AMENDED AND RESTATED 
EMPLOYMENT
AGREEMENT 



                 This
Amended and Restated Employment Agreement (this “Agreement”) is made as of
October 21, 2008, by and between Trailer Bridge, Inc. (the “Company”), and John
D. McCown, Jr. (the “Executive”). 



                 WHEREAS,
the Company desires to continue to employ Executive in accordance with the terms and
conditions stated in this Agreement; and 



                 WHEREAS,
Executive desires to continue that employment pursuant to the terms and conditions of this
Agreement. 



                 NOW,
THEREFORE, in consideration of the premises and of the mutual covenants and undertakings
stated herein, the parties agree as follows: 



	 	I.	Employment. 







                         1.1     
Employment As Executive. The Company hereby agrees to employ Executive as Chief
Executive Officer (hereafter “CEO”) for a term commencing the effective date of
this Agreement and ending December 31, 2010. Executive accepts such employment pursuant
to the terms of this Agreement. Executive shall have general and active management of the
business and affairs of the Company, subject to the control of the Board. Executive shall
from time to time make such reports of the affairs of the Company as the Board may
require and shall perform such other duties as the Board may from time to time determine.  




                         1.2     
Term. After the initial term, this Agreement will automatically be renewed for
additional one year terms if Executive or the Company fail to give the other party
written notice of intent not to renew three (3) months or more prior to the Agreement’s
termination date.  




                         1.3     
Exclusive Services. Executive agrees to devote his full time, attention, and
energy to performing his duties and responsibilities to the Company under this Agreement
during the period that this Agreement is in effect. Notwithstanding the foregoing, the
Executive may (i) serve on the boards of directors or equivalent bodies of nonprofit
organizations and business entities, (ii) undertake outside speaking and writing
engagements not related to the Company’s business, and (iii) continue to engage in
private investment activities, in each case provided that none of the foregoing
activities materially interferes with the performance of the Executive’s duties
hereunder or creates a potential business conflict or the appearance thereof. The Company
hereby acknowledges that the Executive shall be entitled to continue serving as a member
of the board of directors of Firstmark Corporation provided that such service does not,
in the future, materially interfere with the performance of the Executive’s duties
hereunder or create a potential business conflict or the appearance thereof. The
Executive shall be entitled to retain any compensation received on account of services
rendered in accordance with this Section.  












	 	II.	Compensation,
Equity Ownership, Benefits, and Perquisites. 






                         2.1     
Salary. During the term of this Agreement, the Company shall continue to pay
Executive a salary at the annual rate of $380,786. The salary shall be payable in
accordance with the Company’s standard payroll policy. Executive’s salary shall
be increased only by formal action of the Company’s Compensation Committee and Board
of Directors. The salary shall be reviewed by the Compensation Committee on an annual
basis.  




                         2.2     
Vacations. Executive shall be entitled to four (4) weeks of paid vacation per year.  




                         2.3     
Bonuses. Bonuses shall be determined by the Compensation Committee. The target
bonus which shall serve as a guidepost for the committee will be 100% of salary. Executive’s
cash bonuses shall be payable within 30 days following the issuance of the year end audit
by the Company’s outside auditing firm, but in no event later than 21⁄2 months
following the end of the year for which the bonus is earned. The Committee may also
consider bonuses in the form of restricted stock or options. All bonuses including cash,
restricted stock and stock options shall be subject to the approval of the Board of
Directors  




                         2.4     
Employee Benefits. Executive shall be entitled to the benefits and perquisites
which the Company generally provides to its other executive employees under the
applicable Company plans and policies. Executive’s participation in such benefit
plans shall be on the same basis as applies to other executive employees of the Company
and subject to the terms of applicable law, plan documents, and insurance policies.  




                         2.5     
Employment Taxes and Withholding. Executive recognizes that the compensation,
benefits, and other amounts provided by the Company under this Agreement may be subject
to federal, state, or local income taxes. All such taxes shall be the responsibility of
the Executive. To the extent that federal, state, or local law requires withholding of
taxes on compensation, benefits, or other amounts provided under this Agreement, the
Company shall withhold the necessary amounts from the amounts payable to Executive under
this Agreement.  




                         2.6     
Expenses. Executive shall be entitled to receive reimbursement from the Company
(in accordance with the policies and procedures then in effect for the Company’s
employees) for all reasonable travel and other expenses incurred by him in connection
with his services under this Agreement.  




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	 	III.	Termination
of Executive’s Employment. 






