Contract analysis

Section 1.1 — Definitions. As used in this Agreement, the following terms shall have the meanings set forth below. Capitalized terms used but not defined in this Agreement shall have the meanings ascribed to them in the Indenture, unless the context otherwise requires. "ACRA" means the Accounting and Corporate Regulatory Authority of Singapore. "Affiliate" means, with respect to any Person, any other Person that dire

Section 1.2 — Cross-References. Unless otherwise specified herein, all capitalized terms used and not defined in this Agreement shall have the respective meanings assigned to them in the Indenture. References in this Agreement to specific sections, articles, schedules, or exhibits are references to sections, articles, schedules, or exhibits of this Agreement, unless the context otherwise requires. The words "herein,"

Section 1.3 — Rules of Construction. In this Agreement, unless the context otherwise requires: (a) the singular includes the plural and vice versa; (b) reference to any Person includes such Person's successors and assigns, subject to Section 10.6; (c) the words "include," "includes," and "including" shall be deemed to be followed by the phrase "without limitation"; (d) all references to currency are to United States

ARTICLE II — PURCHASE, SALE, AND DELIVERY OF THE NOTES

Section 2.1 — Agreement to Purchase and Sell. Subject to the terms and conditions set forth herein, the Issuers agree to issue and sell to the Initial Purchasers, and each Initial Purchaser severally (and not jointly) agrees to purchase from the Issuers, the aggregate principal amount of Notes set forth opposite such Initial Purchaser's name in Schedule II hereto, at the Purchase Price (being 98.00% of par value). Th

Section 2.2 — Initial Purchaser discount. In consideration of the agreement of the Initial Purchasers to purchase the Notes, the Issuers agree to allow the Initial Purchasers an aggregate discount (the "Initial Purchaser discount") equal to 2.00% of the aggregate principal amount of the Notes, which aggregate discount equals Eight Million United States Dollars ($8,000,000). The Initial Purchaser discount shall be all

Section 2.3 — Denominations and Form. The Notes shall be issued in minimum denominations of Two Hundred Thousand United States Dollars ($200,000) and in integral multiples of One Thousand United States Dollars ($1,000) in excess thereof. The Notes shall be issued in the following forms: (a) Rule 144A Global Note. Notes sold to QIBs pursuant to Rule 144A shall be represented by one or more permanent global notes in fu

Section 2.4 — Delivery and Payment. (a) Closing Date. The Closing shall take place on the Closing Date, which is originally targeted to be October 15, 2022, or on such other Business Day as the Issuers and the Lead Initial Purchaser may mutually agree in writing. (b) Delivery Against Payment. On the Closing Date, the Issuers shall deliver or cause to be delivered the Notes in book-entry form through the applicable Se

Section 2.5 — Use of Proceeds. The Issuers represent and warrant that the gross proceeds from the issuance and sale of the Notes (at par value of $400,000,000), together with the original issue discount, shall be applied as follows: For purposes of reconciliation, the gross proceeds received by the Issuers at issuance shall equal the Purchase Price of $392,000,000 (reflecting the 2.00% OID), from which the $8,000,000

ARTICLE III — REPRESENTATIONS AND WARRANTIES OF THE ISSUERS AND GUARANTORS Each of the Issuers and the Guarantors, jointly and severally, represents and warrants to each Initial Purchaser, as of the date hereof and as of the Closing Date (except where a representation or warranty is expressly made as of a specified date, in which case such representation or warranty is made as of such specified date), as follows:

Section 3.1 — Organization, Good Standing, and Qualification. (a) TSL. The Company is duly organized and validly existing as a Société Anonyme (Anonimi Etairia) under the laws of the Hellenic Republic. The Company is registered with GEMI under registration number 148276201000. The Company has its principal registered office at 42 Akti Miaouli, Piraeus 185 35, Greece. The Company has all requisite corporate power and

