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                                                                   EXHIBIT 10-10



                                    AGREEMENT


      Agreement (this "Agreement") entered into and effective this 3rd day of
June, 1997 between Bradley D. Wiley of Ringwood, New Jersey (the "Executive")
and The Navigators Group, Inc., a corporation with an office located at 123
William Street, New York, N.Y. 10038 (the "Company").


                              W I T N E S S E T H:


      WHEREAS, both the Company and Executive believe there are mutual
advantages to entering into this Agreement, to induce the Executive to remain in
the employ of the Company.

      NOW THEREFORE, in consideration of the material advantages accruing to the
two parties and the mutual covenants herein, the Company and Executive agree
with each other as follows:


      1. DEFINITIONS.

      (a) "Affiliate" means any person that directly, or indirectly through one
or more intermediaries, controls, or is controlled by, or is under common
control with, any other Person.

      (b) "Base Annual Compensation" means the base salary of the Executive on
an annualized basis, exclusive of any bonus and/or other benefits to which the
Executive may be entitled during the Term.

      (c) "Board" means the Board of Directors of the Company.

      (d) "Bonus" means the bonus payment (in addition to Base Annual
Compensation) that has, in the discretion of the Board of the Company, been paid
(or accrued) to Executive following a calendar year to reward the Executive for
performance during such calendar year.

      (e) "Change in Control" means any of (i) the sale by the Company of at
least Fifty Percent (50%) of its assets to any Person, (ii) the merger or
consolidation of the Company with any Person in which the shareholders of the
Company immediately prior to such merger or consolidation receive less than
Fifty (50%) of the outstanding voting shares of the new or continuing Person,
(iii) the sale, exchange, or other disposition to a Person, or Persons under
common control (or the acquisition through a tender offer or exchange offer by a
Person or Persons under common
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control), in one transaction or a series of related transactions of greater than
Thirty-Three (33%) of the outstanding shares of the Company's common stock, or
(iv) Terence N. Deeks no longer holds any office with the Company and is not a
director.

      (f) "Closing Date" means the effective date of any Change in Control
during the Term of this Agreement.

      (g) "Code" means the Internal Revenue Code of 1986 as in effect at the
time with respect to which such term is used.

      (h) "Company" means The Navigators Group, Inc., a Delaware corporation,
and all of the Subsidiaries.

      (i) "Constructive Discharge" shall be deemed to occur upon the occurrence
during the Covered Period of any of the following: (i) a material, adverse
change in the Executive's title or position, for example if the Executive is no
longer Chief Financial Officer of the Company (other than resulting from a
Discharge for Cause), which adverse change continues for more than Thirty (30)
days following written notice from the Executive; (ii) a substantial reduction
in the Executive's responsibilities (including, without limitation, a
termination of Executive by the Company other than a Discharge for Cause), which
reduction continues for more than Thirty (30) days after written notice from the
Executive setting forth in reasonable detail the nature of such reduction in
responsibilities; (iii) any reduction in the Executive's Base Annual
Compensation below the Base Annual Compensation in effect immediately prior to
the Closing Date of a Change in Control (other than a reduction resulting from
or in connection with a Discharge for Cause), which reduction is not cured
within Thirty (30) days following written notice from the Executive; (iv) the
failure, following a Change in Control, of a successor corporation to assume
this Agreement and all obligations and undertakings of the Company hereunder,
which failure continues for more than Thirty (30) days following written notice
from the Executive to such successor corporation; (v) a portfolio transfer by
the Company of Fifty Percent (50%) or more of the aggregate loss reserves of the
Company; and/or (vi) any other transaction by the Company that constitutes a
"runoff" of greater than Fifty Percent (50%) of the Company's insurance
business.

      (j) "Covered Period" means the period commencing on the earlier of the
Pre-Closing Date and the Closing Date and ending Two (2) years after the Closing
Date.

