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                                                                       Exhibit 2


                              EMPLOYMENT AGREEMENT



         EMPLOYMENT AGREEMENT dated July 1, 1998, between Gryphon Holdings Inc.,
a Delaware corporation (the "Company"), and Mr. John A. Dore (the "Executive").


         WHEREAS, the Company wishes to secure for itself and its subsidiaries
the services of the Executive as a key senior executive officer, and the
Executive desires to serve in the employ of the Company upon the terms and
conditions hereinafter provided.


         NOW THEREFORE BE IT AGREED AS FOLLOWS:

1.       Employment, Duties and Acceptance.

         1.1.     Employment by the Company. The Company hereby agrees that upon
                  the acquisition of all of the issued and outstanding capital
                  stock of The First Reinsurance Company of Hartford ("First
                  Re"), it will employ the Executive, for itself and its
                  subsidiaries, to serve as an Executive Vice President of the
                  Company, as Vice Chairman of Gryphon Insurance Group Inc.
                  ("GIG") and as President and CEO of First Re, Oakley
                  Underwriting Agency, Inc. ("Oakley") and F/I Insurance Agency,
                  Incorporated ("F/I"). In his role as Vice Chairman of GIG, the
                  Executive will be the senior executive in charge of a Chicago
                  based profit center that will have exclusive authority within
                  GIG for all non-program professional liability business,
                  except for Architects' and Engineers' E&O business. In
                  addition, the Executive shall perform such other executive
                  duties for the Company and its subsidiaries not inconsistent
                  with the Executive's foregoing positions as he may be
                  authorized or directed to perform from time to time by the
                  Company.

         1.2.     Acceptance of Employment by the Executive. The Executive
                  agrees to accept such employment and shall render the services
                  described above. The Executive shall devote his full business
                  time and energies to the business of the Company and those of
                  its subsidiaries and to faithfully and diligently perform his
                  duties hereunder, subject to illness, vacations and personal
                  affairs consistent with Company policies for its executives
                  generally. The preceding sentence shall not preclude Executive
                  from serving on the Board of Directors (or comparable
                  governing body) of other business enterprises or from
                  participating in the affairs of any governmental, educational
                  or other charitable institutions with the prior permission of
                  the Company (permission to serve on the Boards of Directors
                  listed on Exhibit A hereto having already been given by the
                  Company).

         1.3.     Place of Employment. The Executive's place of employment shall
                  be at 55 West Monroe Street, Chicago, Illinois 60603 or such
                  other location of the principal office of the aforementioned
                  profit center in the Chicago metropolitan area, subject to
                  such travel as the rendering of the services hereunder may
                  require. Office space, furnishings, support staff and
                  facilities and other office amenities will be provided by the
                  Company for the Executive's place of employment at least
                  comparable to those provided to the Executive at the
                  aforementioned address prior to commencement of this
                  Employment Agreement.

         1.4.     Service as Director. During the term of his employment
                  hereunder, the Executive shall be, and serve as, a member of
                  the Board of Directors of each of the Company's subsidiaries
                  listed in Section 1.1 and the Company agrees to elect or
                  appoint, or cause the election or appointment, of Executive to
                  membership on such Boards of Directors as needed to carry out
                  the foregoing commitment. In addition, the Executive will be
                  elected as soon as practical after the date hereof to the
                  Board of Directors of the Company. Upon the expiration of the
                  Executive's initial term as a Director of the Company and
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                  each term thereafter, so long as the Executive remains
                  employed hereunder, the Company shall cause the Executive to
                  be included in the slate of nominees recommended that year by
                  the Board for election as Directors of the Company by the
                  shareholders.

2.       Term of Employment. The term of the Executive's employment under this
         Employment Agreement shall commence on the date of the acquisition of
         First Re, Oakley and F/I by the Company (the "Commencement Date") and
         shall continue until terminated by either party on thirty days prior
         written notice (the "Term").

