Document:

Exhibit 10.14

 

EXECUTION COPY

 

SECOND
AMENDMENT TO REGISTRATION RIGHTS AGREEMENT

 

THIS
SECOND AMENDMENT TO REGISTRATION RIGHTS AGREEMENT (this “Second Amendment”) is made and entered
into as of July 31, 2015 by and among: (i) Chart Acquisition Corp., a Delaware corporation (the “Company”),
(ii) Tempus Applied Solutions Holdings, Inc., a Delaware corporation (“Pubco”); (iii) Chart Acquisition
Group LLC, a Delaware limited liability company (“Sponsor”), (iv) Cowen Investments LLC (as assignee
of the Common Stock of Cowen Overseas Investment LP) (“Cowen”) and (v) certain of the other persons
or entities described as Holders in the Registration Rights Agreement (as defined below) and named on the signature pages hereto
who have executed this Second Amendment. Capitalized terms used but not otherwise defined herein shall have the respective meanings
assigned to such terms in the Registration Rights Agreement (and if such term is not defined in the Registration Rights Agreement,
then the Merger Agreement (as defined below)).

 

RECITALS

 

WHEREAS,
the Company, Sponsor, Cowen and the other Holders named therein are parties to that certain Registration Rights Agreement, dated
as of December 13, 2012 (as amended, including as amended by the First Amendment to Registration Rights Agreement, dated as of
June 20, 2015 and as amended by this Second Amendment, the “Registration Rights Agreement”), pursuant
to which the Company granted certain registration rights to the Holders with respect to the Company’s securities; and

 

WHEREAS,
on January 5, 2015, the Company entered into a Plan and Agreement of Merger (as amended, including without limitation by the First
Amendment to the Agreement and Plan of Merger, dated as of March 20, 2015, the Second Amendment to Agreement and Plan of Merger,
dated as of June 10, 2015, and the Third Amendment to Agreement and Plan of Merger, dated as of July 15, 2015, the “Merger
Agreement”), with Tempus Applied Solutions, LLC, a Delaware limited liability company (“Tempus”),
each of the persons or entities set forth on Annex A to the Merger Agreement (the “Members”), Benjamin
Scott Terry and John G. Gulbin III, together in their capacity as Members’ Representative solely for purposes specified
in the Merger Agreement (the “Members’ Representative”), Pubco, Chart Merger Sub Inc., a Delaware
corporation (“Parent Merger Sub”), TAS Merger Sub LLC, a Delaware limited liability company (“Tempus
Merger Sub”), Chart Financing Sub Inc., a Delaware corporation (“Parent Financing Sub”),
TAS Financing Sub Inc., a Delaware corporation (“Tempus Financing Sub”), Chart Acquisition Group LLC,
in its capacity as the representative for the equity holders of the Company and Pubco (other than the Members and their successors
and assigns) in accordance with the terms and conditions of the Merger Agreement, Sponsor, Mr. Joseph Wright and Cowen, solely
for the purposes specified in the Merger Agreement; and

 

WHEREAS,
Pubco and the other parties to the New Investor Purchase Agreements have agreed to amend the New Investor Purchase Agreements,
effective as of July 15, 2015, to among other matters, provide the New Investors with registration rights with respect to the
Pubco securities that they receive in the Mergers pursuant to a Registration Rights Agreement by and among Pubco and the New Investors,
the form of which is attached hereto as Exhibit A (the “New Investor Registration Rights Agreement”);
and

 

WHEREAS,
the parties hereto desire to amend the Registration Rights Agreement to acknowledge the New Investor Registration Rights Agreement
and to agree to certain limitations on their rights under the Registration Rights Agreement in connection with the New Investor
Registration Rights Agreement; and

 

    	 

    	 

    

 

WHEREAS,
pursuant to Section 5.5 of the Registration Rights Agreement, the Registration Rights Agreement can be amended with the written
consent of the Company and the Holders of at least 66-2/3% of the Registrable Securities at the time in question (provided, that
any amendment that adversely affects one Holder, solely in its capacity as a holder of the shares of capital stock of the Company,
in a manner that is materially different from the other Holders (in such capacity) shall require the consent of the Holder so
affected).

 

NOW,
THEREFORE, in consideration of the premises and the mutual promises herein made, and in consideration of the representations,
warranties and covenants herein contained, and intending to be legally bound hereby, the parties hereto agree as follows:

 

1.           Acknowledgement of New Investor Registration Rights Agreement. The parties hereby acknowledge that, notwithstanding Section
5.6 of the Registration Rights Agreement, in connection with the New Investor Purchase Agreements, Pubco will enter into the New
Investor Registration Rights Agreement substantially in the form attached as Exhibit A hereto with respect to the Pubco
securities to be issued in the New Investors in the Mergers, and consent to the foregoing. The parties further acknowledge that
certain terms of the New Investor Registration Rights Agreement may conflict with the terms of the Registration Rights Agreement
and may restrict the rights of the Holders under the Registration Rights Agreement, including the rights of the Holders to exercise
Demand Registrations or Piggy-back Registrations. The parties hereby waive any such conflicts and any breach of the Registration
Rights Agreement that may result from Pubco’s compliance with the terms of the New Investor Registration Rights Agreement.

