Document:

Exhibit 10.21

OneBeacon
Insurance

2006
Management Incentive Plan

Performance Goals

	
  1.

  	
  Achieve economic combined ratio of 96% or better

  
	
   

  	
   

  
	
  2.

  	
  Be opportunistic on new business / keep our best
  renewal business / price it right

  
	
   

  	
   

  
	
  3.

  	
  Conform to changing demands to maintain Claims Loss
  Triangle at 25.8%

  
	
   

  	
   

  
	
  4.

  	
  Integrate reciprocals and other new business
  opportunities into OneBeacon including: Lawyers Liability, Community Banking,
  Middle Market MGA initiative, AIE conversion and HGIE expansion

  
	
   

  	
   

  
	
  5.

  	
  Continue to manage aggregate catastrophic exposures
  for wind, earthquake, flood, and terrorism

  
	
   

  	
   

  
	
  6.

  	
  Complete transactions that build long term economic
  value for OneBeacon

  

 

ONEBEACON’S
2006 MANAGEMENT INCENTIVE PLAN

Purpose

The Management Incentive Plan (MIP) is an integral
part of the total compensation program for senior Home Office and Field Office
management. Its primary purpose is to focus attention on 2006 profitability
goals and to reward eligible participants for the achievement of those goals.

 

Eligibility

The Plan is limited to home office and field office
senior staff who have a significant impact on OneBeacon’s operating results.

 

Target Awards

Target awards for all participants, expressed as a
percent of salary, will be set and approved by the Board of OneBeacon Insurance
Group LLC.

 

Performance Measure

The Corporate MIP pool will be established based upon
achievement of a 96% economic combined ratio for total OneBeacon operations,
computed on an adjusted calendar year basis. This measurement will be used to
establish a pool of money to be allocated to business units and Home Office
departments. At a corporate combined ratio of 96%, the plan will fund an amount
equal the sum of each of the plan’s participant’s potential award at their
target bonus percentage. The OneBeacon Board of Managers may adjust the size of
the pool based on under or over achievement of the company’s target combined
ratio and other objectives that will be communicated during first quarter,
2006.

 

Individual Awards

Each business unit will be judged against a number of
metrics including, where appropriate, a combined ratio result target, agreed to
in advance with the President of OneBeacon. Generally these targets will relate
to the aggregate financial plan rolled up by branch and line of business, but
the targets will not always match the plan (in many cases, the targets are more
aggressive). If the combined ratio target is achieved, in conjunction with
other business metrics, the business may be awarded 100% of its indicated share
of the corporate pool. Businesses failing to reach target may or may not, at
the discretion of the President, receive a reduced, partial allocation of the
pool. Businesses exceeding objectives may receive greater than 100% of indicated
allocation. In no event will the sum of the performance adjusted business unit
pools be greater than the performance adjusted company pool.

 

Within each business, it will be the prerogative of
the business leader, with guidance from and after consultation with the company
President, to further allocate the business’s pool amount to the constituent
branches, lines of business and individuals, based upon performance against
targets established within the business. It will be the responsibility of the
business leader, with guidance from the President, to establish appropriate
targets for the constituent branches, lines of business, departments, or
individuals at the outset of the MIP year.

 

 

For
corporate or administrative functions that support all or multiple regions or
businesses, MIP individuals will receive allocations from the corporate pool
based upon attainment of their department and individual MIP goals for 2006.

Review and evaluation of performance will be conducted
during the first quarter following the end of the plan year. Incentive payments
will be paid once plan year results have been produced and evaluated.

The
salary used to determine the amount of the individual awards will be that in
effect at the end of the plan year (12/31/06).

Plan Participation for New Hires

Employees
hired during the plan year are eligible to participate in the MIP. Awards will
be pro-rated specifically based on date of hire.

Special Circumstances

The OneBeacon
Board of Managers may, in its sole discretion, also recognize extraordinary
conditions or circumstances in determining payment levels.

