EXHIBIT 10.1

AMENDED AND RESTATED
WINTRUST FINANCIAL CORPORATION
EMPLOYEE STOCK PURCHASE PLAN
1.Purpose
The purpose of the Wintrust Financial Corporation Employee Stock Purchase Plan
is to encourage employee stock ownership, thereby enhancing employee commitment
to Wintrust Financial Corporation (“Wintrust” or the “Corporation”) and
providing an opportunity to share in the Corporation’s success. The Plan is
amended and restated effective as of the date provided in Paragraph 21 hereof,
as set forth herein.
2.Definitions
(a)“Bank” means any banking subsidiary of the Corporation designated by the
Committee with respect to any offering.
(b)“Board” means the Board of Directors of the Corporation.
(c)“Code” means the Internal Revenue Code of 1986, as amended.
(d)“Committee” means the Compensation Committee of the Board or any other
committee designated by the Board to administer this Plan.
(e)“Common Stock” means Common Stock, no par value, of the Corporation.
(f)“Considered Compensation” means compensation as defined by the Committee in
accordance with Section 423 of the Code and applicable regulations, including
total compensation or base compensation for any pay period during or at the
beginning of, an Offering Period.
(g)“Fair Market Value” means the closing price as recorded by the NASDAQ
National Market on the relevant valuation date or if no closing price has been
recorded on such date, on the next preceding day on which such a closing price
was recorded; provided, however, the Committee may specify some other definition
of Fair Market Value.
(h)“Maximum Share Limit” means 364,135 shares of Common Stock.
(i)“Offering Period” means the term of any offering under the Plan as determined
by the Committee which shall be at least three months in duration, but no more
than 26 months in duration.
(j)“Participating Subsidiary” means any subsidiary or affiliate corporation of
Wintrust designated by the Committee if on the first date of the Offering
Period, Wintrust or a subsidiary of Wintrust, individually or collectively, owns
50% or more of the total combined voting power of all classes of stock of such
corporation.
(k)“Plan” means this Wintrust Financial Corporation Employee Stock Purchase
Plan.
(l)“Purchase Date” means the last day of an Offering Period or any other day or
days the Committee may prescribe under Paragraph 8(c)(ii).
(m)“Purchase Savings Account” means that portion of an aggregate account
established with the Bank on behalf all participating employees that is
attributable to a particular participating employee.
(n)“Wintrust” or “Corporation” means Wintrust Financial Corporation, an Illinois
corporation.
The masculine pronoun wherever used herein is deemed to include the feminine,
and the singular shall be deemed to include the plural whenever the context
requires.

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3.Administration
The Plan shall be administered by the Committee. The Committee, by majority
action thereof (whether taken during a meeting or by written consent), is
authorized to interpret the Plan, to prescribe, amend, and rescind rules and
regulations relating to the Plan, to provide for conditions and assurances
deemed necessary or advisable to protect the interests of the Corporation, and
to make all other determinations necessary or advisable for the administration
of the Plan. To the extent deemed necessary or advisable for purposes of Rule
16b-3 under the Securities Exchange Act of 1934, as amended, any member of the
Committee who is not a “non-employee director” under such Rule may abstain or
recuse himself from any action of the Committee, in which case a majority action
of the remaining members shall constitute a majority action of the Committee.
The Committee may employ such agents, attorneys, accountants or any other
persons and delegate to them such powers, rights and duties, as the Committee
may consider necessary to properly carry out the administration of the Plan. The
interpretation and construction by the Committee of any provisions of the Plan
and the terms and conditions of an offering including employee participation
thereunder and any determination by the Committee pursuant to any provision of
the Plan shall be final and conclusive.
4.Offerings Under the Plan
The Committee shall determine whether Wintrust shall make an offering to all of
the then eligible employees, provided, however, that it shall be under no
obligation to do so. In the event of an offering under the Plan, an offering
prospectus, or such other document as may then be required under applicable law,
shall be prepared which outlines the specific terms and conditions of such
offering.
