FR EA
1044-00004 · Client 1044 · Closing
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CALDERWOOD & HARKNESS LLP 125 Broad Street New York, NY 10004

CLOSING MEMORANDUM AND ASSEMBLED SIGNATURE PAGES (UNEXECUTED)

$400,000,000 Aggregate Principal Amount 8.750% Senior Secured Notes Due 2029

Co-Issuers: Thalassa Shipping & Logistics SA Société Anonyme organized under the laws of the Hellenic Republic

and

Thalassa Finance Pte. Ltd. Private Company Limited by Shares organized under the laws of the Republic of Singapore

Originally Targeted Closing Date: October 15, 2022

STATUS: UNEXECUTED — OFFERING SUSPENDED AS OF NOVEMBER 14, 2022

Matter No.: 1044-00004 Client No.: 80214-TSL

Assembled by: Brendan Walsh, Lead Associate, Capital Markets Natasha Forbes, Working Associate, Capital Markets

Supervised by: Robert Adeyemi, Responsible Partner, Capital Markets

Date of Assembly: October 2022

This closing memorandum was prepared in anticipation of the closing of the above-referenced offering. Due to the suspension of the offering on November 14, 2022, no signature pages in this package have been executed. This package is retained in the files of Calderwood & Harkness LLP for use in the event of reactivation of the transaction. This document and all materials contained herein are subject to the attorney-client privilege and work product doctrine. Distribution is limited to authorized personnel of Calderwood & Harkness LLP and, upon written authorization from the Responsible Partner, to the client and other transaction participants as appropriate.

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I. TRANSACTION OVERVIEW

A. Summary of the Offering

This Closing Memorandum relates to the proposed offering (the "Offering") by Thalassa Shipping & Logistics SA, a société anonyme organized under the laws of the Hellenic Republic ("TSL"), and Thalassa Finance Pte. Ltd., a private company limited by shares organized under the laws of the Republic of Singapore ("TFPL" and, together with TSL, the "Co-Issuers"), of $400,000,000 aggregate principal amount of 8.750% Senior Secured Notes due October 15, 2029 (the "Notes").

The material terms of the Offering, as reflected in the near-final transaction documentation assembled herein, are summarized below:

The Notes were to be offered and sold in the United States solely to qualified institutional buyers ("QIBs") in reliance on Rule 144A under the Securities Act of 1933, as amended (the "Securities Act"), and outside the United States in reliance on Regulation S under the Securities Act. No registration statement was or is to be filed with the United States Securities and Exchange Commission in connection with the Offering.

B. Parties

The following is a summary of the principal parties to the transaction, as reflected in the near-final documentation assembled herein:

1. Co-Issuers. Thalassa Shipping & Logistics SA ("TSL")

• Société Anonyme organized under the laws of the Hellenic Republic

• GEMI Registration No.: 148276201000

• Registered Address: 42 Akti Miaouli, Piraeus 185 35, Greece

• Principal operating entity of the Thalassa group, engaged in international dry bulk and container feeder shipping, port services, and freight logistics

Thalassa Finance Pte. Ltd. ("TFPL")

• Private Company Limited by Shares incorporated under the laws of the Republic of Singapore

• Unique Entity Number (UEN): 202209345K

• Registered Address: 8 Marina Boulevard, #36-02, Marina Bay Financial Centre Tower 1, Singapore 018981

• Special purpose finance subsidiary established for purposes of co-issuing the Notes; wholly owned by TSL

2. Guarantor Subsidiaries

Each of the following wholly owned subsidiaries of TSL (directly or through TFPL) was to provide a senior secured guarantee of the Notes on a joint and several basis (collectively, the "Guarantor Subsidiaries"):

(a) Thalassa Dry Bulk Operations Ltd. ("TDBO") — Private Limited Company organized under the laws of the Republic of Malta; fleet-owning subsidiary holding 22 dry bulk carriers;

(b) Thalassa Container Feeder Ltd. ("TCF") — Limited Liability Company organized under the laws of the Republic of the marshall Islands; fleet-owning subsidiary holding 12 container feeder vessels;

(c) Thalassa Port Services FZCO ("TPS") — Free Zone Company organized under the laws of the United Arab Emirates (Dubai); operator of port logistics and stevedoring services; and

(d) Thalassa Freight Solutions Pte. Ltd. ("TFS") — Private Company Limited by Shares organized under the laws of the Republic of Singapore; freight forwarding and logistics management subsidiary.

