Stock Compensation Plans and Other Employee Benefit Plans
Stock Incentive Plan

In May 2025, the Company’s shareholders approved the 2025 Stock Incentive Plan (“the 2025 Plan”) which provides for the issuance of up to 1,825,000 shares of common stock plus any shares of common stock that were available for awards under the 2022 Stock Incentive Plan (“the 2022 Plan”) as of the effective date of the 2025 Plan. The 2025 Plan replaced the 2022 Plan, and similarly, the 2022 Plan replaced the 2015 Stock Incentive Plan (“the 2015 Plan”) and the 2015 Plan replaced the 2007 Stock Incentive Plan (“the 2007 Plan”) and the 2007 Plan replaced the 1997 Stock Incentive Plan (“the 1997 Plan”). The 2025 Plan, 2022 Plan, 2015 Plan, 2007 Plan and the 1997 Plan are collectively referred to as “the Plans.” The 2025 Plan has substantially similar terms to the predecessor plans. Awards granted under the Plans for which common shares are not issued by reason of cancellation, forfeiture, lapse of such award or settlement of such award in cash, are again available under the 2025 Plan. All grants made after the approval of the 2025 Plan are made pursuant to the 2025 Plan. As of December 31, 2025, approximately 2,185,493 shares were available for future grants assuming the maximum number of shares are issued for the performance awards outstanding. The Plans cover substantially all employees of Wintrust. The Compensation Committee of the Board of Directors administers all stock-based compensation programs and authorizes all awards granted pursuant to the Plans.

The Plans permit the grant of incentive stock options, non-qualified stock options, stock appreciation rights, stock awards, restricted share or unit awards, performance awards and other incentive awards valued in whole or in part by reference to the Company’s common stock, all on a stand-alone, combination or tandem basis. The Company historically awarded stock-based compensation in the form of time-vested non-qualified stock options and time-vested restricted share unit awards (“restricted shares”). The grants of options provide for the purchase of shares of the Company’s common stock at the fair market value of the stock on the date the options are granted. Stock options generally vest ratably over periods of three to five years and have a maximum term of ten years from the date of grant. Restricted shares entitle the holders to receive, at no cost, shares of the Company’s common stock. Restricted shares generally vest over periods of one to five years from the date of grant.

Beginning in 2011, the Company has awarded annual grants under the Long-Term Incentive Program (“LTIP”), which is administered under the Plans. The LTIP is designed in part to align the interests of management with interests of shareholders, foster retention, create a long-term focus based on sustainable results and provide participants a target long-term incentive opportunity. LTIP grants in 2025, 2024, and 2023 consisted of a combination of performance-based stock awards with a
performance condition metric, performance-based stock awards with a market condition metric and time-vested restricted shares. Performance-based stock awards granted under the LTIP are contingent upon the achievement of pre-established long-term performance goals set in advance by the Compensation Committee over a three-year period starting at the beginning of each calendar year. Performance-based stock awards with a market condition metric are contingent on the total shareholder return performance over a three-year period relative to the KBW Regional Bank Index. These performance awards are granted at a target level, and based on the Company’s achievement of the pre-established long-term goals, the actual payouts can range from 0% to a maximum of 150% of the target award. The awards typically vest in the quarter after the end of the performance period upon certification of the payout by the Compensation Committee of the Board of Directors. Holders of performance-based stock awards are entitled to receive, at no cost, the shares earned based on the achievement of the pre-established long-term goals.

Holders of restricted share awards and performance-based stock awards received under the Plans are not entitled to vote or receive cash dividends (or cash payments equal to the cash dividends) on the underlying common shares until the awards are vested and shares are issued. Shares that are vested but are not issuable pursuant to deferred compensation arrangements accrue additional shares based on the value of dividends otherwise paid. Except in limited circumstances, awards granted pursuant to the Plans are canceled upon termination of employment without any payment of consideration by the Company.

