<PAGE>

                                                                    EXHIBIT 10.2

                          MUTUAL RISK MANAGEMENT LTD.


                    DEBENTURE REGISTRATION RIGHTS AGREEMENT
<PAGE>

                               TABLE OF CONTENTS

<TABLE>
<CAPTION>
                                                                                                    Page
                                                                                                    ----
<S>                                                                                                 <C>
1.   Definitions............................................................................           2

     1.1     Other Definitions..............................................................           5

2.   Registration Rights....................................................................           5

     2.1     Demand Registrations...........................................................           6
     2.2     Piggyback Registration.........................................................           9
     2.3     Obligations of the Issuers.....................................................           9
     2.4     Furnish Information............................................................          11
     2.5     Expenses of Registration.......................................................          11
     2.6     Underwriting Requirements......................................................          12
     2.7     Indemnification................................................................          13
     2.8     Termination of Registration Rights.............................................          16
     2.9     "Lock-Up" Agreement............................................................          16

3.   Indenture..............................................................................          16

4.   Miscellaneous..........................................................................          16

     4.1     Amendments; Waivers............................................................          16
     4.2     After-Acquired Shares..........................................................          17
     4.3     Successors and Assigns.........................................................          17
     4.4     Rights and Obligations of Transferees..........................................          17
     4.5     Further Assurances.............................................................          17
     4.6     Notices........................................................................          18
     4.7     Governing Law; Waiver of Jury Trial............................................          20
     4.8     Severability; Interpretation...................................................          21
     4.9     Table of Contents; Headings....................................................          21
     4.10    Entire Agreement...............................................................          21
     4.11    Counterparts...................................................................          21
     4.12    No Third-Party Beneficiaries...................................................          21
     4.13    Execution by Newco.............................................................          21
</TABLE>

                                      (i)
<PAGE>

                    DEBENTURE REGISTRATION RIGHTS AGREEMENT

         THIS DEBENTURE REGISTRATION RIGHTS AGREEMENT (this "Agreement") is made
                                                             ---------
as of May 17, 2001, by and among Mutual Risk Management Ltd., a company
organized under the laws of Bermuda (the "Company"), and XL Insurance Ltd
                                          -------
("XL"), First Union Merchant Banking 2001, LLC, High Ridge Capital Partners II,
  --
L.P., Century Capital Partners II, L.P., Robert A. Mulderig and Taracay
Investors Company (each, a "Purchaser" and, collectively, the "Purchasers") and
                            ---------                          ----------
Intrepid Funding Master Trust (the "RHINOS Debenture Holder").
                                    -----------------------

                                   RECITALS

         WHEREAS, the Company, the Purchasers and the RHINOS Debenture Holder
are parties to that certain securities purchase agreement dated as of May 8,
2001 (the "Securities Purchase Agreement") pursuant to which the Purchasers have
           -----------------------------
agreed to purchase 9 3/8% convertible exchangeable debentures due 2006 of the
Company in an aggregate principal amount of $112,500,000 (such debentures,
together with any RHINOS Debentures issued on or prior to the closing date in
respect of the purchase of debentures by the Purchasers, the "MRM Debentures")
                                                              --------------
and the RHINOS Debenture Holder has agreed to exchange RHINOS (as defined in the
Securities Purchase Agreement) for RHINOS Debentures having a principal amount
equal to the aggregate liquidation preference of the RHINOS tendered in exchange
therefor;

         WHEREAS, the MRM Debentures are convertible into Company Shares or
exchangeable for Newco Shares and/or Newco Debentures; and

         WHEREAS, in order to induce the Purchasers to enter into the Securities
Purchase Agreement and to purchase the MRM Debentures, the Company, Newco and
the Purchasers desire to enter into this Agreement for the purpose, among
others, of establishing certain registration and other rights of the Holders (as
defined below);

         NOW, THEREFORE, in consideration of the mutual covenants contained
herein and other good and valuable consideration, the receipt and sufficiency of
which are hereby acknowledged, the parties hereby agree as follows:
<PAGE>

                                      -2-

         1.    Definitions.


               (a)  "Act" shall mean the Securities Act of 1933, as amended.
                     ---

               (b)  "Agreement" shall have the meaning set forth in the Preamble
                     ---------
to this Agreement.

               (c)  "Business Day" shall mean any day that is not a Saturday,
                     ------------
Sunday or a day on which (i) commercial banks in New York City are authorized or
required to close or (ii) the New York Stock Exchange is not open for trading.

               (d)  "Common Stock" shall mean the common stock or common shares
                     ------------
of the referenced Person.

               (e)  "Common Stock Equivalents" shall mean securities convertible
                     ------------------------
into or exercisable or exchangeable for Common Stock of the referenced Person.

               (f)  "Company" shall have the meaning set forth in the Preamble
                     -------
to this Agreement.

               (g)  "Company Securities" shall mean, collectively, the MRM
                     ------------------
Debentures and the Company Shares.

               (h)  "Company Shares" shall mean shares of Common Stock of the
                     --------------
Company issuable upon conversion of the MRM Debentures.

               (i)  "Debentures" shall mean, collectively, the MRM Debentures
                     ----------
and the Newco Debentures. For all purposes of this Agreement, references to
Debentures shall be deemed to include a reference to the Voting Preferred Stock
issued in connection therewith.

               (j)  "Demand Registration" shall mean a Company Demand
                     -------------------
Registration and/or a Newco Demand Registration.
<PAGE>

                                      -3-

               (k)  "Holder" shall mean, as applicable, any Person owning or
                     ------
having the right to acquire a Registrable Security from time to time.

               (l)  "Issuer" shall mean either the Company or Newco, or both as
                     ------
the context requires.

               (m)  "MRM Debentures" shall have the meaning set forth in the
                     --------------
Preamble to this Agreement. For all purposes of this Agreement, references to
MRM Debentures shall be deemed to include a reference to the Voting Preferred
Stock issued in connection therewith.