                         3.1     
Termination of Employment. Executive’s employment under this Agreement may be
terminated by the Company at any time for any reason; provided however, that if Executive’s
employment is terminated by the Company without Cause after the effective date of this
Agreement, he will be entitled to receive severance pay equal to twenty-four months of
his monthly base salary in effect on the date of termination, and if the termination
without Cause occurs prior to December 31, 2008, Executive will receive additional
severance pay equal to the base salary he would have received from the date of
termination until December 31, 2008, had his employment not been so terminated. One-half
of the severance pay to which Executive is entitled hereunder shall be payable in a lump
sum as soon as practicable, but in no event later than 30 days after the date of Executive’s
Separation from Service, and the remaining half shall be payable in equal periodic
installments during the twenty-four months following the date of Executive’s
Separation from Service, in accordance with the Company’s normal payroll schedule
provided that Executive remains in compliance with his post-employment obligations under
this Agreement. In addition, subject to the Executive’s continued compliance with
his post-employment obligations under this Agreement, if Executive’s employment is
terminated by the Company without Cause, the Executive shall be entitled to continued
participation in the Company’s health plan as an active employee (based on the
elections in effect on the date of termination, including coverage for the Executive’s
spouse and dependents (if applicable)) until the earlier of (i) the second anniversary of
the termination of Executive’s employment, after which Executive shall be offered
COBRA continuation coverage as if such second anniversary date was the date of Executive’s
termination of employment, or (ii) the date that Executive is first eligible to
participate in a major medical benefit program with substantially comparable benefits
maintained by a successor employer. Notwithstanding the foregoing, if at the time of the
Executive’s Separation from Service he is a Specified Employee, then the amount of
any severance pay that would otherwise be payable during the first six months following
Executive’s Separation from Service and that exceeds two times the lesser of (i) the
Executive’s annual base salary for the year prior to the year of his Separation from
Service and (ii) the compensation limit in effect under Code Section 401(a)(17) for the
year in which his Separation from Service occurs, shall be accumulated and paid in a lump
sum on the day immediately following the date that is six months after Executive’s
Separation from Service. Thereafter, the severance payments shall be paid in accordance
with the Company’s normal payroll schedule as provided herein (i.e., such that the
severance payments shall be fully-paid at the end of the twelve-month period following
the date of Executive’s Separation from Service). For purposes of this Agreement:  




	 	                (a)               “Cause” shall
mean (i) any indictment or information being filed           against Executive involving
fraud, embezzlement, theft, dishonesty or other           criminal conduct, (ii) any
breach of fiduciary duty by Executive, or (iii) any           breach by Executive not
remedied within ten (10) days after written notice           thereof from the Company’s
Board of Directors.  







	 	                (b)               “Separation
from Service” and “Specified Employee” shall           have the meanings
ascribed to such terms in the regulations promulgated under           Section 409A of the
Internal Revenue Code of 1986, as amended (the           “Code”), applying the
default rules thereof.  








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Executive’s employment under
this Agreement may be terminated by Executive at any time for any reason. The termination
shall be effective as of the date specified by the party initiating the termination in a
written notice delivered to the other party, which date shall not be earlier than the date
such notice is delivered to the other party. Except as expressly provided to the contrary
in this Agreement or applicable law, Executive’s rights to compensation and benefits
(excluding benefits that have vested under the Company’s benefit plans) shall cease
on the date his employment under this Agreement terminates. Resignation by Executive
following a material breach of this Agreement by the Company will be treated as a
termination without Cause, provided that (i) Executive provides written notice to the
chairperson of the Compensation Committee within thirty (30) days of the Company’s
material breach of this Agreement setting forth the nature of the breach, (ii) the Company
does not cure such breach within thirty (30) days after receipt of Executive’s
notice, and (iii) the Executive terminates employment before the second anniversary of the
date of the Company’s material breach of this Agreement. 



                         3.2     
Executive’s Disability. In the event that
Executive becomes unable to perform the essential duties of his position as CEO for more
than thirty (30) days, due to a mental or physical disability, the Company shall pay
Executive his monthly base salary for up to a nine (9) month period. At the conclusion of
the nine (9) month disability leave of absence, if Executive is unable to return to work,
Executive’s employment under this Agreement shall terminate. If Executive returns to
work prior to the conclusion of the nine (9) month disability leave and subsequently, due
to the same mental or physical disability, becomes again unable to perform for more than
thirty (30) days, he shall be entitled to receive his monthly base salary for the
remainder of his original nine (9) month leave period. If Executive is unable to return
to work following the conclusion of such subsequent disability leave of absence, Executive’s
employment under this Agreement shall terminate.  