3.       Compensation

         3.1.     Salary. As compensation for all services to be rendered
                  pursuant to this Employment Agreement, the Company shall pay
                  the Executive, during the Term, a base salary of $300,000 per
                  annum, payable in installments in accordance with the payroll
                  policies of the Company as in effect from time to time for its
                  executives generally, less such deductions as shall be
                  required to be withheld by applicable law and regulations. The
                  foregoing base salary may be increased from time to time at
                  the discretion of the Board of Directors of the Company.

         3.2.     Annual Bonus. In addition to the salary set forth in Section
                  3.1 hereof, the Executive shall be entitled to participate in
                  the Company's annual bonus incentive plan for members of its
                  senior management subject to the terms and conditions of such
                  plan.

         3.3.     Stock Options. Promptly following the acquisition of First Re,
                  Oakley and F/I by the Company, the Executive shall be granted,
                  subject to the approval of the Compensation Committee of the
                  Company, options to purchase 45,000 shares of Common Stock of
                  the Company under the Company's 1993 Stock Option Plan, as
                  amended. Twenty-five percent (25%) of the foregoing options
                  shall be incentive stock options and seventy-five percent
                  (75%) shall be non-qualified options.

         3.4.     Benefits. The Executive shall be permitted during the Term, to
                  participate in any life insurance, health, disability, pension
                  and other benefit programs which may be available to other
                  executives of the Company generally, on the same terms and
                  subject to the same conditions as such other executives. The
                  Executive shall be entitled to paid vacation and all customary
                  holidays each year during the Term in accordance with the
                  Company's policies as the same may be modified from time to
                  time on the same terms as other executives, except to the
                  extent that First Re elects to maintain separate though
                  comparable programs for its employees. In such event,
                  Executive shall participate in such programs. For purposes of
                  the foregoing benefits, any service requirements relative to
                  such benefits shall treat employment service with Dearborn
                  Risk Management Inc. or First Re prior to your employment
                  hereunder as the equivalent of service with the Company.

         3.5.     Expenses. Subject to such policies as may from time to time be
                  established by the Company's Board of Directors for the
                  Company's executives generally, the Company shall pay or
                  reimburse the Executive for all reasonable expenses actually
                  incurred or paid by the Executive during the Term in the
                  performance of the Executive's services under this Employment
                  Agreement upon presentation of expense statements or vouchers
                  or such other supporting information as it may require of
                  other senior executive officers of the Company. The Company
                  also will provide the Executive, at Company expense, with (i)
                  a new car, leased by the Company (with an equivalent purchase
                  price of not more than $50,000) or, at Executive's choice,
                  (ii) a car currently under lease to First Re and acceptable to
                  the Executive, with the Company paying in either case all
                  related gasoline, maintenance and insurance expenses. The
                  Company will reimburse the Executive during


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                  the Term for his membership dues in the clubs listed on
                  Exhibit B or such other clubs as may be substituted by mutual
                  agreement of the parties for the original clubs.

4.       Definitions. For the purpose of Section 5 of this Agreement, the
         following terms shall be defined as follows:

         4.1.     Cause. "Cause" means:

                  A.       the determination by a majority of the Board of
                           Directors of the Company (the "Board"), other than
                           the Executive, that the Executive has failed to
                           perform his duties to the Company (other than as a
                           result of death or Disability, as hereinafter
                           defined), which failure amounts to an intentional and
                           extended neglect of the Executive's duties hereunder;

                  B.       the commission by the Executive of an act of fraud or
                           embezzlement against the Company or the determination
                           by a majority of the Board of Directors, other than
                           the Executive, that the Executive has willfully taken
                           actions injurious to the business or prospects of the
                           Company; or

