Document:

First Supplemental Agreement dated July 30, 2009 to a loan agreement

 Exhibit 4.21 
 Dated 30 July 2009 
 BOONE STAR OWNERS INC. and

 IOKASTI OWNING COMPANY LIMITED 
 as Borrowers 
 -and- 
 PIRAEUS BANK A.E 
 as Lender 
  
  
 FIRST SUPPLEMENTAL AGREEMENT 
  
  
 in relation to a
Loan Agreement dated 5 October 2007 
 in respect of a loan facility of (originally) US$90,000,000 
 WATSON, FARLEY & WILLIAMS 
 Piraeus 

 INDEX 
  

					
	 Clause
	 	 	  	Page
			
	 1
	 	DEFINITIONS	  	1
			
	 2
	 	REPRESENTATIONS AND WARRANTIES	  	3
			
	 3
	 	AGREEMENT OF THE LENDER	  	4
			
	 4
	 	CONDITIONS	  	4
			
	 5
	 	VARIATIONS TO LOAN AGREEMENT AND FINANCE DOCUMENTS	  	6
			
	 6
	 	CONTINUANCE OF LOAN AGREEMENT AND FINANCE DOCUMENTS	  	13
			
	 7
	 	EXPENSES	  	13
			
	 8
	 	NOTICES	  	13
			
	 9
	 	APPLICABLE LAW	  	13

 THIS FIRST SUPPLEMENTAL AGREEMENT is dated 30 July 2009 and made 
 BETWEEN: 
  

	(1)	BOONE STAR OWNERS INC. (“Boone”), and IOKASTI OWNING COMPANY LIMITED (“Iokasti”), each a corporation incorporated in the
Marshall Islands whose registered office is at Ajeltake Road, Ajeltake Island, Majuro MH96960, Marshall Islands (together the “Borrowers” and each a “Borrower”); and 

  

	(2)	PIRAEUS BANK A.E., acting through its branch at 47-49 Akti Miaouli, 185 36 Piraeus, Greece as “Lender” 

 IS SUPPLEMENTAL to a Loan Agreement dated 5 October 2007 made between (i) the Borrowers as joint and several borrowers and (ii) the
Lender as lender whereby the Lender has made available to the Borrowers a loan facility of (originally) Ninety million United States Dollars (US$90,000,000) (the “Loan”) of which the current outstandings amount to $80,000,000 upon
the terms and for the purposes therein specified. 
 WHEREAS pursuant to a request from the Borrowers, and subject to the terms and
conditions herein contained, the Lender has agreed to waive the applications of certain covenants during the period 31 December 2008 until 31 March 2011 subject to the following conditions: 
  

	(A)	the Lender will receive certain additional security for the obligations of the Borrowers under the Loan Agreement and the other Finance Documents; and

  

	(B)	the entry by the Borrowers into this First Supplemental Agreement whereby certain provisions of the Loan Agreement and certain other Finance Documents will be amended
and/or varied. 

 NOW THEREFORE IT IS HEREBY AGREED 
  

	1	DEFINITIONS 

  

	1.1	Words and expressions defined in the Loan Agreement (as hereby amended) and the recitals hereto and not otherwise defined herein shall have the same meanings
when used in this First Supplemental Agreement. 

  

	1.2	In this First Supplemental Agreement the words and expressions specified below shall have the meanings attributed to them below: 

 “Additional Charterparty Assignment” means, in relation to each Additional Ship, a second priority specific
assignment of any Approved Charter in respect thereof executed or to be executed by the Additional Owner owning that Additional Ship in favour of the Lender in such form as the Lender may approve or require and, in the plural, means both of them;

 “Additional Account” means, in relation to each Additional Owner, an account opened or to be
opened in the name of that Additional Owner with the Lender for receipt of the Earnings of its Additional Ship or such other account or accounts as may be established for this purpose with the prior consent of the Lender and, in the plural, means
both of them; 
 “Additional Account Pledge” means, in relation to each Additional Account, a
second priority pledge over that Additional Account to be executed by the relevant Additional Owner in favour of the Lender in such form as the Lender may approve or require and, in the plural, means both of them; 
 “Additional Finance Documents” means, together, the Additional Guarantees, the Additional Mortgages, the
Additional Deeds of Covenant, the Additional General Assignments, any Additional Charterparty Assignments and the Additional Account Pledges and, in the singular, means any of them; 

 “Additional General Assignment” means, in relation to each Additional Ship,
a second priority general assignment of the Earnings, Insurances and Requisition Compensation in respect thereof executed or to be executed by the Additional Owner owning that Additional Ship in favour of the Lender in such form as the Lender may
approve or require and, in the plural, means both of them; 
 “Additional Guarantee” means, in relation to each
Additional Owner, the guarantee of the obligations of the Borrowers under the Loan Agreement executed or to be executed by that Additional Owner in favour of the Lender in such form as the Lender may approve or require and, in the plural, means both
of them; 
 “Additional Mortgage” means, in relation to each Additional Ship, the second priority Maltese
statutory mortgage over that Additional Ship executed or to be executed by the Additional Owner owning that Additional Ship in favour of the Lender in such form as the Lender may approve or require and, in the plural, means both of them; 

“Additional Owner” means each of Farat and Lotis and, in the plural, means both them; 
 “Additional Ship” means each of “DELRAY” and “TORO” and, in the plural, means both of them; 