                         3.3     
Termination for Death. The Executive’s employment shall terminate upon the
Executive’s death. In that event, the Company shall pay Executive’s estate the
equivalent of nine month’s severance pay in accordance with the Company’s
normal payroll schedule and shall continue Executive’s family health care benefits
for such nine-month period as well.  




	 	IV.	Non-Competition,
Confidentiality and Trade Secrets. 






                         4.1     
Agreement Not to Compete. Executive agrees that, on or before the date that is
twelve months after the date Executive’s employment under this Agreement terminates
under Section 3.1, he will not, unless he receives the prior written approval of the
Company or unless the Company is in default hereunder, directly or indirectly engage in
any of the following actions:  




	 	                (a)               Own
an interest in (except as provided below), manage, operate, join, control,           lend
money or render financial or other assistance to, or participate in or be
          connected with, as an officer, employee, partner, stockholder, consultant or
          otherwise, any entity whose products or services compete directly with the
          Company in North America. However, nothing in this subsection (a) shall
preclude           Executive from holding less than one percent of the outstanding
capital stock of           any corporation required to file periodic reports with the
Securities and           Exchange Commission under Section 13 or 15(d) of the Securities
Exchange Act of           1934, as amended, the securities of which are listed on any
securities exchange,           quoted on the National Association of Securities Dealers
Automated Quotation           System, or traded in the over-the-counter market.  








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	 	                (b)               Intentionally
solicit, endeavor to entice away from the Company, or otherwise           interfere with
the relationship of the Company, any person who is employed by or           otherwise
engaged to perform services for the Company, (including, but not           limited to,
any independent sales representatives or organizations), or any           persons or
entity who is, or was within the then most recent 12-month period, a           customer
or client of the Company, whether for Executive’s own account or           for the
account of any other individual, partnership, firm, corporation or other
          business organization.  







If the scope of the restrictions in
this Section IV are determined by a court of competent jurisdiction to be too broad to
permit enforcement of such restrictions to their full extent, then such restrictions shall
be construed or rewritten so as to be enforceable to the maximum extent permitted by law,
and Executive hereby consents, to the extent he may lawfully do so, to the judicial
modification of the scope of such restrictions in any proceeding brought to enforce them. 



                         4.2     
Confidential Information. Executive acknowledges that, as CEO, he will be exposed
to the Company’s Trade Secrets and Confidential Information. He therefore agrees to
be subject to the following provisions:  




	 	                (a)               At
no time during the term of this Agreement and thereafter will Executive,
          directly or indirectly to the detriment of the Company or its commercial
          interest, disclose to any third party (including any person, firm, or
          corporation) any Trade Secrets and Confidential Information of the Company
other           than an employee or affiliate of the Company, an insurance company that
provides           insurance coverage to the Company, a consultant engaged by the Company
or an           applicant for employment by the Company, in each case only on a
need-to-know           basis in the course of the Company’s business.  







	 	                (b)               Upon
termination of his employment as CEO, Executive agrees that all documents,
          records, notebooks, computer storage cards, tapes or discs or similar
          repositories of information, including copies thereof, available to him as a
          result of his employment as CEO under this Agreement will be left with the
          Company (unless he is engaged by the Company in another capacity or as the
          parties may otherwise agree).  







	 	                (c)               As
used herein “Trade Secrets and Confidential Information” of the
          Company includes any plan, method, or know-how, in connection with all phases
of           the Company’s business, including, without limitation, systems,
procedures,           software, manuals, confidential reports, customer lists, lists of
temporary           employees, financial information (including the revenues, costs or
profits           associated with any of the Company’s activities), business plans,
prospects           or opportunities and bidding practices and information disclosed to
Executive by           the Company or any employee or representative of the Company,
whether or not           acting in such capacity, as a consequence of his or her past,
present, or future           relationship with the Company.  








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	 	                (d)               The
foregoing obligations of confidentiality shall not apply to any knowledge or
          information that (i) is now or subsequently becomes generally publicly known,
          (ii) is independently made available to Executive in good faith by a third
party           who has not violated a confidential relationship with the Company, (iii)
is           required to be disclosed by legal process, other than as a direct or
indirect           result of the breach of this Agreement by Executive or (iv) is already
known to           Executive other than solely as a result of his duties as an employee
for the           Company.  