               (n)  "Newco" shall mean a new company organized under the laws of
                     -----
Bermuda and formed in connection with the Restructuring.

               (o)  "Newco Debentures" means the convertible debentures due 2006
                     ----------------
of Newco issued in exchange for MRM Debentures. For all purposes of this
Agreement, references to Newco Debentures shall be deemed to include a reference
to the Newco Voting Preferred Stock issued in connection therewith.

               (p)  "Newco Securities" shall mean, collectively, the Newco
                     ----------------
Debentures and the Newco Shares.

               (q)  "Newco Shares" shall mean shares of Common Stock of Newco
                     ------------
issuable upon exchange of MRM Debentures or upon conversion of Newco Debentures.

               (r)  "Newco Voting Preferred Stock" shall have the meaning
                     ----------------------------
assigned thereto in the Securities Purchase Agreement.

               (s)  "1934 Act" shall mean the Securities Exchange Act of 1934,
                     --------
as amended.

               (t)  "Person" shall mean any individual or a corporation,
                     ------
company, partnership, trust, incorporated or unincorporated association, joint
venture, joint stock company, limited liability company, government (or agency
or political subdivision thereof) or other entity of any kind.
<PAGE>

                                      -4-

               (u)  "Purchaser(s)" shall have the meaning set forth in the
                     ------------
Preamble to this Agreement.

               (v)  "register," "registered" and "registration" shall mean a
                     --------    ----------       ------------
registration effected by preparing and filing with the SEC a registration
statement or similar document in compliance with the Act, and the declaration or
ordering of effectiveness of such registration statement or document.

               (w)  "Registrable Securities" shall mean (i) the Company Shares,
                     ----------------------
(ii) the Newco Shares, (iii) the MRM Debentures (including the Voting Preferred
Stock issued in connection therewith) and/or (iv) the Newco Debentures
(including the Newco Voting Preferred Stock issued in connection therewith), in
each case until such time as such securities have been sold pursuant to an
effective registration statement or an applicable exemption from registration
under the Act and are no longer subject to restrictions on transfer the Act.

               (x)  "Requisite Holders" shall mean the holders of a majority of
                     -----------------
the Registrable Securities (assuming, solely for purposes of this definition,
that all MRM Debentures and Newco Debentures have been converted into Company
Shares and Newco Shares, respectively, at the then applicable conversion price);
provided, however, that at any time when XL holds a majority of the Registrable
--------  -------
Securities (other than RHINOS Debentures), "Requisite Holders" shall mean a
majority of the Registrable Securities (other than RHINOS Debentures); and
provided, further, however, that so long as XL owns at least $50.0 million
--------  -------  -------
principal amount of Debentures, XL will be deemed to own a majority of the
Registrable Securities.

               (y)  "Restructuring" shall have the meaning assigned thereto in
                     -------------
the Securities Purchase Agreement.


               (z)  "RHINOS Debenture Holder" shall have the meaning set forth
                     -----------------------
in the preamble to this Agreement.


               (aa) "RHINOS Debentures" shall have the meaning assigned thereto
                     -----------------
in the Securities Purchase Agreement.


               (bb) "Rule 144" shall mean Rule 144 promulgated under the Act.
                     --------
<PAGE>

                                      -5-

               (cc) "SEC" shall mean the Securities and Exchange Commission.
                     ---

               (dd) "Securities Purchase Agreement" shall have the meaning set
                     -----------------------------
forth in the Recitals to this Agreement.


               (ee) "Voting Preferred Stock" shall have the meaning set forth
                     ----------------------
in the Securities Purchase Agreement.


               (ff) "XL" shall have the meaning set forth in the preamble to
                     --
this Agreement.

          1.1  Other Definitions
<TABLE>
<CAPTION>
                                                                                             Defined
        Term                                                                                 in Section
        ----                                                                                 ----------
        <S>                                                                                  <C>
        "Company Demand Registration"......................................................  Section 2.1(a)
         ---------------------------
        "Indemnified Party"................................................................  Section 2.7(a)
         -----------------
        "Indemnified Person(s)"............................................................  Section 2.7(b)
         ---------------------
        "Indenture"........................................................................  Section 3
         ---------
        "Initiating Holders"...............................................................  Section 2.1(d)
         ------------------
        "Newco Demand Registration"........................................................  Section 2.1(b)
         -------------------------
        "selling security holder"..........................................................  Section 2.6
         -----------------------
        "Violation"........................................................................  Section 2.7(a)
         ---------
</TABLE>

Other capitalized terms used herein and not otherwise defined herein shall have
the meanings given to such terms in the Securities Purchase Agreement.

         2.    Registration Rights.  The Company and Newco, jointly and
severally, covenant and agree as follows:
<PAGE>

                                      -6-

         2.1   Demand Registrations.


               (a)  Holders of MRM Debentures/Company Shares. The Holders of (i)
                    ----------------------------------------
at least $10.0 million in principal amount of MRM Debentures or (ii) at least
9.0% of the then outstanding Company Shares shall have the right at any time to
make a written request of the Company to register and, upon the receipt of such
written request, the Company shall register under the Act the number or
aggregate principal amount, as applicable, of Registrable Securities which are
the subject of such request (each, a "Company Demand Registration").
                                      ---------------------------

               (b)  Holders of Debentures/Newco Shares. (i) The Holders of at
least 20% of the outstanding Registrable Securities (other than Company Shares)
shall have the right, with the prior written consent of XL (so long as XL owns
at least 20% of the outstanding Registrable Securities (other than Company
Shares) at such time), at any time to make a written request of Newco to
register and, upon receipt of such written request, Newco shall register under
the Act the number of Newco Shares that are the subject of such request or that
are issuable upon exchange of the Debentures that are the subject of such
request (each, a "Newco Demand Registration").
                  -------------------------

               (ii) The Holders of at least 20% of the outstanding Registrable
Securities (other than Company Shares) may also require, with the prior written
consent of XL (so long as XL owns at least 20% of the outstanding Registrable
Securities (other than Company Shares) at such time), the Company to distribute
up to 20% of the Common Stock of Newco owned by the Company to the holders of
Common Stock of the Company in order to create a liquid trading market for such
Common Stock of Newco.

