AMENDED AND RESTATED EMPLOYMENT AGREEMENT

2.             Extent of Employment

(a)           During the Term of Employment, the Executive shall perform his obligations hereunder faithfully and to the best of his ability at the principal executive offices of the Company, under the direction of the Board of Directors and/or Chairman of the Board, President and Chief Executive Officer of the Company, and shall abide by the rules, customs and usages from time to time established by the Companies.

(b)           During the Term of Employment, the Executive shall devote all of his business time, energy and skill as may be reasonably necessary for the performance of his duties, responsibilities and obligations hereunder (except for vacation periods and reasonable periods of illness or other incapacity), consistent with past practices and norms in similar positions.

(c)           Nothing contained herein shall require Executive to follow any directive or to perform any act which would violate any laws, ordinances, regulations or rules of any governmental, regulatory or administrative body, agent or authority, any court or judicial authority, or any public, private or industry regulatory authority (collectively, the “ Regulations ”).  Executive shall act in good faith in accordance with all Regulations.

3.             Term of Employment; Termination

(a)           The “ Term of Employment ” shall commence on October 1, 2005 and shall continue until December 31, 2008 (the “ Initial Term ”); provided , that, (i) such term shall continue for the twelve month period following such Initial Term, and for each twelve month period thereafter (each, an “ Additional Term ”), unless at least 180 days prior to the scheduled expiration date of the Initial Term or any Additional Term, either the Executive or the Company notifies the other of its decision not to continue such term and (ii) should the Executive’s employment by the Company be earlier terminated pursuant to Section 3(b)  or by the Executive pursuant to Section 3(c) , the Term of Employment shall end on the date of such earlier termination.

(b)           Subject to the payments contemplated by Sections 3(f)  through 3(i) , the Term of Employment may be terminated at any time by the Company:

(i)            upon the death of Executive;

(ii)           in the event that because of physical or mental disability Executive is unable to perform, and does not perform, in the view of the Company and as certified in writing by a competent medical physician, his duties hereunder for a continuous period of three consecutive months or any sixty working days out of any consecutive six month period;

(iii)          for Cause (as defined in Section 3(d) ) or Material Breach (as defined in Section 3(e) );

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(iv)          upon the continuous poor or unacceptable performance of the Executive’s duties to the Companies (other than due to a physical or mental disability), which has remained uncured for a period of 90 days after delivery of notice by the Company to the Executive of such dissatisfaction with Executive’s performance, which notice shall describe in reasonable detail the areas of dissatisfaction; or

(v)           for any other reason or no reason, it being understood that no reason is required.

Executive acknowledges that no representations or promises have been made concerning the grounds for termination or the future operation of the Companies’ business, and that nothing contained herein or otherwise stated by or on behalf of any of the Companies modifies or amends the right of the Company to terminate Executive at any time, with or without Material Breach or Cause.  Termination shall become effective upon the delivery by the Company to the Executive of notice specifying such termination and the reasons therefor (i.e., Section 3 (b)(i)-(v) ), subject to the requirements for advance notice and an opportunity to cure provided in this Agreement, if and to the extent applicable.  Notwithstanding anything to the contrary in this Agreement, for purposes of this Agreement, any reference to “termination,” as it relates to a termination of the Executive’s employment, shall refer to a termination of employment which constitutes a “separation from service” within the meaning of Section 409A of the Internal Revenue Code of 1986, as amended and the regulations promulgated thereunder (“ Section 409A ”).

(c)           Subject to the payments contemplated by Section 3(f)  and 3(i) , the Term of Employment may be terminated at any time by the Executive:

(i)            upon the death of Executive;

(ii)           as a result of a material reduction in Executive’s authority, perquisites, position or responsibilities (other than such a reduction in perquisites which affects all of the Company’s senior executives on a substantially equal or proportionate basis), the relocation of the Company’s primary place of business or the relocation of Executive by any of the Companies to another office more than 75 miles from Boston, Massachusetts, or the Company’s willful, material violation of its obligations under this Agreement, in each case, after 60 days’ prior written notice to the Company and its Board of Directors and the Company’s failure thereafter to cure such reduction or violation; or

(iii)          as a result of the Company’s willful and material violation of this Agreement, the 2002 Management Omnibus Incentive Plan (the “ Incentive Plan ”), or any agreement between Executive and any of the Companies pertaining to awards made pursuant to the Incentive Plan or the Executive Incentive Compensation Plan, in each case as such agreements or plans may be amended from time to time.