“Collateral Loan Agreement” means a loan agreement dated 13 March 2008 (as amended and supplemented by supplemental
agreements dated 12 December 2008 and July 2009 respectively) made (originally) between (i) Annapolis Shipping Company Limited, Atlas Owning Company Limited, Farat and Lansat Shipping Company Limited (the “Collateral
Borrowers”) as joint and several borrowers and (ii) the Lender as lender, in respect of a loan facility of (originally) US$130,000,000; 
 “Deed of Covenant” means, in relation to each Additional Ship, the second priority deed of covenant collateral to the relevant Additional Mortgage executed or to be executed by the
Additional Owner owning that Additional Ship in favour of the Lender in such form as the Lender may approve or require and, in the plural, means both of them; 
 “DELRAY” means the 1994-built bulk carrier vessel of 71,860 metric tons deadweight tons, having IMO Number 9071600 and registered in the ownership of Lotis under Maltese flag with the
name “DELRAY”; 
 “Farat” means Farat Shipping Company Limited a company incorporated in Malta, whose
registered office is at 5/2, Merchants Street, Valletta, Malta; 
 “Lotis” means Lotis Trading Inc., a
corporation incorporated under the laws of Republic of Marshall Islands with its registered office at Trust Company Complex, Ajeltake Road, Ajeltake Island, Majuro, Marshall Islands MH-96960; 
 “Mortgage Addendum” means, in relation to each Original Ship, the first addendum, to the Mortgage on that Original Ship,
executed or to be executed by: 
  

	 	(a)	in the case of “TRANSATLANTIC”, Boone; and 

  

	 	(b)	in the case of “VOC GALAXY” Iokasti, 

 in favour of the Lender in such form as the Lender may approve or require and, in the plural, means both of them; 
  

 2 

 “Original Ship” means each of “TRANSATLANTIC” and “VOC
GALAXY” and, in the plural, means both of them; 
 “TORO” means the 1995-built bulk carrier vessel of
73,034 metric tons deadweight tons, haying IMO Number 9075735 registered in the ownership of Farat under Maltese flag with the name “TORO”; and 
 “Waiver Period” has the meaning ascribed to it in Recital (A) above. 
  

	1.3	Where the context so admits words importing the singular number only shall include the plural and vice versa and words importing persons shall include firms and
corporations. Clause headings are inserted for convenience of reference only and shall be ignored in construing this First Supplemental Agreement. References to Clauses are to clauses of this First Supplemental Agreement save as may be otherwise
expressly provided in this First Supplemental Agreement. 

  

	2	REPRESENTATIONS AND WARRANTIES 

  

	2.1	Each Borrower hereby jointly and severally represents and warrants to the Lender, as at the date of this First Supplemental Agreement, that the representations
and warranties set forth in Clause 8 of the Loan Agreement (updated mutatis mutandis to the date of this First Supplemental Agreement) are true and correct as if all references therein to “this Agreement” were references to the Loan
Agreement as further amended by this First Supplemental Agreement. 

  

	2.2	Each Borrower hereby further jointly and severally represents and warrants to the Lender that as at the date of this First Supplemental Agreement:

  

	(a)	each Borrower is duly incorporated and validly existing and in good standing under the laws of Malta and has full power to enter into and perform its obligations under
this First Supplemental Agreement and has complied with all statutory and other requirements relative to its business, and does not have an established place of business in any part of the United Kingdom or the United States of America;

  

	(b)	all necessary governmental or other official consents, authorisations, approvals, licences, consents or waivers for the execution, delivery, performance, validity
and/or enforceability of this First Supplemental Agreement and all other documents to be executed in connection with the amendments to the Loan Agreement as contemplated hereby have been obtained and will be maintained in full force and effect, from
the date of this First Supplemental Agreement and so long as any moneys are owing under any of the Finance Documents and while all or any part of the Commitment remains outstanding; 

  

	(c)	each Borrower has taken all necessary corporate and other action to authorise the execution, delivery and performance of its obligations under this First Supplemental
Agreement and such other documents to which it is a party and such documents do or will upon execution thereof constitute the valid and binding obligations of each Borrower enforceable in accordance with their respective terms;

  

	(d)	the execution, delivery and performance of this First Supplemental Agreement and all such other documents as contemplated hereby does not and will not, from the date of
this First Supplemental Agreement and so long as any moneys are owing under any of the Finance Documents and while all or any part of the Commitment remains outstanding, constitute a breach of any contractual restriction or any existing applicable
law, regulation, consent or authorisation binding on each Borrower or on any of its property or assets and will not result in the creation or imposition of any security interest, lien, charge or encumbrance (other than under the Finance Documents)
on any of such property or assets; and 

  

 3 

	(e)	each Borrower has fully disclosed in writing to the Lender all facts which it knows or which it should reasonably know and which are material for disclosure to the
Lender in the context of this First Supplemental Agreement and all information furnished by such Borrower or on its behalf relating to its business and affairs in connection with this First Supplemental Agreement was and remains true, correct and
complete in all material respects and there are no other material facts or considerations the omission of which would render any such information misleading. 

  

	3	AGREEMENT OF THE LENDER 

  

	3.1	The Lender, relying upon each of the representations and warranties set out in Clauses 2.1 and 2.2 of this First Supplemental Agreement, hereby agrees with the
Borrowers, subject to and upon the terms and conditions of this First Supplemental Agreement and in particular, but without limitation, subject to the fulfillment of the conditions precedent set out in Clause 4, to: 

  

	(a)	waive the application of certain covenants contained within the Loan Agreement; and 

  

	(b)	the amendments and/or variations of certain other provisions of the Loan Agreement set out in this First Supplemental Agreement. 