      (k) "Discharge for Cause" shall, during the Covered Period, be deemed to
occur only following the termination of Executive's employment by the Board upon
a good faith determination by the Board that any of the following has occurred:
(i) the commission by Executive of any act which, if successfully prosecuted by
the appropriate authorities, would constitute a felony under state or


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federal law; (ii) Executive's embezzlement or intentional misappropriation of
any property of the Company (it being understood that the use by the Executive
of Company office supplies at home to facilitate his performance of his duties
to the Company shall not be construed as embezzlement or intentional
misappropriation of property of the Company); (iii) the intentional or knowing
commission by the Executive of an act that causes the Company or any of its
Affiliates to be in contravention of any material provision of applicable law or
any material rules and regulations of any governmental or other regulatory body
having jurisdiction over the business and affairs of the Company or its
Affiliates; (iv) the continued insubordination of the Executive or his
dereliction of duties after written notice from the Board specifying the
insubordination or dereliction of duties and a reasonable opportunity (not less
than Ten (10) days) to cure have been given to the Executive; or (v) Executive's
having divulged, furnished or made accessible to anyone other than the Company,
its directors, officers, employees, auditors, bankers, rating agencies,
analysts, regulatory agencies and legal advisors, other than in the regular
course of the business of the Company, any confidential knowledge or information
relating to the customers, employees, operations, financial condition, revenues
or projections of the Company, other than information in the public domain which
has not been improperly disclosed by the Executive. Such determination by the
Board may be made only after reasonable written notice to the Executive from a
member of the Board setting forth details of the allegations which may
constitute Discharge for Cause and after an opportunity for such Participant,
together with his counsel, to be heard by the Board. Notwithstanding the
foregoing, in the event Executive disputes, in an arbitration pursuant to
Section 6, below, that an event permitting Discharge for Cause has occurred (a
"Challenged Termination"), then the Company shall, until the Arbitrators render
their judgement with respect to the Challenged Termination (a) permit the
Executive to participate, to the extent Executive continues to be eligible
notwithstanding the Challenged Termination, in all medical, dental, life
insurance and short and long-term disability plans in which Executive was
entitled to participate prior to the Challenged Termination (each a "Plan" and
collectively the "Plans"), subject to the terms and conditions that were in
effect prior to the Challenged Termination, as such terms and conditions may be
amended subsequent to the Challenged Termination, and (b) if the Executive is
not eligible to participate in a Plan or Plans by virtue because of his
termination, pay to the Executive, on a monthly basis, an amount equal to the
aggregate amount paid by the Company on behalf of the Executive with respect to
the Plan or Plans for which the Executive is not eligible because of his
termination.

      (1) "Person" means an individual, partnership, firm, trust, corporation or
other similar entity. When two or more Persons


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act as a partnership, limited partnership, limited liability company, syndicate
or other group for the purpose of acquiring, holding or disposing of securities
of the Company, such partnership, limited partnership, syndicate or group shall
be deemed a "Person" for the purposes of this Agreement.

      (m) "Pre Closing Date" means, with respect to the types of Change in
Control described in Sections 1(e) (i), 1(e) (ii) and/or 1(e) (iii), above, the
effective date of the written agreement for such asset sale, merger or
consolidation, or stock purchase agreement, as the case may be, between the
Company and the Person or Persons to whom the Company's assets or shares of
Common Stock are being sold, or with whom the Company is merging or
consolidating, as the case may be.

      (n) "Primary Benefit" shall have the meaning accorded thereto in Section
3(a).

      (o) "Subsidiary" means any Person of which a majority of the capital stock
having voting power for the election of directors or other governing board is
owned by the Company and/or one or more of the Subsidiaries.

      Any term used in this Agreement in the masculine gender shall include the
feminine gender.

2.    DISCHARGE FOR CAUSE.

      Notwithstanding anything to the contrary in this Agreement, Discharge for
Cause of the Executive by the Board shall not constitute Constructive Discharge.

3.    TERMINATION BY THE EXECUTIVE FOLLOWING CONSTRUCTIVE DISCHARGE.

      (a) In the event of the Constructive Discharge of the Executive during the
Covered Period, the Executive shall, subject to the next succeeding sentence, be
entitled to send written notice (the "Termination Notice") to the Company (or
any successor or continuing Person) stating that he is terminating his
employment with the Company (or such successor or continuing Person) due to such
Constructive Discharge. In the event the Company terminates the Executive other
than a Discharge for Cause, the Termination Notice shall be deemed to have been
sent by Executive on the date of such termination. The Termination Notice with
respect to any other Constructive Discharge must be sent within Six (6) Months
of the effective date of such Constructive Discharge, or the Executive shall be
deemed to have waived his rights under this Section 3 with respect to such
Constructive Discharge. Provided the Executive sends the Termination Notice
within such Six (6) Month period, the Company (or such successor or continuing
Person) shall pay to the Executive:


