Document:

exv10w21

Exhibit 10.21

RETENTION AGREEMENT

     This retention agreement, dated March 15, 2011 (this “Agreement”), is made by and between Wind
River Reinsurance Company, Ltd. (the “Employer”) and Troy W. Santora (the “Employee”). Capitalized
terms used but not concurrently defined herein shall have the meanings set forth in Sections 2 and
4 below.

1. Qualifying Period Employment. Subject to Section 2 below, the Employee agrees to remain
employed by the Employer for the Qualifying Period. Nothing in this Agreement alters or modifies
the Employee’s employment relationship with the Employer. This Agreement does not constitute an
agreement by the Employer to continue to employ the Employee during the entire, or any portion of
the, term of this Agreement.

2. Payment of Bonus. If eligible, the Employee will receive the Bonus on the first regular pay
date following the end of the Qualifying Period. Subject to the provisions of the following
paragraph, payment of the Bonus is contingent upon the Employee’s continued employment with the
Employer for the entire Qualifying Period. Payment of the Bonus is also subject to all applicable
payroll withholdings and deductions.

If the Employee’s employment with the Employer terminates before the end of the Qualifying Period
for any reason, including, without limitation, the death or disability of the Employee, other than
solely resulting from (a) the Employee’s resignation with Good Reason or (b) the termination of the
Employee’s employment without Cause, the Employee will not earn and will not be entitled to receive
the Bonus (or any portion thereof), and the Employer shall have no further obligations under this
Agreement. However, notwithstanding any other provision of this Agreement, if the Employee’s
employment terminates before the end of the Qualifying Period because the Employee resigns for Good
Reason or because the Employee’s employment has been terminated without Cause, the Employee will be
entitled to the payment of the Bonus on the first regular pay date following the end of the
Qualifying Period.

     Solely for purposes of determining the Employee’s Bonus eligibility under the terms of
this Agreement:

     (a) “Cause” shall mean each of the following; provided, however, that written
notice to the Employee of a condition constituting Cause has been delivered by the Employer to the
Employee and such condition remains uncured by the Employee for at least thirty (30) days after
receipt of such notice; provided further that any condition otherwise
constituting Cause hereunder that is described under clauses (i) through (iv) below shall only
constitute Cause to the extent it is reasonably expected to have a material adverse economic impact
on the Employer and Global Indemnity plc (the “Company”) and the Company’s controlled affiliates on
a consolidated basis: (i) the engaging by the Employee in any fraud, dishonesty or gross misconduct
adverse to the interests of the Employer or any of its subsidiaries or affiliates; (ii) the
material violation by the Employee of any restrictive covenants contained in the Employee’s
employment agreement (if any) with the Employer as of the date hereof or as it may be amended (the
“Employment Agreement”) or any other agreement with the Employer or any of its
subsidiaries or affiliates to which the Employee is a party; (iii) a breach by the Employee of any
material representation or warranty made in the Employee’s Employment Agreement or any other
agreement with the

 

 

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March 15, 2011

Page 2

Employer or any of its subsidiaries or affiliates to which the Employee is a party; (iv) the
determination by at least a majority of the members of the Board of Directors of the Company (the
“Board”) that the Employee has exhibited gross negligence in the performance of the Employee’s
duties; (v) receipt of a final written directive or order of any governmental or regulatory body or
authority having jurisdiction over the Employer requiring the Employee’s termination or removal; or
(vi) the Employee being convicted of a felony or other crime involving moral turpitude.

     (b) “Good Reason” shall mean:

          (i) the Employee’s termination of employment within thirty (30) days following a written
notice from the Employer that its principal executive offices are being relocated more than thirty
(30) miles from their current location or that the Employee’s principal place of employment is
transferred to an office location more than thirty (30) miles from the Employee’s then current
principal place of employment (unless in either case the effect of such relocation results in the
Employee’s principal place of employment being less than twenty (20) miles from the Employee’s
principal residence); 

          (ii) a reduction in the Employee’s annual base salary as in effect on the date hereof or as
the same may be increased from time to time; or

          (iii) the failure by the Employer or its subsidiaries or affiliates to continue to provide
the Employee with benefits substantially similar to those enjoyed by the Employee under any of the
benefit plans in which the Employee participates on the date hereof or as the same may be increased
from time to time.

