<PAGE>

                                                                   EXHIBIT 10.10

                                PLEDGE AGREEMENT

         This PLEDGE AGREEMENT (this "Agreement") is made and entered into as of
July 31, 2002, by and between WellCare Holdings, LLC, a Delaware limited
liability company ("Holdings"), and Kiran C. Patel, as Stockholder
Representative on behalf of the Stockholders ("Stockholder Representative").

                                    RECITALS

         A.       Pursuant to that certain Purchase Agreement, dated as of May
17, 2002 (the "Purchase Agreement"), by and among WellCare Acquisition Company,
a Delaware corporation and a wholly-owned subsidiary of Holdings ("Buyer"); Well
Care HMO, Inc., Florida corporation, HealthEase of Florida, Inc., a Florida
corporation, Comprehensive Health Management, Inc., a Florida corporation, and
Comprehensive Health Management of Florida, L.C., a Florida limited liability
company (collectively, the "Companies"); and the holders of common stock and/or
other equity securities of the Companies, Buyer is acquiring, on the date
hereof, all of the outstanding Equity Securities of the Companies.

         B.       As partial consideration for the acquisition by Buyer of the
outstanding Equity Securities of the Companies, Buyer is issuing to Stockholder
Representative, on the date hereof, that certain Promissory Note of even date
herewith in the original principal amount of $53,000,000 (the "Note").

         C.       As security for the obligations of Buyer under the Note,
Holdings has agreed to pledge to Stockholder Representative the Pledged Shares
(as defined below), on the terms and subject to the conditions set forth in this
Agreement.

         D.       Holdings acknowledges that it will benefit from the financing
evidenced by the Note, and that such benefits constitute adequate consideration
for the pledge of the Pledged Shares.

         NOW, THEREFORE, in consideration of the covenants, promises,
representations and warranties set forth herein, and for other good and valuable
consideration (the receipt and sufficiency of which are hereby acknowledged by
the parties), intending to be legally bound hereby, the parties agree as
follows:

         1.       Definitions; Interpretation.

                  (a)      All capitalized terms used in this Agreement and not
otherwise defined herein shall have the meanings assigned to them in the
Purchase Agreement or the Note, as applicable.

                  (b)      As used in this Agreement, the following terms shall
have the following meanings:

                  "Obligations" means the indebtedness of Buyer to Stockholder
Representative under the Note including, without limitation, all unpaid
principal of the Note and all interest

<PAGE>

accrued thereon, together with reasonable attorneys' fees, court costs and
expenses arising out of the collection of any amounts due under the Note and the
enforcement of the Note and this Agreement.

                  "Pledged Shares" means (i) until the payment of the First
Payment Amount (as finally determined pursuant to the Note and Exhibit A of the
Purchase Agreement), all of the issued and outstanding capital stock of Buyer,
(ii) after the payment of the First Payment Amount (as finally determined
pursuant to the Note and Exhibit A of the Purchase Agreement) and until the
payment of the Second Payment Amount (as finally determined pursuant to the Note
and Exhibit A of the Purchase Agreement), 70% of the issued and outstanding
capital stock of Buyer, and (iii) from and after the payment of the Second
Payment Amount (as finally determined pursuant to the Note and Exhibit A of the
Purchase Agreement) and continuing until the termination of this Agreement
pursuant to Section 19,51% of the issued and outstanding capital stock of Buyer.

                  "UCC" means the Uniform Commercial Code as the same may, from
time to time, be in effect in the State of New York.

                  (c)      Where applicable and except as otherwise defined
herein, terms used in this Agreement shall have the meanings assigned to them in
the UCC.

                  (d)      In this Agreement, (i) the meaning of defined terms
shall be equally applicable to both the singular and plural forms of the terms
defined; and (ii) the headings are for convenience of reference only and shall
not affect the construction of this Agreement.

         2.       Security Interest.

                  (a)      As security for the payment and performance of the
Obligations, Holdings hereby pledges to Stockholder Representative, and hereby
grants to Stockholder Representative a security interest in, all of Holdings'
right, title and interest in, to and under the Pledged Shares and any
certificates and instruments now or hereafter representing the Pledged Shares.