5.Eligibility
All employees of Wintrust or of any Participating Subsidiary shall be eligible
to participate in an offering under the Plan except that the Committee may, with
respect to any offering, exclude from eligibility (i) any employee who normally
works less than 20 (or such lesser number determined by the Committee) hours a
week, (ii) any employee who normally works less than five (or such lesser number
determined by the Committee) months a year, (iii) any employee who, on the first
date of the applicable Offering Period, has not been employed by Wintrust or a
Participating Subsidiary for at least 24 (or such lesser number determined by
the Committee) months immediately prior thereto and (iv) any employee who is a
highly compensated employee (as defined in Section 414(q) of the Code);
provided, however, that the Committee may exclude employees who have completed a
shorter period of service or whose customary employment is for fewer months in a
calendar year than is specified in (i), (ii) or (iii), provided that the
exclusion is applied in an identical manner to all employees who are granted
options under the Plan or offering. In the case of employees of a Participating
Subsidiary who become employed as a result of the acquisition by Wintrust or a
Participating Subsidiary of all or part of the assets or stock of such
employees’ previous employer and the previous employer does not become a
Participating Subsidiary, the Committee may establish a separate “offering”
under this Plan in accordance with Treasury Regulation §1.423-2(a) and each
employee’s employment date will be considered to be the date he was employed by
his previous employer solely for the purpose of applying provision (iii) above,
unless otherwise determined by the Committee.
6.Stock
The shares of Common Stock offered hereunder may be treasury shares, authorized
and unissued shares, shares purchased in the open market (on an exchange or in
negotiated transactions) or any combination thereof. Subject to adjustment in
accordance with the provisions of Paragraph 8(f), the total number of shares of
Common Stock which may be offered shall not exceed the Maximum Share Limit. If
at any time participating employees elect to purchase more than the Maximum
Share Limit, then the number of shares of Common Stock which may be purchased by
each participating employee shall be reduced pro rata.
In the event that an employee’s participation under the Plan for any reason ends
or is terminated and the shares which are subject to option are not purchased,
such unpurchased shares of Common Stock shall again be available for offering
under the Plan.

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7.Number of Shares Which an Employee May Purchase
Wintrust may grant to each participating employee, on a nondiscriminatory basis,
an option to purchase such number of shares of Common Stock with respect to a
given offering as shall have an aggregate purchase price not in excess of the
lesser of (i) 20 percent of such employee’s Considered Compensation determined
on the first date of the Offering Period or (ii) $50,000 or (iii) such lesser
amount as the Committee may determine as of the first date of the Offering
Period.
Alternatively, Wintrust may grant to each participating employee, on a
nondiscriminatory basis, an option to purchase a fixed or maximum number of
shares of Common Stock determined on the first date of the Offering Period,
provided that the aggregate purchase price must comply with limitations set
forth in the preceding sentence.
Notwithstanding the foregoing provisions of this Plan, no employee may
participate in an offering under the Plan (i) if such participation would permit
the employee to purchase shares of Common Stock under all the employee stock
purchase plans of Wintrust and its Participating Subsidiaries qualified under
Section 423 of the Code at a rate which exceeds $25,000 in fair market value of
such shares for each calendar year during which an option granted to the
employee under the Plan is outstanding (determined based on the fair market
value of the stock at the time the option was granted), or (ii) if such
employee, immediately after his participation commences, owns stock possessing
five percent or more of the total combined voting power or value of all classes
of stock of Wintrust or any Participating Subsidiary. For such purpose, the
rules of Section 424(d) of the Code, as amended, shall apply in determining the
stock ownership of an employee, and stock which the employee may purchase
pursuant to his participation in the Plan and under all other plans or options
of Wintrust or any Participating Subsidiary shall be treated as stock owned by
the employee.