               (c)  (i) In connection with a Company Demand Registration made
pursuant to Section 2.1(a), the Company shall:

               (A)  within ten (10) days of the receipt thereof, give written
     notice of such request to all Holders of Company Securities; and

               (B)  file as soon as practicable, and in any event within ninety
     (90) days of the receipt of such request, a registration statement under
     the Act covering all Company Securities constituting Registrable Securities
     (subject to the limitations of Section 2.1(d) and subject to the provisions
     of Section 2.6), which the Holders of the ap-
<PAGE>

                                      -7-

     plicable Company Security request to be registered, within twenty (20) days
     of the mailing of such notice by the Issuer in accordance with Section 4.6.

               (ii) In connection with a Newco Demand Registration made
pursuant to Section 2.1(b), Newco shall:

               (A)  within ten (10) days of the receipt thereof, give written
         notice of such request to all Holders of Newco Securities; and

               (B)  file as soon as practicable, and in any event within ninety
         (90) days of the receipt of such request, a registration statement
         under the Act covering all Newco Securities constituting Registrable
         Securities (subject to the limitations of Section 2.1(d) and subject to
         the provisions of Section 2.6), which the Holders of the applicable
         Newco Security request to be registered; within twenty (20) days of the
         mailing of such notice by the Issuer in accordance with Section 4.6.

               (d)  If the Holders initiating a registration request pursuant to
Section 2.1(a) and (b) (any such Holders, the "Initiating Holders") intend to
                                               ------------------
distribute the applicable Registrable Securities covered by their request by
means of an underwriting, they shall so advise the applicable Issuer as a part
of their request made pursuant to Section 2.1(a) or (b), as the case may be, and
such Issuer shall include such information in the applicable written notice
referred to in Section 2.1(c)(i)(A) or 2.1(c)(ii)(A). The managing underwriter
will be selected by the majority in interest of the Initiating Holders and shall
be reasonably acceptable to the applicable Issuer, or, if such Initiating
Holders so direct, the applicable Issuer shall select the managing underwriter,
which shall be reasonably acceptable to the Initiating Holders. In any such
event, the right of any Holder to include such Holder's Registrable Securities
in such registration shall be conditioned upon such Holder's participation in
such underwriting and the inclusion of such Holder's Registrable Securities in
the underwriting (unless otherwise mutually agreed by a majority in interest of
the Initiating Holders and such Holder) to the extent provided herein. All
Holders proposing to distribute their securities through such underwriting shall
enter into an underwriting agreement, a custody agreement and a power of
attorney, each in customary form with the underwriter or underwriters selected
for such underwriting and deliver an opinion of counsel in customary form to
such underwriter or underwriters.

               (e)  Notwithstanding the foregoing, if the applicable Issuer
shall furnish to Holders requesting a registration statement pursuant to this
Section 2.1 a certificate signed by the president or chief executive officer of
the applicable Issuer stating that in the good faith
<PAGE>

                                      -8-

judgment of its board of directors it would be materially adverse to such Issuer
and its security holders for such registration statement to be filed at that
time and it is therefore essential to defer the filing of such registration
statement, or the filing of such registration statement would materially
interfere with or otherwise adversely affect in any material respect any
financing, acquisition, corporate reorganization or other material transaction
or development involving such Issuer, such Issuer shall have the right to defer
such filing for a period of not more than 90 days after receipt of the request
of the Initiating Holders; provided, however, that each Issuer may utilize this
                           --------  -------
right no more than once in any twelve-month period.

               (f)  Notwithstanding anything else in this Agreement to the
contrary, neither Issuer shall be obligated to effect, or to take any action to
effect, any Demand Registration pursuant to this Section 2.1 for an Initiating
Holder (other than an Initiating Holder that (x) holds at least $15.0 million in
principal amount of Debentures or 13.0% of the then outstanding Company Shares
and (y) has not previously initiated a Demand Registration) after the Issuers
have, in the aggregate, effected three (3) Demand Registrations pursuant to this
Section 2.1 and such Demand Registrations have been declared or ordered
effective; provided, however, that such registrations remain effective under the
           --------  -------
Act until the earlier of (x) an aggregate of 120 days after the effective date
thereof or (y) the consummation of the distribution by the Holders participating
in such registration of all of the Registrable Securities covered thereby;
provided, further, that a registration shall not constitute a Demand
--------  -------
Registration if (A) after such Demand Registration has become effective such
registration or the related offer, sale or distribution of Registrable
Securities thereunder is interfered with by any stop order, injunction or other
order or requirement of the SEC or other governmental agency or court for any
reason not attributable to the Initiating Holders and such interference is not
thereafter eliminated or (B) the conditions specified in the underwriting
agreement, if any, entered into in connection with such Demand Registration are
not satisfied or waived (other than any conditions, the satisfaction of which is
solely within the control of the selling Holders).

               (g)  A registration will not count as a Demand Registration until
it has become effective (unless the Initiating Holders withdraw the Registrable
Securities or if such failure to become effective results solely from the
failure of the Initiating Holders to fulfill an obligation or satisfy a
condition under this Agreement, in which cases such demand will count as a
Demand Registration unless the Initiating Holders agree to pay all expenses of
such registration (as described in Section 2.5)). Except as provided above, the
Company will pay all expenses in connection with any registration initiated as a
Demand Registration, whether or not it becomes effective.
<PAGE>

                                      -9-

         2.2   Piggyback Registration.


               (a)  Debentures. If either Issuer proposes to register (including
                    ----------
for this purpose a registration effected by the applicable Issuer for security
holders other than the Holders) any debt securities solely for cash, then the
applicable Issuer shall, at such time, promptly give each Holder of Company
Debentures or Newco Debentures, as the case may be, written notice of such
registration setting forth the date on which such Issuer proposes to file such
registration statement (which date shall be no earlier than 20 days from the
date of such notice). Upon the written request of any such Holder given within
twenty (20) days after mailing of such notice by such Issuer in accordance with
Section 4.6, the applicable Issuer shall cause to be registered under the Act
and include in the same registration statement all of the Company Debentures or
Newco Debentures, as the case may be, that each such Holder has requested to be
registered and take any and all other actions reasonably necessary under United
States federal or state laws or otherwise to permit such Holders to effect the
proposed sale or other disposition of the Company Debentures or Newco
Debentures, as the case may be.

