1044-00003 · Client 1044 · documents

legal-opinion-no-conflicts.docx DOCUMENT Finance & Banking

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CALDERWOOD & HARKNESS LLP Attorneys at Law

780 Third Avenue New York, NY 10017

Telephone: (212) 558-4000 Facsimile: (212) 558-3588 www.calderwoodharkness.com

June 30, 2023

Nordbank International AG as Administrative Agent and Collateral Agent under the Senior Secured Credit Agreement (as defined below) Bahnhofstrasse 78 8001 Zürich, Switzerland

Attention: Henrik Lüdemann, Managing Director, Shipping & Offshore Finance

and the Lenders party to the Credit Agreement referred to below

Ladies and Gentlemen:

Calderwood & Harkness LLP ("we," "us," or "this Firm") acts as counsel to Thalassa Americas Inc., a corporation organized and existing under the laws of the State of Delaware ("TAI" or the "Company"), in connection with the transactions contemplated by the Restructuring Support Agreement dated March 14, 2023 (the "RSA"), among the Company, Thalassa Shipping & Logistics Société Anonyme ("TSL"), Nordbank International AG, as Administrative Agent and Collateral Agent, and the consenting lenders party thereto.

This opinion is delivered in connection with C&H Matter Number 1044-00003. This opinion is delivered pursuant to Section 4.01(g)(ii) of Amendment No. 1 to the Credit Agreement (each as defined below) as a condition precedent to the effectiveness of such Amendment No. 1 and the closing of the transactions contemplated by the RSA on the date hereof. This opinion is delivered concurrently with, and should be read together with, our separate opinion letter of even date addressed to the same parties regarding the due authorization, execution, delivery, and enforceability of the Company Transaction Documents (as defined below) by TAI.

1. BACKGROUND AND TRANSACTION DOCUMENTS DEFINED

For purposes of this opinion letter, the following capitalized terms shall have the meanings set forth below:

"Credit Agreement" means the Senior Secured Credit Agreement originally dated as of June 15, 2019 (as amended, restated, supplemented, or otherwise modified from time to time), among Thalassa Shipping & Logistics Société Anonyme, a société anonyme organized under the laws of the Hellenic Republic ("TSL"), as Borrower, Thalassa Americas Inc., a Delaware corporation ("TAI"), as Co-Borrower with respect to the U.S. Tranche, Nordbank International AG, a bank organized under the laws of Switzerland ("Nordbank"), as Administrative Agent and Collateral Agent, and the several banks and other financial institutions from time to time party thereto as lenders (collectively, the "Lenders"). The Credit Agreement provided for aggregate commitments in the original principal amount of Six Hundred Eighty-Five Million Dollars ($685,000,000), comprising: (i) a Term Loan A facility in the original principal amount of Four Hundred Million Dollars ($400,000,000) (the "TLA"; CUSIP: 87265BAA7), (ii) a Revolving Credit Facility in the original principal amount of Two Hundred Million Dollars ($200,000,000) (the "Revolving Facility"), and (iii) a U.S. Tranche Term Loan B facility in the original principal amount of Eighty-Five Million Dollars ($85,000,000) (the "TLB"), for which TAI is the designated Co-Borrower.

"Amendment No. 1" means Amendment No. 1 to the Senior Secured Credit Agreement, dated as of May 15, 2023, among TSL, TAI, Nordbank (as Administrative Agent and Collateral Agent), and the Lenders signatory thereto, implementing the restructuring terms agreed upon pursuant to the RSA. Amendment No. 1 effects, among other things, the following modifications to the Credit Agreement: (a) an extension of the maturity date from June 15, 2024 to June 15, 2027; (b) the conversion of Seventy-Five Million Dollars ($75,000,000) of outstanding TLA principal to payment-in-kind ("PIK") obligations; (c) a reduction of the aggregate Revolving Facility commitments from Two Hundred Million Dollars ($200,000,000) to One Hundred Fifty Million Dollars ($150,000,000); (d) a resetting of the financial maintenance covenants, including (I) a Maximum Net Leverage Ratio of 7.00 to 1.00 stepping down to 5.50 to 1.00 by the fourth fiscal quarter of 2025, (II) a Minimum Liquidity covenant of Thirty Million Dollars ($30,000,000), and (III) a waiver of the Interest Coverage Ratio covenant through the fourth fiscal quarter of 2023; (e) an amendment fee in the amount of Five Million Four Hundred Thousand Dollars ($5,400,000), payable in the form of PIK additions to the outstanding TLA principal; and (f) a retroactive waiver of default interest that had accrued under the Credit Agreement.

"Amended and Restated Intercreditor Agreement" means the Amended and Restated Intercreditor Agreement, dated as of May 15, 2023, by and between Nordbank International AG, in its capacity as first-lien agent and collateral agent under the Credit Agreement (as amended), and Dralvecen Mezzanine Capital LLC, in its capacity as second-lien holder and collateral agent under the New Second-Lien Notes (as defined below), which agreement amends, restates, and supersedes in its entirety the original Intercreditor Agreement dated as of June 15, 2019.

"Amended and Restated Intercompany Promissory Note" means the Amended and Restated Intercompany Promissory Note, dated as of May 25, 2023, made by TAI (as maker) in favor of TSL (as holder), in the original principal amount of Seventy-Six Million Four Hundred Thousand Dollars ($76,400,000), which amends and restates the original intercompany promissory note in the same principal amount. Pursuant to the Amended and Restated Intercompany Promissory Note, the maturity date has been extended to December 2028 and the per annum interest rate has been reduced from 5.0% to 2.0%.

In addition to the foregoing, we have reviewed or been made aware of the following related documents executed or delivered in connection with the transactions contemplated by the RSA:

(a) the Joinder Agreement — Consenting Lenders, dated as of March 14, 2023, pursuant to which certain Lenders became parties to the RSA and agreed to be bound by its terms (the "Joinder Agreement");

(b) the Restructuring Support Agreement, dated as of March 14, 2023, among TSL, TAI, Nordbank (as Administrative Agent and Collateral Agent), and the consenting lenders signatory thereto, as supplemented by the Joinder Agreement (the "RSA");

(c) the Side Letter Agreement re Vessel Disposition Undertaking, dated as of March 14, 2023, between TSL and Nordbank (as Administrative Agent), setting forth certain obligations of TSL with respect to the disposition of identified vessels within specified timeframes;

(d) the KFO Equity Subscription Agreement, dated as of May 22, 2023, pursuant to which Kronos Family Office S.A. (as the controlling shareholder of TSL) agreed to contribute additional equity capital to TSL in support of the restructuring; and

(e) the New Second-Lien Note Purchase Agreement, dated as of May 18, 2023, among TSL, TAI, and Dralvecen Mezzanine Capital LLC, as purchaser, providing for the issuance and sale of Sixty Million Dollars ($60,000,000) in aggregate principal amount of second-lien secured notes (the "New Second-Lien Notes"), together with the related New Second-Lien Notes Indenture dated as of May 18, 2023.

The documents described above are referred to collectively herein as the "Transaction Documents." Those Transaction Documents to which TAI is a party — namely, Amendment No. 1, the Amended and Restated Intercreditor Agreement (to the extent TAI is bound thereby or has obligations thereunder), the Amended and Restated Intercompany Promissory Note, the RSA, and the Joinder Agreement — are referred to herein as the "Company Transaction Documents."

2. DOCUMENTS EXAMINED

In connection with the opinions expressed herein, we have examined originals or copies (certified or otherwise identified to our satisfaction) of the following documents:

1. Certificate of Incorporation of Thalassa Americas Inc. (as amended through the date hereof), as filed with the Secretary of State of the State of Delaware.

2. Bylaws of Thalassa Americas Inc. (as amended and currently in effect as of the date hereof).

3. Resolutions of the Board of Directors of TAI adopted at a meeting held on or about May 2023 and by unanimous written consent dated on or about June 2023, authorizing the execution, delivery, and performance by TAI of the Company Transaction Documents and the consummation of the transactions contemplated thereby, and authorizing the officers of TAI to execute and deliver such documents and instruments as may be necessary or appropriate in connection therewith.