 

2.           Amendments to Registration Rights Agreement. The Parties hereby agree to the following amendments to the Registration Rights
Agreement:

 

(a)            Section 1.1 of the Registration Rights Agreement is hereby amended to add the following definition:

 

“New
Investor Registration Rights Agreement” shall mean that certain Registration Rights Agreement, dated as of July
31, 2015, by and among Pubco and the New Investors (as such term is defined in the Merger Agreement).

 

“Tempus
Registration Rights Agreement” shall mean that certain Registration Rights Agreement, by and among Pubco and the
Members to be entered into by Pubco in connection with the Mergers.

 

(b)            Section 5.6 of the Registration Rights Agreement is hereby deleted and replaced in its entirety by the following:

 

“5.6          Other
Registration Rights. The Company and Pubco represent and warrant that, other than the parties to the New Investor Registration
Rights Agreement and the Tempus Registration Rights Agreement, no person, other than a Holder of Registrable Securities, has any
right to require the Company or Pubco to register any securities of the Company or Pubco for sale or to include such securities
of the Company or Pubco in any Registration filed by the Company or Pubco for the sale of securities for its own account or for
the account of any other person. Further, the Company and Pubco represent and warrant that, other than with respect to the New
Investor Registration Rights Agreement, this Agreement supersedes any other registration rights agreement or agreement with similar
terms and conditions and in the event of a conflict between any such agreement or agreements and this Agreement, the terms of
this Agreement shall prevail; provided, that in the event of any conflict between the New Investor Registration Rights
Agreement and this Agreement, including any provisions of this Agreement that are prohibited by the terms of the New Investor
Registration Rights Agreement, the terms of the New Investor Registration Rights Agreement will prevail.”

 

    	2

    	 

    

 

3.           Miscellaneous. Except as expressly provided in this Second Amendment, all of the terms and provisions in the Registration
Rights Agreement are and shall remain in full force and effect, on the terms and subject to the conditions set forth therein.
This Second Amendment does not constitute, directly or by implication, an amendment or waiver of any provision of the Registration
Rights Agreement, or any other right, remedy, power or privilege of any party thereto, except as expressly set forth herein. Any
reference to the Registration Rights Agreement in the Registration Rights Agreement or any other agreement, document, instrument
or certificate entered into or issued in connection therewith shall hereinafter mean the Registration Rights Agreement, as amended
by this Second Amendment (or as the Registration Rights Agreement may be further amended or modified after the date hereof in
accordance with the terms thereof). The terms of this Second Amendment shall be governed by and construed in a manner consistent
with the provisions of the Registration Rights Agreement, including Sections 5.4 thereof.

 

[REMAINDER
OF PAGE INTENTIONALLY LEFT BLANK; SIGNATURE PAGES FOLLOW]

 

    	3

    	 

    

 

IN
WITNESS WHEREOF, each party hereto has signed or has caused to be signed by its officer thereunto duly authorized this Second
Amendment to Registration Rights Agreement as of the date first above written.

 

	 	Company:
	 	 
	 	CHART
    ACQUISITION CORP.
	 	 
	 	By:	 
	 	 	Name:  Christopher
    D. Brady
	 	 	Title:  President
	 	 	 
	 	Pubco:
	 	 
	 	TEMPUS
    APPLIED SOLUTIONS HOLDINGS, INC.
	 	 
	 	By:	 
	 	 	Name:  Christopher
    D. Brady
	 	 	Title:  President
	 	 	 
	 	Holders:
	 	 
	 	CHART
    ACQUISITION GROUP LLC
	 	 
	 	By:
    	The
    Chart Group L.P.
	 	 	 
	 	By:	 
	 	 	Name:  Christopher
    D. Brady
	 	 	Title:  Manager
	 	 	 
	 	COWEN
    INVESTMENTS LLC
	 	 
	 	By:	 
	 	 	Name:
	 	 	Title:
	 	 
	 	THE
    CHART GROUP L.P.
	 	 
