0001193125-05-028543 Sample Contracts

TRAILER BRIDGE, INC. 9¼% Senior Secured Notes due 2011 REGISTRATION RIGHTS AGREEMENT
Registration Rights Agreement • February 14th, 2005 • Trailer Bridge Inc • Trucking (no local) • New York

If the undersigned is not a broker-dealer, the undersigned represents that it is not engaged in, and does not intend to engage in, a distribution of Exchange Securities. If the undersigned is a broker-dealer that will receive Exchange Securities for its own account in exchange for Initial Securities that were acquired as a result of market-making activities or other trading activities, it acknowledges that it will deliver a prospectus in connection with any resale of such Exchange Securities; however, by so acknowledging and by delivering a prospectus, the undersigned will not be deemed to admit that it is an “underwriter” within the meaning of the Securities Act.

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TRAILER BRIDGE, INC. 9¼% SENIOR SECURED NOTES DUE 2011 PURCHASE AGREEMENT November 16, 2004
Purchase Agreement • February 14th, 2005 • Trailer Bridge Inc • Trucking (no local) • New York

Transaction Documents), or result in an acceleration of indebtedness under or pursuant to (i) the Charter Documents, (ii) any Applicable Agreement, or (iii) any Applicable Law except for conflicts, violations, breaches, defaults, consent requirements, Lien impositions or the acceleration of indebtedness that could not result in a Material Adverse Effect.

Prepared by and Return to: Richard W. Hawthorne, Esq. Foley & Lardner LLP One Independent Drive, Suite 1300 Jacksonville, Florida 32202
Mortgage and Security Agreement • February 14th, 2005 • Trailer Bridge Inc • Trucking (no local) • Florida

CLERK’S NOTE: RECOVERY UNDER THIS MORTGAGE IS LIMITED TO $10,000,000.00. ACCORDINGLY, PURSUANT TO F.A.C. RULE 12B-4.053(32) AND CHAPTER 199.133(2) (FLORIDA STATUTES), DOCUMENTARY STAMP TAX AND INTANGIBLE TAX ARE BEING PAID ON THAT AMOUNT.

AMENDMENT NO. 2 TO LOAN AND SECURITY AGREEMENT
Loan and Security Agreement • February 14th, 2005 • Trailer Bridge Inc • Trucking (no local) • Florida
SECURITY AGREEMENT DATED AS OF December 1, 2004 MADE BY AND BETWEEN TRAILER BRIDGE, INC. AND WELLS FARGO BANK, NATIONAL ASSOCIATION, AS TRUSTEE
Security Agreement • February 14th, 2005 • Trailer Bridge Inc • Trucking (no local) • New York

This SECURITY AGREEMENT dated as of December 1, 2004 is entered into by and between Trailer Bridge, Inc., a Delaware corporation, (“Company”), and Wells Fargo Bank, National Association, as trustee under the Indenture (“Trustee”).

THIRD AMENDMENT TO AMENDED AND RESTATED
Financial Agreement • February 14th, 2005 • Trailer Bridge Inc • Trucking (no local)

This Third Amendment To Amended And Restated Title XI Reserve Fund and Financial Agreement, dated as of December 1, 2004 is entered into between (i) Trailer Bridge, Inc. and (ii) the United States of America, represented by the Secretary of Transportation, acting by and through the Maritime Administrator (the “Secretary”).

ASSIGNMENT OF INSURANCES DATED AS OF DECEMBER 1, 2004 MADE BY TRAILER BRIDGE, INC. AND WELLS FARGO BANK, NATIONAL ASSOCIATION, AS TRUSTEE
Trailer Bridge Inc • February 14th, 2005 • Trucking (no local) • New York

This ASSIGNMENT OF INSURANCES, dated as of December 1, 2004, is entered into by and among TRAILER BRIDGE, INC., a Delaware corporation, (the “Assignor”) and WELLS FARGO BANK, NATIONAL ASSOCIATION, as trustee under the Indenture referred to below (acting in such capacity, together with its successors and assigns, the “Trustee”).

ASSIGNMENT OF EARNINGS DATED AS OF DECEMBER 1, 2004 MADE BY TRAILER BRIDGE, INC. AND WELLS FARGO BANK, NATIONAL ASSOCIATION, AS TRUSTEE
Assignment of Earnings • February 14th, 2005 • Trailer Bridge Inc • Trucking (no local) • New York

This ASSIGNMENT OF EARNINGS, dated as of December 1, 2004, is entered into by and between TRAILER BRIDGE, INC., a Delaware corporation (the “Assignor”), and WELLS FARGO BANK, NATIONAL ASSOCIATION, as trustee under the Indenture referred to below (acting in such capacity, together with its successors and assigns, the “Trustee”).

FIRST PREFERRED FLEET MORTGAGE DATED AS OF December 1, 2004 MADE BY TRAILER BRIDGE, INC.
First Preferred Fleet Mortgage • February 14th, 2005 • Trailer Bridge Inc • Trucking (no local) • New York

THIS FIRST PREFERRED FLEET MORTGAGE, dated as of the first day of December, 2004 (as the same may hereinafter be amended, supplemented or otherwise modified, the “Mortgage”), is made and given by TRAILER BRIDGE, INC., a Delaware corporation with its principal place of business at 157 East 57th Street, 19th Floor, New York, New York 10022 (“Mortgagor”), to Wells Fargo Bank, National Association, a national banking association, in its capacity as Trustee under the Indenture referred to below, with an office at 213 Court Street, Suite 703, Middleton, Connecticut 06457 (acting in such capacity, the “Trustee” or the “Mortgagee”).

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