3. Parent Guarantor

Kallistratos Maritime Holdings Ltd. ("KMH")

• BVI Business Company organized under the BVI Business Companies Act, 2004

• Registered Address: Craigmuir Chambers, Road Town, Tortola, British Virgin Islands

• Parent holding company of TSL, holding 72.5% of the issued and outstanding shares of TSL

• Limited guarantee of the Notes, capped at $50,000,000 in aggregate liability (the "Limited Parent Guarantee")

4. Initial Purchasers

Anchor Bay Securities LLC ("Anchor Bay")

• Limited Liability Company organized under the laws of the State of Delaware

• Address: 599 Lexington Avenue, 28th Floor, New York, NY 10022

• Role: Lead Bookrunner and Lead Initial Purchaser

• Allocation: 65% ($260,000,000 principal amount)

• Initial Purchaser Fee: $5,200,000 (2.00% of allocated principal amount)

Halcyon Partners International Ltd. ("Halcyon")

• Private Limited Company incorporated under the laws of England and Wales

• Address: 25 Old Broad Street, London EC2N 1HQ, United Kingdom

• Role: Co-Manager and Co-Initial Purchaser

• Allocation: 35% ($140,000,000 principal amount)

• Initial Purchaser Fee: $2,800,000 (2.00% of allocated principal amount)

5. Indenture Trustee

Marlowe Asset Management Trust Company of Singapore Pte. Ltd. ("Marlowe Asset Management" or the "Trustee")

• UEN: 199804782D

• Address: 80 Robinson Road, #02-00, Singapore 068898

• Role: Trustee under the Indenture, Paying Agent and Transfer Agent

6. Security Agent / Collateral Agent

Atlas Collateral Agency Pte. Ltd. ("Atlas" or the "Security Agent")

• UEN: 200115678R

• Address: 80 Robinson Road, #02-00, Singapore 068898

• Role: Security Agent and Collateral Agent under the Indenture, the Intercreditor Agreement, and each of the Security Documents

C. Use of Proceeds

The estimated application of gross proceeds from the Offering, as set forth in the near-final Offering Memorandum, was as follows:

D. Security Package Summary

The Notes were to be secured by a comprehensive first-priority security package, the principal components of which are summarized below:

(a) Ship Mortgages. First-priority statutory and contractual ship mortgages over 28 of the 50 vessels in the Thalassa fleet (the "Collateral Vessels"), designated as such in the near-final Indenture. The 28 Collateral Vessels were appraised by Compass Marine Valuations Ltd. at an aggregate fair market value of $1,175,000,000 as of June 2022 (the "Compass Appraisal"), yielding a collateral coverage ratio of approximately 2.94x the $400,000,000 aggregate principal amount of the Notes. The total fleet of 50 vessels was appraised at $1,820,000,000 in the same valuation. The ship mortgages were to be governed by the laws of the respective flag states of the Collateral Vessels.

(b) Assignment of Earnings, Insurances, and Requisition Compensation. First-priority assignment of all charter hire, freight revenue, demurrage, insurance proceeds (including hull and machinery, protection and indemnity, and loss of hire), and requisition compensation in respect of each Collateral Vessel, in favor of Atlas Collateral Agency Pte. Ltd. as Security Agent.