In the
event of termination prior to the payment of awards, no incentive payments will
be made. However, in the event of retirement or reduction in force after the
end of the plan year, but before payment is made, incentive payments may be
made if approved by the senior business leader. These exceptions will be made
on a case by case basis. In the event of death or disability, the plan
participant or beneficiary may be considered for a partial award payment.

Effect on Benefit Plans

Amounts
paid under the terms of this plan will not be counted for purposes of
determining compensation under any employee benefit plan sponsored by
OneBeacon.

Plan Continuation

Notwithstanding any of the aforementioned, the plan
may be amended or terminated, in whole or in part, at any time, by the Board of
Managers.

 

 2Exhibit 10.23

OneBeacon Phantom WTM Share Plan

June 1, 2006

1.              
THE PLAN

This
is the OneBeacon Phantom WTM Share Plan (the “ Plan ”) of
OneBeacon Insurance Group LLC (the “ Company ”).

2.              
ADMINISTRATION

The
Plan shall be administered by the board of managers of the Company or a
committee of managers of the Company (references to the “ Board ” herein shall refer to the board of managers of the Company or
such committee, if any).

The
Board shall have exclusive authority to select the employees to be granted
awards under the Plan (“ Awards ”), to
determine the type, size and terms of the Awards and to prescribe the form of
the instruments embodying Awards. The Board may specify the terms and
conditions applicable to such Awards in an Award agreement, but at minimum will
provide a written grant letter or certificate setting forth the terms of the
Award. The Board shall be authorized to interpret the Plan and the Awards
granted under the Plan, to establish, amend and rescind any rules and regulations
relating to the Plan and to make any other determinations which it believes
necessary or advisable for the administration of the Plan. The Board may
correct any defect or supply any omission or reconcile any inconsistency in the
Plan or in any Award in the manner and to the extent the Board deems desirable
to carry it into effect. Any decision of the Board in the administration of the
Plan, as described herein, shall be final and conclusive. The Board may act
only by a majority of its members in office, except that the members thereof
may authorize any one or more of their number or any officer of the Company to
execute and deliver documents on behalf of the Board. No member of the Company
shall be liable for anything done or omitted to be done by him or by any other
member of the Board in connection with the Plan, except for his own willful
misconduct or as expressly provided by statute.

3.              
AWARDS

(a)          Eligible Participants . Any employee of the
Company or any of its subsidiaries is eligible to receive an Award hereunder.
The Board shall select which eligible employees shall be granted Awards
hereunder. No employee shall have a right to receive an Award hereunder and the
grant of an Award to an employee in one period shall not obligate the Board to
continue to grant Awards to such employee in subsequent periods.

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(b)             Type of Award. All Awards under this Plan
shall be “ Phantom Share Awards ”.

4.              
PHANTOM SHARES

The
grant of a Phantom Share Award to a participant will entitle the participant to
receive, without payment to the Company, all or part of a specified amount (the
“ Actual Value ”) determined by the Board, if the
terms and conditions specified herein and in the Award are satisfied. Payment
in respect of an Award shall be made as provided in Section 4(h). Each Award
shall be subject to the following terms and conditions:

(a)          Each Phantom
Share Award shall consist of a target number of Phantom Shares as determined by
the Board. Phantom Share Awards may be granted in different classes or series
having different terms and conditions.

(b)          The Actual Value
of a Phantom Share Award shall be the product of (i) the target number of
Phantom Shares subject to the Phantom Share Award, (ii) the Performance
Percentage (as defined below) applicable to the Phantom Share Award and (iii)
the market value of a share (a “ Share ”) of Common Stock of White Mountains
Insurance Group, Ltd. (“ White Mountains ”), par value of $1.00 per share, on
the date the Award is paid or becomes payable to the participant. The “ Performance Percentage ” applicable to a Phantom Share Award
shall be a percentage of no less than 0% and no more than 200%, which
percentage shall be determined by the Board based on the extent to which the
Performance Objectives (as defined below) established for such Award are
achieved during the Award Period. The method for determining the applicable
Performance Percentage shall also be established by the Board.