Stock-based compensation is measured as the fair value of an award on the date of grant, and the measured cost is recognized over the period which the recipient is required to provide service in exchange for the award. The fair value of restricted share and performance-based stock awards with a performance metric is determined based on the average of the high and low trading prices on the grant date. The fair value of performance stock awards with a market condition metric is determined using a Monte Carlo simulation model and the fair value of stock options is estimated using a Black-Scholes option-pricing model. The Monte Carlo simulation model and the Black-Scholes option-pricing model require the input of highly subjective assumptions and are sensitive to changes in the award’s expected life and the price volatility of the underlying stock, which can materially affect the fair value estimates. Management periodically reviews and adjusts the assumptions used to calculate the fair value of such awards when granted. No options have been granted since 2016.

Stock-based compensation is recognized based on the number of awards that are ultimately expected to vest, taking into account expected forfeitures. In addition, for performance-based awards with a performance metric, an estimate is made of the number of shares expected to vest as a result of actual performance against the performance criteria in the award to determine the amount of compensation expense to recognize. The estimate is re-evaluated quarterly and total compensation expense is adjusted for any change in estimate in the current period.

Stock-based compensation expense recognized in the Consolidated Statements of Income was $42.0 million, $38.9 million and $33.5 million and the related tax benefits were $9.1 million, $8.3 million and $7.4 million in 2025, 2024 and 2023, respectively.

A summary of the Plans’ stock option activity for the years ended December 31, 2025, 2024 and 2023 is as follows:
Stock OptionsCommon
Shares
Weighted Average
Strike Price
Remaining
Contractual Term(1)
Intrinsic Value(2)
($000)
Outstanding at January 1, 2023
68,093 $41.14 
Exercised(54,993)40.75 
Outstanding at December 31, 2023
13,100 $42.76 4.2$655 
Exercisable at December 31, 2023
13,100 $42.76 4.2$655 
Outstanding at January 1, 2024
13,100 $42.76 
Exercised(2,275)38.00 
Outstanding at December 31, 2024
10,825 $43.76 3.5$876 
Exercisable at December 31, 2024
10,825 $43.76 3.5$876 
Outstanding at January 1, 2025
10,825 $43.76 
Exercised(5,150)42.61 
Outstanding at December 31, 2025
5,675 $44.81 2.7$539 
Exercisable at December 31, 2025
5,675 $44.81 2.7$539 
Vested or expected to vest at December 31, 2025
5,675 $44.81 2.7$539 
(1)Represents the weighted average contractual remaining life in years.
(2)Aggregate intrinsic value represents the total pretax intrinsic value (i.e., the difference between the Company’s stock price at year end and the option exercise price, multiplied by the number of shares) that would have been received by the option holders if they had exercised their options on the last day of the year. Options with exercise prices above the year end stock price are excluded from the calculation of intrinsic value. The intrinsic value will change based on the fair market value of the Company’s stock.

The aggregate intrinsic value of options exercised during the years ended December 31, 2025, 2024 and 2023, was $466,598, $179,664 and $2.5 million, respectively. The actual tax benefit realized for the tax deductions from option exercises totaled
$90,000, $30,000 and $540,000 for 2025, 2024 and 2023, respectively. Cash received from option exercises under the Plans for the years ended December 31, 2025, 2024 and 2023 was $220,000, $86,457 and $2.2 million, respectively.