4. Secretary's Certificate of TAI, dated June 30, 2023, executed by the Secretary of TAI, certifying the authenticity and completeness of the foregoing charter documents and resolutions, and certifying the incumbency and specimen signatures of Marcus Hale, President of TAI, and Diana Restrepo, Vice President, Finance of TAI.

5. Officer's Certificate of TAI, dated June 30, 2023, executed by Marcus Hale, President of TAI, certifying, among other things, the satisfaction of conditions precedent to the effectiveness of Amendment No. 1 and the closing of the transactions contemplated by the RSA.

6. Solvency Certificate of TAI, dated June 30, 2023, executed by Diana Restrepo, Vice President, Finance of TAI, certifying as to the solvency of TAI on a stand-alone basis and giving effect to the transactions contemplated by the Company Transaction Documents.

7. Certificate of Good Standing of TAI, issued by the Secretary of State of the State of Delaware, dated on or about June 2023.

8. Certificate of Good Standing and Certificate of Foreign Qualification of TAI, issued by the Secretary of State of the State of Texas (reflecting TAI's qualification to do business in Texas and its principal office address at 1400 McKinney Street, Suite 2200, Houston, TX 77010), dated on or about June 2023.

9. The Senior Secured Credit Agreement, dated as of June 15, 2019, among TSL, TAI, Nordbank, and the Lenders, including all schedules and exhibits thereto.

10. Amendment No. 1 to the Senior Secured Credit Agreement, dated as of May 15, 2023.

11. The original Intercreditor Agreement, dated as of June 15, 2019, between Nordbank (as first-lien agent) and Dralvecen Mezzanine Capital LLC (as second-lien holder).

12. The Amended and Restated Intercreditor Agreement, dated as of May 15, 2023.

13. The original intercompany promissory note from TAI (as maker) to TSL (as holder), in the principal amount of $76,400,000.

14. The Amended and Restated Intercompany Promissory Note, dated as of May 25, 2023.

15. The Restructuring Support Agreement, dated as of March 14, 2023.

16. The Joinder Agreement — Consenting Lenders, dated as of March 14, 2023.

17. The indenture governing the $50,000,000 aggregate principal amount of 8.25% Senior Unsecured Notes due March 1, 2025, issued by TAI, with Garrison Trust Company as trustee (CUSIP: 87265BAB5) (the "Unsecured Notes Indenture").

18. The Consent and Waiver Letter from Garrison Trust Company, as trustee under the Unsecured Notes Indenture, dated March 20, 2023, pursuant to which Garrison Trust Company, acting at the direction of the holders of a majority in aggregate principal amount of the outstanding Unsecured Notes, waived the event of default arising from the missed semi-annual interest payment due December 1, 2022, in the amount of Two Million Sixty-Two Thousand Five Hundred Dollars ($2,062,500).

19. The documentation relating to the mezzanine notes originally issued in the aggregate principal amount of $100,000,000, with an outstanding balance (including PIK additions) of approximately $112,300,000 as of the date hereof (the "Mezzanine Notes"), and related documentation.

20. The New Second-Lien Note Purchase Agreement, dated as of May 18, 2023, among TSL, TAI, and Dralvecen Mezzanine Capital LLC.

21. The New Second-Lien Notes Indenture, dated as of May 18, 2023.

22. The directors' and officers' liability insurance policy issued by Promontory Indemnity Insurance Co. (Policy No. PII-DO-2022-08847), providing an aggregate coverage limit of Twenty-Five Million Dollars ($25,000,000), as brokered by Seaward & Beckett Insurance Brokers Ltd.

23. Such other documents, records, agreements, certificates, instruments, corporate proceedings, and other matters as we have deemed necessary or appropriate for the purpose of rendering the opinions expressed herein.

We have also reviewed such matters of law and fact as we have considered necessary or appropriate as a basis for the opinions set forth below.

3. ASSUMPTIONS

In rendering the opinions set forth herein, we have, with your consent and without independent investigation or verification, assumed the following:

(a) Genuineness of Signatures. All signatures on all documents examined by us (other than the signatures of officers of TAI) are genuine, and all natural persons who executed such documents had the legal capacity to do so.

(b) Authenticity of Documents. All documents submitted to us as originals are authentic, complete, and accurate, and all documents submitted to us as copies conform to the originals thereof, which originals are authentic, complete, and accurate.

(c) Organization and Authority of Other Parties. Each party to the Transaction Documents (other than TAI) has been duly organized or formed, as applicable, and is validly existing and in good standing under the laws of its jurisdiction of organization or formation, and has the requisite corporate, partnership, or other organizational power and authority to execute, deliver, and perform its respective obligations under each Transaction Document to which it is a party.

(d) Due Authorization by Other Parties. The Transaction Documents have been duly authorized, executed, and delivered by each party thereto other than TAI. As to TAI's due authorization, execution, and delivery of the Company Transaction Documents, we opine separately in our companion opinion letter of even date addressed to the same parties.

(e) Authority of Signatories. Each natural person executing any Transaction Document on behalf of any party thereto (other than TAI) has been duly authorized to do so by all necessary corporate, partnership, or other organizational action.

(f) Accuracy of Representations and Warranties. All factual representations and warranties made by TAI in the Company Transaction Documents and in the certificates delivered to Nordbank (as Administrative Agent and Collateral Agent) and the Lenders at or prior to the closing on the date hereof are accurate and complete in all material respects. We have relied upon such representations and warranties, and upon the Officer's Certificate of Marcus Hale and the Solvency Certificate of Diana Restrepo, without independent verification.

(g) Greek Law Matters. All filings, registrations, consents, approvals, authorizations, and other actions required under the laws of the Hellenic Republic (Greece) in connection with the execution, delivery, and performance of the Transaction Documents, and the consummation of the transactions contemplated thereby, have been duly obtained, made, or taken, as applicable, by each party required to obtain, make, or take the same. We express no opinion as to any matter governed by or arising under Greek law. Greek law matters relating to TSL and the Transaction Documents have been addressed by Vassiliou & Demetriou Law Offices, 15 Vasilissis Sofias Avenue, Athens 10674, Greece (lead partner: Alexandros Vassiliou), in their separate opinion letter of even date.

(h) Supersession of Forbearance Agreement. The Forbearance Agreement, dated as of October 10, 2022, among TSL, TAI, Nordbank, and the forbearing lenders party thereto (as extended by the First Amendment to Forbearance Agreement dated January 8, 2023, and the Second Amendment to Forbearance Agreement dated March 8, 2023), has been validly superseded in all respects by the RSA, and no party thereto has any continuing rights, obligations, or claims arising under or in connection with such Forbearance Agreement (as so amended).

4. OPINIONS

Based upon and subject to the foregoing, and subject to the qualifications and limitations set forth in Section 5 below, we are of the opinion that:

4.1 No Violation of Organizational Documents

The execution, delivery, and performance by TAI of each Company Transaction Document to which it is a party, and the consummation by TAI of the transactions contemplated thereby, do not and will not (a) violate any provision of the Certificate of Incorporation of TAI (as amended through the date hereof) or (b) violate any provision of the Bylaws of TAI (as amended and currently in effect as of the date hereof). In rendering this opinion, we have reviewed the Certificate of Incorporation and Bylaws of TAI and the resolutions of the Board of Directors of TAI adopted in connection with the transactions contemplated by the RSA, and we have confirmed that such resolutions duly authorize the execution, delivery, and performance by TAI of each Company Transaction Document to which it is a party and the consummation by TAI of the transactions contemplated thereby.