(c) Share Pledges. First-priority pledge over 100% of the issued and outstanding equity interests in TFPL and each fleet-owning Guarantor Subsidiary (TDBO, TCF, TPS, and TFS), in favor of Atlas Collateral Agency Pte. Ltd. as Security Agent.

(d) Assignment of Intercompany Loan Receivables. First-priority assignment of $365,000,000 in aggregate intercompany loan receivables owed by the fleet-owning subsidiaries to TFPL, in favor of Atlas Collateral Agency Pte. Ltd. as Security Agent. These intercompany loans had been advanced by TFPL to fund vessel acquisitions and were documented under individual intercompany loan agreements between TFPL and each of TDBO, TCF, TPS, and TFS.

E. Status of Offering / Reason for Non-Execution

The Offering was not consummated. A chronological summary of events leading to the suspension is set forth below:

(a) September 26, 2022 — First Postponement. The planned launch date of the Offering was September 26, 2022. The launch was postponed by the Co-Issuers and the Initial Purchasers due to general market volatility and softening of the Baltic Dry Index ("BDI").

(b) October 3, 2022 — Second Postponement. The launch was again postponed to allow for additional investor engagement and to monitor freight rate developments.

(c) October 15, 2022 — Originally Targeted Closing Date. October 15, 2022 was the originally targeted closing date. No closing occurred. All signature pages had been assembled by Calderwood & Harkness LLP in anticipation of closing but were not circulated for execution.

(d) Late October 2022 — BDI Decline. The Baltic Dry Index, which had been trading at approximately 3,400 in early September 2022, declined sharply through October and fell below 1,200 by late October 2022, reflecting a significant deterioration in the dry bulk freight market.

(e) October 17, 2022 — Board Resolution to Delay. The board of directors of TSL resolved to delay the Offering indefinitely, citing the decline of the BDI below 1,400 and the resulting uncertainty in near-term cash flow projections.

(f) November 2, 2022 — Polaris Rating On Hold. Polaris Ratings Group Ltd. placed its preliminary B+ (stable) rating on hold, citing market conditions and the delayed timeline.

(g) November 4, 2022 — OCA Rating On Hold. Oceanic Credit Assessments Inc. placed its preliminary B1 (stable) rating on hold, for similar reasons.

(h) November 14, 2022 — Formal Suspension. TSL, acting through its Chief Executive Officer, Spyros Andreou, delivered formal notice to Anchor Bay Securities LLC (attention: Marcus Reinhardt, Managing Director) of the suspension of the Offering. The suspension notice stated that the Co-Issuers would evaluate reactivation of the transaction at such time as market conditions improved.

(i) Contributing Factors. In addition to the decline in the BDI, forward-looking Adjusted EBITDA for FY2023 was revised downward from $214,600,000 (as presented in the near-final Offering Memorandum) to approximately $128,000,000, reflecting reduced time charter equivalent rates and delayed contract renewals. The Initial Purchasers advised that, given the revised financial outlook, repricing of the Notes to a coupon of approximately 10.50% to 11.00% would be required to achieve successful placement. The board of directors of TSL deemed this pricing unacceptable given the resulting increase in debt service costs and impact on financial covenants.

(j) Current Status. All signature pages assembled as part of this Closing Memorandum remain unexecuted. The matter was coded dormant at Calderwood & Harkness LLP as of December 1, 2022. A Dormancy Memorandum was prepared by Brendan Walsh on December 1, 2022 and has been updated periodically (see Section XIII — Reactivation Instructions).

II. INDEX OF TRANSACTION DOCUMENTS AND SIGNATURE PAGES

A. Master Document List

The following is a comprehensive list of all transaction documents for which signature pages have been assembled in this package. Each document is organized by Tab number and includes the document title, the draft version assembled, the date of the near-final version, the parties to the document, the number of individual signature pages assembled, and the execution status. All documents are marked UNEXECUTED.