                  (b)      Holdings hereby agrees to deliver to National City
Bank, a national banking association, as escrow agent (the "Escrow Agent"), the
certificates representing the Pledged Shares, which shall be in suitable form
for transfer by delivery, or shall be accompanied by duly executed instruments
of transfer or assignment in blank, to be held in escrow pursuant to that
certain Escrow Agreement of even date herewith (the "Escrow Agreement") by and
among Holdings, Stockholder Representative and the Escrow Agent. The Escrow
Agent shall hold the Pledged Shares in escrow, pursuant to the terms of the
Escrow Agreement, until the termination of this Agreement in accordance with
Section 19, and upon such termination the Escrow Agent shall promptly return all
of the Pledged Shares to Holdings. Upon the delivery of a certificate (a
"Default Notice") from the Stockholder Representative to the Escrow Agent (with
a copy to Holdings and Buyer) certifying that an "Effective Default" has
occurred, the Escrow Agent, pursuant to the terms of the Escrow Agreement, shall
deliver the Pledged Shares to the Stockholder Representative, and the
Stockholder Representative shall have the rights set forth in Section 5(b). An
"Effective Default" shall occur when: (i) an Event of Default (as defined in the
Note) shall have occurred and is continuing; and (ii) either (a) such "Event of
Default" arose

                                        2
<PAGE>

under either subparagraphs (iii) or (iv) of the definition of "Event of Default"
under the Note, (b) a court of competent jurisdiction has entered a final order
or judgment (a copy of which shall be included with the Default Notice) to the
effect that an "Event of Default" has occurred under the Note, or (c) the Buyer
has delivered a certificate executed by it, or the Independent Accountants have
issued a written report, setting forth the applicable Purchase Price Adjustment
(which shall have become final and binding) (a copy of which shall be included
with the Default Notice), in either case that results in a Payment Amount (as
defined in the Note) being due, and Buyer shall not have paid such amount when
due (or within any applicable cure period) in accordance with the terms of the
Note.

                  (c)      Holdings shall execute and deliver to Stockholder
Representative concurrently with the execution of this Agreement, and Holdings
hereby authorizes Stockholder Representative to file (with or without Holdings'
signature), at any time and from time to time thereafter, all financing
statements, assignments, continuation financing statements, termination
statements, and other documents and instruments, in form reasonably satisfactory
to Stockholder Representative, and take all other action, as Stockholder
Representative may reasonably request, to effect a transfer of a security
interest in and pledge of the Pledged Shares to Stockholder Representative
pursuant to the UCC and to continue perfected, maintain the priority of or
provide notice of the security interest of Stockholder Representative in the
Pledged Shares and to accomplish the purposes of this Agreement.

                  (d)      Holdings agrees that this Agreement shall create a
continuing security interest in and pledge of the Pledged Shares which shall
remain in effect until terminated in accordance with Section 19, provided,
however, that Stockholder Representative shall not foreclose on its interest in
the Pledged Shares except in compliance with this Agreement and the Escrow
Agreement. Holdings agrees that the Pledged Shares shall be deemed subject to
the possession of Stockholder Representative for all purposes under the Escrow
Agreement and for purposes of perfecting Stockholder Representative's security
interest in the Pledged Shares.

                  (e)      Upon payment of the First Payment Amount and the
Second Payment Amount (as finally determined pursuant to the Note and Exhibit A
of the Purchase Agreement), the security interests created under this Agreement
with respect to the capital stock of Buyer which no longer constitute Pledged
Shares as of such dates pursuant to the definition of "Pledged Shares" herein
(such shares of capital stock, the "Released Shares") shall automatically
terminate and Stockholder Representative or the Escrow Agent (pursuant to the
terms of the Escrow Agreement) shall promptly (and in any event within three
Business Days) redeliver to Holdings any and all certificates representing the
Released Shares, which shall be in suitable form for transfer by delivery, or
shall be accompanied by duly executed instruments of transfer or assignment in
blank, all in form and substance satisfactory to Holdings, and shall execute and
deliver to Holdings such documents and instruments reasonably requested by
Holdings as shall be necessary to effect the transfer to Holdings of the
Released Shares or to evidence termination of all security interests given by
Holdings to Stockholder Representative hereunder with respect to the Released
Shares.