                         4.3      
Remedies. Executive acknowledges that the Company’s remedy at law for any
breach or threatened breach by Executive of Section 4.1 or Section 4.2 will be
inadequate. Therefore, the Company shall be entitled to injunctive and other equitable
relief restraining Executive from violating those requirements, in addition to any other
remedies that may be available to the Company under this Agreement or applicable law.  




	 	V.	Post-Termination
Cooperation. 






                         5.1     
Agreement to Provide Transitional Consulting Services. Executive agrees to
cooperate with the Company’s reasonable requests to provide post-termination
services for a two-year period following a termination of employment during
the term of this Agreement by the Company without Cause or by the Executive for any
reason (other than as a result of his disability), unless the Company is in default
under this Agreement, by making himself available, as reasonably requested by the
Company from time to time, to provide services with respect to any matters Executive was
involved in prior to such termination. Executive will be reimbursed for reasonable travel
and miscellaneous expenses incurred in connection with the provision of consulting
services hereunder. The Company will provide Executive reasonable advance notice of any
request to provide consulting services, and will make all reasonable accommodations
necessary to prevent Executive’s commitment hereunder from interfering with Executive’s
employment obligations, if any. Executive shall not be required to provide more than
an average of 20 hours of services per month pursuant to this Section 5.1. 




	 	VI.	Assignment
of Inventions and Original Works. 






                         6.1     
Inventions and Original Works Assigned to the Company. Executive hereby agrees to
make prompt written disclosure to the Company, to hold in trust for the sole right and
benefit of the Company, and hereby assigns to the Company all of Executive’s right,
title and interest in and to any patents, ideas, inventions, original works of
authorship, developments, improvements or trade secrets which Executive may solely or
jointly conceive or reduce to practice, or cause to be conceived or reduced to practice,
during the period of this Agreement if such idea, invention, original works of
authorship, developments, improvements, or trade secrets are in any way directly or
indirectly, related to the Company’s business as now conducted or as may be
conducted in the future.  




                         6.2     
Works Made for Hire. Executive acknowledges that all original works of authorship
which are made by Executive (solely or jointly with others) within the scope of this
Agreement and which are protected by copyright are “works made for hire,” as
that term is defined in the United States Copyright Act (17 U.S.C., Section 101).  




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                         6.3     
Obtaining Letters Patent, Copyright Registrations and Other Protections.  




	 	                (a)               Executive
agrees to assist the Company in every proper way to obtain and enforce           United
States and foreign proprietary rights relating to any and all inventions,
          original works of authorship, developments, improvements or trade secrets of
the           Company in any and all countries. To that end, Executive shall execute,
verify           and deliver (A) such documents and perform such other acts (including
appearing           as a witness) as the Company may reasonably request for use in
applying for,           obtaining, perfecting, evidencing, sustaining and enforcing such
proprietary           rights and the assignment thereof and (B) assignments of such
proprietary rights           to the Company or its designee.  







	 	                (b)               Executive’s
obligation to assist the Company with respect to proprietary           rights in any and
all countries shall continue beyond the termination of           Executive’s
employment, but the Company shall compensate Executive at a           reasonable rate
after the termination of this Agreement for the time actually           spent by
Executive at the Company’s request on such assistance.  







	 	                (c)               In
the event the Company is unable for any reason, after reasonable effort, to
          secure Executive’s signature on any document needed in connection with the
          actions specified in the preceding paragraph, Executive hereby irrevocably
          designates and appoints the Company and its duly authorized officers and agents
          as Executive’s agent and attorney-in-fact, to act for and on
          Executive’s behalf to execute, verify and file any such documents and to
do           all other lawfully permitted acts to further the purposes of the preceding
          paragraph with the same legal force and effect as if executed by Executive.
Such           appointment is coupled with an interest. Executive hereby waives and
quitclaims           to the Company any and all claims of any nature whatsoever which
Executive now           or may hereafter have for infringement of any proprietary rights
assigned to the           Company.  







	 	VII.	No
Violation of Other Agreements. 






                         7.1     
Non-contravention. Executive represents and agrees that neither (a) Executive’s
entering into this Agreement nor (b) Executive’s carrying out the provisions of this
Agreement will violate any other agreement (oral or written) to which Executive is a
party or by which Executive is bound.  