4.2 No Breach of Material Agreements

The execution, delivery, and performance by TAI of each Company Transaction Document to which it is a party, and the consummation by TAI of the transactions contemplated thereby, do not and will not (a) result in a breach of, (b) constitute a default under (or an event that, with the giving of notice or the lapse of time or both, would constitute a default under), or (c) result in the acceleration of any obligation under, any material agreement, indenture, mortgage, deed of trust, note, instrument, or other obligation to which TAI is a party or by which TAI or any of its properties or assets are bound, including without limitation:

(i) the Senior Secured Credit Agreement, dated as of June 15, 2019, as amended by Amendment No. 1 dated May 15, 2023 — in which TAI is a Co-Borrower with respect to the U.S. Tranche (Term Loan B, $85,000,000);

(ii) the indenture governing the $50,000,000 aggregate principal amount of 8.25% Senior Unsecured Notes due March 1, 2025, with Garrison Trust Company as trustee (CUSIP: 87265BAB5) — we note that the event of default arising from the missed semi-annual interest payment due December 1, 2022, in the amount of $2,062,500, has been duly waived by the requisite holders of the Unsecured Notes pursuant to the Consent and Waiver Letter from Garrison Trust Company dated March 20, 2023, and that the missed coupon payment is being paid in full concurrently with the closing on the date hereof;

(iii) the Amended and Restated Intercreditor Agreement, dated as of May 15, 2023;

(iv) the Amended and Restated Intercompany Promissory Note, dated as of May 25, 2023 (original principal amount of $76,400,000; per annum interest rate of 2.0%; maturity date of December 2028);

(v) the Houston terminal lease and other material contracts to which TAI is a party, as more particularly described on Schedule A hereto; and

(vi) each of the other material agreements listed on Schedule A hereto.

We note that this opinion is limited to those agreements that have been identified to us by the officers of TAI and listed on Schedule A attached hereto. We have not undertaken an independent investigation, search of public records, or other inquiry to identify all agreements, instruments, or obligations to which TAI may be a party or by which TAI or its properties may be bound.

4.3 No Violation of Applicable Law

The execution, delivery, and performance by TAI of each Company Transaction Document to which it is a party, and the consummation by TAI of the transactions contemplated thereby, do not and will not result in a violation of any applicable law, statute, rule, or regulation of the State of Delaware, the State of Texas, or the federal laws of the United States of America, in each case to the extent applicable to TAI and the transactions contemplated by the Company Transaction Documents.

Without limiting the generality of the foregoing, we have specifically considered and confirm that the execution, delivery, and performance by TAI of the Company Transaction Documents, and the consummation of the transactions contemplated thereby, do not and will not result in a violation of:

(a) the Delaware General Corporation Law (Title 8 of the Delaware Code);

(b) applicable federal securities laws, including the Securities Act of 1933, as amended, and the Securities Exchange Act of 1934, as amended, and the rules and regulations promulgated thereunder;

(c) applicable provisions of the United States Bankruptcy Code (Title 11 of the United States Code) — we note in this regard that no voluntary or involuntary petition for relief under the Bankruptcy Code has been filed by or against TAI, and the Chapter 11 contingency plan (proposed venue: the United States Bankruptcy Court for the Southern District of Texas, Houston Division) was not activated; and

(d) applicable banking and lending regulations of the United States and the State of Texas.

4.4 No Governmental Consent Required

No consent, approval, authorization, order, registration, qualification, or filing with any governmental authority or regulatory body of the State of Delaware, the State of Texas, or the United States of America is required for the valid execution, delivery, and performance by TAI of the Company Transaction Documents or the consummation by TAI of the transactions contemplated thereby, except for such consents, approvals, authorizations, orders, registrations, qualifications, and filings as have been duly obtained or made prior to the date hereof.

We note in this regard that the closing of the transactions contemplated by the RSA is occurring on June 30, 2023, which is the Effective Date as defined in the RSA. All conditions precedent to the effectiveness of Amendment No. 1 and the consummation of the transactions contemplated by the RSA have been satisfied or duly waived, as certified in the Officer's Certificate of Marcus Hale, President of TAI, dated June 30, 2023, and as set forth in the Closing Memorandum of even date prepared by this Firm.

4.5 No Liens Created

The execution, delivery, and performance by TAI of the Company Transaction Documents do not and will not result in the creation or imposition of any lien, charge, pledge, security interest, encumbrance, or other restriction on title or transfer upon any property or assets of TAI (whether real, personal, or mixed, and whether tangible or intangible), other than liens and security interests expressly created, granted, or permitted by the Transaction Documents. The foregoing exception includes, without limitation, (a) the first-priority liens and security interests securing the obligations of TAI and TSL under the Credit Agreement (as amended by Amendment No. 1), as granted in favor of Nordbank (as Collateral Agent) for the benefit of the Lenders, and (b) the second-priority liens and security interests securing the obligations under the $60,000,000 aggregate principal amount of New Second-Lien Notes issued to Dralvecen Mezzanine Capital LLC, in each case as provided for and described in the Amended and Restated Intercreditor Agreement dated May 15, 2023.

5. QUALIFICATIONS AND LIMITATIONS

The opinions expressed herein are subject to the following qualifications and limitations:

5.1 Jurisdictional Limitation

The opinions expressed herein are limited solely to the laws of the State of New York, the General Corporation Law of the State of Delaware (Title 8 of the Delaware Code), and the federal laws of the United States of America, in each case as in effect on the date hereof. We do not express any opinion as to the laws of any other jurisdiction, including without limitation the laws of the Hellenic Republic (Greece), Switzerland, England and Wales, Singapore, the Federal Republic of Germany, Canada, the United Arab Emirates, the Republic of Cyprus, or Bermuda.

With respect to matters governed by the laws of the Hellenic Republic, including matters relating to the organization, corporate authority, and enforceability of obligations of TSL, we note that such matters have been separately addressed by Vassiliou & Demetriou Law Offices, located at 15 Vasilissis Sofias Avenue, Athens 10674, Greece (lead partner: Alexandros Vassiliou), in their separate opinion letter of even date addressed to Nordbank (as Administrative Agent and Collateral Agent) and the Lenders.

5.2 Bankruptcy and Insolvency Qualification

The opinions expressed herein are subject to the effect of (a) bankruptcy, insolvency, reorganization, receivership, moratorium, arrangement, fraudulent conveyance, fraudulent transfer, preferential transfer, and other similar laws relating to or affecting the enforcement of creditors' rights generally, including without limitation the United States Bankruptcy Code (Title 11 of the United States Code) and applicable state insolvency, receivership, assignment for the benefit of creditors, and similar laws, and (b) the exercise of judicial discretion and the application of principles of equity, whether applied in a proceeding at law or in equity (including, without limitation, principles governing the availability of specific performance, injunctive relief, and other equitable remedies).

We note that the Chapter 11 contingency plan prepared by this Firm and by Kensington Veltrian Partners LLC (as financial advisor to TAI) for the potential filing of a voluntary petition for relief under Chapter 11 of the Bankruptcy Code by TAI (proposed venue: the United States Bankruptcy Court for the Southern District of Texas, Houston Division) was not activated, and no petition for relief under the Bankruptcy Code has been filed by or against TAI as of the date hereof. The foregoing qualification is included as a standard matter and should not be construed as suggesting any concern regarding the solvency or financial condition of TAI.

5.3 Equitable Principles Limitation

The opinions expressed herein are subject to, and may be limited by, general principles of equity, whether applied in a proceeding at law or in equity, including without limitation concepts of materiality, reasonableness, good faith, fair dealing, unconscionability, impracticability, frustration of purpose, and the discretion of the court before which any proceeding may be brought. We express no opinion as to the availability of any particular equitable remedy.

5.4 Material Agreement Limitation

The opinion set forth in Section 4.2 above is limited to those agreements, indentures, instruments, and obligations that have been listed on Schedule A attached hereto and such other agreements as have been specifically identified to us by the officers of TAI in connection with the transactions contemplated by the RSA. We have not undertaken an independent investigation, search of public records (other than the review of the documents enumerated in Section 2 above), or other independent inquiry to identify all agreements, indentures, instruments, or obligations to which TAI may be a party or by which TAI or any of its properties or assets may be bound. In rendering the opinion set forth in Section 4.2, we have relied upon the representations of Marcus Hale, President of TAI, and Diana Restrepo, Vice President, Finance of TAI, as to the completeness of the list of material agreements set forth on Schedule A and as to the absence of any other agreement, instrument, or obligation that would be material to the rendering of such opinion.