                                        3
<PAGE>

         3.       Warranties. Holdings warrants to Stockholder Representative,
as of the date hereof and until the termination of this Agreement pursuant to
Section 19, that:

                  (a)      Holdings is the sole legal and equitable owner of the
Pledged Shares, and Holdings' absolute title thereto is not the subject of any
claim or challenge threatened or asserted by any third party.

                  (b)      The Pledged Shares are not subject to any restriction
of transfer, "buy-sell" agreement, voting agreement, redemption agreement,
option or other agreement, other than this Agreement.

                  (c)      This Agreement provides Stockholder Representative
with a valid pledge of, and a valid first priority security interest in, the
Pledged Shares.

         4.       Covenants. So long as any of the Obligations remain
unsatisfied, Holdings agrees that:

                  (a)      Holdings shall give prompt written notice to
Stockholder Representative (and in any event not later than 30 days following
any change described below in this subsection) of: (i) any change in the
location of Holdings' chief executive office or principal place of business,
(ii) any change in the location of books and records pertaining to Pledged
Shares; (iii) any change in Holdings' name, (iv) any changes in its identity or
structure in any manner which might make any financing statement filed hereunder
incorrect or misleading; (v) any change in its registration as an organization
(or any new such registration); and (vi) any change in its jurisdiction of
organization.

                  (b)      Holdings will not surrender or lose possession of
(other than to Stockholder Representative or, with the prior consent of
Stockholder Representative, to the Escrow Agent or other depositary or financial
intermediary), exchange, sell, convey, transfer, assign or otherwise dispose of
or transfer the Pledged Shares or any right, title or interest therein.

                  (c)      Holdings shall cause Buyer to refrain from issuing to
any person (other than Holdings) any shares of Buyer's capital stock or any
rights, options or warrants to acquire such stock, or any securities convertible
into stock; provided, however, that Buyer may, after the payment of the First
Payment Amount (as finally determined pursuant to the Note and Exhibit A of the
Purchase Agreement), issue shares of stock and/or convertible securities so long
as the Pledged Shares continue to represent the then-applicable requisite
percentage of the issued and outstanding capital stock of Buyer set forth in the
definition of "Pledged Shares."

                  (d)      Holdings shall deliver to Escrow Agent any stock of
Buyer received as a result of ownership of the Pledged Shares immediately upon
receipt, and any such additional stock shall become Pledged Shares hereunder
upon issuance, to the extent necessary such that the Pledged Shares continue to
represent the then-applicable requisite percentage of the issued and outstanding
capital stock of Buyer set forth in the definition of "Pledged Shares."

                                        4
<PAGE>

         5.       Administration of the Pledged Shares.

                  (a)      Until the occurrence of an Effective Default: (i)
Holdings shall be entitled to receive and retain for its own account any cash
dividend in respect of the Pledged Shares (subject to the terms of the Note);
(ii) Holdings shall have the right to vote the Pledged Shares in its sole and
absolute discretion, and shall retain the power to control the direction,
management and policies of Buyer to the same extent as if the Pledged Shares
were not pledged to Stockholder Representative pursuant to this Agreement; (iii)
Holdings shall be the stockholder of record with respect to the Pledged Shares
on the books and records of Buyer and shall retain all incidents, rights and
benefits of the Pledged Shares as if the Pledged Shares were not pledged to
Stockholder Representative pursuant to this Agreement, and none of such
incidents, rights or benefits shall be exercised by the Stockholder
Representative; and (iv) Holdings shall retain and enjoy all title, ownership
and privilege embodied in the Pledged Shares as if the Pledged Shares were not
pledged to Stockholder Representative pursuant to this Agreement, and none of
such title, ownership or privilege shall be exercised or disturbed by
Stockholder Representative. Stockholder Representative shall execute and deliver
(or cause to be executed and delivered) to Holdings all such proxies and other
instruments as Holdings may reasonably request for the purpose of enabling
Holdings to exercise the voting and other rights which it is entitled to
exercise, to receive distributions which it is authorized to receive and retain,
and to exercise all other rights provided herein to the full extent contemplated
by this Section 5(a).