A summary of the Plans’ restricted share activity for the years ended December 31, 2025, 2024 and 2023 is as follows:
 
 202520242023
Restricted SharesCommon
Shares
Weighted
Average
Grant-Date
Fair Value
Common
Shares
Weighted
Average
Grant-Date
Fair Value
Common
Shares
Weighted
Average
Grant-Date
Fair Value
Outstanding at January 1880,866 $90.95 746,123 $79.60 610,155 $73.21 
Granted262,521 132.46 407,046 99.89 270,855 88.06 
Vested and issued(224,769)94.65 (241,415)70.41 (121,534)65.90 
Forfeited or canceled(30,220)110.10 (30,888)95.26 (13,353)83.68 
Outstanding at end of year888,398 $101.63 880,866 $90.95 746,123 $79.60 
Vested, but deferred, at year end102,218 $55.59 100,610 $54.46 98,919 $53.58 

A summary of the Plans’ performance-based stock award activity, based on the target level of the awards, for the years ended December 31, 2025, 2024 and 2023 is as follows:
 202520242023
Performance SharesCommon
Shares
Weighted
Average
Grant-Date
Fair Value
Common
Shares
Weighted
Average
Grant-Date
Fair Value
Common
Shares
Weighted
Average
Grant-Date
Fair Value
Outstanding at January 1454,017 $93.57 553,026 $79.69 545,379 $70.30 
Granted88,310 134.57 111,469 100.47 189,355 92.36 
Added by performance factor at vesting75,461 96.51 96,952 58.78 23,925 62.82 
Vested and issued(230,957)95.26 (295,644)58.69 (186,344)62.67 
Forfeited or canceled(9,074)105.85 (11,786)95.97 (19,289)81.84 
Outstanding at end of year377,757 $102.38 454,017 $93.57 553,026 $79.69 
Vested, but deferred, at year end13,335 $41.21 21,759 $44.51 29,020 $45.88 

At December 31, 2025, the maximum number of performance-based shares that could be issued on outstanding awards if performance is attained at the maximum amount was approximately 560,000 shares.

The actual tax benefit realized upon the vesting and issuance of restricted shares and performance-based stock is based on the fair value of the shares on the issue date, and the estimated tax benefit of the awards is based on fair value of the awards on the grant date. The actual tax benefit realized upon the vesting and issuance of restricted shares and performance-based stock in 2025 was $3.6 million more than the expected tax benefit for those shares; in 2024 the actual tax benefit was $4.4 million more than the expected tax benefit for those shares and in 2023 the actual tax benefit was $1.8 million more than the expected tax benefit for those shares. These differences in actual and expected tax benefits were recorded to income tax expense.

As of December 31, 2025, there was $47.7 million of total unrecognized compensation cost related to non-vested share based arrangements under the Plans. That cost is expected to be recognized over a weighted average period of approximately two years. The total fair value of shares vested during the years ended December 31, 2025, 2024 and 2023 was $43.7 million, $34.7 million and $22.1 million, respectively.

The Company issues new shares to satisfy its obligation to issue shares granted pursuant to the Plans.

Cash Incentive and Retention Plan

The Cash Incentive and Retention Plan (“CIRP”) allows the Company to provide cash compensation to the Company’s and its subsidiaries’ officers and employees. The CIRP is administered by the Compensation Committee of the Board of Directors. The CIRP generally provides for the grants of cash awards, which may be earned pursuant to the achievement of performance criteria established by the Compensation Committee and/or continued employment. The performance criteria, if any, established by the Compensation Committee must relate to one or more of the criteria specified in the CIRP, which includes: earnings, earnings growth, revenues, stock price, return on assets, return on equity, improvement of financial ratings, achievement of balance sheet or income statement objectives and expenses. These criteria may relate to the Company, a
particular line of business or a specific subsidiary of the Company. The Company had no expense related to the CIRP in 2025, 2024 and 2023, and no awards were paid in those years. There were no outstanding awards under this plan at December 31, 2025.

Other Employee Benefits

Wintrust and its subsidiaries also provide 401(k) Retirement Savings Plans (“401(k) Plans”). The 401(k) Plans cover all employees meeting certain eligibility requirements. Contributions by employees are made through salary deferrals at their direction, subject to certain Plan and statutory limitations. Employer contributions to the 401(k) Plans are made at the employer’s discretion. Eligible participants that have contributed to the 401(k) Plans are eligible to share in an allocation of employer contributions. The Company’s expense for the employer contributions to the 401(k) Plans was approximately $22.0 million in 2025, $19.7 million in 2024, and $19.2 million in 2023.