5.5 Regulatory Limitations

Without limiting the generality of Section 5.1, we do not express any opinion herein with respect to:

(a) compliance with maritime law, admiralty law, the Merchant Marine Act of 1920 (the "Jones Act"), the Shipping Act of 1984, or any other statute, rule, or regulation specific to the shipping, maritime transportation, or logistics industries;

(b) tax matters of any kind, including without limitation federal, state, and local income, excise, franchise, and other taxes — tax opinions in connection with the transactions contemplated by the RSA have been separately addressed by Sylvia Hartwell, Specialist Partner, Tax, Calderwood & Harkness LLP, in a separate tax opinion letter of even date;

(c) compliance with anti-money laundering laws and regulations, including without limitation the Bank Secrecy Act, the USA PATRIOT Act of 2001, and the regulations promulgated by the Financial Crimes Enforcement Network ("FinCEN");

(d) compliance with the sanctions laws and regulations administered by the Office of Foreign Assets Control ("OFAC") of the U.S. Department of the Treasury, including without limitation Executive Orders imposing sanctions on designated persons and entities; and

(e) compliance with environmental laws and regulations, including without limitation the Comprehensive Environmental Response, Compensation, and Liability Act ("CERCLA"), the Resource Conservation and Recovery Act ("RCRA"), the Clean Water Act, the Clean Air Act, and corresponding state environmental laws and regulations.

5.6 No Implied Opinions

We express no opinion, and no opinion is to be implied or inferred, beyond those opinions expressly stated herein. The opinions expressed herein are limited in all respects to the matters expressly set forth in Section 4, and no expansion of such opinions may be made by implication or otherwise.

6. RELIANCE AND BENEFIT

This opinion letter is furnished solely for the benefit of Nordbank International AG, in its capacity as Administrative Agent and Collateral Agent under the Credit Agreement (as amended), and the Lenders party to the Credit Agreement (as amended), in each case solely in connection with the closing of the transactions contemplated by the RSA on June 30, 2023.

The Lenders currently party to the Credit Agreement (as amended by Amendment No. 1), and the respective commitments of each as of the date hereof, are as follows:

This opinion letter may not be relied upon by any other person or entity, or for any purpose other than the purpose set forth above, without the prior written consent of Calderwood & Harkness LLP. This opinion letter may not be quoted or referred to in any report, document, financial statement, prospectus, or other document, or filed with any governmental authority or other person, without the prior written consent of Calderwood & Harkness LLP.

7. DATE AND CHANGE LIMITATION

This opinion letter speaks only as of the date hereof, June 30, 2023, and is based upon the facts, circumstances, and laws in existence on the date hereof. We have no obligation, and assume no obligation, to update, supplement, revise, or withdraw this opinion letter, or any opinion expressed herein, to reflect any facts, circumstances, developments, or changes in law that may hereafter come to our attention or occur after the date hereof, regardless of whether such facts, circumstances, developments, or changes in law may affect the opinions expressed herein.

We trust that the foregoing opinions are satisfactory for your purposes in connection with the closing of the transactions contemplated by the RSA. Should you have any questions regarding the matters addressed herein, please do not hesitate to contact the undersigned.

Very truly yours,

CALDERWOOD & HARKNESS LLP

By: ________

Name: Nathaniel Bower

Title: Partner, Bankruptcy & Restructuring Group

Calderwood & Harkness LLP 780 Third Avenue New York, NY 10017 Telephone: (212) 558-4000

SCHEDULE A

Material Agreements of Thalassa Americas Inc. Reviewed in Connection with Opinion 4.2

The following is an enumerated list of all material agreements, indentures, instruments, and obligations to which Thalassa Americas Inc. ("TAI") is a party or by which TAI or any of its properties or assets are bound, in each case as identified to Calderwood & Harkness LLP by the officers of TAI and reviewed in connection with the opinion set forth in Section 4.2 of this opinion letter:

1. Senior Secured Credit Agreement, dated as of June 15, 2019 (as amended by Amendment No. 1 to the Senior Secured Credit Agreement dated as of May 15, 2023), among TSL (as Borrower), TAI (as Co-Borrower with respect to the U.S. Tranche (Term Loan B, $85,000,000)), Nordbank International AG (as Administrative Agent and Collateral Agent), and the Lenders party thereto.

2. Amended and Restated Intercreditor Agreement, dated as of May 15, 2023, by and between Nordbank International AG (as first-lien agent and collateral agent) and Dralvecen Mezzanine Capital LLC (as second-lien holder and collateral agent).

3. Amended and Restated Intercompany Promissory Note, dated as of May 25, 2023, from TAI (as maker) to TSL (as holder), in the original principal amount of $76,400,000, bearing interest at 2.0% per annum, with a maturity date of December 2028.

4. Restructuring Support Agreement, dated as of March 14, 2023, among TSL, TAI, Nordbank (as Administrative Agent and Collateral Agent), and the consenting lenders signatory thereto.

5. Joinder Agreement — Consenting Lenders, dated as of March 14, 2023, pursuant to which certain Lenders became parties to the RSA.

6. Houston Terminal Lease, providing for TAI's principal office and terminal operations at 1400 McKinney Street, Suite 2200, Houston, TX 77010, together with all amendments, supplements, and modifications thereto.

7. Vessel Charter Agreements to which TAI is a party, consisting of Jones Act–exempt foreign-flag vessel scheduling contracts entered into in the ordinary course of TAI's business.

8. Domestic Freight Brokerage Agreements to which TAI is a party, entered into in the ordinary course of TAI's freight brokerage and logistics operations.

9. Directors' and Officers' Liability Insurance Policy, issued by Promontory Indemnity Insurance Co. (Policy No. PII-DO-2022-08847), providing an aggregate coverage limit of $25,000,000, as brokered by Seaward & Beckett Insurance Brokers Ltd.

10. Engagement Letters with Professional Advisors, including:

(a) Engagement letter with Calderwood & Harkness LLP, dated October 25, 2022 (as supplemented by the Supplemental Engagement Letter dated November 5, 2022), for legal advisory services in connection with the restructuring of TAI's and TSL's indebtedness.

(b) Engagement letter with Kensington Veltrian Partners LLC (financial advisor), providing for a monthly advisory fee of $250,000 and a completion fee of $4,500,000 upon the consummation of the restructuring.

11. Standby Engagement with Pendleton Claim Services Inc., dated November 15, 2022, for claims management and administration services in connection with a potential Chapter 11 filing. This engagement was terminated on July 10, 2023, following the successful consummation of the out-of-court restructuring.

12. Registered Agent Agreement with Capitol Registered Agents LLC (1209 Orange Street, Wilmington, DE 19801), for the provision of registered agent services in the State of Delaware.

13. Such other agreements as have been identified to us by Marcus Hale, President of TAI, and Diana Restrepo, Vice President, Finance of TAI, and listed on the certificate of such officers delivered at the closing on June 30, 2023, which certificate has been reviewed by this Firm and is incorporated by reference into this Schedule A.