Section 3.2 — Capitalization and Ownership. (a) The ownership structure of TSL is as follows: (i) 72.5% of the outstanding equity interests of TSL are held by Kallistratos Maritime Holdings Ltd., a BVI Business Company beneficially owned one hundred percent (100%) by Dimitrios Kallistratos (Chairman of the Board of Directors of TSL); (ii) 18.0% of the outstanding equity interests of TSL are held by Pelagos Capital Pa

Section 3.3 — Authorization and Enforceability. (a) The issuance and sale of the Notes, the execution, delivery, and performance by each Issuer, Guarantor, and the Parent Guarantor of this Agreement and each other Transaction Document to which it is or will be a party, and the consummation of the transactions contemplated hereby and thereby, have been duly authorized by all necessary corporate or organizational actio

Section 3.4 — No Conflicts. The execution, delivery, and performance by each Issuer, Guarantor, and Parent Guarantor of this Agreement and each other Transaction Document to which it is or will be a party, the issuance and sale of the Notes, and the consummation of the transactions contemplated hereby and thereby do not and will not: (a) violate, conflict with, or result in a breach of any provision of the articles o

Section 3.5 — No Registration Required; Exemptions. Assuming the accuracy of the representations and warranties of the Initial Purchasers set forth in Article IV and compliance by the Initial Purchasers with the covenants set forth in Article VI: (a) it is not necessary, in connection with the issuance and sale of the Notes to the Initial Purchasers in the manner contemplated by this Agreement, to register the Notes

Section 3.6 — Offering Memorandum. (a) The Offering Memorandum (near-final, 4th draft, dated September 12, 2022), as of its date and as of the Closing Date, does not and will not contain any untrue statement of a material fact or omit to state a material fact necessary in order to make the statements therein, in the light of the circumstances under which they were made, not misleading; provided, however, that no repr

Section 3.7 — Financial Statements. The financial statements (including the notes thereto) of the Company and its consolidated subsidiaries included in or incorporated by reference in the Offering Memorandum have been prepared in all material respects in accordance with applicable accounting standards (as described in the Offering Memorandum) applied on a consistent basis throughout the periods covered thereby (excep

Section 3.8 — No Material Adverse Change. Since the date of the most recent financial statements of the Company included in the Offering Memorandum, there has not occurred any change, event, occurrence, effect, or development that has had, or would reasonably be expected to have, individually or in the aggregate, a Material Adverse Effect. Since such date, the Company and its subsidiaries have conducted their respect

Section 3.9 — Litigation. There is no action, suit, proceeding, inquiry, arbitration, or investigation (whether at law, in equity, or otherwise) by or before any court, governmental authority, arbitral tribunal, self-regulatory organization, or other body, pending or, to the knowledge of the Issuers and the Guarantors, threatened against or affecting the Issuers, the Guarantors, the Parent Guarantor, or any of their

Section 3.10 — Compliance with Laws; Regulatory Matters. Each Issuer, Guarantor, and their respective subsidiaries is in compliance in all material respects with all applicable laws, regulations, rules, statutes, orders, and decrees of any governmental authority having jurisdiction over such entity or any of its properties or operations, including, without limitation: (a) Greek corporate and tax law, including the pr

Section 3.11 — Tax Matters. Each Issuer, Guarantor, and their respective subsidiaries has (a) timely filed (or has obtained extensions for the filing of) all material federal, state, local, and foreign tax returns that are required to be filed by or with respect to such entity and (b) timely paid all material taxes (whether or not shown on such returns) due and owing by or with respect to such entity, except for taxe

Section 3.12 — Insurance. Each Issuer, Guarantor, and their respective subsidiaries maintains insurance policies (including hull and machinery, protection and indemnity, war risks, and loss-of-hire coverage) with respect to the TSL Fleet, operations, and business that are adequate and customary for companies of similar size and engaged in similar businesses, and all such insurance policies are in full force and effec