               (b)  Company/Newco Shares. If either Issuer proposes to register
                    --------------------
any of its Common Stock or Common Stock Equivalents under the Act in connection
with the public offering of Common Stock or Common Stock Equivalents solely for
cash, then such Issuer shall, at such time, promptly give each Holder of Company
Shares or Newco Shares, as the case may be, written notice of such registration
setting forth the date on which such Issuer proposes to file such registration
statement (which date shall be no earlier than 20 days from the date of such
notice). Upon the written request of any such Holder given within twenty (20)
days after mailing of such notice by such Issuer in accordance with Section 4.6,
such Issuer shall cause to be registered under the Act and include in the same
registration statement all of the Company Shares or Newco Shares, as the case
may be, that each such Holder has requested to be registered and take any and
all other actions reasonably necessary under United States federal or state laws
or otherwise to permit such Holders to effect the proposed sale or other
disposition of the Company Shares or Newco Shares, as the case may be.

          2.3  Obligations of the Issuers. Whenever required under this Section
2 to effect the registration of any Registrable Securities, the applicable
Issuer shall promptly:

               (a)  prepare and file with the SEC a registration statement with
         respect to such Registrable Securities and use its best efforts to
         cause such registration statement to become effective, and keep such
         registration statement effective for a period of up to one hundred
         twenty (120) days or until the distribution contemplated in the
         Registration Statement has been completed; provided, however, that
                                                    --------  -------
         before filing any such
<PAGE>

                                     -10-

         registration statement or amendments thereto, the applicable Issuer
         will furnish to the Holders of Registrable Securities proposed to be
         included in any such registration statement copies of all such
         documents proposed to be filed and afford such Holders a reasonable
         opportunity to comment thereon;

               (b)  prepare and file with the SEC such amendments and
         supplements to such registration statement and the prospectus used in
         connection with such registration statement as may be necessary to
         comply with the provisions of the Act with respect to the disposition
         of all securities covered by such registration statement;

               (c)  furnish to the Holders of Registrable Securities proposed
         to be included in any such registration statement such numbers of
         copies of a prospectus, including a preliminary prospectus, in
         conformity with the requirements of the Act, and such other documents
         as they may reasonably request in order to facilitate the disposition
         of Registrable Securities owned by them;

               (d)  use its best efforts to register and qualify the securities
         covered by such registration statement under the securities or Blue Sky
         laws of such jurisdictions as shall be reasonably requested by the
         Holders; provided, however, that the Issuer shall not be required in
                  --------  -------
         connection therewith or as a condition thereto to qualify to do
         business or to file a general consent to service of process in any such
         jurisdictions;

               (e)  in the event of any underwritten public offering, enter into
         and perform its obligations under an underwriting agreement in usual
         and customary form with the managing underwriter of such offering and,
         in connection therewith, the applicable Issuer shall cooperate with the
         managing underwriter and shall attend such meetings and travel to such
         places to aid in the marketing of such underwritten public offering as
         the underwriters may reasonably request;

               (f)  notify each Holder of Registrable Securities covered by such
         registration statement at any time when a prospectus relating thereto
         is required to be delivered under the Act of the happening of any event
         as a result of which the prospectus included in such registration
         statement, as then in effect, includes an untrue statement of a
         material fact or omits to state a material fact required to be stated
         therein or necessary to make the statements therein not misleading in
         the light of the circumstances then existing;
<PAGE>

                                     -11-

               (g)  use its best efforts to cause all such Registrable
         Securities registered pursuant hereunder to be listed on each
         securities exchange on which similar securities issued by the
         applicable Issuer are then listed;

               (h)  provide a transfer agent and registrar for all Registrable
         Securities registered pursuant hereunder and a CUSIP number for all
         such Registrable Securities, in each case not later than the effective
         date of such registration statement;

               (i)  in the event of an underwritten public offering, use its
         best efforts to obtain, at the request of any Holder requesting
         registration of Registrable Securities pursuant to this Section 2, (i)
         an opinion, dated such date, of the counsel representing the applicable
         Issuer for the purposes of such registration, in form and substance as
         is customarily given to underwriters in an underwritten public
         offering, addressed to the underwriters, if any, and to the Holders
         requesting registration of Registrable Securities and (ii) a letter,
         dated such date, from the independent certified public accountants of
         the applicable Issuer, in form and substance as is customarily given by
         independent certified public accountants to underwriters in an
         underwritten public offering, addressed to the underwriters, if any,
         and to the Holders requesting registration of Registrable Securities;
         and

               (j)  take such other customary and reasonable actions as the
         Holders of a majority of the Registrable Securities to be included in
         such registration statement or the underwriters, if any, reasonably
         request in order to facilitate the distribution of such Registrable
         Securities.

         2.4   Furnish Information. It shall be a condition precedent to the
obligations of the applicable Issuer to take any action pursuant to this Section
2 with respect to the Registrable Securities of any selling Holder that such
Holder shall furnish to such Issuer such information regarding itself, the
Registrable Securities held by it and the intended method of disposition of such
Registrable Securities as shall be reasonably required to effect the
registration of such Holder's Registrable Securities.