  

	3.2	Each Borrower agrees and confirms that the Loan Agreement and the Finance Documents to which it is a party shall remain in full force and effect and that Borrower shall
remain liable under the Loan Agreement and the Finance Documents to which it is a party for all obligations and liabilities assumed by it thereunder. 

  

	4	CONDITIONS 

  

	4.1	The agreements of the Lender contained in Clause 3.1 of this First Supplemental Agreement shall all be expressly subject to the condition that the Lender shall
have received in form and substance satisfactory to the Lender and its legal advisers on or before the date of this First Supplemental Agreement: 

  

	(a)	evidence that the persons executing this First Supplemental Agreement on behalf of each Borrower are duly authorised to execute the same on behalf of such Borrower;

  

	(b)	a certificate from an officer of each Additional Owner confirming the names of all the directors and Shareholders of that Additional Owner and having attached thereto
true and complete copies of its incorporation and constitutional documents; 

  

	(c)	true and complete copies of the resolutions passed at separate meetings of all the directors and shareholders of each Borrower and each Additional Owner authorising and
approving the execution of, in the case of each Borrower the Mortgage Addendum and in the case of each Additional Owner the Additional Finance Documents to which it is a party and any other document or action to which it is or is to be a party and
authorising its directors or other representatives to execute the same on its behalf; 

  

	(d)	the original of any power of attorney issued by each Borrrower and each Additional Owner pursuant to such resolutions aforesaid; 

  

	(e)	evidence that each Additional Ship is: 

  

	 	(i)	registered in the ownership of the relevant Additional Owner under the laws and flag of the Malta; and 

  

 4 

	 	(ii)	insured in accordance with the relevant provisions of the Additional Deed of Covenant relative to that Additional Ship and all requirements thereof in respect of such
insurance have been fulfilled; and 

  

	(f)	the Additional Finance Documents and the Mortgage Addenda, duly executed by the Additional Owners or, in the case of each Mortgage Addendum, each Borrower together with
evidence that: 

  

	 	(i)	each Additional Mortgage has been registered against the relevant Additional Ship with first priority in accordance with the laws of Malta; 

  

	 	(ii)	each Mortgage Addendum in connection with the relevant Original Ship has been duly registered in accordance with the laws of Malta; 

  

	 	(iii)	all notices required to be given under each Additional Deed of Covenant, each Additional General Assignment and each Additional Charterparty Assignment have been given
and acknowledged in the manner therein provided (other than in the case of a Charterparty Assignment in which case the Borrower or, as the case may be, Additional Owner which is a party thereto shall procure that the Lender receives the relevant
acknowledgement only if an Event of Default has occurred); and 

  

	 	(iv)	save for the charges created by or pursuant to: 

  

	 	(A)	any Finance Document (as defined in the Collateral Loan Agreement) which has been executed pursuant to the Collateral Loan Agreement; and 

  

	 	(B)	the Additional Mortgages, the Additional Deeds of Covenant, the Additional General Assignments and the Additional Charterparty Assignments, 

 there is no lien, charge or encumbrance of any kind whatsoever on either Additional Ship or her Earnings, Insurances or Requisition
Compensation. 
  

	(g)	a certified true copy of any Approved Charter entered into in respect of either Additional Ship; 

  

	(h)	the original of any mandates or other documents required in connection with the opening or operation of the Additional Accounts; 

  

	(i)	documents establishing that each Additional Ship is managed by the Approved Manager; 

  

	(j)	a letter of undertaking executed by the Approved Manager in favour of the Lender in the terms required by the Lender agreeing certain matters in relation to the
management of each Additional Ship and subordinating the rights of the Approved Manager against that Additional Ship and the Additional Owner owning that Additional Ship to the rights of the Lender under the Finance Documents;

  

	(k)	copies of ISM DOC and SMC and the International Ship Security Certificate under the ISPS Code in respect of each Additional Ship; 

  

	(l)	each Additional Ship maintains the highest available class with such first-class classification society which is a member of the IACS as the Lender may approve free of
all recommendations and conditions of such classification society; 

  

	(m)	evidence that each Additional Owner is a direct or indirect subsidiary of the Corporate Guarantor; 

  

 5 

	(n)	certified copies of all documents (with a certified translation if an original is not in English) evidencing any other necessary action, approvals or consents with
respect to this First Supplemental Agreement and the Additional Finance Documents (including without limitation) all necessary governmental and other official approvals and consents in such pertinent jurisdictions as the Lender deems appropriate;

  

	(o)	such legal opinions as the Lender may require in respect of the matters contained in this First Supplemental Agreement and the Additional Finance Documents and the
Mortgage Addenda; and 

  

	(p)	evidence that the agent referred to in Clause 9.4 has accepted its appointment as agent for service of process under this First Supplemental Agreement and the
Additional Finance Documents. 