                  (b)      From and after the occurrence of an Effective
Default, then for so long as such Effective Default shall remain uncured or
shall be continuing: (i) Stockholder Representative shall be entitled to receive
all distributions and payments of any nature with respect to the Pledged Shares,
to be held by Stockholder Representative as part of the Pledged Shares; (ii)
Stockholder Representative shall have the right following prior written notice
to Holdings to vote or consent to take any action with respect to the Pledged
Shares and exercise all rights of conversion, exchange, subscription or any
other rights, privileges or options pertaining to the Pledged Shares as if
Stockholder Representative were the absolute owner thereof; (iii) subject to the
terms of the Escrow Agreement, Stockholder Representative shall have the right,
for and in the name, place and stead of Holdings, to execute endorsements,
assignments or other instruments of conveyance or transfer with respect to all
or any of the Pledged Shares, to endorse any checks, drafts, money orders and
other instruments relating thereto, to sue for, collect, receive and give
acquittance for all moneys due or to become due in connection with the Pledged
Shares and otherwise to file any claims, take any action or institute, defend,
settle or adjust any actions, suits or proceedings with respect to the Pledged
Shares, execute any and all such other documents and instruments, and do any and
all such acts and things, as Stockholder Representative may reasonably deem
necessary or desirable to protect, collect, realize upon and preserve the
Pledged Shares, to enforce Stockholder Representative's rights with respect to
the Pledged Shares and to accomplish the purposes of this Agreement; and (iv)
Stockholder Representative may, upon thirty (30) days' notice to Holdings, sell
the Pledged Shares or any part thereof at public or private sale or at any
appropriate broker's board or securities exchange, for cash, credit or future
delivery. In any such sale:

                           (A)      Stockholder Representative may be the
purchaser of any or all of the Pledged Shares sold at any public sale, or, to
the extent permitted by law, at any private sale.

                                        5
<PAGE>

                           (B)      At or prior to any sale of the Pledged
Shares, Stockholder Representative may, in its sole discretion, restrict
prospective purchasers to persons who will represent that they will purchase for
their own account for investment and not with view to the distribution or sale
of any of the Pledged Shares and who will agree that the Pledged Shares so
purchased may bear an appropriate restrictive legend.

                           (C)      At or prior to any sale, Stockholder
Representative may, in its sole discretion, require that prospective purchasers
establish, to Stockholder Representative's satisfaction, that they are investors
of sufficient financial means or business acumen to qualify as "accredited
investors" under federal and state securities laws.

                           (D)      At any sale, Stockholder Representative
shall have the right to transfer to the purchaser thereof the Pledged Shares
sold. Stockholder Representative is hereby appointed Holdings' attorney-in-fact
for the purpose of supplying any endorsements necessary to effect such transfer.
Each purchaser at any such sale (including, without limitation, Stockholder
Representative) shall hold the property sold free from any claim or right of any
kind, including any equity or rights or redemption of Holdings, which hereby
specifically waives all rights of redemption, stay or appraisal which Holdings
has or may have under any rule of law or statute now existing or hereafter
adopted.

                           (E)      At any sale, the Pledged Shares may be sold
in one lot as an entirety or in separate portions, as Stockholder Representative
may determine.

                           (F)      Stockholder Representative shall not be
obliged to make any sale pursuant to any notice given and may, without notice or
publication, adjourn any public or private sale or cause the same to be
adjourned from time to time by announcement at the time and place fixed for the
sale, and such sale may be resumed at any time and place to which the same may
be so adjourned.

                           (G)      In the case of any sale of all or any part
of the Pledged Shares on credit or for future delivery, payments made by the
purchaser shall reduce the outstanding balance of the Obligations as payments
are received, and the outstanding principal balance of the Obligations shall
continue to accrue interest over the time that such payments are made, until the
principal and accrued interest constituting the Obligations have been paid in
full. Stockholder Representative shall not incur any liability in case of the
failure of such purchaser to completely pay for the Pledged Shares so sold and,
in the case of any such failure, the Pledged Shares may again be sold pursuant
to the provisions hereof.

                  (c)      Distributions and other payments which are received
by Holdings but which it is not entitled to retain as a result of the operation
of Section 5(b) shall be held in trust for the benefit of Stockholder
Representative, be segregated from the other property or funds of Holdings, and
be forthwith paid over or delivered to Stockholder Representative in the same
form as so received.