         2.5   Expenses of Registration. All expenses (other than underwriting
discounts and commissions) incurred in connection with registrations, filings or
qualifications pursuant to Section 2.1 or 2.2, including (without limitation)
all registration, filing and qualification fees, SEC and state "Blue Sky"
filings, printers' and accounting fees (including the cost of "cold comfort"
letters, if required), fees and disbursements of counsel for the applicable
Issuer
<PAGE>

                                     -12-

and the reasonable fees and disbursements of one counsel for the Holders of
Registrable Securities (selected by the Holders of a majority of Registrable
Securities to be registered) included in each registration made pursuant to this
Agreement shall be borne by such Issuer; provided, however, that such Issuer
                                         --------  -------
shall not be required to pay for any expenses of any registration proceeding
begun pursuant to Section 2.1 if the registration request is subsequently
withdrawn or the registration statement does not become effective, in each case,
in the circumstances described in Section 2.1(g) (in which case all
participating Holders shall severally and proportionately bear such expenses),
unless the Requisite Holders agree to forfeit their right to one (1) demand
registration right pursuant to Section 2.1(g).

         2.6   Underwriting Requirements. (a) In connection with any offering
involving an underwriting of Registrable Securities, such Issuer shall not be
required under Section 2.2 to include any Registrable Securities of a Holder in
such underwriting unless such Holder accepts the terms of the underwriting as
agreed upon between the applicable Issuer and the underwriters; provided,
                                                                --------
however, that under no circumstances will any Holder be obligated to make
-------
representations or provide indemnities except with respect to information
reasonably required to be furnished pursuant to Section 2.4.

         (b)   With respect to a registration pursuant to Section 2.1, if the
total amount of securities, including Registrable Securities, requested by
security holders to be included in such offering exceeds the amount of
securities that the managing underwriters with respect to such registration
determine in their sole discretion is compatible with the success of the
offering, then the applicable Issuer shall be required to include in the
offering only that number of such securities which the managing underwriters
determine in their sole discretion will not jeopardize the success of the
offering (the securities so included to be apportioned pro rata among the
Holders according to the total amount of securities entitled to be included
therein owned by each such Holder or in such other proportions as shall be
mutually agreed to by such Holders); provided, however, that in no event shall
                                     --------  -------
any Registrable Securities proposed to be included in any registration be
excluded from such offering if the securities of any selling security holder
other than a Holder of Registrable Securities or any securities offered by
either Issuer are included.

         (c)   With respect to a registration pursuant to Section 2.2, if the
total amount of securities, including Registrable Securities, requested by
security holders to be included in such offering exceeds the amount of
securities that the managing underwriters with respect to such registration
determine in their sole discretion is compatible with the success of the
offering, then the applicable Issuer shall be required to include in the
offering only that number of such securities which the managing underwriters
determine in their sole discretion
<PAGE>

                                      -13-


will not jeopardize the success of the offering (the securities so included to
be apportioned pro rata among the applicable Issuer and the selling security
holders, including the Registrable Securities, according to the total amount of
securities entitled to be included therein owned by each such selling security
holder or in such other proportions as shall mutually be agreed to by such
selling security holders).

     2.7  Indemnification.  In the event any Registrable Securities are included
in a registration statement under this Section 2:

          (a)  To the extent permitted by law, each Issuer will indemnify and
     hold harmless each selling Holder, and each officer, director, employee,
     affiliate and each person, if any, who controls such Holder within the
     meaning of the Act or the 1934 Act (any of the foregoing persons, an
     "Indemnified Party"), against any losses, claims, damages, or liabilities
      -----------------
     (joint or several) to which they may become subject under the Act, or the
     1934 Act or other federal or state securities law, insofar as such losses,
     claims, damages, or liabilities (or actions in respect thereof) arise out
     of or are based upon any of the following statements, omissions or
     violations (collectively, a "Violation"): (i) any untrue statement or
                                  ---------
     alleged untrue statement of a material fact contained in such registration
     statement, including any preliminary prospectus or final prospectus
     contained therein or any amendments or supplements thereto, (ii) the
     omission or alleged omission to state therein a material fact required to
     be stated therein, or necessary to make the statements therein not
     misleading, or (iii) any violation or alleged violation by the Issuer of
     the Act, the 1934 Act, any state securities law or any rule or regulation
     promulgated under the Act, or the 1934 Act or any state securities law; and
     the applicable Issuer will pay to each Indemnified Party, as incurred, any
     legal or other expenses reasonably incurred by them in connection with
     investigating or defending any such loss, claim, damage, liability, or
     action; provided, however, that the indemnity agreement contained in this
             --------  -------
     Section 2.7(a) shall not apply to amounts paid in settlement of any such
     loss, claim, damage, liability or action if such settlement is effected
     without the consent of the applicable Issuer (which consent shall not be
     unreasonably withheld or delayed). Nor shall any Issuer be liable in any
     such case for any such loss, claim, damage, liability or action to the
     extent that it arises out of or is directly based upon a Violation which
     occurs in reliance upon and in conformity with written information
     reasonably required by Section 2.4 furnished for use in connection with
     such registration by any Indemnified Party, or which results from the
     failure of an Indemnified Party to deliver a final, amended or supplemental
     prospectus furnished an Indemnified Party and required to be delivered if
     the Violation would not have occurred if the delivery had been made.
<PAGE>