  

	5	VARIATIONS TO LOAN AGREEMENT AND FINANCE DOCUMENTS 

  

	5.1	In consideration of the agreement of the Lender contained in Clause 3.1 of this First Supplemental Agreement the Borrowers hereby agree with the Lender that upon
satisfaction of the conditions referred to in Clause 4.1, the provisions of the Loan Agreement and the Guarantee shall be varied and/or amended and/or supplemented as follows: 

  

	(a)	by inserting in clause 1.1 of the Loan Agreement the definitions of “Additional Guarantee”, “Additional Owner”, “Additional Ships,
“Collateral Loan Agreement”, “DELRAY”, “Farat”, “Lotis”, “Mortgage Addendum”, “Original Ship”, and “TORO” set out in Clause 1.2 of this First Supplemental Agreement;

  

	(b)	the definition of, and references throughout each of the Finance Documents to, the Mortgage relevant to each Original Ship, shall be construed as if the same referred
to that Mortgage as amended and supplemented by the relevant Mortgage Addendum; 

  

	(c)	by adding the following new definition of “Collateral Loan” in clause 1.1 of the Loan Agreement: 

 ““Collateral Loan” means the principal amount outstanding at any relevant time under the Collateral Loan
Agreement;”; 
  

	(d)	by adding the following new paragraphs (c) and (d) in the definition of “Account” contained in clause 1.1 of the Loan Agreement;

  

	 	“(c)	in the case of “DELRAY”, an earnings account in the name of Lotis with the Lender designated “Lotis Traders Inc.—Earnings Account; and

  

	 	(d)	in the case of “TORO”, an earnings account in the name of Farat with the Lender designated “Farat Owning Company Limited - Earnings Account”;”;

  

	(e)	by deleting the word “either” and replacing it with the word “any” in the first line of the definition of “Account” contained in clause
1.1 of the Loan Agreement; 

  

	(f)	by deleting the word “and” after the words “Charter Assignment;” in sub-paragraph (j) in the definition of “Finance Documents” in
clause 1.1 of the Loan Agreement; 

  

	(g)	by adding the following new paragraph (k) in the definition of “Finance Documents” in clause 1.1 of the Loan Agreement: 

  

	 	“(k)	the Additional Guarantees;”; 

  

 6 

	(h)	by redesignating the existing sub-paragraph (k) of the definition of “Finance Documents” in clause 1.1 thereof as a new sub-paragraph (l);

  

	(i)	by adding the words “each Additional Owner,” after the word “mean” and before the words “the Corporate Guarantor” in the definition of
“Security Party” in clause 1.1 of the Loan Agreement; 

  

	(j)	by adding the following new definition of “Relevant Charter” in clause 1.1 of the Loan Agreement: 

 ““Relevant Charter” has the meaning given to it in Clause 14.3;”; 
  

	(k)	by deleting the definition of “Ship” contained in clause 1.1 of the Loan Agreement and substituting the same with the following: 

 ““Ship” means each of “TRANSATLANTIC”, “VOC GALAXY” and each Additional Ship and in the plural
means all of them;”; 
  

	(l)	by deleting the definition “VOC GALAXY” in clause 1.1 of the Loan Agreement and replacing it with the following new definition: 

 ““VOC GALAXY” means the 2002-built bulk carrier vessel of 30,928 gross registered tons and 16,341 net registered tons,
having IMO Number 9257060 previously registered in the ownership of the relevant Seller under the flag of Antigua & Bermuda with the name “VOC GALAXY”, purchased by Iokasti pursuant to the relevant MOA and currently registered in
its ownership under Maltese flag with the name “PACHINO”;”; 
  

	(m)	by adding the words “or, as the case may be, Additional Owner” after the words “Borrower” in: 

  

	 	(i)	the second line of the definition of “Account Pledge” in clause 1.1 of the Loan Agreement; 

  

	 	(ii)	the second line of the definition of “Approved Charter” in clause 1.1 of the Loan Agreement; 

  

	 	(iii)	the fifth line of the definition of “Approved Manager’s Undertaking” in clause 1.1 of the Loan Agreement; 

  

	 	(iv)	the second line of sub-paragraph (a) in the definition of “Charter Assignment” in clause 1.1 of the Loan Agreement; 

  

	 	(v)	the second line of sub-paragraph (a) in the definition of “Earnings” in clause 1.1 of the Loan Agreement; 

  

	 	(vi)	the third line of the definition of “General Assignment” in clause 1.1 of the Loan Agreement; 

  

	 	(vii)	the fifth line of sub-paragraph (e) of the definition of “Permitted Security Interests” in clause 1.1 of the Loan Agreement; 

  

	 	(viii)	the second line of sub-paragraph (b)(ii) of the definition of “Total Loss Date” in clause 1.1 of the Loan Agreement; 

  

	 	(ix)	the second line of the definition of “obligatory insurances” in clause 1.2 of the Loan Agreement; and 

  

 7 

	 	(x)	in the second line of clause 18.1(k) of the Loan Agreement; 

  

	(n)	by deleting the definition of “Margin” in clause 1.1 of the Loan Agreement and substituting the same with the following new definition:

 ““Margin” means: 
  

	 	(a)	during the period commencing on 1 April 2009 and ending on the last day of the Waiver Period, 2 per cent. per annum; and 

  

	 	(b)	at all times thereafter and subject to the terms of Clause 4.10, 1.5 per cent per annum;”; 

  

	(o)	by deleting clauses 4.4 to 4.12 (inclusive) of the Loan Agreement and substituting the same with the following new clauses: 

  

	 	“4.4	Notification of market disruption. The Lender shall promptly notify the Borrowers if: 

  

	 	(a)	no rate is quoted on Reuters BBA Page LIBOR 01; or 

  

	 	(b)	for any reason the Lender is unable to obtain Dollars in the London Interbank Market in order to fund or continue to fund the Loan (or any part thereof) during any
Interest Period; or 

  

	 	(c)	LIBOR for that Interest Period does not adequately reflect the Lender’s cost of funding for that Interest Period. 