         6.       Stockholder Representative's Duties. Stockholder
Representative shall have no duty to exercise any of the rights, privileges or
powers afforded to it by virtue of its security interest in the Pledged Shares
and shall not be responsible to Holdings or any other Person for

                                        6
<PAGE>

any failure to do so or delay in doing so. Beyond the exercise of reasonable
care to assure the safe custody of the Pledged Shares if held by the Stockholder
Representative and the accounting for moneys actually received by Stockholder
Representative hereunder, except as specifically provided herein, Stockholder
Representative shall have no duty or liability to exercise or preserve any
rights, privileges or powers pertaining to the Pledged Shares.

         7.       Notices. All notices, requests and other communications
hereunder must be in writing and will be deemed to have been duly given only if
delivered personally against written receipt or by facsimile transmission
against facsimile confirmation or mailed by internationally recognized overnight
courier prepaid, to the parties at the following addresses or facsimile numbers:

         If to Stockholder Representative:      Kiran C. Patel, M.D.
                                                11609 Carrollwood Drive
                                                Tampa, FL 33618

                                                Facsimile No.: (727) 535-6163

         with a copy to:                        Sandip I. Patel, Esq.
                                                1408 North Westshore Boulevard
                                                Suite 611
                                                Tampa, FL 33607

                                                Facsimile No.: (813) 289-8849

         If to Holdings:                        WellCare Holdings, LLC
                                                67 East 11th Street, Suite 318
                                                New York, NY 10003

                                                Attn: Todd S. Farha
                                                Facsimile No.: (212) 388-1659

         with a copy to:                        Brobeck, Phleger & Harrison LLP
                                                2100 Reston Parkway, Suite 203
                                                Reston, VA 20191

                                                Attn: Thaddeus Bereday, Esq.
                                                Facsimile No.: (703) 621-3001

All such notices, requests and other communications will (a) if delivered
personally to the address as provided herein, be deemed given upon delivery, (b)
if delivered by facsimile transmission to the facsimile number as provided
herein, be deemed given upon facsimile confirmation, and (c) if delivered by
overnight courier to the address as provided herein, be deemed given on the
earlier of the first Business Day following the date sent by such overnight
courier or upon receipt (in each case regardless of whether such notice, request
or other communication is received by any other Person to whom a copy of such
notice is to be delivered

                                        7
<PAGE>

pursuant hereto). Either party from time to time may change its address,
facsimile number or other information for the purpose of notices to that party
by giving notice specifying such change to the other party hereto.

         8.       Waiver. Any term or condition of this Agreement may be waived
at any time by the party that is entitled to the benefit thereof, but no such
waiver shall be effective unless set forth in a written instrument duly executed
by or on behalf of the party waiving such term or condition. No waiver by any
party of any term or condition of this Agreement, in any one or more instances,
shall be deemed to be or construed as a waiver of the same or any other term or
condition of this Agreement on any future occasion. All remedies, either under
this Agreement or by law or otherwise afforded, will be cumulative and not
alternative.

         9.       Costs and Expenses. Buyer shall reimburse Stockholder
Representative for all reasonable costs and expenses incurred by Stockholder
Representative, including the reasonable fees and disbursements of one counsel
to Stockholder Representative, in connection with the enforcement of this
Agreement and the Note at any time during the continuance of an Event of Default
(as finally determined pursuant to the Note), including in any out-of-court
workout or other refinancing or restructuring or in any bankruptcy case, and the
protection, sale or collection of, or other realization upon, any of the Pledged
Shares.

         10.      No Assignment; Binding Effect. Neither this Agreement nor any
right, interest or obligation hereunder may be assigned (by operation of law or
otherwise) by either party without the prior written consent of the other party
and any attempt to do so will be void. Subject to the preceding sentence, this
Agreement is binding upon, inures to the benefit of and is enforceable by the
parties hereto and their respective successors and assigns.

         11.      Governing Law. This Agreement shall be governed by, and
construed in accordance with, the law of the State of New York, except as
required by mandatory provisions of law and to the extent the validity or
perfection of the security interests hereunder, or the remedies hereunder, in
respect of any Pledged Shares are governed by the law of a jurisdiction other
than New York.