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            (i) an amount (the "Primary Benefit") equal to One Hundred Fifty
            Percent (150%) of the Base Annual Compensation of the Executive in
            effect immediately prior to the effective date of the Constructive
            Discharge. The Primary Benefit shall be paid to the Executive in
            twelve (12) equal monthly installments, commencing on the first
            business day of the first calendar month following receipt of the
            Termination Notice; and

            (ii) within Thirty (30) Days following receipt of the Termination
            Notice, the amount (the "Pro Rata Bonus") that results from the
            following calculation: (A) the Bonus paid (or accrued and to be
            paid) to the Executive with respect to the calendar year immediately
            preceding the calendar year of the Constructive Discharge,
            multiplied by (B) a fraction, the numerator of which is the number
            of days elapsed in the calendar year of the Constructive Discharge,
            and the denominator of which is 365.

The Primary Benefit and Pro Rata Bonus shall be in satisfaction of any and all
other compensation, bonus, severance and/or other payments of any kind
whatsoever, otherwise due or to be paid to the Executive, except for accrued,
but not paid, Base Annual Compensation and accrued and to be paid bonus from any
prior period, and except for the payments to the Executive pursuant to Section 3
(b).

      (b) In addition to the Primary Benefit and the Pro Rata Bonus, the Company
shall, for the twelve (12) month period commencing with receipt of the
Termination Notice: (i) permit the Executive to participate, to the extent
Executive continues to be eligible, in all medical, dental, life insurance,
short and long-term disability plans, 401K and Money Purchase Plans (or their
successor plans) in which Executive was entitled to participate prior to
delivery of the Termination Notice (each a "Plan" and collectively the "Plans"),
subject to the terms and conditions that were in effect prior to the delivery
of the Termination Notice, as such terms and conditions may be amended
subsequent to delivery of the Termination Notice, and (ii) if the Executive is
not eligible to participate in a Plan or Plans by virtue of his termination, pay
to the Executive, on the first business day of each of the twelve months
subsequent to receipt of the Termination Notice, an amount equal to the
aggregate amount paid by the Company on behalf of the Executive with respect to
the Plan or Plans for which the Executive is not eligible because of his
termination.

      (c) Notwithstanding anything to the contrary in this Agreement and/or any
other agreement between the Company and the Executive in effect on the date
hereof, in the event a


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Constructive Discharge shall occur, then each Award under the Company's Phantom
Stock Appreciation Rights Plan theretofore granted to the Executive, and each
other option theretofore granted to the Executive by the Company shall, to the
extent not theretofore exercised or expired, become immediately exercisable in
full and shall expire on the earlier to occur of (i) the expiration of the
period of twelve (12) months after the date of such Constructive Discharge and
(ii) the date specified in such Award.

4.    TERM; TERMINATION.

      The term of this Agreement (the "Term") shall commence on the date first
written above and continue for so long as the Executive is employed by the
Company (or any successor or continuing Person); provided, however, that the
obligations of the Company (or any successor or continuing Person) under Section
3 shall survive such termination.

5.    NOTICES.

      Any notice or other communication to the Executive or the Company (or any
successor or continuing Person) pursuant to this Agreement shall be in writing
and shall be deemed given when personally delivered or sent by registered or
certified mail, return receipt requested, at the addresses set forth below, or
at such other address as the Executive or the Company (or any successor or
continuing Person) shall have specified by notice to the other in the manner
herein provided:

      If to Executive:

            Bradley D. Wiley
            35 Olive Lane
            Ringwood, N.J. 07456


      If to the Company (or any successor or continuing Person):

            The Navigators Group, Inc.
            Attention: Terence N. Deeks
            123 William Street
            New York, N.Y. 10038

6.    Arbitration

      (a) Any dispute or difference of opinion arising out of, with respect to
or in connection with this Agreement shall be submitted to binding arbitration
before an arbitration panel consisting of one arbitrator to be chosen by the
Company, the other by Executive, and the third arbitrator (the "Umpire") to be
chosen by the two arbitrators. All of the arbitrators shall be active or retired
disinterested executive officers of insurance


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or reinsurance companies or Lloyd's Underwriters. In the event that either party
fails to choose an arbitrator within thirty (30) days following a written
request by the other party to do so, the requesting party may choose a second
arbitrator on behalf of the other party. If the two arbitrators fail to agree
upon the selection of an Umpire within thirty (30) days following their
appointment, each arbitrator shall nominate three candidates within ten (10)
days thereafter, two of whom the other shall decline, and the decision between
the remaining two candidates shall be made by drawing lots.