8.Terms and Conditions of Participation in an Offering Under the Plan
An eligible employee’s participation in an offering under this Plan shall comply
with and be subject to the following:
(a)Purchase Price. The purchase price per share of Common Stock shall be
determined by the Committee at the outset of the offering; provided, however,
the purchase price may not be lower than the lesser of 85 percent of the Fair
Market Value of the shares of Common Stock on the first date of the Offering
Period or 85 percent of the Fair Market Value of the shares of Common Stock on
the Purchase Date.
(b)Purchase Savings Account. A participating employee shall authorize the
withholding from his compensation, throughout the Offering Period, of a dollar
amount or percent of salary per pay period, the maximum of which is subject to
the limits of Paragraph 7 or other lesser limitations set by the Committee.
Withheld amounts will be credited to the employee’s Purchase Savings Account.
Subject to the applicable limitations contained in Paragraph 7 hereof, the
employee shall not be entitled to make any other deposits to his Purchase
Savings Account, unless the Committee so determines, and then, only to the
extent permitted by the Committee and in accordance with Treasury Regulation
§1.423-2. No interest shall accrue at any time for any amount credited to a
Purchase Savings Account.
After the employee’s withholding election has been received and approved by
Wintrust, the employee shall not be entitled change such election during the
Offering Period unless, subject to the applicable limitations contained in
Paragraph 7 hereof, the Committee so determines, and then, only to the extent
permitted by the Committee and in accordance with Treasury Regulation §1.423-2.
Notwithstanding the foregoing, the employee may withdraw funds accumulated in
his Purchase Savings Account at any time, except as the Committee may otherwise
provide. The Bank reserves the right, as a condition of any Purchase Savings
Account, to demand and receive thirty days’ notice, in writing, as a condition
of the withdrawal of any sum or sums whenever such requirement may be deemed
advisable by the Bank, in its discretion.

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(c)Purchase of Shares.
(i)     Subject to earlier purchase pursuant to Paragraphs 8(c)(ii), 8(e) and
8(g) hereof, each employee shall specify on or before the Purchase Date whether
he desires to purchase all, a portion or none of the shares of Common Stock
which he is entitled to purchase as a result of his participation in the
offering. Except as set forth in the next paragraph, if the employee fails to
deliver the notification referred to in this paragraph, such failure shall be
deemed an election by the employee to exercise his right to purchase on the
Purchase Date all of the shares of Common Stock which he is entitled to
purchase.
On the Purchase Date, the Bank shall cause the funds then credited to the
employee’s Purchase Savings Account to be applied to the purchase price of the
shares of Common Stock the employee elected to purchase. Any funds remaining in
the Purchase Savings Account after such purchase will be paid to the employee
and the Purchase Savings Account will be closed; provided, however, any payroll
deductions accumulated in an employee’s Purchase Savings Account which are not
sufficient to purchase a full share of Common Stock shall be retained in the
Purchase Savings Account for the next subsequent Offering Period, subject to
earlier withdrawal by the employee as provided in this Section 8.
(ii)     The Committee may determine that Wintrust shall make an offering which
shall have more than one Purchase Date and, in such case, the Committee shall
establish the dates (each a “Purchase Date”) on which purchases of shares of
Common Stock can or will be made by participating employees during an Offering
Period. The Committee shall set the terms, conditions and other procedures
necessary for the proper administration of such Offering.
(d)Termination of Participation by Employee. An employee who participates in an
offering may at any time on or before the expiration of the Offering Period
terminate participation by written notice of such termination on a form
prescribed by the Committee and delivered to Wintrust. As soon as practicable
thereafter, all funds then credited to his Purchase Savings Account will be paid
to the employee and his Purchase Savings Account will be closed.
(e)Termination of Employment. In the event that a participating employee’s
employment with Wintrust and/or a Participating Subsidiary terminates during the
term of an Offering Period, his participation under the Plan shall terminate
immediately and within a reasonable time thereafter all funds then credited to
his Purchase Savings Account will be paid to the employee. However, if any
termination of employment is for reasons of death, total and permanent
disability, or retirement (as determined by the Committee), then, as of the
earlier of (i) the end of the three month period commencing on the date of his
death, total and permanent disability, or retirement and (ii) the last day of
the Offering Period, the employee (or his estate, personal representative, or
beneficiary) shall have the right to elect to purchase all or fewer than all of
the shares of Common Stock which he is entitled to purchase or to receive the
proceeds of his Purchase Savings Account in cash.