	 	VIII.	Miscellaneous. 






                         8.1     
Amendment. This Agreement may be amended only in a writing that is signed by both
parties.  




                         8.2     
Entire Agreement. This Agreement contains the entire understanding of the parties
with regard to the employment of the Executive by the Company. There are no other
agreements, conditions, or representations, oral or written, expressed or implied, with
regard thereto. This Agreement supersedes all prior agreements, promises, and
representations relating to the employment of Executive by the Company, including but not
limited to the Employment Agreement between the Company and Executive dated as of August
5, 2004.  





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                         8.3     
Assignment. The Company may in its sole discretion assign this Agreement to any
entity which succeeds to the business of the Company through merger, consolidation, a
sale of all or substantially all of the assets of the Company, or any similar
transaction. Executive acknowledges that the services to be rendered by him are unique
and personal. Accordingly, Executive may not assign any of his rights or obligations
under this Agreement.  




                         8.4     
Successors. Subject to Section 8.3, the provisions of this Agreement shall be
binding upon the parties hereto, upon any successor to or assign of the Company, and upon
Executive’s heirs and the personal representative of Executive or Executive’s
estate.  




                         8.5     
Notices. Any notice, consent, waiver or other communication required or permitted
to be given under the terms of this Agreement shall be in writing and shall be deemed to
have been delivered: (a) upon receipt, when delivered personally; (b) upon
receipt, when sent by facsimile (provided confirmation of transmission is mechanically or
electronically generated and kept on file by the sending party); or (c) one business day
after deposit for next-day delivery with a nationally-recognized overnight courier
service, in each case properly addressed to the party to receive the same addressed as
follows:  





If to the Company, to: 




William G. Gotimer, Jr. 
Executive
Vice President & General Counsel 
Trailer Bridge, Inc. 
1120
Avenue of the Americas 
Suite 1503 
New York,
NY 10036




If to Executive, to: 




John D. McCown, Jr. 
25
Miller Road 
Pound Ridge, NY 10576



or to such other addresses as either
party may be designate in writing to the other party from time to time. 



                         8.6     
Return of Records and Property. Upon termination of his employment with the
Company, Executive shall promptly deliver to the Company any and all Company records and
any and all Company property in his possession or under his control, including without
limitation manuals, books, blank forms, documents, letters, memoranda, notes, notebooks,
reports, printouts, computer disks, computer tapes, source codes, data, tables or
calculations and all copies thereof, documents that in whole or in part contain any trade
secrets or confidential, proprietary or other secret information of the Company and all
copies thereof, and keys, access cards, access codes, passwords, credit cards, personal
computers, telephones and other electronic equipment belonging to the Company.  




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                         8.7     
Separate Representation. Executive hereby acknowledges that he has sought and
received independent advice from counsel of Executive’s own selection in connection
with this Agreement and has not relied to any extent on any representative or counsel of
the Company in deciding to enter into this Agreement.  




                         8.8     
Waiver of Breach. Any waiver by either party of compliance with any provision of
this Agreement by the other party shall not operate or be construed as a waiver of any
other provision of this Agreement or of any subsequent breach by such party of a
provision of this Agreement. No waiver by the Company shall be valid unless in writing
and signed by a person authorized to do so by the Board of Directors of the Company.  




                         8.9     
Severability. If any one or more of the provisions (or portions thereof) of this
Agreement shall for any reason be held by a final determination of a court of competent
jurisdiction to be invalid, illegal, or unenforceable in any respect, such invalidity,
illegality, or unenforceability shall not affect any other provisions (or portions of the
provisions) of this Agreement, and the invalid, illegal, or unenforceable provision shall
be deemed replaced by a provision that is valid, legal, and enforceable and that comes
closest to expressing intention of the parties.  




                         8.10     
Governing Law. This Agreement shall be interpreted and enforced in accordance with
the laws of the State of New York, without giving effect to conflict of law principles.  




                         8.11     
Headings. The headings of articles and sections herein are included solely for
convenience and reference and shall not control the meaning of interpretation of any of
the provisions of this Agreement.  




                         8.12     
Counterparts. This Agreement may be executed by either of the parties in
counterparts, each of which shall be deemed to be an original, but all such counterparts
shall constitute a single instrument.  














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                IN
WITNESS WHEREOF, the parties have executed this Agreement effective as of the date set
forth above. 



		Trailer Bridge, Inc. 
		

By:  /s/ Douglas E. Schimmel 
		Name:    Douglas E. Schimmel
		Its:          Chairman, Compensation Committee
		


By:  /s/ John D. McCown, Jr. 
		        John D. McCown, Jr.