	 	By:	 
	 	 	Name:  Christopher
    D. Brady
	 	 	Title:  Manager

  

[Signature Page to Second
Amendment to Registration Rights Agreement]

 

    	 

    	 

    

 

Holders
(cont.):

 

	 	 	 
	Abdulwahab
    Al-Nakib	 	Geoffry
    Nattans
	 	 	 
	 	 	 
	Joseph
    Boyle	 	Governor
    Thomas Ridge
	 	 	 
	 	 	 
	Christopher
    Brady	 	Charlene
    Ryan
	 	 	 
	 	 	 
	David
    Collier	 	Margaret
    Saracco
	 	 	 
	 	 	 
	Senator
    Joseph Robert Kerrey 	 	Timothy
    N. Teen
	 	 	 
	 	 	 
	Deirdre
    Kilmartin	 	Cole
    Van Nice
	 	 	 
	 	 	 
	Michael
    LaBarbera	 	H.
    Whitney Wagner
	 	 	 
	 	 	 
	Khaled
    El-Marsafy (Fourth and Market)	 	Joseph
    R. Wright
	 	 	 
	 	 	 
	Matthew
    McCooe	 	Young-Gak
    Yun
	 	 	 
	 	 	 
	Manuel
    D. Medina	 	 

 

[Signature Page to Second Amendment to Registration
Rights Agreement]

 

    	 

    	 

    

 

Exhibit
A

Form
of New Investor Registration Rights Agreement

 

See
Attachment.Exhibit 10.15

 

July 30, 2015

 

Christopher D. Brady

Chart Acquisition Corp.

c/o The Chart Group, L.P.

555 Fifth Avenue, 19th Floor

New York, New York 10017

 

	 	Re: Waiver

 

Dear Mr. Brady:

 

Reference is made to that certain
Third Amended and Restated Warrant Agreement (the “Agreement”) dated June 11, 2015, by and between Chart Acquisition
Corp. (the “Company”) and Continental Stock Transfer & Trust Company. Pursuant to Section 4.4 of the Agreement,
in the event of a Fundamental Transaction, the Company is obligated to purchase the Warrants held by a Registered Holder (if so
requested) for cash in an amount equal to the Black Scholes Value of the remaining unexercised portion of such Warrant on the date
of such Fundamental Transaction (the “Repurchase Right”). All capitalized terms not defined herein shall have the meaning
specified to them in the Agreement.

 

Each of the undersigned, on its
own behalf and on behalf of its successors, transferees and assigns, hereby agrees, for good and valuable consideration, the receipt
and sufficiency of which is hereby acknowledged, (i) to waive the Repurchase Right as set forth in the Agreement for the number
of Warrants set forth opposite its name on Exhibit A (the “Subject Warrants”) and (ii) not to sell, offer to sell,
contract or agree to sell, hypothecate, pledge, grant any option to purchase or otherwise dispose of or agree to dispose of, directly
or indirectly, or enter into any swap or other arrangement that transfers to another, in whole or in part, any of the economic
consequences of ownership of, any of the Subject Warrants unless the transferee enters into a written agreement with the parties
hereto agreeing to be bound by the terms of this waiver.

 

Except as expressly set forth herein,
this waiver shall not be deemed to be a waiver, amendment or modification of any provisions of the Agreement or of any right,
power or remedy of the undersigned, nor shall it constitute a waiver of any provision of any other document, instrument and/or
agreement executed or delivered in connection therewith, in each case whether arising before or after the date hereof or as a result
of performance hereunder or thereunder.

 

Please confirm that the foregoing
is in accordance with your understanding of our agreement by signing and returning to us a copy of this letter. This letter may
be executed in counterparts and by facsimile or other electronic transmission.

 

[Signature page follows]

 

    	 

    	 

    

  

	 	Very truly yours,
	 	 
	 	CHART ACQUISITION GROUP LLC
	 	 	 
	 	By:	/s/ Christopher D. Brady
	 	 	Name: Christopher D. Brady
	 	 	Title:
	 	 	 
	 	 	/s/ Joseph R. Wright
	 	 	JOSEPH R. WRIGHT
	 	 	 
	 	COWEN INVESTMENTS LLC
	 	 	 
	 	By:	/s/ Owen Littman
	 	 	Name: Owen Littman
	 	 	Title: Authorized Signatory

 

AGREED TO AND ACCEPTED AS

OF THE 30th DAY OF JULY, 2015:

 

CHART ACQUISITION CORP.

 

	By:	/s/ Christopher D. Brady	 
	Name:	Christopher D. Brady	 
	Title:	President	 

 

Signature Page to Warrant Agreement Waiver

 

    	 

    	 

    

 

Exhibit A

 

Subject Warrants

 

	Name	 	Number of Subject Warrants
	Chart Acquisition Group LLC	 	1,921,933
	Joseph R. Wright	 	103,884
	Cowen Investments LLC	 	1,090,824

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