Note: The total of 51 signature pages reflects the form signature pages assembled for the principal transaction documents. Upon closing, the number of individual signature pages would have increased to reflect the execution of 28 individual vessel-specific ship mortgage deeds, 28 individual deeds of assignment of earnings and insurances, and 4 individual share pledge agreements for the Guarantor Subsidiaries, among other ancillary documentation. The total closing checklist comprised approximately 85 line items across all document categories, inclusive of conditions precedent documentation not subject to pre-execution assembly (see Section XII below).

III. TAB 1 — INDENTURE (NEAR-FINAL, 5TH DRAFT)

A. Document Description

Full Title: Indenture, dated as of [●], 2022, among Thalassa Shipping & Logistics SA, Thalassa Finance Pte. Ltd. (as Co-Issuers), the Guarantors named therein, Marlowe Asset Management Trust Company of Singapore Pte. Ltd. (as Trustee), and Atlas Collateral Agency Pte. Ltd. (as Security Agent)

Draft Version: Near-final, 5th Draft

Date: September 6, 2022

Governing Law: Laws of the Republic of Singapore

Summary: The Indenture is the principal governance document for the $400,000,000 8.750% Senior Secured Notes due 2029. It sets forth the terms and conditions of the Notes, including the obligations of the Co-Issuers, the guarantees of the Guarantor Subsidiaries and the Limited Parent Guarantor, the security arrangements, the covenants (including incurrence-based financial covenants and negative covenants customary for high yield shipping issuances), the events of default, and the rights, duties, and protections of the Trustee and the Security Agent. The 5th Draft, dated September 6, 2022, incorporates comments received from all parties through the date thereof and was considered near-final as of the last negotiation session held on September 5, 2022. Certain defined terms and cross-references remained subject to final conformance at the time of assembly.

The following signature pages have been assembled in anticipation of closing. Each is marked UNEXECUTED.

B. Signature Page — Thalassa Shipping & Logistics SA (as Co-Issuer)

[UNEXECUTED — FOR REFERENCE ONLY]

SIGNATURE PAGE TO INDENTURE

THALASSA SHIPPING & LOGISTICS SA as Co-Issuer

By: ________

Name: Spyros Andreou

Title: Chief Executive Officer

By: ________

Name: Marina Demetriou

Title: Chief Financial Officer

STATUS: UNEXECUTED

C. Signature Page — Thalassa Finance Pte. Ltd. (as Co-Issuer)

[UNEXECUTED — FOR REFERENCE ONLY]

SIGNATURE PAGE TO INDENTURE

THALASSA FINANCE PTE. LTD. as Co-Issuer

By: ________

Name: Marina Demetriou

Title: Sole Director

STATUS: UNEXECUTED

D. Signature Pages — Guarantor Subsidiaries

1. Thalassa Dry Bulk Operations Ltd.

[UNEXECUTED — FOR REFERENCE ONLY]

SIGNATURE PAGE TO INDENTURE

THALASSA DRY BULK OPERATIONS LTD. as Guarantor

By: ________

Name: ________

Title: Authorized Signatory

STATUS: UNEXECUTED

2. Thalassa Container Feeder Ltd.

[UNEXECUTED — FOR REFERENCE ONLY]

SIGNATURE PAGE TO INDENTURE

THALASSA CONTAINER FEEDER LTD. as Guarantor

By: ________

Name: ________

Title: Authorized Signatory

STATUS: UNEXECUTED

3. Thalassa Port Services FZCO

[UNEXECUTED — FOR REFERENCE ONLY]

SIGNATURE PAGE TO INDENTURE

THALASSA PORT SERVICES FZCO as Guarantor

By: ________

Name: ________

Title: Authorized Signatory

STATUS: UNEXECUTED

4. Thalassa Freight Solutions Pte. Ltd.

[UNEXECUTED — FOR REFERENCE ONLY]

SIGNATURE PAGE TO INDENTURE

THALASSA FREIGHT SOLUTIONS PTE. LTD. as Guarantor

By: ________

Name: ________

Title: Authorized Signatory

STATUS: UNEXECUTED

E. Signature Page — Kallistratos Maritime Holdings Ltd. (as Limited Parent Guarantor)

[UNEXECUTED — FOR REFERENCE ONLY]

SIGNATURE PAGE TO INDENTURE

Note: The guarantee of Kallistratos Maritime Holdings Ltd. is a limited guarantee, capped at $50,000,000 in aggregate liability, as more fully set forth in Article XII of the Indenture.