(c)          At the time each
Phantom Share Award is granted to a participant, the Board shall establish
performance objectives (“ Performance
Objectives ”) to be attained within the Award Period (as defined
below) as the means of determining the Performance Percentage applicable to such
Award.

(d)          The award period
(the “ Award Period ”) in respect
of any grant of a Phantom Share Award shall be such period as the Board shall
determine. An Award Period may contain a number of performance periods; each
performance period shall commence on or after the first day of the Award Period
and shall end no later than the last day of the Award Period. If the Board does
not specify in a Phantom Share Award agreement or elsewhere the performance
periods contained in an Award Period, each 12-month period beginning with the
first day of such Award Period shall be deemed to be a performance period.

 

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(e)          Except as
otherwise determined by the Board, Phantom Shares shall be canceled without any
payment to the participant if the participant’s continuous employment with the
Company or any of its subsidiaries shall terminate for any reason prior to the
end of the Award Period, except by reason of a period of Related Employment as
defined in Section 6, and except as otherwise specified in this Section 4(e) or
in Section 4(f). Notwithstanding the foregoing and without regard to Section
4(g), if an employee participant shall:

(i)           while in
such employment, die or become disabled as described in Section 5 prior to the
end of an Award Period, the Phantom Shares for such Award Period shall be
immediately canceled and the participant, or the participant’s legal
representative, as the case may be, shall receive as soon as administratively
feasible a payment in respect of such canceled Phantom Shares equal to the
product of (A) (i) the target number of Phantom Shares for such Award
multiplied by (ii) a fraction, the numerator of which is equal to the number of
full or partial months within the Award Period during which employee was
continuously employed by the Company or its subsidiaries (including, for this
purpose, the month in which the death or disability occurs), and the
denominator of which is equal to the total number of months within such Award
Period, multiplied by (B) the market value of a Share on the last day of
the performance period in which the death or disability occurred, multiplied
by (C) the Performance Percentage determined by the Board to have been
achieved through the end of the performance period in which the death or
disability occurred (but which in no event shall be less than 50%); or

(ii)          while in such
employment, retire on or after the participant’s 60 th birthday by mutual agreement with the Company
prior to the end of the Award Period, the Phantom Shares shall be immediately
canceled and the participant shall receive as soon as administratively feasible
a payment in respect of such canceled Phantom Shares equal to the product of
(A) (i) the target number of Phantom Shares for such Award multiplied by (ii) a
fraction, the numerator of which is equal to the number of full or partial
months within the Award Period during which employee was continuously employed
by the Company or its subsidiaries (including, for this purpose, the month in
which the mutually agreed retirement occurs), and the denominator of which is
equal to the total number of months within such Award Period, multiplied by
(B) the market value of a Share on the last day of the performance period in
which the retirement occurred, multiplied by (C) the Performance
Percentage determined by the Board to have been achieved through the end of the
performance period in which the retirement occurred.

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(f)            
If after a Change in Control as defined in Section 7(a):

(i)           
there is a Termination Without Cause, as defined in Section 8, of the
employment of a participant;

(ii)          
there is a Constructive Termination, as defined in Section 9, of the employment
of a participant; or

(iii)           there
occurs an Adverse Change in the Plan, as defined in Section 10, in respect of a
participant

