Exhibit 4.19




 




FIRST AMENDMENT TO
DEBENTURE AGREEMENT




 




6.75% Convertible

Subordinated Debenture, Series B No. 2 Due July 3, 2007


Original Principal Amount up to $1,000,000




 




THIS FIRST AMENDMENT TO DEBENTURE AGREEMENT

(the “Amendment”) is made and entered into on this 23rd day of December, 2002,

by and between William H. White, an individual, or his assigns (“Holder”) and

Pioneer Drilling Company, a Texas corporation (the “Company”).




 




R E C I T A L S




 




A.                                   On the Subsequent

Closing Date, the Company issued that certain 6.75% Convertible Subordinated

Debenture, Series B, No. 2, due July 3, 2007 in the original principal amount

of $1,000,000 to William H. White (referred to as the “Debenture” or the

“Note”) in accordance with those terms and conditions as set forth in those

certain Debenture Agreements on each of those dates therewith (collectively the

“Debenture Agreement”).




 




B.                                     The Company’s

subsidiary, Pioneer Drilling Services, Ltd., has simultaneously entered into

that certain loan agreement with Merrill Lynch Capital, a division of Merrill

Lynch Business Financial Services Inc. (“Merrill Lynch”) in the principal

amount of Fourteen Million Five Hundred Thousand and No/100 Dollars

($14,500,000.00), to retire the loan with American Banc, to acquire new

drilling rigs and for working capital purposes.




 




C.                                     As a result of the

transaction to be entered into with Merrill Lynch, the parties desire to amend

the terms of the Debenture Agreement to (i) modify certain defined terms as

outlined below, and (ii) to modify Section 6.08 to include additional events

which will not impair the rights of the holders of Superior Indebtedness to

enforce subordination of the Subordinated Indebtedness.




 




D.                                    All capitalized

terms not otherwise defined in this First Amendment, or modified in Article I

below, shall have the same meanings as set forth in the Debenture Agreement.




 




NOW, THEREFORE, in consideration of the

premises and of the mutual agreements hereinafter set forth, the parties hereto

agree as follows:




 





























 




ARTICLE I


Amendment




 




1.01                           Amendment to the

definition “Holder”.  The term

“Holder” shall be amended as follows:




 




“1.07                     Holder.  The term “Holder” shall collectively mean

WEDGE Energy Services, L.L.C., a Delaware limited liability company, and

William H. White, an individual, or any one of their Affiliates.”




 




1.02                           Amendment to the

definition “Subsequent Closing Date”. 

The term “Subsequent Closing Date” shall be amended as follows:




 




“1.17.                  Subsequent Closing Date.  The term Subsequent Closing Date shall mean

July 29, 2002.”




 




1.03                           Amendment to the

definition Superior Indebtedness. 

The term “Superior Indebtedness” shall be amended as follows:




 




“1.20                     Superior Indebtedness.  The term Superior Indebtedness shall mean

the indebtedness owed by the Company to (i) Frost National Bank as disclosed in

the subordination agreement previously entered into between Holder and Frost

National Bank and (ii) the Company’s guarantee of Pioneer Drilling Services,

Ltd.’s Fourteen Million Five Hundred Thousand and No/100 Dollars

($14,500,000.00) term loan from Merrill Lynch Capital, a division of Merrill

Lynch Business Financial Services, Inc.”




 




1.04                           Amendment to Section 6.08

Obligations Unimpaired.  Section

6.08 is amended in its entirety as follows:




 




“Section 6.08.  Subordination Not Affected,

etc.  The terms of this

Article VI, the subordination effected hereby, and the rights of the holders of

the Superior Indebtedness shall not be affected by (a) any amendment of or

addition or supplement to any Superior Indebtedness or any instrument or

agreement relating thereto, (b) any exercise or non-exercise of any right,

power, or remedy under or in respect of any Superior Indebtedness or any

instrument or agreement relating thereto, (c) any waiver, consent, release,

indulgence, extension, renewal, modification, delay, or other action, inaction

or omission, in respect of any Superior Indebtedness or any instrument or

agreement relating thereto or any security therefor or guaranty thereof, or (d)

the failure of any Superior Indebtedness to perfect any 




 




2





























 




security interest, or the lapse in perfection

of any security interest in any such collateral, whether or not any holder of

any Subordinated Indebtedness shall have had notice or knowledge of any of the

foregoing.  In addition, in the event

that any holder or prospective holder of Superior Indebtedness reasonably

requires a modification or amendment of the terms of this Article VI with

respect to the subordination of the Subordinated Indebtedness, the Holder

agrees to execute any such reasonable and necessary modification or amendment

to this Article VI with respect thereto.”




 




ARTICLE II


ENFORCEABILITY OF REMAINING PROVISIONS




 




All other

provisions of the Debenture Agreement, and the Exhibit attached thereto, shall

remain in full force and effect and any inconsistencies between this Amendment

and the Agreement shall be construed in favor of this Amendment.




 




ARTICLE III


MISCELLANEOUS




 




3.01                           Counterparts.  This Amendment may be executed by the

parties hereto in multiple counterparts. 

It shall not be necessary that the signatures of the parties appear on

the same counterparts.




 




3.02                           Governing

Law.  This Amendment shall be

governed by and construed in accordance with the laws of the state of Texas.




 




IN WITNESS

WHEREOF, the parties hereto have caused this Amendment to be duly executed as

of the day and year first above written.




 




 




	

  COMPANY:


  	

  HOLDER:


  
	

   


  	

   


  
	

  PIONEER DRILLING COMPANY


  	

   


  
	

   


  	

   


  
	

   


  	

   


  
	

  By:


  	

   


  	

   


  	

  By:


  	

   


  
	

  Name:


  	

   


  	

   


  	

   


  	

  William H. White, an individual


  
	

  Title:


  	

   


  	

   


  	

   


  
							





 




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