  

	 	4.5	Suspension of drawdown. If the Lender’s notice under Clause 4.4 is served before the Loan is made, the Lender’s obligation to make the Loan
shall be suspended while the circumstances referred to in the Lender’s notice continue. 

  

	 	4.6	Application of alternative rate of interest. Following the service of a notice by the Lender pursuant to Clause 4.4, but before the commencement of the
Interest Period to which that notice relates, the Lender shall have the right to: 

  

	 	(a)	reduce (in its sole discretion) the duration of the Interest Period selected by the Borrowers, unless a shorter period is not available in which case the Lender shall
have the right to amend (in its sole discretion) the duration of the Interest Period selected by the Borrowers; and/or 

  

	 	(b)	determine (in its sole discretion) the relevant rate of interest which shall apply to the Loan during that Interest Period and which shall be the aggregate of
(i) the applicable Margin and (ii) either: 

  

	 	(i)	the arithmetic mean of the rates per annum offered, on the relevant Quotation Date, for deposits in Dollars for a period equal to, or as near as possible to, the
relevant Interest Period which appear on the electronic pages (together, the “Applicable Screen Rates”) of (aa) KLIEMM (Carl Kliem GmbH), (bb) USDDEPO=ICAP (Icap Plc) and (cc) USDDEPO=TTLK (Tullet Prebon Plc) on the Reuters Money
News Services or 

  

	 	(ii)	if: 

  

	 	(A)	for any reason, there are no Applicable Screen Rates available on the relevant Quotation Date; or 

  

 8 

	 	(B)	the Applicable Screen Rates (or any of them) do not reflect the rates given in the interbank market on that Quotation Date, 

 the rate per annum, expressed as a percentage, which reflects the cost to the Lender of funding the Loan (or any part thereof) during that
Interest Period from whichever alternative sources are available to the Lender (and as it may select in its sole discretion) in Dollars or in any available currency, 
 (the “Alternative Rate”). 
 The Lender shall promptly notify the
Borrowers in writing of any Alternative Rate and any change to the Interest Period selected initially by the Borrower arising through the operation of this Clause 4.6. 
  

	 	4.7	Negotiation of alternative basis for funding. If the Borrowers do not agree with the Alternative Rate they shall notify the Lender in writing not later than 2
days after the date on which the Lender serves its notice pursuant to Clause 4.6. The Borrowers and the Lender shall use reasonable endeavours to agree, within 10 days after the date on which the Borrowers serve their notice of objection to the
Alternative Rate (the “Negotiation Period”), an alternative basis (including, but not limited to, an alternative interest period, funding in an alternative currency or currencies and an alternative margin which, for the avoidance of doubt,
shall reflect the Lender’s cost of funding) for the Lender to continue to fund the Loan during the Interest Period concerned. 

  

	 	4.8	Application of alternative rate of interest. Any Alternative Rate or an alternative basis for the Lender to continue to fund the Loan shall take effect in
accordance with the terms notified by the Lender pursuant to Clause 4.6 or, as the case may be, upon the terms agreed pursuant to Clause 4.7. The alternative basis shall continue to apply if the relevant circumstances are continuing at the end of
the applicable Interest Period (in the case of the Alternative Rate) or interest period so set by the Lender (in each other case) and for so long as the Lender and the Borrowers are in agreement as to the alternative basis for funding.

  

	 	4.9	Prepayment. If the Borrowers do not agree with the Interest Period and/or Alternative Rate set by the Lender pursuant to Clause 4.6 and an alternative basis for
funding the Loan (or any part thereof) is not agreed pursuant to Clause 4.7 within the Negotiation Period, the Borrowers shall prepay the Loan upon demand by the Lender together with all accrued interest thereon at the applicable rate plus the
applicable Margin. 

  

	 	4.10	Application of Margin. The Margin shall be reduced at the end of the Waiver Period to 1.5 per cent. per annum and shall at all times thereafter remain at
such rate Provided that at any relevant time: 

  

	 	(a)	no Event of Default or Potential Event of Default has occurred; and 

  

	 	(b)	the Borrowers are in compliance with the terms of Clause 14.1.”; 

  

	(p)	by deleting the number “1,” at the beginning of clause 5.2(a) of the Loan Agreement; 

  

	(q)	by deleting clause 7.7 of the Loan Agreement and substituting the same with the following: 

  

	 	“7.7	Mandatory prepayment. The Borrowers shall be obliged to prepay (1) the Total Amount if an Original Ship is sold or becomes a Total Loss during the Waiver
Period or (2) the Relevant Fraction of the Loan if an Original Ship is sold or becomes a Total Loss at any other time: 

  

	 	(a)	if an Original Ship is sold, on or before the date on which the sale is completed by delivery of such Ship to the buyer; or 

  

 9 

	 	(b)	if an Original Ship becomes a Total Loss, on the earlier of the date falling 180 days after the Total Loss Date and the date of receipt by the Lender of the proceeds of
insurance relating to such Total Loss, 

 and in this Clause 7.7: 
 “Total Amount” means, in relation to an Original Ship which has been sold or become a Total Loss during the Waiver Period,
an amount equal to the whole of the sale or insurance proceeds relating to the Total Loss of that Original Ship; 
 “Relevant Fraction” is a fraction whose: 
  

	 	(i)	numerator is the Market Value of the Original Ship being sold or which has become a Total Loss on the date on which such sale is completed or (as the case may be) the
date on which the Total Loss occurred; and 

  

	 	(ii)	denominator is the aggregate Market Value of all the Original Ships on the date on which the relevant Original Ship which is subject to a Mortgage is sold or becomes a
Total Loss. 