(f)Recapitalization. The aggregate number of shares of Common Stock which may be
offered under the Plan, the number of shares of Common Stock which each employee
is entitled to purchase as a result of his participation in an offering and the
purchase price per share for each such offering shall all be proportionately
adjusted for any increase or decrease in the number of issued shares of Common
Stock resulting from a subdivision or consolidation of shares or other capital
adjustment, or the payment of a stock dividend, or other increase or decrease in
such shares of Common Stock, effected without receipt of consideration by
Wintrust; provided, however, that any fractional shares of Common Stock
resulting from any such adjustment shall be eliminated.
Subject to any required action by stockholders, if Wintrust shall be the
surviving or resulting corporation in any merger or consolidation, excluding for
this purpose a merger or consolidation which, or the approval of which by the
stockholders of Wintrust, constitutes a Change of Control (and, thus, the
consequences of which are otherwise provided for in Paragraph 8(g) hereof), any
employee’s rights to purchase stock pursuant

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to participation in an offering hereunder shall pertain to and apply to the
shares of stock to which a holder of the number of shares of Common Stock
subject to such rights would have been entitled; but a dissolution or
liquidation of Wintrust or a merger or consolidation in which Wintrust is not
the surviving or resulting corporation, excluding for this purpose a merger or
consolidation which, or the approval of which by the stockholders of Wintrust,
constitutes a Change of Control (and, thus, the consequences of which are
otherwise provided for in Paragraph 8(g) hereof), shall cause all participation
in any offering made under the Plan which is then in effect to terminate, except
that the surviving or resulting corporation may, in its absolute and
uncontrolled discretion, tender an offer to purchase its shares on terms and
conditions both as to the number of shares and otherwise, which will
substantially preserve the rights and benefits of employees participating in an
offering then in effect under the Plan.
In the event of a change in Common Stock which is limited to a change in the
designation thereof to “Capital Stock” or other similar designation, or to a
change in par value thereof, or from par value to no par value, without increase
in the number of issued shares, the shares resulting from any such change shall
be deemed to be Common Stock within the meaning of the Plan.
(g)     Change of Control. Anything in the Plan to the contrary notwithstanding,
the date on which a “Change of Control” (as defined below) occurs shall be
considered to be a Purchase Date with respect to all Offering Periods under the
Plan and each employee who is a participant in the Plan shall thereupon have the
right to purchase all or fewer than all of the shares of Common Stock which he
is entitled to purchase as a result of his participation in the offering with
the funds then credited to his Purchase Savings Account or to be promptly paid
in cash all funds credited to his Purchase Savings Account. For this purpose, a
“Change of Control” shall mean:
(i)The acquisition, other than from the Corporation, by any individual, entity
or group (within the meaning of Section 13(d)(3) or 14(d)(2) of the Securities
Exchange Act of 1934, as amended (the “Exchange Act”)) of beneficial ownership
(within the meaning of Rule 13d-3 promulgated under the Exchange Act) of 50% or
more of either the then outstanding shares of Common Stock of the Corporation or
the combined voting power of the then outstanding voting securities of the
Corporation entitled to vote generally in the election of directors, but
excluding, for this purpose, any such acquisition by the Corporation or any of
its subsidiaries, or any employee benefit plan (or related trust) of the
Corporation or its subsidiaries, or any corporation with respect to which,
following such acquisition, more than 50% of, respectively, the then outstanding
shares of common stock of such corporation and the combined voting power of the
then outstanding voting securities of such corporation entitled to vote
generally in the election of all or substantially all directors is then
beneficially owned, directly or indirectly, by the individuals and entities who
were the beneficial owners, respectively, of the Common Stock and voting
securities of the Corporation immediately prior to such acquisition in
substantially the same proportion as their ownership, immediately prior to such