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(d)                                  For the purposes of this Section 3 , “ Cause ” shall mean any of the following:

(i)            Executive’s commission or conviction of any crime or criminal offense involving monies or other property or any felony;

(ii)           Executive’s commission or conviction of fraud or embezzlement;

(iii)          Executive’s material and knowing violation of any obligations imposed upon Executive, personally, as opposed to upon the Company, whether as a stockholder or otherwise, under this Agreement, the Incentive Plan or any other agreement between the Executive, on the one hand, and any of the Companies, on the other hand, the Amended and Restated Certificate of Incorporation, or the By-Laws of the Company, in each case as may be amended from time to time; provided , that the Executive has been given written notice describing any such violation in reasonable detail and fails to cure the violation within 90 days from such notice; or

(iv)          Executive engages in egregious misconduct involving serious moral turpitude to the extent that Executive’s credibility and reputation no longer conform to the standard of the Company’s executives.

(e)                                   For the purposes of this Section 3 , “ Material Breach ” shall mean any of the following:

(i)            Executive’s breach of any of his fiduciary duties to the Companies or their stockholders or making of a willful misrepresentation or omission which breach, misrepresentation or omission would reasonably be expected to materially adversely affect the business, properties, assets, condition (financial or other) or prospects of the Companies;

(ii)           Executive’s willful, continual and material neglect or failure to discharge his duties, responsibilities or obligations prescribed by this Agreement or any other agreement between the Executive and any of the Companies (other than arising solely due to physical or mental disability);

(iii)          Executive’s habitual drunkenness or substance abuse which materially interferes with Executive’s ability to discharge his duties, responsibilities or obligations prescribed by this Agreement or any other agreement between the Executive and any of the Companies; and

(iv)          Executive’s willful and material violation of any non-competition, non-disparagement, or confidentiality agreement with any of the Companies, including without limitation, those set forth in Sections 7 , 8 and 9 of this Agreement, or any other agreements with any of the Companies;

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in each case, for purposes of clauses (i) through (iv), after the Company or the Board of Directors of the Company has provided Executive with 60 days’ written notice describing such circumstances and the possibility of a Material Breach in reasonable detail, and Executive fails to cure such circumstances and Material Breach within those 60 days.  No act or omission shall be deemed willful if done, or omitted to be done, in good faith by the Executive based upon a resolution duly adopted by the Company’s Board of Directors.

(f)            In the event Executive’s employment is terminated by the Company under any circumstances described in Section 3(b)(v)  or by Executive under the circumstances described in Section 3(c)(ii)  or (iii) ,

(i)            the Company shall pay or cause to be paid to the Executive, (A) within five business days after the date of termination, any earned but unpaid base salary and, subject to the provisions of Section 5, any expense reimbursement payments owed to the Executive, and (B) any earned but unpaid annual bonus payments relating to the prior year to be paid in accordance with the terms and conditions of the Safety Insurance Group, Inc. Annual Performance Incentive Plan, or any successor plan thereto (collectively, the “ Accrued Obligations ”);

(ii)           the Company shall pay or cause to be paid to the Executive, within thirty business days after the date of termination, a lump-sum payment equal to the annual base salary the Executive would have received over the remaining Term of Employment if his employment had not terminated, assuming for this purpose that a notice not to extend the Term of Employment was provided on the date of termination (the “ Severance Period ”), based on the Executive’s base salary in effect immediately prior to the date of termination; and

(iii)          subject to the provisions of Section 5 , during the Severance Period, the Company will provide or cause to be provided to the Executive (and any covered dependents), with life and health insurance benefits (but not disability insurance benefits) substantially similar to those the Executive and any covered dependents were receiving immediately prior to the date of termination and at the same dollar cost to the Executive as in effect immediately prior to the termination of employment.  Nothing in this Section 3(f)(iii)  will extend the COBRA continuation coverage period.

(g)           In the event the Executive’s employment is terminated within three years after a Change of Control (provided the Term of Employment has not already expired) under any circumstances described in Section 3(b)(v)  or by Executive under the circumstances described in Section 3(c)(ii)  or (iii) ,

(i)            the Company shall pay or cause to be paid to the Executive any Accrued Obligations in accordance with Section 3(f)(i );

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(ii)           the Company shall pay or cause to be paid to the Executive, within thirty business days after the date of termination, a lump-sum payment equal to two (2) times the sum of (A) the Executive’s annual base salary in effect immediately prior to the date of termination and (B) the most recent annual bonus paid to the Executive prior to the Change in Control; and

(iii)          subject to the provisions of Section 5 , for a two (2) year period after the date of termination, the Company will provide or cause to be provided to the Executive (and any covered dependents), with life and health insurance benefits (but not disability insurance benefits) substantially similar to those the Executive and any covered dependents were receiving immediately prior to the date of termination and at the same dollar cost to the Executive as in effect immediately prior to the termination of employment.  Nothing in this Section 3(g)(iii)  will extend the COBRA continuation coverage period.