 If at any time during the Waiver Period an Original Ship is sold or becomes a Total Loss, the Total
Amount relative to that Original Ship is greater than the Advance relative to that Original Ship, the amount by which the Total Amount exceeds the relevant Advance shall be applied in prepayment of the Collateral Loan in accordance with clause 7 of
the Collateral Loan Agreement.”; 
  

	(r)	by adding: 

  

	 	(i)	the words “or either Additional Owner” after the word “Borrower” in the first line; and 

  

	 	(ii)	the words “or, as the case may be, such Additional Owner” after the word “Borrower” in the second line, 

 of clause 10.18 of the Loan Agreement; 
  

	(s)	by adding new clauses 10.19 and 10.20 in the Loan Agreement as follows: 

  

	 	“10.19	Information on Relevant Charter. The Borrowers shall, and shall procure that each Additional Owner shall, immediately inform the Lender if the charterer which
has entered into a Relevant Charter with that Borrower or, as the case may be, Additional Owner is in breach of its obligations under that Relevant Charter. 

  

	 	10.20	No amendment to Relevant Charter etc. No Borrower or, as the case may be, Additional Owner will agree to any amendment or supplement to, or waive or fail to
enforce the Relevant Charter to which it is or will become a party or any of its provisions.”; 

  

	(t)	by adding a new sub-paragraph (g) in clause 11.3 of the Loan Agreement: 

  

	 	“(g)	during the period 31 December 2008 to 31 December 2009, pay any dividends or make any other form of distribution (other than any dividends which are
distributed in the form of shares);”; 

  

 10 

	(u)	by adding the words “at any time (other than during the Waiver Period)” after the word “Borrowers” in the second line of clause 14.1 of the Loan
Agreement; 

  

	(v)	by deleting clause 14.3 of the Loan Agreement and substituting the same as follows: 

  

	 	“14.3	Valuation of Ships. The Market Value of a Ship or, as the case may be, a Fleet Vessel at any date is that shown by a valuation prepared:

  

	 	(a)	as at a date not more than 14 days previously; 

  

	 	(b)	by an independent sale and purchase shipbroker which the Lender has appointed and the Borrowers have approved (such approval not to be unreasonably withheld) for the
purpose; 

  

	 	(c)	with or without physical inspection of the relevant Ship (as the Lender may require); 

  

	 	(d)	on the basis of a sale for prompt delivery for cash on normal arm’s length commercial terms as between a willing seller and a willing buyer;

  

	 	(e)	free of any existing charter or other contract of employment (other than: 

  

	 	(i)	in the case of a Ship, any Relevant Charter to which that Ship may be subject and which has an unexpired duration of at least 11 months; and 

 

	 	(ii)	in the case of a Fleet Vessel, any charterparty to which that Fleet Vessel may be subject, which is made between the owner of that Fleet Vessel and a charterer
acceptable to the Lender and has an unexpired duration of at least 11 months, 

 in which case such Relevant
Charter or, as the case may be, charterparty, shall be taken into account in determining the Market Value of the relevant Ship Provided that, in the case of a Relevant Charter, the Lender is satisfied that the parties to such Relevant Charter are in
full compliance with the terms thereof); and 
  

	 	(f)	after deducting the estimated amount of the usual and reasonable expenses which would be incurred in connection with the sale. 

 In this Clause 14.3 “Relevant Charter” means, in relation to a Ship, any time charter party in respect of that Ship entered
into by the relevant Borrower or, as the case may be, Additional Owner and a charterer in all respects acceptable to the Lender, exceeding or which, by virtue of any optional extensions is capable of exceeding, 11 months in duration (as the same may
be amended or supplemented from time to time) on terms and substance in all respects acceptable to the Lender.”; 
  

	(w)	by deleting clause 14.6 and 14.7 of the Loan Agreement and substituting the same as follows: 

  

	 	“14.6	Frequency of valuation. The Borrowers acknowledge and agree that the Lender may commission a valuation of each Ship: 

  

	 	(a)	at the end of each 3-month period ending on 31 March, 30 June, 30 September and 31 December in each year; 

  

 11 

	 	(b)	if the Lender provides its consent pursuant to Clause 10.18 in respect of any amendment and/or variation of a Relevant Charter, immediately after such amendment and/or
variation has been effected, and 

  

	 	(c)	at any other time as the Lender may determine (including, but not limited to, if, in the opinion of the Lender, any charterer in respect of a Relevant Charter is not in
compliance with the terms of that Relevant Charter) in its absolutely discretion. 