      (b) The decision of a majority of the arbitrators shall be final and
binding on both parties. The arbitrators shall not have the right or authority
to award punitive damages.

      (c) (i) All expenses of the Company in any arbitration hereunder and/or
any action or proceeding to confirm, vacate or modify any judgement rendered in
an arbitration hereunder, including, without limitation, all legal fees, all
costs and expenses of its arbitrator and 50% of the costs and expenses of the
Umpire, and any and all other costs of the Company arising out of such
arbitration, action or proceeding, shall be borne by the Company, whether or not
it is the prevailing party.

      (ii) Except as provided in Section 6(c) (iii), below, all expenses of the
Executive in any arbitration hereunder and/or any action or proceeding to
confirm, vacate or modify any judgement rendered in an arbitration hereunder,
including, without limitation, all legal fees, all costs and expenses of the
Executive's arbitrator and 50% of the costs and expenses of the Umpire, and any
and all other costs of the Executive arising out of such arbitration, action or
proceeding, shall be borne by the Executive.

      (iii) In the event the arbitrators award the Executive any amount that the
Executive claimed was due him and that the Company refused to pay, then all
expenses of the Executive in the arbitration and/or any action or proceeding to
confirm, vacate or modify the judgement rendered, including, without limitation,
all legal fees, all costs and expenses of the Executive's arbitrator and 100% of
the costs and expenses of the Umpire, and any and all other costs of the
Executive arising out of such arbitration, action or proceeding, shall be borne
by the Company.


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7. VENUE; GOVERNING LAW.

       Any arbitration proceedings shall take place in New York, New York unless
another location is mutually agreed upon by the parties to this Agreement or by
a majority of the arbitrators. Notwithstanding the situs of the arbitration, the
arbitrators, shall apply the law of New York (but not the arbitration law of
that state, the intent of the parties being that the United States Arbitration
Act, 9 U.S.C. ss. 1, et seq. shall control questions of arbitrability,
confirmation, modification, vacatur and the like.) This Agreement shall be
governed by the laws of the State of New York.

8. JURISDICTION. Judgment upon the final decision of the arbitrators may be
entered in, and any actions or proceedings regarding confirmation, modification
or vacatur of such judgement may be brought in, the courts of the United States
for the Southern District of New York or (to the extent exclusive jurisdiction
exists therefor) of the State of New York, New York County, and the parties
hereto irrevocably submit to the non-exclusive jurisdiction of such courts in
respect of any such action, proceedings or dispute.

      The parties hereto irrevocably waive, to the fullest extent permitted by
law, any objection that they may now or hereafter have to the laying of venue of
any such action or proceeding in the courts of the State of New York, New York
County or in the United States District Court for the Southern District of New
York and any claim that any such action, proceeding or dispute brought in any
such court has been brought in any inconvenient forum.

9. ENTIRE AGREEMENT. This Agreement constitutes the entire agreement between the
parties and contains all the agreements between them with respect to the subject
matter hereof. It also supersedes any and all other agreements or contracts,
either oral or written, between the parties with respect to the subject matter
hereof.

10. AMENDMENT. The terms and conditions of this Agreement may be amended only by
a writing executed by the Company (or any successor or continuing Person) and by
Executive.

11. SEVERABILITY. The invalidity or unenforceability of any particular provision
of this Agreement shall not affect its other provisions, and this Agreement
shall be construed in all respects as if such invalid or unenforceable provision
had been omitted.

12. SUCCESSORS AND ASSIGNS. This Agreement shall be binding upon the Company,
its successors and assigns, including, without limitation any Person into which
the Company may be merged or by which it may be acquired, and shall be binding
upon and shall inure to the benefit of Executive, his administrators, executors,


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legatees, heirs, and assigns. The Executive shall not assign all or any portion
of his rights and/or responsibilities under this Agreement.

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


                                       THE NAVIGATORS GROUP, INC.


                                       By: /s/ Terence N. Deeks
                                           ----------------------------
                                           Terence N. Deeks,
                                           President

                                           /s/ Bradley D. Wiley
                                           ----------------------------
                                           Bradley D. Wiley


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