                                      -14-

          (b)  To the extent permitted by law, each selling Holder will
     indemnify and hold harmless the applicable Issuer, each of its directors,
     officers, employees and affiliates, and each person, if any, who controls
     the applicable Issuer within the meaning of the Act or the 1934 Act, any
     other Holder selling securities in such registration statement and any
     controlling person of any such other Holder (any of the foregoing persons,
     an "Indemnified Person(s)"), against any losses, claims, damages or
         ---------------------
     liabilities (joint or several) to which any of such Indemnified Persons may
     become subject under the Act, or the 1934 Act or other federal or state
     securities law, insofar as such losses, claims, damages or liabilities (or
     actions in respect thereto) arise out of or are directly based upon any
     Violation, in each case to the extent (and only to the extent) that such
     Violation occurs in reliance upon and in conformity with written
     information reasonably required by Section 2.4 furnished by such Holder for
     use in connection with such registration; and each such Holder will pay, as
     incurred, any legal or other expenses reasonably incurred by any such
     Indemnified Person in connection with investigating or defending any such
     loss, claim, damage, liability, or action; provided, however, that the
                                                --------  -------
     indemnity agreement contained in this Section 2.7(b) shall not apply to
     amounts paid in settlement of any such loss, claim, damage, liability or
     action if such settlement is effected without the consent of the Holder,
     which consent shall not be unreasonably withheld or delayed. Nor shall such
     Holder be liable in any such case for any such loss, claim, damage,
     liability, or action to the extent that it arises out of or is based upon a
     Violation which results from the failure of any Indemnified Person to
     deliver a final, amended or supplemental prospectus furnished to any
     Indemnified Person, and required to be delivered, if the Violation would
     not have occurred if the delivery had been made; provided, however, that in
                                                      --------  -------
     no event shall any indemnity under this Section 2.7(b) exceed the gross
     proceeds from the offering received by such Holder.

          (c)  Promptly after receipt by an indemnified party under this Section
     2.7 of notice of the commencement of any action (including any governmental
     action), such indemnified party will, if a claim in respect thereof is to
     be made against any indemnifying party under this Section 2.7, deliver to
     the indemnifying party a written notice of the commencement thereof and the
     indemnifying party shall have the right to participate in, and, to the
     extent the indemnifying party so desires, jointly with any other
     indemnifying party similarly noticed, to assume the defense thereof with
     counsel mutually and reasonably satisfactory to the parties; provided,
                                                                  --------
     however, that an indemnified party (together with all other indemnified
     -------
     parties which may be represented without conflict by one counsel) shall
     have the right to retain one separate counsel, reasonably acceptable to the
     indemnifying party, with the reasonable fees and expenses of such counsel
     to be paid by the indemnifying party, if representation of such indemnified
     party by the counsel retained by the indemnifying party would be
     inappropriate due to actual or potential differing interests between such
     indemnified party and any other
<PAGE>

                                      -15-

     party represented by such counsel in such proceeding. The failure to
     deliver written notice to the indemnifying party within a reasonable time
     of the commencement of any such action, if prejudicial to its ability to
     defend such action, shall relieve such indemnifying party of any liability
     to the indemnified party under this Section 2.7, but the omission so to
     deliver written notice to the indemnifying party will not relieve the
     indemnifying party of any liability that the indemnifying party may have to
     any indemnified party otherwise under this Section 2.7.

          (d)  If the indemnification provided for in this Section 2.7 is held
     by a court of competent jurisdiction to be unavailable to an indemnified
     party or is insufficient to hold any indemnified party harmless with
     respect to any loss, liability, claim, damage, or expense referred to
     herein, then the indemnifying party, in lieu of indemnifying such
     indemnified party hereunder, shall contribute to the amount paid or payable
     by such indemnified party as a result of such loss, liability, claim,
     damage, or expense in such proportion as is appropriate to reflect the
     relative benefits received by the indemnified party on the one hand and the
     indemnifying party on the other, and the relative fault of the indemnifying
     party on the one hand and of the indemnified party on the other in
     connection with the statements or omissions that resulted in such loss,
     liability, claim, damage, or expense as well as any other relevant
     equitable considerations. The relative fault of the indemnifying party and
     of the indemnified party shall be determined by reference to, among other
     things, whether the untrue or alleged untrue statement of a material fact
     or the omission to state a material fact relates to information supplied by
     the indemnifying party or by the indemnified party and the parties'
     relative intent, knowledge, access to information, and opportunity to
     correct or prevent such statement or omission.

          (e)  Notwithstanding the foregoing, to the extent that the provisions
     on indemnification and contribution contained in the underwriting agreement
     entered into in connection with the underwritten public offering are in
     conflict with the foregoing provisions, the provisions in the underwriting
     agreement shall control; provided, however, that any party hereto who is
                              --------  -------
     adversely affected thereby has consented in writing to such provisions in
     the underwriting agreement.

          (f)  The obligations of the Issuers and the Holders under this Section
     2.7 shall survive the completion of any offering of Registrable Securities
     in a registration statement under this Section 2, and otherwise.
<PAGE>

                                      -16-

     2.8  Termination of Registration Rights. This Agreement (other than the
provisions of Sections 2.7, 2.9, 3, 4.6 and 4.7) shall terminate and be of no
further force and effect on the first date on which no Registrable Securities
are outstanding.

     2.9  "Lock-Up" Agreement. Each Issuer hereby acknowledges and agrees
that for a period of 90 days after any date upon which any Holders have made a
Company Demand Registration and for a period of 180 days after any date upon
which any Holders have made a Newco Demand Registration, it shall not (i) offer,
pledge, announce the intention to sell, sell, contract to sell, sell any option
or contract to purchase, purchase any option or contract to sell, grant any
option, right or warrant to purchase or otherwise transfer or dispose of,
directly or indirectly, in respect of any of its debt securities or capital
stock, or any securities convertible into or exercisable or exchangeable
therefor or (ii) enter into any swap, option, future, forward or other agreement
that transfers, in whole or in part, any of the economic consequences of
ownership of such securities, whether any such transaction described in clause
(i) or (ii) above is to be settled by delivery of such securities, in cash or
otherwise or (iii) file or cause to become effective any registration statement
under the Act other than that related solely to a Demand Registration, in each
case, other than such securities to be sold pursuant to the Securities Purchase
Agreement and other than any securities issued pursuant to an employee benefit
or employee stock option plan of the Issuer.

     3.   Indenture. Upon registration of any Debentures pursuant to this
Agreement, the applicable Issuer will provide a trust indenture (the
"Indenture") with an independent institutional trustee meeting the qualification
requirements under the Trust Indenture Act of 1939, as amended. The Indenture
shall govern the terms of the Debentures so registered and contain terms
substantially identical to the terms of the Debentures so registered.