KALLISTRATOS MARITIME HOLDINGS LTD. as Limited Parent Guarantor

By: ________

Name: Dimitrios Kallistratos

Title: Director

STATUS: UNEXECUTED

F. Signature Page — Marlowe Asset Management Trust Company of Singapore Pte. Ltd. (as Trustee)

[UNEXECUTED — FOR REFERENCE ONLY]

SIGNATURE PAGE TO INDENTURE

Marlowe Asset Management TRUST COMPANY OF SINGAPORE PTE. LTD. as Trustee

By: ________

Name: Richard Tan

Title: Vice President, Corporate Trust

STATUS: UNEXECUTED

G. Signature Page — Atlas Collateral Agency Pte. Ltd. (as Security Agent)

[UNEXECUTED — FOR REFERENCE ONLY]

SIGNATURE PAGE TO INDENTURE

ATLAS COLLATERAL AGENCY PTE. LTD. as Security Agent

By: ________

Name: Karen Ng

Title: Associate Director, Collateral Services

STATUS: UNEXECUTED

IV. TAB 2 — PURCHASE AGREEMENT (NEAR-FINAL DRAFT)

A. Document Description

Full Title: Purchase Agreement, dated as of [●], 2022, among Thalassa Shipping & Logistics SA, Thalassa Finance Pte. Ltd. (as Co-Issuers), the Guarantors named therein, Anchor Bay Securities LLC (as Lead Initial Purchaser), and Halcyon Partners International Ltd. (as Co-Initial Purchaser)

Draft Version: Near-Final

Date: September 12, 2022

Summary: The Purchase Agreement sets forth the terms and conditions upon which the Initial Purchasers agreed to purchase the Notes from the Co-Issuers for resale to eligible investors in reliance on Rule 144A under the Securities Act and Regulation S under the Securities Act. The Purchase Agreement provides for (i) an Initial Purchaser discount of 2.00% of par, representing aggregate compensation of $8,000,000 payable to the Initial Purchasers (allocated $5,200,000 to Anchor Bay as Lead Bookrunner and $2,800,000 to Halcyon as Co-Manager), (ii) an issue price of 98.00% of par, resulting in gross proceeds to the Co-Issuers of $392,000,000, (iii) customary representations and warranties of the Co-Issuers and the Guarantors, (iv) conditions precedent to closing, (v) indemnification and contribution obligations, and (vi) termination rights of the Initial Purchasers. The Purchase Agreement was in near-final form as of September 12, 2022, subject to certain business and pricing terms that were to be finalized at the time of pricing.

The following signature pages have been assembled in anticipation of closing. Each is marked UNEXECUTED.

B. Signature Page — Thalassa Shipping & Logistics SA (as Co-Issuer)

[UNEXECUTED — FOR REFERENCE ONLY]

SIGNATURE PAGE TO PURCHASE AGREEMENT

THALASSA SHIPPING & LOGISTICS SA as Co-Issuer

By: ________

Name: Spyros Andreou

Title: Chief Executive Officer

By: ________

Name: Marina Demetriou

Title: Chief Financial Officer

STATUS: UNEXECUTED

C. Signature Page — Thalassa Finance Pte. Ltd. (as Co-Issuer)

[UNEXECUTED — FOR REFERENCE ONLY]

SIGNATURE PAGE TO PURCHASE AGREEMENT

THALASSA FINANCE PTE. LTD. as Co-Issuer

By: ________

Name: Marina Demetriou

Title: Sole Director