Lender	Commitment (USD)
Nordbank International AG	$137,000,000
Aegean Capital Bank SA	$110,000,000
Harborstone Bank plc	$95,000,000
Pacifica Trade Finance Corp.	$82,000,000
Continental Maritime Lending GmbH	$72,000,000
Triton Credit Partners LP	$68,000,000
Laurentian Shipping Fund II	$55,000,000
Caspian Asset Management Ltd.	$40,000,000
Pelagos Institutional Credit Fund	$26,000,000
Total	$685,000,000

CALDERWOOD & HARKNESS LLP Attorneys at Law
780 Third Avenue New York, NY 10017
Telephone: (212) 558-4000 Facsimile: (212) 558-3588 www.calderwoodharkness.com
June 30, 2023
Nordbank International AG as Administrative Agent and Collateral Agent under the Senior Secured Credit Agreement (as defined below) Bahnhofstrasse 78 8001 Zürich, Switzerland
Attention: Henrik Lüdemann, Managing Director, Shipping & Offshore Finance
and the Lenders party to the Credit Agreement referred to below
Ladies and Gentlemen:
Calderwood & Harkness LLP ("we," "us," or "this Firm") acts as counsel to Thalassa Americas Inc., a corporation organized and existing under the laws of the State of Delaware ("TAI" or the "Company"), in connection with the transactions contemplated by the Restructuring Support Agreement dated March 14, 2023 (the "RSA"), among the Company, Thalassa Shipping & Logistics Société Anonyme ("TSL"), Nordbank International AG, as Administrative Agent and Collateral Agent, and the consenting lenders party thereto.
This opinion is delivered in connection with C&H Matter Number 1044-00003. This opinion is delivered pursuant to Section 4.01(g)(ii) of Amendment No. 1 to the Credit Agreement (each as defined below) as a condition precedent to the effectiveness of such Amendment No. 1 and the closing of the transactions contemplated by the RSA on the date hereof. This opinion is delivered concurrently with, and should be read together with, our separate opinion letter of even date addressed to the same parties regarding the due authorization, execution, delivery, and enforceability of the Company Transaction Documents (as defined below) by TAI.
1. BACKGROUND AND TRANSACTION DOCUMENTS DEFINED
For purposes of this opinion letter, the following capitalized terms shall have the meanings set forth below:
"Credit Agreement" means the Senior Secured Credit Agreement originally dated as of June 15, 2019 (as amended, restated, supplemented, or otherwise modified from time to time), among Thalassa Shipping & Logistics Société Anonyme, a société anonyme organized under the laws of the Hellenic Republic ("TSL"), as Borrower, Thalassa Americas Inc., a Delaware corporation ("TAI"), as Co-Borrower with respect to the U.S. Tranche, Nordbank International AG, a bank organized under the laws of Switzerland ("Nordbank"), as Administrative Agent and Collateral Agent, and the several banks and other financial institutions from time to time party thereto as lenders (collectively, the "Lenders"). The Credit Agreement provided for aggregate commitments in the original principal amount of Six Hundred Eighty-Five Million Dollars ($685,000,000), comprising: (i) a Term Loan A facility in the original principal amount of Four Hundred Million Dollars ($400,000,000) (the "TLA"; CUSIP: 87265BAA7), (ii) a Revolving Credit Facility in the original principal amount of Two Hundred Million Dollars ($200,000,000) (the "Revolving Facility"), and (iii) a U.S. Tranche Term Loan B facility in the original principal amount of Eighty-Five Million Dollars ($85,000,000) (the "TLB"), for which TAI is the designated Co-Borrower.
"Amendment No. 1" means Amendment No. 1 to the Senior Secured Credit Agreement, dated as of May 15, 2023, among TSL, TAI, Nordbank (as Administrative Agent and Collateral Agent), and the Lenders signatory thereto, implementing the restructuring terms agreed upon pursuant to the RSA. Amendment No. 1 effects, among other things, the following modifications to the Credit Agreement: (a) an extension of the maturity date from June 15, 2024 to June 15, 2027; (b) the conversion of Seventy-Five Million Dollars ($75,000,000) of outstanding TLA principal to payment-in-kind ("PIK") obligations; (c) a reduction of the aggregate Revolving Facility commitments from Two Hundred Million Dollars ($200,000,000) to One Hundred Fifty Million Dollars ($150,000,000); (d) a resetting of the financial maintenance covenants, including (I) a Maximum Net Leverage Ratio of 7.00 to 1.00 stepping down to 5.50 to 1.00 by the fourth fiscal quarter of 2025, (II) a Minimum Liquidity covenant of Thirty Million Dollars ($30,000,000), and (III) a waiver of the Interest Coverage Ratio covenant through the fourth fiscal quarter of 2023; (e) an amendment fee in the amount of Five Million Four Hundred Thousand Dollars ($5,400,000), payable in the form of PIK additions to the outstanding TLA principal; and (f) a retroactive waiver of default interest that had accrued under the Credit Agreement.
"Amended and Restated Intercreditor Agreement" means the Amended and Restated Intercreditor Agreement, dated as of May 15, 2023, by and between Nordbank International AG, in its capacity as first-lien agent and collateral agent under the Credit Agreement (as amended), and Dralvecen Mezzanine Capital LLC, in its capacity as second-lien holder and collateral agent under the New Second-Lien Notes (as defined below), which agreement amends, restates, and supersedes in its entirety the original Intercreditor Agreement dated as of June 15, 2019.
"Amended and Restated Intercompany Promissory Note" means the Amended and Restated Intercompany Promissory Note, dated as of May 25, 2023, made by TAI (as maker) in favor of TSL (as holder), in the original principal amount of Seventy-Six Million Four Hundred Thousand Dollars ($76,400,000), which amends and restates the original intercompany promissory note in the same principal amount. Pursuant to the Amended and Restated Intercompany Promissory Note, the maturity date has been extended to December 2028 and the per annum interest rate has been reduced from 5.0% to 2.0%.
In addition to the foregoing, we have reviewed or been made aware of the following related documents executed or delivered in connection with the transactions contemplated by the RSA:
(a) the Joinder Agreement — Consenting Lenders, dated as of March 14, 2023, pursuant to which certain Lenders became parties to the RSA and agreed to be bound by its terms (the "Joinder Agreement");
(b) the Restructuring Support Agreement, dated as of March 14, 2023, among TSL, TAI, Nordbank (as Administrative Agent and Collateral Agent), and the consenting lenders signatory thereto, as supplemented by the Joinder Agreement (the "RSA");
(c) the Side Letter Agreement re Vessel Disposition Undertaking, dated as of March 14, 2023, between TSL and Nordbank (as Administrative Agent), setting forth certain obligations of TSL with respect to the disposition of identified vessels within specified timeframes;
(d) the KFO Equity Subscription Agreement, dated as of May 22, 2023, pursuant to which Kronos Family Office S.A. (as the controlling shareholder of TSL) agreed to contribute additional equity capital to TSL in support of the restructuring; and
(e) the New Second-Lien Note Purchase Agreement, dated as of May 18, 2023, among TSL, TAI, and Dralvecen Mezzanine Capital LLC, as purchaser, providing for the issuance and sale of Sixty Million Dollars ($60,000,000) in aggregate principal amount of second-lien secured notes (the "New Second-Lien Notes"), together with the related New Second-Lien Notes Indenture dated as of May 18, 2023.
The documents described above are referred to collectively herein as the "Transaction Documents." Those Transaction Documents to which TAI is a party — namely, Amendment No. 1, the Amended and Restated Intercreditor Agreement (to the extent TAI is bound thereby or has obligations thereunder), the Amended and Restated Intercompany Promissory Note, the RSA, and the Joinder Agreement — are referred to herein as the "Company Transaction Documents."
2. DOCUMENTS EXAMINED
In connection with the opinions expressed herein, we have examined originals or copies (certified or otherwise identified to our satisfaction) of the following documents:
1.  Certificate of Incorporation of Thalassa Americas Inc. (as amended through the date hereof), as filed with the Secretary of State of the State of Delaware.
2.  Bylaws of Thalassa Americas Inc. (as amended and currently in effect as of the date hereof).
3.  Resolutions of the Board of Directors of TAI adopted at a meeting held on or about May 2023 and by unanimous written consent dated on or about June 2023, authorizing the execution, delivery, and performance by TAI of the Company Transaction Documents and the consummation of the transactions contemplated thereby, and authorizing the officers of TAI to execute and deliver such documents and instruments as may be necessary or appropriate in connection therewith.