3. Grantor Trust. Prior to the consummation of a Qualifying Transaction, the Employer shall
contribute an amount equal to the Bonus to an irrevocable “rabbi trust” (which shall be a grantor
trust within the meaning of Sections 671-678 of the United States Internal Revenue Code, as amended
(the “Code”)) for the Employee’s benefit.

4. Definitions. For purposes of this Agreement:

     (a) “Qualifying Transaction” means, whether effected directly or indirectly or in one or a
series of transactions: (i) any merger, amalgamation, scheme of arrangement, consolidation or other
business combination transaction pursuant to which the business, assets or divisions of the
Employer or any direct or indirect parent of the Employer is combined with that of a
third party not affiliated with the Employer or any of its subsidiaries or affiliates; or
(ii) any sale, transfer, exchange or other disposition of 50% or more of the issued common shares
of the Employer, any direct or indirect parent of the Employer, or all or substantially all of the
Employer’s assets or the assets of any direct or indirect parent of the Employer is transferred to
a third party not affiliated with the Employer or any of its subsidiaries or
affiliates, including, without limitation, by means of a purchase or exchange of capital stock or
assets, a merger, amalgamation, scheme of arrangement, consolidation, other business combination, a
tender or exchange or takeover offer, a leveraged buy-out, lease or license, the formation of a
partnership, joint or collaborative venture or similar arrangement or otherwise; provided,
however, that the Compensation Committee of the Board (the “Committee”) shall have
sole discretion with respect to the determination as to whether a Qualifying Transaction has
occurred.

 

 

Troy W. Santora

March 15, 2011

Page 3

     (b) “Bonus” means a cash bonus in the pre-tax amount of US$125,000; and

     (c) “Qualifying Period” means the twelve (12)-month period following the consummation of
a Qualifying Transaction.

5. Governing Law. This Agreement shall be governed by and construed in accordance with the
laws of Bermuda without regard to its conflict of laws provisions; provided,
however, that if the Employee’s Employment Agreement (if any) provides for a different
choice of law, then the provision in the Employee’s Employment Agreement shall govern this
Agreement.

6. Dispute Resolution; Venue. In the event that any disagreement or dispute whatsoever shall arise
between the parties concerning this Agreement, such disagreement or dispute shall be exclusively
submitted to the Judicial and Mediation Services Inc. (“JAMS”) for resolution in a confidential
private arbitration in accordance with the comprehensive rules and procedures of JAMS, including
the internal appeal process provided for in Rule 34 of the JAMS rules with respect to any initial
judgment rendered in an arbitration. Any such arbitration proceeding shall take place in
Philadelphia, Pennsylvania or another location agreed upon in writing by the parties, before a
single arbitrator (rather than a panel of arbitrators). Subject to applicable law, the parties
agree that the arbitrator shall have no authority to award any punitive or exemplary damages and
waive, to the full extent permitted by applicable law, any right to recover such damages in such
arbitration. Each party shall each bear their respective costs (including attorneys’ fees, and
there shall be no award of attorney’s fees) and shall split the fees and expenses of the
arbitrator. Judgment upon the final award rendered by such arbitrator, after giving effect to the
JAMS internal appeal process, may be entered in any court having jurisdiction thereof. If JAMS is
not in business or is no longer providing arbitration services, then the American Arbitration
Association shall be substituted for JAMS for the purposes of the foregoing provisions. Each party
agrees that, except to the extent otherwise required by applicable law, it shall maintain absolute
confidentiality in respect to any dispute between them under this Agreement.

7. Successors. This Agreement shall inure to the benefit of, and be binding upon, any successor or
assign of the Employer, specifically including, without limitation, the purchaser of the stock or
assets of the Employer or the survivor upon any other Qualifying Transaction. In the event of the
Employee’s death, this Agreement shall inure to the benefit of, and be binding upon, any executor,
personal representative or heirs of the Employee and, in the event of the Employee’s Disability,
this Agreement shall inure to the benefit of, and be binding upon, any personal representative or
guardian of the Employee.