acquisition, of the then outstanding shares of Common Stock of the Corporation
or the combined voting power of the then outstanding voting securities of the
Corporation entitled to vote generally in the election of directors, as the case
may be; or
(ii)Individuals who, as of the date hereof, constitute the Board (as of the date
hereof the “Incumbent Board”) cease for any reason to constitute at least a
majority of the Board, provided that any individual becoming a director
subsequent to the date hereof whose election, or nomination for election by the
Corporation’s shareholders, was approved by a vote of at least a majority of the
directors then comprising the Incumbent Board shall be considered as though such
individual were a member of the Incumbent Board, but excluding, for this
purpose, any such individual whose initial assumption of office is in connection
with an actual or threatened election contest relating to the election of the
directors of the Corporation (as such terms are used in Rule 14a-11 of
Regulation 14A promulgated under the Exchange Act); or
(iii)The consummation of a reorganization, merger or consolidation of the
Corporation, in each case, with respect to which all or substantially all of the
individuals and entities who were the respective beneficial owners of the Common
Stock and voting securities of the Corporation immediately prior to such
reorganization, merger or consolidation do not, following such reorganization,
merger or consolidation, beneficially own, directly or indirectly, more than 50%
of, respectively, the then outstanding shares of Common Stock and the combined
voting power of the then outstanding voting securities entitled to vote
generally in the election of directors, as the case may be, of the corporation
resulting from such reorganization, merger or consolidation, or a complete
liquidation or dissolution of

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the Corporation or of the sale or other disposition of all or substantially all
of the assets of the Corporation.
(h)Assignability. No Purchase Savings Account, or option to purchase shares of,
Common Stock hereunder shall be assignable, by pledge or otherwise, or
transferable except by will or by the laws of descent and distribution; and no
right of any employee to purchase stock pursuant to an offering made hereunder
shall be subject to any obligation or liability of such employee or have a lien
imposed upon it. During the lifetime of an employee, the shares of Common Stock
which he is entitled to purchase under the Plan may be purchased only by the
employee.
(i)Restrictions on Transferability. If, at the time of the purchase of shares of
Common Stock under the Plan, in the opinion of counsel for Wintrust, it is
necessary or desirable, in order to comply with any applicable laws or
regulations relating to the purchase or sale of securities, that the employee
purchasing such shares shall agree not to purchase or dispose of such shares
otherwise than in compliance with the Securities Act of 1933 or the Exchange
Act, as amended, and the rules and regulations promulgated thereunder, the
employee will, upon the request of Wintrust, execute and deliver to Wintrust an
agreement to such effect.
(j)Rights as Stockholder. An employee who is a participant hereunder shall have
no rights as a stockholder with respect to shares of Common Stock which he is
entitled to purchase under the Plan until the date of the issuance of the shares
of Common Stock to the employee.
(k)Miscellaneous. The terms and conditions of participation under the Plan may
include such other provisions as the Board shall deem advisable, including
without limitation, provisions which may require participants to notify Wintrust
promptly in writing if such participant disposes of stock acquired hereunder
prior to the expiration of applicable holding periods under Section 423 of the
Code.
9.    Conformance With Tax and Securities Laws
The Plan and all offerings under the Plan are intended to comply in all aspects
with Section 423 of the Code (or its successor section) and Rule 16b-3
promulgated under the Exchange Act, as amended from time to time. Should any of
the terms of the Plan or offerings be found not to be in conformity with the
terms of Section 423 or Rule 16b-3, such terms shall be invalid and shall be
omitted from the Plan or the offering but the remaining terms of the Plan shall
not be affected. However, to the extent permitted by law, any provisions which
could be deemed invalid and omitted shall first be construed, interpreted or
revised retroactively to permit this Plan to be construed in compliance with all
applicable laws (including Rule 16b-3) so as to foster the intent of this Plan.