4.  Secretary's Certificate of TAI, dated June 30, 2023, executed by the Secretary of TAI, certifying the authenticity and completeness of the foregoing charter documents and resolutions, and certifying the incumbency and specimen signatures of Marcus Hale, President of TAI, and Diana Restrepo, Vice President, Finance of TAI.
5.  Officer's Certificate of TAI, dated June 30, 2023, executed by Marcus Hale, President of TAI, certifying, among other things, the satisfaction of conditions precedent to the effectiveness of Amendment No. 1 and the closing of the transactions contemplated by the RSA.
6.  Solvency Certificate of TAI, dated June 30, 2023, executed by Diana Restrepo, Vice President, Finance of TAI, certifying as to the solvency of TAI on a stand-alone basis and giving effect to the transactions contemplated by the Company Transaction Documents.
7.  Certificate of Good Standing of TAI, issued by the Secretary of State of the State of Delaware, dated on or about June 2023.
8.  Certificate of Good Standing and Certificate of Foreign Qualification of TAI, issued by the Secretary of State of the State of Texas (reflecting TAI's qualification to do business in Texas and its principal office address at 1400 McKinney Street, Suite 2200, Houston, TX 77010), dated on or about June 2023.
9.  The Senior Secured Credit Agreement, dated as of June 15, 2019, among TSL, TAI, Nordbank, and the Lenders, including all schedules and exhibits thereto.
10.  Amendment No. 1 to the Senior Secured Credit Agreement, dated as of May 15, 2023.
11.  The original Intercreditor Agreement, dated as of June 15, 2019, between Nordbank (as first-lien agent) and Dralvecen Mezzanine Capital LLC (as second-lien holder).
12.  The Amended and Restated Intercreditor Agreement, dated as of May 15, 2023.
13.  The original intercompany promissory note from TAI (as maker) to TSL (as holder), in the principal amount of $76,400,000.
14.  The Amended and Restated Intercompany Promissory Note, dated as of May 25, 2023.
15.  The Restructuring Support Agreement, dated as of March 14, 2023.
16.  The Joinder Agreement — Consenting Lenders, dated as of March 14, 2023.
17.  The indenture governing the $50,000,000 aggregate principal amount of 8.25% Senior Unsecured Notes due March 1, 2025, issued by TAI, with Garrison Trust Company as trustee (CUSIP: 87265BAB5) (the "Unsecured Notes Indenture").
18.  The Consent and Waiver Letter from Garrison Trust Company, as trustee under the Unsecured Notes Indenture, dated March 20, 2023, pursuant to which Garrison Trust Company, acting at the direction of the holders of a majority in aggregate principal amount of the outstanding Unsecured Notes, waived the event of default arising from the missed semi-annual interest payment due December 1, 2022, in the amount of Two Million Sixty-Two Thousand Five Hundred Dollars ($2,062,500).
19.  The documentation relating to the mezzanine notes originally issued in the aggregate principal amount of $100,000,000, with an outstanding balance (including PIK additions) of approximately $112,300,000 as of the date hereof (the "Mezzanine Notes"), and related documentation.
20.  The New Second-Lien Note Purchase Agreement, dated as of May 18, 2023, among TSL, TAI, and Dralvecen Mezzanine Capital LLC.
21.  The New Second-Lien Notes Indenture, dated as of May 18, 2023.
22.  The directors' and officers' liability insurance policy issued by Promontory Indemnity Insurance Co. (Policy No. PII-DO-2022-08847), providing an aggregate coverage limit of Twenty-Five Million Dollars ($25,000,000), as brokered by Seaward & Beckett Insurance Brokers Ltd.
23.  Such other documents, records, agreements, certificates, instruments, corporate proceedings, and other matters as we have deemed necessary or appropriate for the purpose of rendering the opinions expressed herein.
We have also reviewed such matters of law and fact as we have considered necessary or appropriate as a basis for the opinions set forth below.
3. ASSUMPTIONS
In rendering the opinions set forth herein, we have, with your consent and without independent investigation or verification, assumed the following:
(a) Genuineness of Signatures. All signatures on all documents examined by us (other than the signatures of officers of TAI) are genuine, and all natural persons who executed such documents had the legal capacity to do so.
(b) Authenticity of Documents. All documents submitted to us as originals are authentic, complete, and accurate, and all documents submitted to us as copies conform to the originals thereof, which originals are authentic, complete, and accurate.
(c) Organization and Authority of Other Parties. Each party to the Transaction Documents (other than TAI) has been duly organized or formed, as applicable, and is validly existing and in good standing under the laws of its jurisdiction of organization or formation, and has the requisite corporate, partnership, or other organizational power and authority to execute, deliver, and perform its respective obligations under each Transaction Document to which it is a party.
(d) Due Authorization by Other Parties. The Transaction Documents have been duly authorized, executed, and delivered by each party thereto other than TAI. As to TAI's due authorization, execution, and delivery of the Company Transaction Documents, we opine separately in our companion opinion letter of even date addressed to the same parties.
(e) Authority of Signatories. Each natural person executing any Transaction Document on behalf of any party thereto (other than TAI) has been duly authorized to do so by all necessary corporate, partnership, or other organizational action.
(f) Accuracy of Representations and Warranties. All factual representations and warranties made by TAI in the Company Transaction Documents and in the certificates delivered to Nordbank (as Administrative Agent and Collateral Agent) and the Lenders at or prior to the closing on the date hereof are accurate and complete in all material respects. We have relied upon such representations and warranties, and upon the Officer's Certificate of Marcus Hale and the Solvency Certificate of Diana Restrepo, without independent verification.
(g) Greek Law Matters. All filings, registrations, consents, approvals, authorizations, and other actions required under the laws of the Hellenic Republic (Greece) in connection with the execution, delivery, and performance of the Transaction Documents, and the consummation of the transactions contemplated thereby, have been duly obtained, made, or taken, as applicable, by each party required to obtain, make, or take the same. We express no opinion as to any matter governed by or arising under Greek law. Greek law matters relating to TSL and the Transaction Documents have been addressed by Vassiliou & Demetriou Law Offices, 15 Vasilissis Sofias Avenue, Athens 10674, Greece (lead partner: Alexandros Vassiliou), in their separate opinion letter of even date.
(h) Supersession of Forbearance Agreement. The Forbearance Agreement, dated as of October 10, 2022, among TSL, TAI, Nordbank, and the forbearing lenders party thereto (as extended by the First Amendment to Forbearance Agreement dated January 8, 2023, and the Second Amendment to Forbearance Agreement dated March 8, 2023), has been validly superseded in all respects by the RSA, and no party thereto has any continuing rights, obligations, or claims arising under or in connection with such Forbearance Agreement (as so amended).
4. OPINIONS
Based upon and subject to the foregoing, and subject to the qualifications and limitations set forth in Section 5 below, we are of the opinion that:
4.1 No Violation of Organizational Documents
The execution, delivery, and performance by TAI of each Company Transaction Document to which it is a party, and the consummation by TAI of the transactions contemplated thereby, do not and will not (a) violate any provision of the Certificate of Incorporation of TAI (as amended through the date hereof) or (b) violate any provision of the Bylaws of TAI (as amended and currently in effect as of the date hereof). In rendering this opinion, we have reviewed the Certificate of Incorporation and Bylaws of TAI and the resolutions of the Board of Directors of TAI adopted in connection with the transactions contemplated by the RSA, and we have confirmed that such resolutions duly authorize the execution, delivery, and performance by TAI of each Company Transaction Document to which it is a party and the consummation by TAI of the transactions contemplated thereby.
4.2 No Breach of Material Agreements
The execution, delivery, and performance by TAI of each Company Transaction Document to which it is a party, and the consummation by TAI of the transactions contemplated thereby, do not and will not (a) result in a breach of, (b) constitute a default under (or an event that, with the giving of notice or the lapse of time or both, would constitute a default under), or (c) result in the acceleration of any obligation under, any material agreement, indenture, mortgage, deed of trust, note, instrument, or other obligation to which TAI is a party or by which TAI or any of its properties or assets are bound, including without limitation:
(i) the Senior Secured Credit Agreement, dated as of June 15, 2019, as amended by Amendment No. 1 dated May 15, 2023 — in which TAI is a Co-Borrower with respect to the U.S. Tranche (Term Loan B, $85,000,000);
(ii) the indenture governing the $50,000,000 aggregate principal amount of 8.25% Senior Unsecured Notes due March 1, 2025, with Garrison Trust Company as trustee (CUSIP: 87265BAB5) — we note that the event of default arising from the missed semi-annual interest payment due December 1, 2022, in the amount of $2,062,500, has been duly waived by the requisite holders of the Unsecured Notes pursuant to the Consent and Waiver Letter from Garrison Trust Company dated March 20, 2023, and that the missed coupon payment is being paid in full concurrently with the closing on the date hereof;
(iii) the Amended and Restated Intercreditor Agreement, dated as of May 15, 2023;
(iv) the Amended and Restated Intercompany Promissory Note, dated as of May 25, 2023 (original principal amount of $76,400,000; per annum interest rate of 2.0%; maturity date of December 2028);
(v) the Houston terminal lease and other material contracts to which TAI is a party, as more particularly described on Schedule A hereto; and
(vi) each of the other material agreements listed on Schedule A hereto.
We note that this opinion is limited to those agreements that have been identified to us by the officers of TAI and listed on Schedule A attached hereto. We have not undertaken an independent investigation, search of public records, or other inquiry to identify all agreements, instruments, or obligations to which TAI may be a party or by which TAI or its properties may be bound.
4.3 No Violation of Applicable Law
The execution, delivery, and performance by TAI of each Company Transaction Document to which it is a party, and the consummation by TAI of the transactions contemplated thereby, do not and will not result in a violation of any applicable law, statute, rule, or regulation of the State of Delaware, the State of Texas, or the federal laws of the United States of America, in each case to the extent applicable to TAI and the transactions contemplated by the Company Transaction Documents.
Without limiting the generality of the foregoing, we have specifically considered and confirm that the execution, delivery, and performance by TAI of the Company Transaction Documents, and the consummation of the transactions contemplated thereby, do not and will not result in a violation of:
(a) the Delaware General Corporation Law (Title 8 of the Delaware Code);
(b) applicable federal securities laws, including the Securities Act of 1933, as amended, and the Securities Exchange Act of 1934, as amended, and the rules and regulations promulgated thereunder;
(c) applicable provisions of the United States Bankruptcy Code (Title 11 of the United States Code) — we note in this regard that no voluntary or involuntary petition for relief under the Bankruptcy Code has been filed by or against TAI, and the Chapter 11 contingency plan (proposed venue: the United States Bankruptcy Court for the Southern District of Texas, Houston Division) was not activated; and
(d) applicable banking and lending regulations of the United States and the State of Texas.
4.4 No Governmental Consent Required
No consent, approval, authorization, order, registration, qualification, or filing with any governmental authority or regulatory body of the State of Delaware, the State of Texas, or the United States of America is required for the valid execution, delivery, and performance by TAI of the Company Transaction Documents or the consummation by TAI of the transactions contemplated thereby, except for such consents, approvals, authorizations, orders, registrations, qualifications, and filings as have been duly obtained or made prior to the date hereof.
We note in this regard that the closing of the transactions contemplated by the RSA is occurring on June 30, 2023, which is the Effective Date as defined in the RSA. All conditions precedent to the effectiveness of Amendment No. 1 and the consummation of the transactions contemplated by the RSA have been satisfied or duly waived, as certified in the Officer's Certificate of Marcus Hale, President of TAI, dated June 30, 2023, and as set forth in the Closing Memorandum of even date prepared by this Firm.
4.5 No Liens Created
The execution, delivery, and performance by TAI of the Company Transaction Documents do not and will not result in the creation or imposition of any lien, charge, pledge, security interest, encumbrance, or other restriction on title or transfer upon any property or assets of TAI (whether real, personal, or mixed, and whether tangible or intangible), other than liens and security interests expressly created, granted, or permitted by the Transaction Documents. The foregoing exception includes, without limitation, (a) the first-priority liens and security interests securing the obligations of TAI and TSL under the Credit Agreement (as amended by Amendment No. 1), as granted in favor of Nordbank (as Collateral Agent) for the benefit of the Lenders, and (b) the second-priority liens and security interests securing the obligations under the $60,000,000 aggregate principal amount of New Second-Lien Notes issued to Dralvecen Mezzanine Capital LLC, in each case as provided for and described in the Amended and Restated Intercreditor Agreement dated May 15, 2023.
5. QUALIFICATIONS AND LIMITATIONS
The opinions expressed herein are subject to the following qualifications and limitations:
5.1 Jurisdictional Limitation
The opinions expressed herein are limited solely to the laws of the State of New York, the General Corporation Law of the State of Delaware (Title 8 of the Delaware Code), and the federal laws of the United States of America, in each case as in effect on the date hereof. We do not express any opinion as to the laws of any other jurisdiction, including without limitation the laws of the Hellenic Republic (Greece), Switzerland, England and Wales, Singapore, the Federal Republic of Germany, Canada, the United Arab Emirates, the Republic of Cyprus, or Bermuda.
With respect to matters governed by the laws of the Hellenic Republic, including matters relating to the organization, corporate authority, and enforceability of obligations of TSL, we note that such matters have been separately addressed by Vassiliou & Demetriou Law Offices, located at 15 Vasilissis Sofias Avenue, Athens 10674, Greece (lead partner: Alexandros Vassiliou), in their separate opinion letter of even date addressed to Nordbank (as Administrative Agent and Collateral Agent) and the Lenders.
5.2 Bankruptcy and Insolvency Qualification
The opinions expressed herein are subject to the effect of (a) bankruptcy, insolvency, reorganization, receivership, moratorium, arrangement, fraudulent conveyance, fraudulent transfer, preferential transfer, and other similar laws relating to or affecting the enforcement of creditors' rights generally, including without limitation the United States Bankruptcy Code (Title 11 of the United States Code) and applicable state insolvency, receivership, assignment for the benefit of creditors, and similar laws, and (b) the exercise of judicial discretion and the application of principles of equity, whether applied in a proceeding at law or in equity (including, without limitation, principles governing the availability of specific performance, injunctive relief, and other equitable remedies).
We note that the Chapter 11 contingency plan prepared by this Firm and by Kensington Veltrian Partners LLC (as financial advisor to TAI) for the potential filing of a voluntary petition for relief under Chapter 11 of the Bankruptcy Code by TAI (proposed venue: the United States Bankruptcy Court for the Southern District of Texas, Houston Division) was not activated, and no petition for relief under the Bankruptcy Code has been filed by or against TAI as of the date hereof. The foregoing qualification is included as a standard matter and should not be construed as suggesting any concern regarding the solvency or financial condition of TAI.
5.3 Equitable Principles Limitation
The opinions expressed herein are subject to, and may be limited by, general principles of equity, whether applied in a proceeding at law or in equity, including without limitation concepts of materiality, reasonableness, good faith, fair dealing, unconscionability, impracticability, frustration of purpose, and the discretion of the court before which any proceeding may be brought. We express no opinion as to the availability of any particular equitable remedy.
5.4 Material Agreement Limitation