8. Entire Agreement; Amendment; Termination; Waiver, etc. This Agreement contains all the
terms and conditions of the Employee’s Agreement. The Employee’s signature below acknowledges that
the Employee has not relied on any promises or representations concerning the subject matter hereof
not contained in this Agreement. No provision of this Agreement may be amended or modified,
in whole or in part, nor any waiver or consent given, unless approved in writing by the Employer
and the Employee in the case of an amendment or modification or by the party to be charged in the
case of a waiver or consent, which writing specifically refers to this Agreement and the provision
so amended or modified or for which such waiver or consent is given. This Agreement and all of the
rights, benefits and

 

 

Troy W. Santora

March 15, 2011

Page 4

obligations hereunder shall terminate and be of no further force and effect if a Qualifying
Transaction has not been effected or entered into within two years from the date of this Agreement;
provided that if a Qualifying Transaction is entered into within such two-year
period, and after the cessation of such two-year period such Qualifying Transaction is not
subsequently consummated, this Agreement and all of the rights, benefits and obligations hereunder
shall terminate and be of no further force and effect; provided further
that the Committee may terminate this Agreement prior to a Qualifying Transaction upon the
recommendation of the Chief Executive Officer of the Company.

9. Other Matters. The invalidity or unenforceability of any provision of this Agreement shall not
affect the validity or enforceability of any other provisions of this Agreement, which shall remain
in full force and effect. It is understood and agreed that no failure or delay by a party in
exercising any right, power or privilege hereunder shall operate as a waiver thereof, nor shall any
single or partial exercise thereof preclude any other or further exercise thereof or the exercise
of any right, power or privilege hereunder. This Agreement may be executed in counterparts, each
such counterpart shall be deemed an original and all such counterparts shall together constitute
one instrument. The headings contained in this Agreement are for reference purposes only and shall
not modify, expand, define or otherwise affect, in any way, the meaning or interpretation of the
terms and provisions of this Agreement.

10. Section 280G. Notwithstanding any other provisions of this Agreement, in the event that any
payment or benefit received or to be received by the Employee (including any payment or benefit
received or to be received in connection with a Qualifying Transaction or the termination of the
Employee’s employment, whether pursuant to the terms of this Agreement or any other plan,
arrangement or agreement) (all such payments and benefits being hereinafter referred to as the
“Total Payments”) would be subject (in whole or part), to any excise tax imposed under Section 4999
of the Code (the “Excise Tax”), then, after taking into account any reduction in the Total Payments
provided by reason of Section 280G of the Code in such other plan, arrangement or agreement, the
cash Total Payments that do not constitute deferred compensation within the meaning of Section 409A
of the Code (“Section 409A”) shall first be reduced, all other Total Payments that do not
constitute deferred compensation within the meaning of Section 409A shall be next reduced, and all
other Total Payments that do constitute deferred compensation within the meaning of Section 409A
shall thereafter be reduced (beginning with those payments last to be paid), to the extent
necessary so that no portion of the Total Payments is subject to the Excise Tax but only if (a) the
net amount of such Total Payments, as so reduced (and after subtracting the net amount of foreign,
federal, state and local income taxes on such reduced Total Payments and after taking into account
the phase out of itemized deductions and personal exemptions attributable to such reduced Total
Payments) is greater than or equal to (b) the net amount of such Total Payments without such
reduction (but after subtracting the net amount of foreign, federal, state and local income taxes
on such Total Payments and the amount of Excise Tax to which the Employee would be subject in
respect of such unreduced Total Payments and after taking into account the phase out of itemized
deductions and personal exemptions attributable to such unreduced Total Payments).

(The remainder of this page is intentionally left blank.

 

 

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

	 	 	 	 	 
	WIND RIVER REINSURANCE COMPANY, LTD.

 	 
	By:  	/s/ Larry A. Frakes
 	 
	 	Name:  	Larry A. Frakes 	 
	 	Title:  	Director 	 
	 
	EMPLOYEE

 	 
	/s/ Troy W. Santora
 	 
	Troy W. Santoraexv10w23

Exhibit 10.23

RETENTION AGREEMENT

     This retention agreement, dated March 15, 2011 (this “Agreement”), is made by and between
United America Indemnity, Ltd. (the “Employer”) and Thomas M. McGeehan (the “Employee”).
Capitalized terms used but not concurrently defined herein shall have the meanings set forth in
Sections 2 and 4 below.