10.Amendments
The Board may alter, amend, suspend or discontinue the Plan or at any time prior
to a Change of Control (as defined in Paragraph 8(g)) alter or amend any and all
terms of participation in an offering made thereunder.
11.Application of Funds
The proceeds received by Wintrust from the sale of Common Stock under the Plan,
except as otherwise provided herein, will be used for general corporate
purposes.
12.No Obligation to Purchase Shares
Participation under the Plan shall impose no obligation upon the employee to
purchase any shares of Common Stock which are the subject of his participation.
13.Withholding
Any amounts to be paid or shares of Common Stock to be delivered by Wintrust
under the Plan shall be reduced to the extent permitted or required under
applicable law by any sums required to be withheld by Wintrust or any
Participating Subsidiary.
14.Governing Law
Except where such laws may be superseded by Federal Law, this Plan and the terms
and conditions of participation in the Plan, shall be construed in accordance
with and governed by the laws of the State of Illinois; provided, however, in
the event the Corporation’s state of incorporation shall be changed, then the
law of such new state of incorporation shall govern.

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15.Regulatory Authorities
Each and every obligation and undertaking of Wintrust hereunder is subject to
the proviso that if at any time the Board determines that the listing,
registration or qualification of the shares covered hereby or by an option
issued hereunder upon any securities exchange or under any state or federal law,
or the consent or approval of any governmental agency or regulatory body, is
necessary or desirable as a condition to or in connection with the grant or
exercise of any option hereunder, such grant or exercise shall be deemed to be
without effect hereunder until such listing, registration, qualification,
consent or approval shall have been effected or obtained free of any conditions
not acceptable to the Board.
16.Designation of Beneficiary
Each employee may designate any person or entity as such employee’s beneficiary
who shall, in the event of the employee’s death, receive shares of Common Stock
under the Plan or the funds in the employee’s Purchase Savings Account. Each
designation of a beneficiary by an employee will revoke all previous
designations under the Plan made by that employee and will be effective only
when filed in writing with Wintrust in accordance with procedures established by
the Committee during the employee’s lifetime. If any employee fails to designate
a beneficiary in the manner provided above, or if the beneficiary designated by
an employee dies before the employee or before issuance of all shares of Common
Stock due to the employee under the Plan is completed, the Board or the
Committee shall distribute the employee’s shares to the legal representative or
representatives of the estate of the later to die of the employee or the
employee’s designated beneficiary.
17.    Indemnification
Any person who is or was a director, officer, or employee of Wintrust or a
Participating Subsidiary and each member of the Committee shall be indemnified
and saved harmless by Wintrust to the extent legally permissible from and
against any and all liability or claim of liability to which such person may be
subjected by reason of any act done or omitted to be done in good faith with
respect to the administration of the Plan, including all expenses reasonably
incurred in his defense in the event that Wintrust fails to provide such
defense.
18.    Rights to Employment
Participation under the Plan shall not confer upon any employee any right with
respect to continued employment by Wintrust or a Participating Subsidiary.
19.    Expenses
All expenses of administering the Plan shall be borne by Wintrust.
20.    Facility of Payment
Whenever the Committee considers that an employee or a beneficiary entitled to
shares of Common Stock or proceeds under the Plan is under a legal disability or
is incapacitated in any way so as to be unable to manage his financial affairs,
the Committee may direct that such shares of Common Stock or proceeds be issued
directly to such employee or beneficiary, to the legal guardian or conservator
of such employee or beneficiary, to a relative of such employee or beneficiary
to be expended by such relative for the benefit of such employee or beneficiary,
to a custodian for such beneficiary under a Uniform Transfers or Gifts to Minors
Act or comparable statute of any state, or expended for the benefit of such
employee or beneficiary, as the Committee considers advisable.
21.    Effective Date
This Plan, as amended and restated as set forth herein, is effective April 3,
2018, subject to approval by the shareholders of the Corporation at the 2018
annual meeting of the Corporation.

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