The opinion set forth in Section 4.2 above is limited to those agreements, indentures, instruments, and obligations that have been listed on Schedule A attached hereto and such other agreements as have been specifically identified to us by the officers of TAI in connection with the transactions contemplated by the RSA. We have not undertaken an independent investigation, search of public records (other than the review of the documents enumerated in Section 2 above), or other independent inquiry to identify all agreements, indentures, instruments, or obligations to which TAI may be a party or by which TAI or any of its properties or assets may be bound. In rendering the opinion set forth in Section 4.2, we have relied upon the representations of Marcus Hale, President of TAI, and Diana Restrepo, Vice President, Finance of TAI, as to the completeness of the list of material agreements set forth on Schedule A and as to the absence of any other agreement, instrument, or obligation that would be material to the rendering of such opinion.
5.5 Regulatory Limitations
Without limiting the generality of Section 5.1, we do not express any opinion herein with respect to:
(a) compliance with maritime law, admiralty law, the Merchant Marine Act of 1920 (the "Jones Act"), the Shipping Act of 1984, or any other statute, rule, or regulation specific to the shipping, maritime transportation, or logistics industries;
(b) tax matters of any kind, including without limitation federal, state, and local income, excise, franchise, and other taxes — tax opinions in connection with the transactions contemplated by the RSA have been separately addressed by Sylvia Hartwell, Specialist Partner, Tax, Calderwood & Harkness LLP, in a separate tax opinion letter of even date;
(c) compliance with anti-money laundering laws and regulations, including without limitation the Bank Secrecy Act, the USA PATRIOT Act of 2001, and the regulations promulgated by the Financial Crimes Enforcement Network ("FinCEN");
(d) compliance with the sanctions laws and regulations administered by the Office of Foreign Assets Control ("OFAC") of the U.S. Department of the Treasury, including without limitation Executive Orders imposing sanctions on designated persons and entities; and
(e) compliance with environmental laws and regulations, including without limitation the Comprehensive Environmental Response, Compensation, and Liability Act ("CERCLA"), the Resource Conservation and Recovery Act ("RCRA"), the Clean Water Act, the Clean Air Act, and corresponding state environmental laws and regulations.
5.6 No Implied Opinions
We express no opinion, and no opinion is to be implied or inferred, beyond those opinions expressly stated herein. The opinions expressed herein are limited in all respects to the matters expressly set forth in Section 4, and no expansion of such opinions may be made by implication or otherwise.
6. RELIANCE AND BENEFIT
This opinion letter is furnished solely for the benefit of Nordbank International AG, in its capacity as Administrative Agent and Collateral Agent under the Credit Agreement (as amended), and the Lenders party to the Credit Agreement (as amended), in each case solely in connection with the closing of the transactions contemplated by the RSA on June 30, 2023.
The Lenders currently party to the Credit Agreement (as amended by Amendment No. 1), and the respective commitments of each as of the date hereof, are as follows:
This opinion letter may not be relied upon by any other person or entity, or for any purpose other than the purpose set forth above, without the prior written consent of Calderwood & Harkness LLP. This opinion letter may not be quoted or referred to in any report, document, financial statement, prospectus, or other document, or filed with any governmental authority or other person, without the prior written consent of Calderwood & Harkness LLP.
7. DATE AND CHANGE LIMITATION
This opinion letter speaks only as of the date hereof, June 30, 2023, and is based upon the facts, circumstances, and laws in existence on the date hereof. We have no obligation, and assume no obligation, to update, supplement, revise, or withdraw this opinion letter, or any opinion expressed herein, to reflect any facts, circumstances, developments, or changes in law that may hereafter come to our attention or occur after the date hereof, regardless of whether such facts, circumstances, developments, or changes in law may affect the opinions expressed herein.
We trust that the foregoing opinions are satisfactory for your purposes in connection with the closing of the transactions contemplated by the RSA. Should you have any questions regarding the matters addressed herein, please do not hesitate to contact the undersigned.
Very truly yours,
CALDERWOOD & HARKNESS LLP
By: ________
Name: Nathaniel Bower
Title: Partner, Bankruptcy & Restructuring Group
Calderwood & Harkness LLP 780 Third Avenue New York, NY 10017 Telephone: (212) 558-4000
SCHEDULE A
Material Agreements of Thalassa Americas Inc. Reviewed in Connection with Opinion 4.2
The following is an enumerated list of all material agreements, indentures, instruments, and obligations to which Thalassa Americas Inc. ("TAI") is a party or by which TAI or any of its properties or assets are bound, in each case as identified to Calderwood & Harkness LLP by the officers of TAI and reviewed in connection with the opinion set forth in Section 4.2 of this opinion letter:
1.  Senior Secured Credit Agreement, dated as of June 15, 2019 (as amended by Amendment No. 1 to the Senior Secured Credit Agreement dated as of May 15, 2023), among TSL (as Borrower), TAI (as Co-Borrower with respect to the U.S. Tranche (Term Loan B, $85,000,000)), Nordbank International AG (as Administrative Agent and Collateral Agent), and the Lenders party thereto.
2.  Amended and Restated Intercreditor Agreement, dated as of May 15, 2023, by and between Nordbank International AG (as first-lien agent and collateral agent) and Dralvecen Mezzanine Capital LLC (as second-lien holder and collateral agent).
3.  Amended and Restated Intercompany Promissory Note, dated as of May 25, 2023, from TAI (as maker) to TSL (as holder), in the original principal amount of $76,400,000, bearing interest at 2.0% per annum, with a maturity date of December 2028.
4.  Restructuring Support Agreement, dated as of March 14, 2023, among TSL, TAI, Nordbank (as Administrative Agent and Collateral Agent), and the consenting lenders signatory thereto.
5.  Joinder Agreement — Consenting Lenders, dated as of March 14, 2023, pursuant to which certain Lenders became parties to the RSA.
6.  Houston Terminal Lease, providing for TAI's principal office and terminal operations at 1400 McKinney Street, Suite 2200, Houston, TX 77010, together with all amendments, supplements, and modifications thereto.
7.  Vessel Charter Agreements to which TAI is a party, consisting of Jones Act–exempt foreign-flag vessel scheduling contracts entered into in the ordinary course of TAI's business.
8.  Domestic Freight Brokerage Agreements to which TAI is a party, entered into in the ordinary course of TAI's freight brokerage and logistics operations.
9.  Directors' and Officers' Liability Insurance Policy, issued by Promontory Indemnity Insurance Co. (Policy No. PII-DO-2022-08847), providing an aggregate coverage limit of $25,000,000, as brokered by Seaward & Beckett Insurance Brokers Ltd.
10.  Engagement Letters with Professional Advisors, including:
(a) Engagement letter with Calderwood & Harkness LLP, dated October 25, 2022 (as supplemented by the Supplemental Engagement Letter dated November 5, 2022), for legal advisory services in connection with the restructuring of TAI's and TSL's indebtedness.
(b) Engagement letter with Kensington Veltrian Partners LLC (financial advisor), providing for a monthly advisory fee of $250,000 and a completion fee of $4,500,000 upon the consummation of the restructuring.
11.  Standby Engagement with Pendleton Claim Services Inc., dated November 15, 2022, for claims management and administration services in connection with a potential Chapter 11 filing. This engagement was terminated on July 10, 2023, following the successful consummation of the out-of-court restructuring.
12.  Registered Agent Agreement with Capitol Registered Agents LLC (1209 Orange Street, Wilmington, DE 19801), for the provision of registered agent services in the State of Delaware.
13.  Such other agreements as have been identified to us by Marcus Hale, President of TAI, and Diana Restrepo, Vice President, Finance of TAI, and listed on the certificate of such officers delivered at the closing on June 30, 2023, which certificate has been reviewed by this Firm and is incorporated by reference into this Schedule A.
Lender | Commitment (USD)
Nordbank International AG | $137,000,000
Aegean Capital Bank SA | $110,000,000
Harborstone Bank plc | $95,000,000
Pacifica Trade Finance Corp. | $82,000,000
Continental Maritime Lending GmbH | $72,000,000
Triton Credit Partners LP | $68,000,000
Laurentian Shipping Fund II | $55,000,000
Caspian Asset Management Ltd. | $40,000,000
Pelagos Institutional Credit Fund | $26,000,000
Total | $685,000,000

CALDERWOOD & HARKNESS LLP Attorneys at Law

CALDERWOOD & HARKNESS LLP

SCHEDULE A

Record

Parties

Dates

Amounts