The Wintrust Financial Corporation Employee Stock Purchase Plan (“ESPP”) is designed to encourage greater stock ownership among employees, thereby enhancing employee commitment to the Company. The ESPP gives eligible employees the right to accumulate funds over an offering period to purchase shares of common stock. All shares offered under the ESPP will be either newly issued shares of the Company or shares issued from treasury, if any. In accordance with the ESPP, beginning January 1, 2015, the purchase price of the shares of common stock is equal to 95% of the closing price of the Company’s common stock on the last day of the offering period. During 2025, 2024 and 2023, 29,708, 32,942 and 46,034, shares of common stock, respectively, were purchased by participants and no compensation expense was recorded. The Company plans to continue to offer common stock through this ESPP on an ongoing basis and, in 2021, increased the shares authorized under the ESPP by 200,000 shares. At December 31, 2025, the Company had an obligation to issue 6,038 shares of common stock to participants and had 103,788 shares available for future grants under the ESPP.

The Company does not currently offer other postretirement benefits such as health care or other pension plans.

Directors Deferred Fee and Stock Plan

The Wintrust Financial Corporation Directors Deferred Fee and Stock Plan (“DDFS Plan”) allows directors of the Company and its subsidiaries to choose to receive payment of directors’ fees in either cash or common stock of the Company and to defer the receipt of the fees. The DDFS Plan is designed to encourage stock ownership by directors. All shares offered under the DDFS Plan will be either newly issued shares of the Company or shares issued from treasury. The number of shares issued is determined on a quarterly basis based on the fees earned during the quarter and the fair market value per share of the common stock on the last trading day of the preceding quarter. The shares are issued annually and the directors are entitled to dividends and voting rights upon the issuance of the shares. During 2020, an additional 200,000 shares were authorized under the DDFS Plan. During 2025, 2024 and 2023, a total of 17,546 shares, 14,927 shares and 63,001 shares, respectively, were issued to directors. For those directors that elect to defer the receipt of the common stock, the Company maintains records of stock units representing an obligation to issue shares of common stock. The number of stock units equals the number of shares that would have been issued had the director not elected to defer receipt of the shares. Additional stock units are credited at the time dividends are paid, however no voting rights are associated with the stock units. The shares of common stock represented by the stock units are issued in the year specified by the directors in their participation agreements. At December 31, 2025, the Company has an obligation to issue 313,281 shares of common stock to directors and has 24,218 shares available for future grants under the DDFS Plan.

Historical Timeline

Fiscal YearFiled
2025Feb 26, 2026Showing above
2024Feb 28, 2025
2023Feb 28, 2024
2022Feb 28, 2023
2021Feb 25, 2022
2020Feb 26, 2021
2019Feb 28, 2020
2018Feb 28, 2019
2017Feb 28, 2018
2016Feb 28, 2017
2015Feb 29, 2016

About Stock Compensation Disclosures

Stock-based compensation disclosures detail the equity awards granted to employees and executives — including stock options, restricted stock units (RSUs), and performance shares — along with the valuation methods and assumptions used to expense them. This section reveals the true cost of talent retention and the alignment between management incentives and shareholder interests.

Key signals: total unrecognized compensation expense and its expected recognition period signal future earnings headwinds from already-granted awards. For stock options, examine Black-Scholes assumptions — expected volatility, risk-free rate, and expected term — as understating any of these reduces reported compensation expense. Compare stock compensation expense as a percentage of revenue against peers to assess dilution cost. Watch vesting schedules for acceleration clauses tied to change-of-control events. Performance-based awards with undemanding targets may indicate weak governance. Add back stock compensation to operating cash flow to calculate a more conservative free cash flow figure.