  (any such occurrence under the above clauses (i), (ii) or (iii), a “
Trigger Event ”), then:

with
respect to Phantom Share Awards that were granted prior to the Change in
Control for which the Award Period was still outstanding on the date of the
Trigger Event (each, an “ Applicable Award ”),
each such Applicable Award shall be immediately canceled and, in respect of
each Applicable Award, such participant shall be entitled to receive a cash
payment equal to the product of (A) (i) the target number of Phantom Shares for
such Applicable Award multiplied by (ii) a fraction, the numerator of which is
equal to the number of full months within the Award Period during which the
participant was continuously employed by the Company or its subsidiaries, and
the denominator of which is equal to the total number of months within such
Award Period, multiplied by (B) the greater of (i) the market value of a
Share immediately prior to the Change in Control and (ii) the market value of a
Share on the date the applicable Trigger Event occurs, multiplied by (C)
the greater of (i) the Performance Percentage that would have been calculated
immediately prior to the Trigger Event and (ii) a Performance Percentage equal
to 100%. If following a Change in Control, a Participant’s employment remains
continuous through the end of an Award Period, then the Participant shall be
paid with respect to such Awards for which the participant would have been paid
had there not been a Change in Control and the Actual Value shall be determined
in accordance with Section 4(g) below.

(g)          Except as
otherwise provided in Section 4(f), as soon as practicable after the end of the
Award Period or such earlier date as the Board in its sole discretion may
designate, the Board shall (i) determine, based on the extent to which the
applicable Performance Objectives have been achieved, the Performance
Percentage applicable to an Award of Phantom Shares, (ii) calculate the Actual
Value of the Phantom Share Award and (iii) cause the Company to cause an amount
equal to the Actual Value of the Phantom Shares earned by the participant to be
paid to the participant or the participant’s beneficiary.

(h)          Unless payment
is deferred in accordance with an election made by the participant in
accordance with procedures adopted by the Company,

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payment
of any amount in respect of the Phantom Shares shall be made by the Company no
later than 2 1/2 months after the end of the Company’s fiscal year in which such
Phantom Shares are earned and shall be made in cash.

5.              
DISABILITY

For
the purposes of this Plan, a participant shall be deemed to be disabled if the
participant has been approved for the payment of benefits under the long-term
disability plan of the Company or its subsidiary.

6.              
RELATED EMPLOYMENT

For
the purposes of this Plan, Related Employment shall mean the employment of a
participant by an employer which is neither the Company nor a subsidiary
provided: (i) such employment is undertaken by the participant and continued at
the request of the Company or a subsidiary; (ii) immediately prior to
undertaking such employment, the participant was an officer or employee of the
Company or a subsidiary, or was engaged in Related Employment as herein
defined; and (iii) such employment is recognized by the Board, in its sole
discretion, as Related Employment for the purposes of this Section 6. The death
or disability of a participant during a period of Related Employment as herein
defined shall be treated, for purposes of this Plan, as if the death or onset
of disability had occurred while the participant was an officer or employee of
the Company.

7.              
CHANGE IN CONTROL

(a)            For
purposes of this Plan, a “ Change in Control ”
within the meaning of this Plan shall occur if:

(i)           Any person
or group (within the meaning of Section 13(d) and 14(d)(2) of the Exchange
Act), other than John J. Byrne, Berkshire Hathaway, Inc. or one of its wholly
owned subsidiaries, or an underwriter temporarily holding Shares in connection
with a public issuance thereof or an employee benefit plan of White Mountains
or its affiliates, becomes the beneficial owner (within the meaning of Rule
13d-3 under the Exchange Act) of thirty-five percent (35%) or more of the then
outstanding White Mountains Shares;

(ii)          the Continuing
Directors, as defined in Section 7(b), cease for any reason to constitute a
majority of the board of directors of White Mountains; or

(iii)         the business of the Company or the subsidiary
for which the participant’s services are principally performed is disposed of
by White Mountains or the Company pursuant to a sale or other

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disposition
of all or substantially all of the business or business-related assets of the
Company or such subsidiary (including the disposition of the stock of the
Company or a subsidiary of the Company).