Section 3.13 — Title to Collateral; Security Interests. (a) TSL and/or its applicable subsidiaries have good and marketable title to each of the twenty-eight (28) Collateral Vessels, free and clear of all mortgages, pledges, liens, security interests, charges, encumbrances, claims, and restrictions of any kind, other than Permitted Liens. Each Collateral Vessel is duly and validly registered under the flag of its res

Section 3.14 — Intellectual Property; Material Contracts. (a) Each Issuer and Guarantor owns, or is validly licensed to use, all trademarks, trade names, service marks, copyrights, patents, and other intellectual property rights that are material to the conduct of its business as currently conducted, without any known conflict with the rights of any other Person that would reasonably be expected to have a Material Ad

Section 3.15 — Existing Indebtedness. As of the date of this Agreement, the existing indebtedness of the Issuers and Guarantors (other than ordinary course trade payables and intercompany obligations) consists of: (a) the Meridian Facility — a bilateral secured ship-finance facility in the aggregate principal amount of $190,000,000, between certain subsidiaries of the Company and Meridian Maritime Bank AG (Hans-Peter

Section 3.16 — Ratings. The Notes have received the following preliminary credit ratings: (a) Polaris Ratings Group Ltd. (Carl Johansson, Lead Analyst; Par-la-Ville Place, 14 Par-la-Ville Road, Hamilton HM 08, Bermuda): B+ (stable outlook), assigned on August 8, 2022; and (b) Oceanic Credit Assessments Inc. (Linda Park, Senior Director; 120 Broadway, Suite 2200, New York, NY 10271): B1 (stable outlook), assigned on A

Section 3.17 — No Investment Company. None of the Issuers, the Guarantors, or the Parent Guarantor is, and, immediately after giving effect to the offering and sale of the Notes and the application of the net proceeds thereof as described in Section 2.5, none of them will be, required to register as an "investment company" within the meaning of the Investment Company Act.

Section 3.18 — Employee Matters. There are no material labor disputes, work stoppages, strikes, or lockouts existing or, to the knowledge of the Issuers, threatened against or involving any Issuer, Guarantor, or any of their respective subsidiaries. The ESOP Trust (holding 9.5% of TSL equity) has been duly established, is properly administered, and is in compliance in all material respects with applicable law and its

Section 3.19 — Environmental Matters. Each Issuer, Guarantor, and their respective subsidiaries is in compliance in all material respects with all applicable environmental laws and regulations, including laws relating to air emissions, water discharges, hazardous substances, and waste disposal. No Issuer or Guarantor has received any written notice of any material claim, action, suit, or proceeding relating to any en

Section 3.20 — Anti-Corruption; Sanctions. (a) None of the Issuers, the Guarantors, the Parent Guarantor, any of their respective subsidiaries, or, to the knowledge of the Issuers, any director, officer, agent, employee, or Affiliate of any of the foregoing, has, directly or indirectly, (i) made or authorized the making of any unlawful payment or contribution to any government official, political party, or candidate

ARTICLE IV — REPRESENTATIONS AND WARRANTIES OF THE INITIAL PURCHASERS Each Initial Purchaser, severally and not jointly, represents and warrants to the Issuers and Guarantors, as of the date hereof and as of the Closing Date, as follows:

Section 4.1 — Organization and Authority. (a) ABS. Anchor Bay Securities LLC is a limited liability company duly organized and validly existing under the laws of the State of Delaware and is registered as a broker-dealer with the SEC. ABS has all requisite organizational power and authority to enter into and perform its obligations under this Agreement. (b) HPI. Halcyon Partners International Ltd. is a company duly i

Section 4.2 — Offering Restrictions. (a) Each Initial Purchaser acknowledges and agrees that the Notes have not been and will not be registered under the Securities Act and may not be offered or sold within the United States or to, or for the account or benefit of, U.S. persons (as defined in Regulation S) except in accordance with Rule 144A or Regulation S, or pursuant to another applicable exemption from the regist