                  C.       the Executive's conviction of any felony or a
                           misdemeanor involving moral turpitude.

         4.2.     Constructive Termination. "Constructive Termination" means the
                  occurrence of one or more of the following events: (i) without
                  the Executive's express written consent, the assignment to the
                  Executive of any duties or the reduction of the Executive's
                  duties, either of which results in a significant diminution in
                  the Executive's position or responsibilities with the Company,
                  GIG, First Re or Oakley in effect immediately prior to such
                  assignment, or the removal of the Executive from such position
                  and responsibilities; (ii) a material reduction by the Company
                  in the base compensation of the Executive as in effect
                  immediately prior to such reduction or a material reduction by
                  the Company in the kind or level of employee benefits to which
                  the Executive is entitled immediately prior to such reduction
                  with the result that the Executive's overall benefits package
                  is significantly reduced, unless any such reduction applies
                  generally to all employees at the Executive's level; (iii) the
                  relocation of the Executive to a facility or a location more
                  than fifty (50) miles from the Executive's then present
                  location, without the Executive's express written consent; or
                  (iv) any purported termination by the Company for which the
                  grounds relied upon are not valid; provided that, in each
                  case, the Executive has given the Company written notice
                  stating the Executive's intention to resign for reason of
                  Constructive Termination citing the reason(s), and the Company
                  has not cured the Constructive Termination within fifteen (15)
                  days after receipt of such notice.

         4.3.     Disability. "Disability" means that the Executive is unable by
                  reason of accident or illness (including mental illness) to
                  perform the material duties of the Executive's regular
                  position with the Company and is not expected to recover from
                  such disability within a reasonable period of time. If at any
                  time the Executive or the Company claims that the Executive is
                  disabled, a physician acceptable to both the Company and the
                  Executive (which acceptance will not be unreasonably withheld)
                  will be appointed by the Company to examine the Executive. The
                  Executive will cooperate fully with the physician. If the
                  physician determines that the Executive is disabled, the
                  physician will certify to the Company that the Executive is
                  disabled. The physician's determination will be conclusive.
                  The Company will pay the physician's fee.

         4.4.     Person. "Person" means an individual, partnership, joint stock
                  company, corporation, trust or unincorporated organization, a
                  government or agency or political subdivision


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                  thereof, or any "person" as such term is used in Sections
                  13(d) and 14(d) of the Securities Exchange Act of 1934.


         4.5.     Change in Control. "Change in Control" shall be deemed to
                  occur when any Person is or becomes the "beneficial owner" (as
                  defined in Rule 13d-3 under the Securities Exchange Act of
                  1934), directly or indirectly, of securities of the Company
                  representing twenty percent (20%) or more of the Company's
                  then outstanding voting stock.

5.       Termination Benefits. Upon the Executive's termination of employment,
         the Executive shall be entitled to receive severance and other benefits
         as follows:

         5.1.     Severance Pay.

                  A.       Involuntary Termination; Constructive Termination. If
                           the Company terminates the Executive's employment
                           other than for Cause or Disability, or if the
                           Executive resigns as a result of a Constructive
                           Termination, then, in lieu of any severance benefits
                           to which the Executive may otherwise be entitled
                           under any Company severance plan or program, the
                           Executive shall be entitled to severance benefits as
                           follows:

                           (i)      Except as provided in subsection 5.1.A.(ii)
                                    hereof, the Company will make monthly
                                    payments to the Executive as severance pay
                                    for a period of six (6) to twelve (12)
                                    months (the exact number of months to be
                                    determined by the Board of Directors at the
                                    time of termination) from the date of
                                    termination, provided, that the Executive as
                                    a condition of such payments complies with
                                    the Executive's obligations under Section 6
                                    hereof. Each monthly payment will be equal
                                    to one (1) month of the Executive's base
                                    salary at the rate in effect immediately
                                    prior to the date of termination and will be
                                    paid on or before the first day of the
                                    month.

                           (ii)     Subsection 5.1.A.(i) notwithstanding, if the
                                    date of termination of employment occurs
                                    within twenty-four (24) months after a
                                    Change in Control, the Company will pay the
                                    Executive, in a single lump sum, an amount
                                    equal to 36 months base salary, at the rate
                                    in effect immediately prior to the date of
                                    termination, such amount to be paid within
                                    30 days after such date of termination;
                                    provided, however, that in the event the
                                    Company's independent auditors determine
                                    that such payments would be treated as
                                    "excess parachute payments" within the
                                    meaning of Section 280G of the Internal
                                    Revenue Code of 1986, or any successor
                                    provision, such payments shall be reduced by
                                    the minimum amount necessary to avoid such
                                    treatment. The amount of any such reduction
                                    shall be calculated by the Company's
                                    independent auditors and such calculations
                                    shall be provided, in writing, to the
                                    Executive not later than 20 days after the
                                    date of termination of employment.