     4.   Miscellaneous.

     4.1  Amendments; Waivers. The provisions of this Agreement may be modified
or amended, and waivers and consents to the performance and observance of the
terms hereof may be given, only by written instrument executed and delivered by
each of the Company, Newco (if then a signatory) and the Requisite Holders;
provided, however, that any modification or amendment which adversely affects
--------  -------
the rights of any Holder shall require the consent of such Holder unless the
modification or amendment adversely affects the rights of all Holders in the
same manner. The failure at any time to require performance of any provision
hereof shall in no way affect the full right to require such performance at any
time thereafter (unless performance thereof has been waived in accordance with
the terms hereof for all pur-
<PAGE>

                                      -17-

poses and at all times by the party to whom the benefit of such performance is
to be rendered). The waiver by any party to this Agreement of a breach of any
provision hereof shall not be taken or held to be a waiver of any succeeding
breach of such provision or any other provision or as a waiver of the provision
itself.

     4.2  After-Acquired Shares. All provisions of this Agreement shall apply
to all securities and instruments (i) received by a Holder as a dividend on or
other payment made to holders of shares of capital stock of the Company, or (ii)
issued in connection with a split of shares of capital stock of the applicable
Issuer, or as a result of any exchange for or reclassification of shares of
capital stock of the applicable Issuer, or a reorganization, recapitalization
consolidation or merger.

     4.3  Successors and Assigns. This Agreement and all covenants and
agreements contained in this Agreement by or on behalf of the parties hereto
shall bind, and inure to the benefit of, the respective successors and permitted
assigns of the parties hereto.

     4.4  Rights and Obligations of Transferees. If a Holder transfers any or
all of its Registrable Securities to any person in accordance with the terms of
the Debentures and the Securities Purchase Agreement, such person and each
subsequent transferee shall have the same rights hereunder as are given to such
Holder, and shall be subject to the same obligations as are imposed upon such
Holder by the terms hereof (and all references herein to a Holder shall include
such transferee), unless otherwise provided herein. Any such transferee shall
execute and deliver to the applicable Issuer an instrument acknowledging such
transferee's rights and obligations hereunder to be consistent with this Section
4.4.

     4.5  Further Assurances. (a) Subject to the terms and conditions of this
Agreement, each of the parties hereto agrees to use best efforts to take, or
cause to be taken, all action, and to do, or cause to be done, all things
necessary, proper or advisable under applicable legal requirements, to
consummate and make effective the transactions contemplated by this Agreement.

          (b)  If at any time after the closing any further action is necessary
or reasonably desirable to carry out the purposes of this Agreement, the parties
hereto shall take or cause to be taken all such necessary or convenient action
and execute, and deliver and file, or cause to be executed, delivered and filed,
all necessary or convenient documentation.
<PAGE>

                                      -18-

          (c)  Each of the Issuers agrees that after the date of this Agreement,
it shall not grant any Person registration rights other than piggyback
registration rights which are subordinate to the Holders hereunder with respect
to any class of debt or equity security of the Issuers without the consent of
the Requisite Holders, which consent shall not be unreasonably withheld.

     4.6  Notices. All notices or other communications required or permitted
to be given hereunder shall be in writing and shall be delivered by hand or
sent, postage prepaid, by registered, certified or express mail or reputable
overnight courier service and shall be deemed given when so delivered by hand,
or if mailed, three Business Days after mailing (two Business Days in the case
of express mail or overnight courier service), as follows:

          (i)  If to the Company:


               Mutual Risk Management Ltd.
               44 Church Street
               Hamilton HM12
               Bermuda
               Attention:  Chief Executive Officer
               Telephone:  (441) 295-5688
               Facsimile:  (441) 292-1867

          with a copy to:


               Mayer, Brown & Platt
               190 South LaSalle Street
               Chicago, Illinois 60603
               Attention:  Richard W. Shepro
               Telephone:   (312) 782-0600
               Facsimile:   (312) 701-7711
<PAGE>

                                      -19-

          (ii)   If to the Purchasers:


                 XL Insurance Ltd
                 c/o XL Capital Ltd.
                 XL House
                 One Bermudiana Road
                 Hamilton HM 11
                 Bermuda
                 Attention: Paul Giordano
                 Telephone:   (441) 294-7162
                 Facsimile:   (441) 292-5280

                 First Union Merchant Banking 2001, LLC
                 One First Union Center - 12th Floor
                 201 South College Street
                 Charlotte, North Carolina 28288-0732
                 Attention:   Wellford Tabor
                 Telephone:   (704) 374-4540
                 Facsimile:   (704) 374-6711


                 High Ridge Capital Partners II, L.P.
                 105 Rowayton Avenue
                 Rowayton, Connecticut 06853
                 Attention:   James L. Zech
                 Telephone:   (203) 831-0104
                 Facsimile:   (203) 831-0480

                 Century Capital Partners II, L.P.
                 c/o Century Capital Management Inc.
                 One Liberty Square
                 Boston, Massachusetts 02109
                 Attention:   Craig Eisenacher
                 Telephone:   (617) 482-3060
                 Facsimile:   (617) 542-9398


                 Taracay Investors Company
                 104 Wallacks Point
                 Stamford, Connecticut 06902
<PAGE>

                                      -20-

                 Attention:  Robert Clements
                 Telephone:  (203) 862-4343
                 Facsimile:  (203) 625-8366


         (iii)   If to the RHINOS Debenture Holders:


                 Intrepid Funding Master Trust
                 c/o Wilmington Trust Company,
                 as Owner-Trustee
                 Rodney Square North
                 1100 North Market Street
                 Wilmington, Delaware 19890
                 Attention:   Mary Kay Pupillo
                 Telephone:   (302) 651-8558
                 Facsimile:   (302) 651-8882