1. Qualifying Period Employment. Subject to Section 2 below, the Employee agrees to remain
employed by the Employer for the Qualifying Period. Nothing in this Agreement alters or modifies
the Employee’s employment relationship with the Employer. This Agreement does not constitute an
agreement by the Employer to continue to employ the Employee during the entire, or any portion of
the, term of this Agreement.

2. Payment of Bonus. If eligible, the Employee will receive the Bonus on the first regular pay
date following the end of the Qualifying Period. Subject to the provisions of the following
paragraph, payment of the Bonus is contingent upon the Employee’s continued employment with the
Employer for the entire Qualifying Period. Payment of the Bonus is also subject to all applicable
payroll withholdings and deductions.

If the Employee’s employment with the Employer terminates before the end of the Qualifying Period
for any reason, including, without limitation, the death or disability of the Employee, other than
solely resulting from (a) the Employee’s resignation with Good Reason or (b) the termination of the
Employee’s employment without Cause, the Employee will not earn and will not be entitled to receive
the Bonus (or any portion thereof), and the Employer shall have no further obligations under this
Agreement. However, notwithstanding any other provision of this Agreement, if the Employee’s
employment terminates before the end of the Qualifying Period because the Employee resigns for Good
Reason or because the Employee’s employment has been terminated without Cause, the Employee will be
entitled to the payment of the Bonus on the first regular pay date following the end of the
Qualifying Period; provided, however, that the Bonus shall be reduced (but not
below zero) by any cash severance payments made to the Employee due to such termination of
employment pursuant to the terms of the Employee’s employment agreement (if any) with the
Employer as of the date hereof or as it may be amended (the “Employment Agreement”). If the Bonus
is paid hereunder, then following the payment of such Bonus, the Employee agrees that he or she
shall forfeit any right to receive cash severance payments under the Employment Agreement upon any
subsequent termination of employment.

     Solely for purposes of determining the Employee’s Bonus eligibility under the terms of
this Agreement:

     (a) “Cause” shall mean each of the following; provided, however, that written
notice to the Employee of a condition constituting Cause has been delivered by the Employer to the
Employee and such condition remains uncured by the Employee for at least thirty (30) days after
receipt of such notice; provided further that any condition otherwise
constituting Cause hereunder that is described under clauses (i) through (iv) below shall only
constitute Cause to the extent it is reasonably expected to have a material adverse economic impact
on the Employer and Global Indemnity plc (the “Company”) and the Company’s controlled affiliates on
a consolidated

 

 

Thomas M. McGeehan

March 15, 2011

Page 2

basis: (i) the engaging by the Employee in any fraud, dishonesty or gross misconduct adverse to the
interests of the Employer or any of its subsidiaries or affiliates; (ii) the material violation by
the Employee of any restrictive covenants contained in the Employment Agreement or any
other agreement with the Employer or any of its subsidiaries or affiliates to which the Employee is
a party; (iii) a breach by the Employee of any material representation or warranty made in the
Employee’s Employment Agreement or any other agreement with the Employer or any of its subsidiaries
or affiliates to which the Employee is a party; (iv) the determination by at least a majority of
the members of the Board of Directors of the Company (the “Board”) that the Employee has exhibited
gross negligence in the performance of the Employee’s duties; (v) receipt of a final written
directive or order of any governmental or regulatory body or authority having jurisdiction over the
Employer requiring the Employee’s termination or removal; or (vi) the Employee being convicted of a
felony or other crime involving moral turpitude.

     (b) “Good Reason” shall mean:

          (i) the Employee’s termination of employment within thirty (30) days following
a written notice from the Employer that its principal executive offices are being relocated more
than thirty (30) miles from their current location or that the Employee’s principal place of
employment is transferred to an office location more than thirty (30) miles from the Employee’s
then current principal place of employment (unless in either case the effect of such relocation
results in the Employee’s principal place of employment being less than twenty (20) miles from the
Employee’s principal residence); 

          (ii) a reduction in the Employee’s annual base salary as in effect on the date hereof or as
the same may be increased from time to time; or

          (iii) the failure by the Employer or its subsidiaries or affiliates to continue to provide
the Employee with benefits substantially similar to those enjoyed by the Employee under any of the
benefit plans in which the Employee participates on the date hereof or as the same may be increased
from time to time.