                  B.       Other Termination. If the Executive's employment
                           terminates for any reason other than as described in
                           Section 5.1.A. above, including by reason of the
                           Executive's death, Disability, termination by the
                           Company for Cause or resignation other than for
                           Constructive Termination, then the Executive shall be
                           entitled to receive severance, if any, and any other
                           benefits only as may then be established under the
                           Company's existing severance and benefit plans and
                           policies at the time of such termination.


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         5.2.     Health and Life Insurance. If the Executive's employment
                  terminates as described in subsection 5.1.A.(i) above, the
                  Executive will receive Company-paid medical and life insurance
                  as provided to such Executive immediately prior to the
                  Executive's termination of employment. If the Executive's
                  medical and life insurance coverage included the Executive's
                  dependents immediately prior to the Executive's termination,
                  such dependents shall also be covered at the Company's
                  expense. Company-paid coverage referred to above shall
                  continue as long as the monthly payments continue under
                  subsection 5.1.A.(i). For purposes of the continuation health
                  coverage required under Section 4980B of the Internal Revenue
                  Code of 1986, as amended ("COBRA"), the date of the
                  "qualifying event" giving rise to the Executive's COBRA
                  election period (and that of the Executive's "qualifying
                  beneficiaries") shall be the date of termination.

         5.3.     No Mitigation. The Executive shall not be required to mitigate
                  the amount of any payment contemplated by this Employment
                  Agreement (whether by seeking new employment or in any other
                  manner). The Executive's payments under this Agreement shall
                  not be affected by payments received from any future employer,
                  except that the Company's obligation to provide medical and
                  life insurance under Section 5.2. shall terminate to the
                  extent the Executive receives substantially equivalent
                  benefits from another employer.

6.       Confidentiality; Covenant Not to Solicit.

         6.1.     Acknowledgment. The Executive acknowledges that (i) the
                  Company, which for the purposes of this Section 6 includes all
                  of the subsidiaries and affiliates of the Company, whether now
                  existing or as may be acquired, formed or incorporated during
                  the Executive's employment hereunder, is engaged in the
                  business of property and casualty insurance and reinsurance
                  and may become engaged during the period during which the
                  Executive is employed by the Company in certain other
                  businesses through the acquisition thereof or otherwise
                  (collectively the "Business"); (ii) the Business is conducted
                  throughout the United States and Canada; (iii) his work for
                  the Company has given him, and will continue to give him,
                  access to trade secrets of, and confidential information
                  concerning, the Company; and (iv) the agreements and covenants
                  contained in this Section 6 are essential to protect the
                  Business and goodwill of the Company.


         6.2.     Confidential Information. During the term of the Executive's
                  employment with the Company and for the period ending two
                  years thereafter, the Executive shall keep secret and retain
                  in strictest confidence, and shall not use for the benefit of
                  himself or others, all confidential matters of the Company
                  (other than such matters in the public domain and other than
                  general knowledge of the Executive relating to the Business),
                  including without limitation, trade secrets, client lists,
                  details of client or consultant contracts, pricing policies,
                  operational methods, marketing plans or strategies, product
                  development techniques or plans, business acquisition plans,
                  new personnel acquisition plans and research projects of the
                  Company learned by the Executive heretofore or hereafter. All
                  memoranda, notes, lists, records and other documents or papers
                  (and copies thereof), including such items stored in computer
                  memories, on microfiche or by any other means, made or
                  compiled by or on behalf of the Executive, or made available
                  to the Executive relating to the Company, are and shall be the
                  Company's property and shall be delivered to the Company
                  promptly upon the termination of the Executive's employment
                  (whether such termination is for Cause or otherwise) or at any
                  other time on request of the Company.