(b)          For the purposes
of this Plan, “ Continuing Director ”
shall mean a member of the board of directors of White Mountains (the “ White Mountains Board ”) (i) who is not an
employee of White Mountains or its subsidiaries or of a holder of, or an
employee or an affiliate of an entity or group that holds, thirty-five percent
(35%) or more of White Mountains’ Shares and (ii) who either was a member of
the White Mountains Board on March 31, 2006, or who subsequently became a
director of White Mountains and whose election, or nomination for election, by
White Mountains’ shareholders was approved by a vote of a majority of the
Continuing Directors then on the White Mountains Board (which term, for
purposes of this definition, shall mean the whole board and not any committee
thereof).

(c)          In the event of
a Change in Control, the Board as constituted immediately prior to the Change
in Control shall determine the manner in which “market value” of Shares will be
determined following the Change in Control.

(d)          In the event of
a Change in Control of a type described in Section 7(a)(iii), the Board may
determine, in its sole discretion, to amend the definition of “Shares” under
any or all then outstanding Phantom Share Awards in order that “Shares” would
instead refer to the shares of the acquiring company. In any such case, the
Board would make such adjustments as it deems appropriate in its sole
discretion to affected Phantom Share Awards so that the Award immediately after
the alteration shall be of comparable value to the Award immediately prior
thereto. Such an amendment by the Board will not under any circumstances
constitute an Adverse Change to the Plan or a basis for Constructive
Termination.

8.            
TERMINATION WITHOUT CAUSE

For
purposes of this Plan, “ Termination Without
Cause ” shall mean a termination of the participant’s employment
with the Company or a subsidiary by the Company or the subsidiary other than
(i) for death or total permanent disability or (ii) for Cause. “ Cause ” shall mean (a) an act or omission
by the participant that constitutes a felony or any crime involving moral
turpitude; or (b) willful gross negligence or willful gross misconduct by the
participant in connection with his employment by the Company or by a subsidiary
which causes, or is likely to cause, material loss or damage to the Company.
Notwithstanding anything herein to the contrary, if the participant’s
employment with the Company or one of its subsidiaries shall terminate due to a
Change in Control as described in

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Subsection
7(a)(iii), where the purchaser, as described in such subsection, formally
assumes the Company’s obligations under this Plan or places the participant in
a similar or like plan with no diminution of the value of the awards, such
termination shall not be deemed to be a “Termination Without Cause.”

9.              
CONSTRUCTIVE TERMINATION

“ Constructive Termination ” shall mean a
termination of employment with the Company or a subsidiary at the initiative of
the participant that the participant declares by prior written notice delivered
to the Secretary of the Company to be a Constructive Termination by the Company
or a subsidiary and which follows (a) a material decrease in the participant’s
salary or (b) a material diminution in the authority, duties or
responsibilities of the participant’s position as a result of which the
participant determines in good faith that the he/she cannot continue to carry
out his/her job in substantially the same manner as it was intended to be
carried out immediately before such diminution. Notwithstanding anything herein
to the contrary, Constructive Termination shall not occur within the meaning of
this Section 9 until and unless 30 days have elapsed from the date the Company
receives such written notice from the participant and, during that period, the
Company fails to cure, or cause to be cured, the circumstance serving as the
basis on which the declaration of Constructive Termination is given.

10.           
ADVERSE CHANGE IN THE PLAN

An “ Adverse Change in the Plan ” shall mean

(a)          termination
of the Plan;

(b)          amendment of the
Plan pursuant to Section 14 that materially diminishes the value of Awards that
may be granted under the Plan, either to individual participants or in the
aggregate, unless there is substituted concurrently authority to grant
long-term incentive awards of comparable value to individual participants in
the Plan or in the aggregate, as the case may be, or

(c)          in respect of
any holder of an Award a material diminution in the participant’s rights held
under such Award (except as may occur under the terms of the Award as originally
granted) unless there is substituted concurrently a long-term incentive award
with a value at least comparable to the loss in value attributable to such
diminution in rights

In no
event shall any amendment of the Plan or any Award contemplated by Section 7(d)
or Section 11 be deemed an Adverse Change in the Plan.