         12.      Cumulative Remedies. The remedies provided to the parties in
this Agreement are not exclusive of any other remedies that may be available
under any other document or at law or equity.

         13.      Jurisdiction; Venue. All actions and proceedings arising out
of or relating to this Agreement shall be heard and determined in any New York
state or federal court sitting in the City of New York, and each party hereby
irrevocably accepts and consents to the exclusive personal jurisdiction of those
courts for such purpose. In addition, each party hereby irrevocably waives, to
the fullest extent permitted by law, any objection which it may now or hereafter
have to the laying of venue of any action or proceeding arising out of or
relating to this Agreement or any judgment entered by any court in respect
thereof brought in any state or federal court sitting in the city of New York
and further irrevocably waives any claim that any action or proceeding brought
in any such court has been brought in an inconvenient forum.

                                        8
<PAGE>

         14.      Waiver of Trial by Jury. IN ANY ACTION OR PROCEEDING ARISING
HEREFROM, THE PARTIES HERETO CONSENT TO TRIAL WITHOUT A JURY IN ANY ACTION,
PROCEEDING OR COUNTERCLAIM BROUGHT BY ANY PARTY HERETO AGAINST THE OTHER OR
THEIR SUCCESSORS IN RESPECT OF ANY MATTER ARISING OUT OF OR IN CONNECTION WITH
THIS AGREEMENT, REGARDLESS OF THE FORM OF ACTION OR PROCEEDING.

         15.      Entire Agreement; Modification. This Agreement, the Note and
the Escrow Agreement constitute the entire agreement of the parties with respect
to the subject matter hereof and supersedes all prior agreements and
understandings, both written and oral, between the parties with respect to the
subject matter hereof. This Agreement may be amended or modified only by an
instrument in writing duly executed by the parties to this Agreement.

         16.      Third-party Beneficiaries. The terms and provisions of this
Agreement are intended solely for the benefit of each party hereto and their
respective successors or permitted assigns, and it is not the intention of the
parties to confer third-party beneficiary rights, and this Agreement does not
confer any such rights, upon any other Person.

         17.      Severability. Any term or provision of this Agreement that is
invalid, illegal or unenforceable in any situation in any jurisdiction shall not
affect the validity, legality or enforceability of the offending term or
provision in any other situation or in any other jurisdiction. If such
invalidity, illegality or unenforceability is caused by length of time or size
of area, or both, the otherwise invalid provision shall be, without further
action by the parties, automatically amended to such reduced period or area as
would cure such invalidity, illegality or unenforceability; provided, however,
that such amendment shall apply only with respect to the operation of such
provision in the particular jurisdiction in which such determinations is made.

         18.      Counterparts. This Agreement may be executed in any number of
counterparts, each of which will be deemed to be an original, but all of which
taken together shall constitute one and the same agreement.

         19.      Termination. This Agreement and the security interests created
under this Agreement shall terminate on the payment in full of the Note or other
event that results in its cancellation or satisfaction in accordance with its
terms. Upon any such termination of this Agreement, Stockholder Representative
or the Escrow Agent shall promptly (and in any event within three Business Days)
redeliver to Holdings all certificates representing the Pledged Shares, which
shall be in suitable form for transfer by delivery, or shall be accompanied by
duly executed instruments of transfer or assignment in blank, all in form and
substance satisfactory to Holdings, and shall execute and deliver to Holdings
such documents and instruments reasonably requested by Holdings as shall be
necessary to evidence termination of all security interests given by Holdings to
Stockholder Representative hereunder.

                            [SIGNATURE PAGE FOLLOWS]

                                        9
<PAGE>

                  IN WITNESS WHEREOF, Holdings and Stockholder Representative
have executed this Agreement as of the date first written above.

                                      WELLCARE HOLDINGS, LLC

                                      By: /s/ Todd S. Farha
                                          --------------------------------------
                                          Todd S. Farha
                                          President and Chief Executive Officer

                                      KIRAN C. PATEL, M.D., as Stockholder
                                      Representative on behalf of the
                                      Stockholders

                                      /s/ Kiran C. Patel
                                      ------------------------------------------

                                       10