         6.3.     Non-Solicitation. During the term of the Executive's
                  employment with the Company and for a period ending two years
                  thereafter, the Executive shall not: (i) solicit or initiate
                  any other action which is intended to induce any other
                  employee of the Company to


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                  terminate employment with the Company, or (ii) solicit, or
                  disclose to any person the identity of, any of the Company's
                  clients, customers, policyholders, vendors, consultants or
                  agents in order to induce any such party to terminate its
                  existing business relationship with the Company.

7.       Enforcement. In the event of the breach by the Executive of any of the
         provisions of Section 6, the Company, in addition to other rights and
         remedies existing in its favor, may apply to any court of law or equity
         of competent jurisdiction for specific performance and/or injunctive
         relief in order to enforce, or prevent any violations of, the
         provisions hereof.

8.       Employment At-Will. The Executive shall be deemed an "At-Will" employee
         of the Company. Nothing in this Agreement shall be construed to confer
         upon the Executive any right with respect to continuation of employment
         by the Company, nor shall it interfere in any way with the Company's
         right to terminate the Executive's employment at any time, with or
         without Cause.

9.       Successors and Assigns. This Agreement and the rights and obligations
         of the parties hereto will bind and inure to the benefit of any
         successor or successors of the Company by reorganization, merger or
         consolidation and any assignee of all or substantially all of its
         business and properties which assignee shall as a condition of such
         assignment assume all of the Company's obligations hereunder. This
         Agreement shall be binding upon and inure to the benefit of the heirs,
         executors, administrators and successors or assignees of the parties
         hereto; provided, however, that neither this Agreement nor any rights
         or benefits hereunder may be assigned by the Company or by the
         Executive without the prior written consent of the other party.

10.      Severability. Whenever possible, each provision of this Agreement will
         be interpreted in such a manner as to be effective and valid under
         applicable law, but if any provision of this Agreement is held to be
         invalid, illegal or unenforceable in any respect under any applicable
         law or rule in any jurisdiction, such invalidity, illegality, or
         unenforceability will not affect any other provision, but this
         Agreement will be reformed, construed and enforced in such jurisdiction
         as if such invalid, illegal or unenforceable provision had never been
         contained herein.

11.      Notices. Unless otherwise provided herein, any notice, request,
         instruction or other document to be given hereunder by any party to the
         other shall be in writing and delivered in person or by courier,
         telegraphed, telexed or by facsimile transmission (in each such case to
         be effective on the date of receipt) or mailed by certified mail,
         postage prepaid, return receipt requested (such mailed notice to be
         effective on the date such receipt is acknowledged), as follows:

                           (a) If to the Executive:


                                   c/o The First Reinsurance Company of Hartford
                                           55 W. Monroe Street
                                           Chicago, IL 60603
                                           Facsimile: 312-357-3525


                           (b) If to the Company:


                                    Gryphon Holdings Inc.
                                            30 Wall Street
                                            New York, NY 10005
                                            Attn.:  Robert M. Coffee, Esq.
                                            Facsimile: 212-825-0200


or to such other place as either party may designate by written notice to the
other.


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12.      Waivers. If either party should waive any breach of any provision of
         this Agreement, he or it will not thereby be deemed to have waived any
         preceding or succeeding breach of the same or any other provision of
         this Agreement.

13.      Complete Agreement: Amendments. This Agreement is the entire agreement
         of the parties with respect to the subject matter hereof and may not be
         amended, except by written instrument approved by resolution of the
         Board of Directors of the Company and executed by the parties.

14.      Headings. The headings of the sections hereof are inserted for
         convenience only. They are not a part of nor do they affect the meaning
         of the sections.

15.      Governing Law. This Agreement will be interpreted and enforced in
         accordance with the laws of the State of Illinois as applied to
         agreements between Illinois residents made and performed within
         Illinois.


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


                                   GRYPHON HOLDINGS INC.





                                   By:
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                                          Stephen A. Crane
                                          President & Chief Executive Officer


                                   EXECUTIVE:






                                  ---------------------------------------------
                                  John A. Dore


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