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11.           
DILUTION AND OTHER ADJUSTMENTS

In the
event of any change in the outstanding Shares of White Mountains by reason of
any stock split, stock or extraordinary cash dividend, recapitalization,
merger, consolidation, reorganization, combination or exchange of Shares or
other similar event, and if the Board shall determine, in its sole discretion,
that such change equitably requires an adjustment in the number or kind of
Phantom Shares that may be issued under the Plan pursuant to Section 4, in the
target number of Phantom Shares which have been awarded to any participant, or
in any measure of performance, then such adjustment shall be made by the Board
and shall be conclusive and binding for all purposes of the Plan.

In the
event that the Company or one of its subsidiaries were to publicly offer shares
for which a regular and liquid public market existed (the “ Liquid Shares ”), the Board may determine,
in its sole discretion, to amend the definition of “Shares” under the Plan, or
any or all then outstanding Phantom Share Awards, in order that “Shares” would
instead refer to the Liquid Shares. In any such case, the Board would make such
adjustments as it deems necessary and appropriate in its sole discretion to
affected Phantom Share Awards so that the Award immediately following the
alteration shall be of comparable value to the Award immediately prior thereto.
Such an amendment by the Board will not under any circumstances constitute an
Adverse Change to the Plan or a basis for Constructive Termination.

12.           
DESIGNATION OF BENEFICIARY BY PARTICIPANT

A
participant may name a beneficiary to receive any payment to which the
participant may be entitled in respect of Phantom Shares under the Plan in the
event of his/her death, on a form to be provided by the Board. A participant
may change his/her beneficiary from time to time in the same manner. If no
designated beneficiary is living on the date on which any amount becomes
payable to a participant’s executors or administrators, the term “beneficiary”
as used in the Plan shall include such person or persons.

13.          
MISCELLANEOUS PROVISIONS

(a)          No employee or
other person shall have any claim or right to be granted an Award under the
Plan. Neither the Plan nor any action taken hereunder shall be construed as
giving an employee any right to be retained in the employ of the Company or any
subsidiary.

(b)          A participant’s
rights and interest under the Plan may not be assigned or transferred in whole
or in part either directly or by operation of law or otherwise (except in the
event of a participant’s death), including but not

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limited
to, execution, levy, garnishment, attachment, pledge, bankruptcy or in any
other manner and no such right or interest of any participant in the Plan shall
be subject to any obligation or liability or such participant.

(c)          The Company and
its subsidiaries shall have the right to deduct from any payment made under the
Plan any federal, state or local income or other taxes required by law to be
withheld with respect to such payment.

(d)          The expenses of
the Plan shall be borne by the Company. However, if an Award is made to an
employee of a subsidiary, if such Award results in payment of cash to the
participant, such subsidiary shall pay to the Company an amount equal to such
cash payment.

(e)          The Plan shall
be unfunded. The Company shall not be required to establish any special or
separate fund or to make any other segregation of assets to assure the payment
of any Award under the Plan.

(f)           By accepting
any Award or other benefit under the Plan, each participant and each person
claiming under or through him shall be conclusively deemed to have indicated
his/her acceptance and ratification of, and consent to, any action taken under
the Plan by the Company, the Board or any committee designated by the Board.

(g)          The Plan shall be
governed by and construed in accordance with the laws of New York applicable to
contracts made and to be performed in the State of New York.

(h)          It is the intent of
the Board that the Plan will govern the outstanding Phantom Share awards that
were previously made to OneBeacon employees in 2004, 2005 and 2006.

14.           
AMENDMENT OR TERMINATION

The
Plan may be amended, altered, discontinued or terminated at any time and from
time to time by resolution of the Board but no amendment, alteration,
discontinuation or termination shall be made which would impair any of the
accrued rights or obligations under any Award theretofore granted to a
participant without such Participant’s consent; provided, however, that Board
may amend the Plan in such manner as it deems necessary to permit the granting
of Awards meeting the requirements of the Code or other applicable laws.

 9

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