  

	 	14.7	Provision of information. Each Borrower shall promptly provide the Lender and any independent sale and purchase shipbroker or expert acting under Clause 14.4
with any information which the Lender or the independent sale and purchase shipbroker or expert may request for the purposes of the valuation; and, if a Borrower fails to provide the information by the date specified in the request, the valuation
may be made on any basis and assumptions which the independent sale and purchase shipbroker or the Lender (or the expert appointed by it) considers prudent.”; 

  

	(x)	by adding the words “(other than during the period 31 December 2008 to 31 December 2009)” after the words “financial year” in the second
line of clause 11.11(b) of the Corporate Guarantee; 

  

	(y)	by adding the words “(other than any reorganisation, spin-off, redomiciliation or transfer of ownership of the Guarantor (i) in respect of any corporate
entity whose business primarily consists of activities in the oil and gas sector and is a subsidiary of the Guarantor and (ii) which will (A) include the transfer of any Security Interest currently existing in respect of or registered over
such corporate entity or any of its assets (other than any Security Interest created or registered in connection with any guarantee which has been executed by the Guarantor securing such entity’s obligations under an existing loan agreement to
which such entity is a borrower), (B) be made on terms consistent with the conditions applying in the international debt and equity markets on the date of such reorganisation, spin-off, redomiciliation or transfer, (C) not create any
Financial Indebtedness (other than any Financial Indebtedness which may occur in connection with any guarantee which has or will be executed by the Guarantor securing such entity’s obligations under a loan agreement to which such entity is or
will be a borrower) to, or any Security Interest over, the assets (or any of them) of, the Guarantor or the Group and (D) not cause any material adverse change in the financial position, state of affairs or prospects of the Guarantor or the
Group)” after the words “reorganisation” in the second line of clause 11.14 of the Corporate Guarantee; 

  

	(z)	by adding in the first line of clause 11.15 of the Corporate Guarantee after the word “that” the words “(other than during the Waiver Period subject to
no Event of Default being in existence at the relevant time)”; 

  

	(aa)	by construing all references therein to “this Agreement” where the context admits as being references to “this Agreement as the same is amended and
supplemented by this First Supplemental Agreement and as the same may from time to time be further supplemented and/or amended”; and 

  

	(bb)	by construing references to each of the Finance Documents as being references to each such document as it is from time to time supplemented and/or amended.

  

	5.2	Amendments to Finance Documents. With effect on and from the date of this First Supplemental Agreement each of the Finance Documents other than the Loan
Agreement shall be, and shall be deemed by this Agreement to have been, amended as follows: 

  

	(a)	the definition of, and references throughout each of the Finance Documents to, the Loan Agreement and any of the other Finance Documents shall be construed as if the
same referred to the Loan Agreement and those Finance Documents as amended and supplemented by this First Supplemental Agreement; and 

  

 12 

	(b)	by construing references throughout each of the Finance Documents to “this Agreement”, “this Deed”, “hereunder and other like expressions as if
the same referred to such Finance Documents as amended and supplemented by this First Supplemental Agreement. 

  

	5.3	Finance Documents to remain in full force and effect. The Finance Documents shall remain in full force and effect as amended and supplemented by:

  

	(a)	the amendments to the Finance Documents contained or referred to in Clauses 5.1 and 5.2; and 

  

	(b)	such further or consequential modifications as may be necessary to make the same consistent with, and to give full effect to, the terms of this First Supplemental
Agreement. 

  

	6	CONTINUANCE OF LOAN AGREEMENT AND FINANCE DOCUMENTS 

 Save for the alterations to the Loan Agreement made or to be made pursuant to this First Supplemental Agreement and such further modifications (if any) thereto as may be necessary to make the same
consistent with the terms of this First Supplemental Agreement, the Loan Agreement shall remain in full force and effect and the security constituted by the security Documents shall continue and remain valid and enforceable. 
  

	7	EXPENSES 

 The Borrowers
agree to pay to the Lender upon demand and from time to time all costs, charges and expenses (including legal fees) incurred by the Lender in connection with the preparation, negotiation, execution and (if required) registration or preservation of
rights under the enforcement or attempted enforcement thereof, this First Supplemental Agreement and the Finance Documents or otherwise in connection with the Loan or any part of thereof. Without prejudice to the foregoing, the Borrowers hereby
irrevocably authorise the Lender to debit any of the Accounts with the amount necessary to settle the Lender’s lawyers’ legal fees and disbursements. 
  

	8	NOTICES 

 The provisions
of Clause 27 (Notices) of the Loan Agreement shall apply to this First Supplemental Agreement as if the same were set out herein in full. 
  

	9	APPLICABLE LAW 

  

	9.1	This First Supplemental Agreement shall be governed by and construed in accordance with English law. 

  

	9.2	Subject to Clause 9.3, the courts of England shall have exclusive jurisdiction to settle any Disputes which may arise out of or in connection with this First
Supplemental Agreement. 

  

	9.3	Clause 9.2 is for the exclusive benefit of the Lender which reserves the right: 

  

	(a)	to commence proceedings in relation to any matter which arises out of or in connection with this First Supplemental Agreement in the courts of any country other than
England and which have or claim jurisdiction to that matter; and 

  

 13 

	(b)	to commence such proceedings in the courts of any such country or countries concurrently with or in addition to proceedings in England or without commencing proceedings
in England. 

 None of the Borrowers shall commence any proceedings in any country other than England in relation
to a matter which arises out of or in connection with this First Supplemental Agreement. 
  

	9.4	Each Borrower irrevocably appoints Ince Process Agents Ltd. for the time being presently of 5th Floor, International House, 1 St. Katharine’s Way, London
E1W lAY, England for the time being to act as its agent to receive and accept on its behalf any process or other document relating to any proceedings in the English courts which are connected with this First Supplemental Agreement.

  

	9.5	Nothing in this Clause 9 shall exclude or limit any right which the Lender may have (whether under the law of any country, an international convention or
otherwise) with regard to the bringing of proceedings, the service of process, the recognition or enforcement of a judgment or any similar or related matter in any jurisdiction. 

  

	9.6	In this Clause 9, “proceedings” means proceedings of any kind, including an application for a provisional or protective measure.