         4.7   Governing Law; Waiver of Jury Trial. THIS AGREEMENT SHALL BE
GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE INTERNAL LAWS OF THE STATE OF
NEW YORK. ANY DISPUTE UNDER THIS AGREEMENT THAT IS NOT SETTLED BY MUTUAL CONSENT
SHALL BE FINALLY ADJUDICATED BY ANY FEDERAL OR STATE COURT SITTING IN THE CITY,
COUNTY AND STATE OF NEW YORK, AND THE ISSUER CONSENTS TO THE EXCLUSIVE
JURISDICTION OF SUCH COURTS (OR ANY APPELLATE COURT THEREFROM) OVER ANY SUCH
DISPUTE. EACH OF THE COMPANY AND NEWCO HEREBY IRREVOCABLY SUBMITS TO THE
EXCLUSIVE JURISDICTION OF THE FEDERAL AND NEW YORK STATE COURTS LOCATED IN NEW
YORK COUNTY IN CONNECTION WITH ANY SUIT, ACTION OR PROCEEDING RELATED TO THIS
AGREEMENT OR ANY OF THE MATTERS CONTEMPLATED HEREBY, IRREVOCABLY WAIVES ANY
DEFENSE OF LACK OF PERSONAL JURISDICTION AND IRREVOCABLY AGREES THAT ALL CLAIMS
IN RESPECT OF ANY SUIT, ACTION OR PROCEEDING MAY BE HEARD AND DETERMINED IN ANY
SUCH COURT. EACH OF THE COMPANY AND NEWCO IRREVOCABLY WAIVES, TO THE FULLEST
EXTENT IT MAY EFFECTIVELY DO SO UNDER APPLICABLE LAW, ANY OBJECTION WHICH IT MAY
NOW OR HEREAFTER HAVE TO THE LAYING OF VENUE OF ANY SUCH SUIT, ACTION OR
PROCEEDING BROUGHT IN ANY SUCH COURT AND ANY CLAIM THAT ANY SUCH SUIT, ACTION OR
PROCEEDING BROUGHT IN ANY SUCH COURT HAS BEEN BROUGHT IN AN INCONVENIENT FORUM.
<PAGE>

                                      -21-

         4.8   Severability; Interpretation. If any provision in this Agreement
is agreed by the parties hereto to be, is deemed to be or becomes invalid,
illegal, void or unenforceable under any law that is applicable hereto, (i) such
provision will be deemed amended to conform to applicable laws so as to be valid
and enforceable or, if it cannot be so amended without materially altering the
intention of the parties hereto, it will be deleted, with effect from the date
of such agreement or such earlier date as the parties hereto may agree, and (ii)
the validity, legality and enforceability of the remaining provisions of this
Agreement shall not be impaired or affected in any way.

         4.9   Table of Contents; Headings. The table of contents and section
headings herein are for convenience only and shall not affect the construction
hereof.

         4.10  Entire Agreement. This Agreement constitutes the entire agreement
among the parties hereto relating to the subject matter hereof and supersedes
any and all prior oral or written agreements, representations or warranties,
contracts, understandings, correspondence, conversations and memoranda, whether
written or oral, between the parties hereto, or between or among any agents,
representatives, parents, subsidiaries, affiliates, predecessors in interest or
successors in interest, with respect to the subject matter hereof.

         4.11  Counterparts. This Agreement may be executed in one or more
counterparts, all of which shall be considered one and the same agreement, and
shall become effective when one or more such counterparts have been signed by
each of the parties other than Newco and delivered to the other party.

         4.12  No Third-Party Beneficiaries. This Agreement is intended for the
benefit of the parties hereto and the Holders and is not intended to confer any
benefit upon any other person or entity or infringe upon any rights or remedies,
except as contemplated in this Section 4.

         4.13  Execution by Newco. Promptly after the formation of Newco, the
Company will cause Newco to execute and deliver a counterpart to this Agreement
by signing in the space provided on the signature page hereof, pursuant to which
Newco shall, by so executing this Agreement, become a party to this Agreement as
if Newco were an original party hereto and upon which this Agreement shall
constitute a valid and binding agreement of Newco, enforceable in accordance
with its terms.
<PAGE>

                                      -22-


                           [Signature Pages Follow]
<PAGE>

                                      -23-



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

                                          MUTUAL RISK MANAGEMENT LTD.




                                          By:  /s/ Elizabeth B. Price
                                              ---------------------------------
                                              Name:  Elizabeth B. Price
                                              Title: Secretary




                                          XL INSURANCE LTD



                                          By:  /s/ Clive Tobin
                                              ---------------------------------
                                              Name:  Clive Tobin
                                              Title: President & Chief Executive
                                                     Officer



                                          FIRST UNION MERCHANT BANKING 2001,
                                          LLC




                                          By:  /s/ Frederick W. Eubank, II
                                              ---------------------------------
                                              Name:  Frederick W. Eubank, II
                                              Title: Partner

<PAGE>

                                      -24-

                              HIGH RIDGE CAPITAL PARTNERS II, L.P.




                              By: /s/ Steve Tynan
                                  --------------------------------
                                  Name:  Steve Tynan
                                  Title: President, Liberty Street Corp.,
                                         as general partner of Liberty Street
                                                Partners, LP,
                                         as member of High Ridge GP II LLC,
                                         as general partner of High Ridge
                                              Capital Partners II, L.P.

                              CENTURY CAPITAL PARTNERS II, L.P.
                              By:  CCP CAPITAL II LLC, its general partner




                              By:  /s/ Craig Eisenacher
                                  --------------------------------
                                  Name:   Craig Eisenacher
                                  Title:  Managing Member


                               /s/ Robert A. Mulderig
                              -------------------------------------
                              Robert A. Mulderig


                              TARACAY INVESTORS COMPANY




                              By:  /s/ Robert Clements
                                  --------------------------------
                                  Name:  Robert Clements
                                  Title:
<PAGE>

                                      -25-


                             INTREPID FUNDING MASTER TRUST




                             By: /s/ Mary Kay Pupillo
                                 --------------------------------
                                 Name:  Mary Kay Pupillo
                                 Title: Senior Financial Services Officer