3. Grantor Trust. Prior to the consummation of a Qualifying Transaction, the Employer shall
contribute an amount equal to the Bonus to an irrevocable “rabbi trust” (which shall be a grantor
trust within the meaning of Sections 671-678 of the United States Internal Revenue Code, as amended
(the “Code”)) for the Employee’s benefit.

4. Definitions. For purposes of this Agreement:

     (a) “Qualifying Transaction” means, whether effected directly or indirectly or in one or a
series of transactions: (i) any merger, amalgamation, scheme of arrangement, consolidation or other
business combination transaction pursuant to which the business, assets or divisions of the
Employer or any direct or indirect parent of the Employer is combined with that of a
third party not affiliated with the Employer or any of its subsidiaries or affiliates; or
(ii) any sale, transfer, exchange or other disposition of 50% or more of the outstanding shares of
capital stock of the Employer, any direct or indirect parent of the Employer, or all or
substantially all of the Employer’s assets or the assets of any direct or indirect parent of the
Employer is transferred to a third party not affiliated with the Employer or any of its
subsidiaries or affiliates, including, without limitation, by means of a purchase or exchange of
capital stock or assets, a merger,

 

 

Thomas M. McGeehan

March 15, 2011

Page 3

amalgamation, scheme of arrangement, consolidation, other business combination, a tender or
exchange or takeover offer, a leveraged buy-out, lease or license, the formation of a partnership,
joint or collaborative venture or similar arrangement or otherwise; provided,
however, that the Compensation Committee of the Board (the “Committee”) shall have
sole discretion with respect to the determination as to whether a Qualifying Transaction has
occurred.

     (b) “Bonus” means a cash bonus in the pre-tax amount of US$450,000; and

     (c) “Qualifying Period” means the twelve (12)-month period following the consummation of
a Qualifying Transaction.

5. Governing Law. This Agreement shall be governed by and construed in accordance with the
laws of the Cayman Islands, without regard to its conflict of laws provisions; provided,
however, that if the Employee’s Employment Agreement (if any) provides for a different
choice of law, then the provision in the Employee’s Employment Agreement shall govern this
Agreement.

6. Dispute Resolution; Venue. In the event that any disagreement or dispute whatsoever shall arise
between the parties concerning this Agreement, such disagreement or dispute shall be exclusively
submitted to the Judicial and Mediation Services Inc. (“JAMS”) for resolution in a confidential
private arbitration in accordance with the comprehensive rules and procedures of JAMS, including
the internal appeal process provided for in Rule 34 of the JAMS rules with respect to any initial
judgment rendered in an arbitration. Any such arbitration proceeding shall take place in
Philadelphia, Pennsylvania or another location agreed upon in writing by the parties, before a
single arbitrator (rather than a panel of arbitrators). Subject to applicable law, the parties
agree that the arbitrator shall have no authority to award any punitive or exemplary damages and
waive, to the full extent permitted by applicable law, any right to recover such damages in such
arbitration. Each party shall each bear their respective costs (including attorneys’ fees, and
there shall be no award of attorney’s fees) and shall split the fees and expenses of the
arbitrator. Judgment upon the final award rendered by such arbitrator, after giving effect to the
JAMS internal appeal process, may be entered in any court having jurisdiction thereof. If JAMS is
not in business or is no longer providing arbitration services, then the American Arbitration
Association shall be substituted for JAMS for the purposes of the foregoing provisions. Each party
agrees that, except to the extent otherwise required by applicable law, it shall maintain absolute
confidentiality in respect to any dispute between them under this Agreement.

7. Successors. This Agreement shall inure to the benefit of, and be binding upon, any successor or
assign of the Employer, specifically including, without limitation, the purchaser of the stock or
assets of the Employer or the survivor upon any other Qualifying Transaction. In the event of the
Employee’s death, this Agreement shall inure to the benefit of, and be binding upon, any executor,
personal representative or heirs of the Employee and, in the event of the Employee’s Disability,
this Agreement shall inure to the benefit of, and be binding upon, any personal representative or
guardian of the Employee.