 IN WITNESS WHEREOF the parties hereto have caused this First Supplemental Agreement to be duly executed the day and year
first above written. 
  

					
	 BORROWERS
	 		 	/s/ Alexandros Mylonas
	  
 SIGNED
by
	 	)	 
	

	 	)	 
	 for and on behalf of
	 	)	 
	 BOONE STAR OWNERS INC.
	 	)	 
	  
 /s/ Pat Skala
 PAT SKALA
 WATSON,
FARLEY & WILLIAMS
 89 AKTI MIAOULI
 in the presence of: PIRAEUS 185 38 - GREECE
	 	)	 

  

					
	 SIGNED by
	 	)	 	/s/ Alexandros Mylonas
	
 

	 	)	 
	 for and on behalf of
	 	)	 
	 IOKASTI OWNING COMPANY LIMITED
	 	)	 
	  
 /s/ Pat Skala
 PAT SKALA
 WATSON,
FARLEY & WILLIAMS
 89 AKTI MIAOULI
 in the presence of: PIRAEUS 185 38 - GREECE
	 	)	 

  

					
	 LENDER
	 		 	/s/ Jason Dallas        /s/ Krikor Janikian
	  
 SIGNED
by
	 	)	 
	

	 	)	 
	 for and on behalf of
	 	)	 
	PIRAEUS BANK A.E.	 	)	 
	  
 /s/ Pat Skala
 PAT SKALA
 WATSON,
FARLEY & WILLIAMS
 89 AKTI MIAOULI
 in the presence of: PIRAEUS 185 38 - GREECE
	 	)	 

  

 14 

 COUNTERSIGNED this 30 July 2009 by Dryships Inc. which, by its execution hereof confirms and
acknowledges that it has read and understood the terms and conditions of the above First Supplemental Agreement, that it agrees in all respects to the same and that the Finance Documents to which each is a party shall remain in full force and effect
and shall continue to stand as security for the obligations of the Borrowers under the Loan Agreement. 
  

	
	/s/ Alexandros Mylonas
	 for and on behalf of

	DRYSHIPS INC.

 Dated 30 July 2009 
  

 15Waiver Letter, dated February 24, 2010 to a loan agreement

 Exhibit 4.23 

 

 

  

	To:	Iason Owing Company Limited 

 Trust Company Complex 
 Ajeltake Road 
 Ajeltake Island 
 Majuro 
 Marshall Islands MH96960 
 and 
 DryShips Inc. 
 Trust Company Complex 
 Ajeltake Road 
 Ajeltake Island 
 Majuro 
 Marshall Islands MH96960 
 24th February 2010 
 Dear Sirs 
 US$47,000,000 loan facility to Iason Owing Company Limited 
 We refer to the facility
agreement dated 16 November 2007 in connection with the above facility (the “Facility Agreement”). Words and expressions defined therein shall, unless the context otherwise requires or unless otherwise defined herein, have the
same meanings when used in this letter. 
 Following our discussions and subject to documentation satisfactory in all respects to ourselves, we
confirm that the Bank is prepared to agree to the following arrangements in connection with the Facility Agreement and the Security Documents: 
  

	1	 to waive the application of clause 5.3 of the Corporate Guarantee for a period of commencing on the date of this letter and ending on 1st January 2011 (the “Waiver Period”);

  

	2	to waive the application of clause 8.3.1 of the Facility Agreement (in relation to financial covenants) for the Waiver Period; 

  

	3	to waive the application of clause 7.1.10 of the Facility Agreement in respect solely of the representation and warranty concerning the ultimate beneficial ownership of
no less than 25% of the total issued voting share capital of the Corporate Guarantor, and, consequently, to waive the application of paragraph (b) of clause 10.1.28 of the Facility Agreement, in either case, until the final Repayment Date (the
“Maturity Date”); 

  

	4	to waive the application of clause 4.1.10 of the Corporate Guarantee in respect solely of the representation and warranty concerning the ultimate beneficial ownership
of no less than 25% of the total issued voting share capital of the Corporate Guarantor until the Maturity Date; and 

  

	5	to increase the Margin to three per cent (3.0%) per annum at all times during the period commencing on the date of this letter until the Bank notifies the Borrower
that it has determined in its absolute and unfettered discretion that the international financial and credit markets have improved. 

 This letter and any non contractual obligations in connection with this letter shall be governed by, and construed in accordance with, English law. 
 The terms of this letter shall not take effect unless and until the Bank is provided with full documentation (including without limitation, a supplemental agreement to the Facility Agreement and any
security documents required thereunder) on terms and conditions acceptable to the Bank in all respect and in form acceptable to the Bank in its sole discretion. 
  
 ATH-#2747395-v1 
 K.A. 8331/03.08 

 

 

  

	
	 /s/ Lambros Theodorou

	Signed by: Lambros Theodorou
	for and on behalf of
	EFG EUROBANK ERGASIAS S.A.
	
	 /s/ Marina Tzoutzouraki

	 Signed by: Marina Tzoutzouraki
 for and on behalf of

	EFG EUROBANK ERGASIAS S.A.
	
	We agree to the above.
	
	 /s/ Illegible

	Signed by:
	for and on behalf of
	IASON OWNING COMPANY LIMITED
	
	Dated:
	
	Acknowledged by:
	
	 /s/ Illegible

	for and on behalf of
	DRYSHIPS INC.
	Dated:

 ATH-#2747395-v1 
 K.A. 8331/03.08 
  

 2

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