(h)           In the event Executive’s employment is terminated by the Company under the circumstances described in Section 3(b)(iv) ,

(i)            the Company shall pay or cause to be paid to the Executive any Accrued Obligations in accordance with Section 3(f)(i) ;

(ii)           the Company shall pay or cause to be paid to the Executive, within thirty business days after the date of termination, a lump-sum payment equal to three (3) months base salary, based on the Executive’s base salary in effect immediately prior to the date of termination; and

(iii)          subject to the provisions of Section 5 , for a three (3) month period after the date of termination, the Company will provide or cause to be provided to the Executive (and any covered dependents), with life and health insurance benefits (but not disability insurance benefits) substantially similar to those the Executive and any covered dependents were receiving immediately prior to the date of termination and at the same dollar cost to the Executive as in effect immediately prior to the termination of employment.  Nothing in this Section 3(h)(iii)  will extend the COBRA continuation coverage period.

(i)            In the event Executive’s employment is terminated by the Company under the circumstances described in Section 3(b)(i)  or (ii)  or by the Executive under Section 3(c)(i) ,

(i)            the Company will pay or cause to be paid to the Executive (or the Executive’s estate or representative, as the case may be) any Accrued Obligations in accordance with Section 3(f)(i) ;

(ii)           the Company will pay or cause to be paid to the Executive (or the Executive’s estate or representative, as the case may be), within thirty business days after the date of termination, a lump-sum payment equal to 100% of the

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Executive’s annual base salary in effect immediately prior to the date of termination; and

(iii)          subject to the provisions of Section 5 , for a one (1) year period after the date of termination, the Company will provide or cause to be provided to the Executive (and any covered dependents), with life and health insurance benefits (but not disability insurance benefits) substantially similar to those the Executive and any covered dependents were receiving immediately prior to the date of termination and at the same dollar cost to the Executive as in effect immediately prior to the termination of employment.  Nothing in this Section 3(i)(iii)  will extend the COBRA continuation coverage period.

(j)            In the event Executive’s employment is terminated by the Company under any circumstances described in Section 3(b)(iii)  or by Executive as a result of resignation or voluntary termination due to any circumstance other than the material reductions, relocation or violations described in Section 3(c)(ii)  above, there will be no amounts owed to the Executive under Section 4 or any other part of this Agreement, from and after the effectiveness of termination.

(k)           The payments and benefits required by Section 3(f), 3(g), 3(h) or 3(i) , as applicable, constitute severance and liquidated damages, and, except for payments that may be required pursuant to Section 10 , the Company will be obligated to pay or cause to be paid any further amounts to Executive under this Agreement or otherwise be liable to Executive in connection with any termination.

(l)            All determinations pursuant to this Section 3 shall be made by the Company’s Board of Directors (not including Executive) in good faith.

(m)          Termination of the Term of Employment will not terminate Sections 7 through 10 and 12 through 23 , or any other provisions not associated specifically with the Term of Employment.

(n)           In the event the Term of Employment is terminated and the Company is obligated to make or cause to be made payments pursuant to Section 3(f) , the Executive will use his reasonable efforts to seek and obtain alternative employment; provided , however , that the Executive shall not be required to accept a position or positions of a substantially different character than the position(s) held by him under this Agreement; and provided   further , if the Executive shall become physically or mentally disabled, he will not be under such duty.  Moreover, in the event that after the Restricted Period pursuant to Section 8(a) , Executive is employed by or engaged in a Competitive Business as contemplated by Section 8(a)(i) , then the payments under Section 3(f)  will thereupon cease.

(o)           Notwithstanding any provision herein to the contrary, as a condition to payment of any amounts or provision of any benefits pursuant to Sections 3(f)  through 3(i)  or 10 of this Agreement (other than due to the Executive’s death), the Executive shall

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be required to have executed a complete release of the Companies and related parties in such form as is reasonably required by the Company.  Subject to Section 3(p) , all payments and benefits under this Section 3 shall be paid or commenced on the sixtieth (60th) day following the date of termination of the Executive’s employment, provided that the release described in the preceding sentence becomes irrevocable prior to such sixtieth (60th) day.

(p)           Notwithstanding the foregoing, if the Executive is a “specified employee” within the meaning of Section 409A at the time of a termination, any portion of the payments under this Section 3 due hereunder during the first six months following the date of the Executive’s termination, to extent that such payments constitute “deferred compensation” under Section 409A, shall not be paid during such six-month period and instead shall be paid on the first business day following the expiration of such six-month period.  The remaining portion of the payments due hereunder shall be paid as provided in the applicable provisions of this Section 3 .

4.             Compensation

The Company shall pay or cause to be paid to Executive the following compensation:

(a)           During the Term of Employment, the Company shall pay or cause to be paid to Executive as base compensation for his services hereunder, in monthly installments, a base salary at a rate of $150,000 per annum, as increased on an annual basis to reflect the increase in the United States Cost of Living Index for All Urban Consumer (CPI-U) for the Boston, Massachusetts area (the “ CPI-U Index ”).  The January 2004 CPI-U Index shall provide the basis for calculations of such increases.  Notwithstanding the minimum increase set forth above, the Board of Directors of the Company or a committee thereof may establ