8. Entire Agreement; Amendment; Termination; Waiver, etc. This Agreement contains all the
terms and conditions of the Employee’s Agreement. The Employee’s

 

 

Thomas M. McGeehan

March 15, 2011

Page 4

signature below acknowledges that the Employee has not relied on any promises or representations
concerning the subject matter hereof not contained in this Agreement. No provision of this
Agreement may be amended or modified, in whole or in part, nor any waiver or consent given, unless
approved in writing by the Employer and the Employee in the case of an amendment or modification or
by the party to be charged in the case of a waiver or consent, which writing specifically refers to
this Agreement and the provision so amended or modified or for which such waiver or consent is
given. This Agreement and all of the rights, benefits and obligations hereunder shall terminate
and be of no further force and effect if a Qualifying Transaction has not been effected or entered
into within two years from the date of this Agreement; provided that if a
Qualifying Transaction is entered into within such two-year period, and after the cessation of such
two-year period such Qualifying Transaction is not subsequently consummated, this Agreement and all
of the rights, benefits and obligations hereunder shall terminate and be of no further force and
effect; provided further that the Committee may terminate this Agreement
prior to a Qualifying Transaction upon the recommendation of the Chief Executive Officer of the
Company.

9. Other Matters. The invalidity or unenforceability of any provision of this Agreement shall not
affect the validity or enforceability of any other provisions of this Agreement, which shall remain
in full force and effect. It is understood and agreed that no failure or delay by a party in
exercising any right, power or privilege hereunder shall operate as a waiver thereof, nor shall any
single or partial exercise thereof preclude any other or further exercise thereof or the exercise
of any right, power or privilege hereunder. This Agreement may be executed in counterparts, each
such counterpart shall be deemed an original and all such counterparts shall together constitute
one instrument. The headings contained in this Agreement are for reference purposes only and shall
not modify, expand, define or otherwise affect, in any way, the meaning or interpretation of the
terms and provisions of this Agreement.

10. Section 280G. Notwithstanding any other provisions of this Agreement, in the event that any
payment or benefit received or to be received by the Employee (including any payment or benefit
received or to be received in connection with a Qualifying Transaction or the termination of the
Employee’s employment, whether pursuant to the terms of this Agreement or any other plan,
arrangement or agreement) (all such payments and benefits being hereinafter referred to as the
“Total Payments”) would be subject (in whole or part), to any excise tax imposed under Section 4999
of the Code (the “Excise Tax”), then, after taking into account any reduction in the Total Payments
provided by reason of Section 280G of the Code in such other plan, arrangement or agreement, the
cash Total Payments that do not constitute deferred compensation within the meaning of Section 409A
of the Code (“Section 409A”) shall first be reduced, all other Total Payments that do not
constitute deferred compensation within the meaning of Section 409A shall be next reduced, and all
other Total Payments that do constitute deferred compensation within the meaning of Section 409A
shall thereafter be reduced (beginning with those payments last to be paid), to the extent
necessary so that no portion of the Total Payments is subject to the Excise Tax but only if (a) the
net amount of such Total Payments, as so reduced (and after subtracting the net amount of foreign,
federal, state and local income taxes on such reduced Total Payments and after taking into account
the phase out of itemized deductions and personal exemptions attributable to such reduced Total
Payments) is greater than or equal to (b) the net amount of such Total Payments without such
reduction (but after subtracting the net amount of foreign, federal, state and local income taxes
on such Total Payments and the amount of Excise Tax to which the

 

 

Thomas M. McGeehan

March 15, 2011

Page 5

Employee would be subject in respect of such unreduced Total Payments and after taking into account
the phase out of itemized deductions and personal exemptions attributable to such unreduced Total
Payments).

(The remainder of this page is intentionally left blank.

 

 

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

	 	 	 	 	 

	UNITED AMERICA INDEMNITY, LTD.	 	 
	 
	 	 	 	 
	By:

	 	/s/ Larry A. Frakes
 

Name: Larry A. Frakes
	 	 
	 

	 	Title: Director	 	 
	 
	 	 	 	 
	EMPLOYEE	 	 
	 
	 	 	 	 
	/s/ Thomas M. McGeehan	 	 
	 	 	 
	Thomas M. McGeehan

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