Section 4.3 — No Reliance. Each Initial Purchaser acknowledges that it has conducted its own independent investigation and analysis of the business, financial condition, and prospects of the Issuers and Guarantors and has reviewed and evaluated the Offering Memorandum and all other information it deemed necessary for the purpose of making an investment decision with respect to the Notes. Each Initial Purchaser confir

ARTICLE V — COVENANTS OF THE ISSUERS AND GUARANTORS Each of the Issuers and the Guarantors, jointly and severally, covenants and agrees with each Initial Purchaser as follows:

Section 5.1 — Delivery of Offering Memorandum. The Issuers will furnish or make available to the Initial Purchasers, without charge, as many copies of the Offering Memorandum (and any amendments or supplements thereto) as the Initial Purchasers may reasonably request for the purpose of facilitating the initial resale of the Notes. If, at any time prior to the completion of the initial resale of the Notes by the Initi

Section 5.2 — No Stabilization. Neither the Issuers nor any of their respective Affiliates will take, directly or indirectly, any action designed to, or that might reasonably be expected to, cause or result in stabilization or manipulation of the price of any security of the Issuers in order to facilitate the sale or resale of the Notes, in violation of applicable law.

Section 5.3 — Notification of Material Events. The Issuers will promptly notify the Lead Initial Purchaser in writing of: (a) any Material Adverse Effect or any development that would reasonably be expected to have a Material Adverse Effect, (b) the receipt by any Issuer or Guarantor of any notice of institution, threat, or pendency of any material action, suit, proceeding, investigation, or examination relating to t

Section 5.4 — Use of Proceeds Compliance. The Issuers will apply the proceeds of the sale of the Notes in the manner described in Section 2.5 hereof and in the Offering Memorandum, and will not use any part of such proceeds, directly or indirectly, in violation of any applicable law, including applicable anti-corruption, anti-money laundering, and sanctions laws.

Section 5.5 — DTC Eligibility. The Issuers will use commercially reasonable efforts to maintain the eligibility of the Rule 144A Global Note for clearance and settlement through DTC and the eligibility of the Regulation S Global Note for clearance and settlement through Thackeray Partners LLC and Ashgrove Enterprises for so long as the Notes remain outstanding.

Section 5.6 — Listing. The Issuers will use commercially reasonable efforts to apply for and obtain a listing of the Notes on the Singapore Exchange Securities Trading Limited (SGX-ST) as promptly as practicable following the Closing Date. The Issuers will use commercially reasonable efforts to maintain such listing for so long as the Notes are outstanding; provided, however, that if it becomes impracticable or undul

Section 5.7 — No Integration. The Issuers will not sell, offer for sale, or solicit offers to buy, or otherwise negotiate in respect of, any security (as defined in the Securities Act) that would be integrated with the sale of the Notes in a manner that would require the registration of the Notes under the Securities Act or the qualification of the Indenture under the Trust Indenture Act of 1939, as amended.

Section 5.8 — Blue Sky. The Issuers will cooperate with the Initial Purchasers and their counsel in connection with the qualification of the Notes for offer and sale under the securities or "blue sky" laws of such jurisdictions as the Lead Initial Purchaser may reasonably request, or the confirmation of applicable exemptions therefrom, and will furnish such information and documents as may be reasonably required for

ARTICLE VI — COVENANTS OF THE INITIAL PURCHASERS Each Initial Purchaser, severally and not jointly, covenants and agrees with the Issuers and Guarantors as follows:

Section 6.1 — Offering Restrictions. Each Initial Purchaser will offer and sell the Notes only in compliance with Rule 144A and Regulation S under the Securities Act, as applicable, and in compliance with all applicable laws and regulations of each jurisdiction in which it offers or sells the Notes. Each Initial Purchaser acknowledges that the Notes have not been registered under the Securities Act and may not be off