In May 2015, the Company’s shareholders approved the 2015 Stock Incentive Plan (“the 2015 Plan”) which provides for the issuance of up to 5,485,000 shares of common stock. The 2015 Plan replaced the 2007 Stock Incentive Plan (“the 2007 Plan”), which replaced the 1997 Stock Incentive Plan (“the 1997 Plan”). The 2015 Plan, the 2007 Plan and the 1997 Plan are collectively referred to as “the Plans.” The 2015 Plan has substantially similar terms to the 2007 Plan and the 1997 Plan. 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 2015 Plan. All grants made after the approval of the 2015 Plan have been made pursuant to the 2015 Plan. As of December 31, 2019, approximately 3.0 million 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 nonqualified stock options and time-vested restricted share unit awards (“restricted shares”). In general, the grants of options provide for the purchase shares of the Company’s common stock at the fair market value of the stock on the date the options are granted. Options under the 2015 Plan and the 2007 Plan generally vest ratably over periods of three to five years and have a maximum term of seven 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. It is anticipated that LTIP awards will continue to be granted annually. LTIP grants since 2017 have consisted of performance-based stock and performance-based cash awards; however grants had previously included non-qualified stock options. Stock options granted under the LTIP have a term of seven years and will generally vest equally over three years based on continued service. Performance-based stock and cash 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. 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 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. Shares that are vested but are not issuable pursuant to deferred compensation arrangements accrue additional shares based on the value of dividends otherwise paid.

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 values of restricted share and performance-based stock awards are determined based on the average of the high and low trading prices on the grant date, and the fair value of stock options is estimated using a Black-Scholes option-pricing model. The option-pricing model requires the input of highly subjective assumptions and is sensitive to changes in the option’s expected life and the price volatility of the underlying stock, which can materially affect the fair value estimate. Options granted since the inception of the LTIP in 2011 were primarily granted as LTIP awards. Expected life of the options granted since the inception of the LTIP awards has been based on the safe harbor rule of the SEC Staff Accounting Bulletin No. 107 “Share-Based Payment” as the Company believes historical exercise data may not provide a reasonable basis to estimate the expected term of these options. Expected stock price volatility is based on historical volatility of the Company’s common stock, which correlates with the expected life of the options. Management reviews and adjusts the assumptions used to calculate the fair value of an option on a periodic basis to better reflect expected trends during periods when options are 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. Forfeitures are estimated based on historical forfeiture experience. For performance-based stock awards, an estimate is made of the number of shares expected to vest as a result of actual performance against the performance criteria to determine the amount of compensation expense to be recognized. The estimate is reevaluated quarterly and total compensation expense is adjusted for any change in the current period.



Stock Options	Common Shares		Weighted Average Strike Price		Remaining Contractual Term⁽¹⁾	Intrinsic Value⁽²⁾ ($000)
Outstanding at January 1, 2017	1,698,912		$	41.50
Granted	—		—
Exercised	(593,459	)	40.57
Forfeited or canceled	(20,697	)	42.83
Outstanding at December 31, 2017	1,084,756		$	41.98	4.0	$	43,817
Exercisable at December 31, 2017	562,810		$	41.82	3.3	$	22,820
Outstanding at January 1, 2018	1,084,756		$	41.98
Granted	—		—
Exercised	(282,614	)	41.25
Forfeited or canceled	(7,128	)	39.84
Outstanding at December 31, 2018	795,014		$	42.25	3.1	$	19,268
Exercisable at December 31, 2018	613,932		$	42.54	3.1	$	14,705
Outstanding at January 1, 2019	795,014		$	42.25
Granted	—		—
Options outstanding in acquired plans	106,748		38.83
Exercised	(146,430	)	38.84
Forfeited or canceled	—		—
Outstanding at December 31, 2019	755,332		$	42.43	2.8	$	21,503
Exercisable at December 31, 2019	735,396		$	42.42	2.7	$	20,947
Vested or expected to vest at December 31, 2019	755,332		$	42.43	2.8	$	21,503

The aggregate intrinsic value of options exercised during the years ended December 31, 2019, 2018 and 2017, was $4.7 million, $13.3 million and $20.1 million, respectively. The actual tax benefit realized for the tax deductions from option exercises totaled $1.3 million, $3.5 million and $7.8 million for 2019, 2018 and 2017, respectively. Cash received from option exercises under the Plans for the years ended December 31, 2019, 2018 and 2017 was $5.7 million, $11.7 million and $24.1 million, respectively.



	2019				2018				2017
Restricted Shares	Common 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 1	143,263		$	60.80	127,787		$	53.33	133,425		$	49.94
Granted	24,285		68.58		35,654		84.36		16,552		73.16
Vested and issued	(21,529	)	70.99		(18,324	)	54.31		(19,639	)	47.13
Forfeited or canceled	(1,691	)	79.50		(1,854	)	63.50		(2,551	)	52.26
Outstanding at end of year	144,328		$	60.37	143,263		$	60.80	127,787		$	53.33
Vested, but not issuable at end of year	92,183		$	52.24	90,520		$	51.94	89,723		$	51.64



	2019				2018				2017
Performance Shares	Common 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 1	396,855		$	67.71	359,196		$	54.37	298,180		$	43.64
Granted	175,823		71.56		134,380		88.27		145,853		72.60
Added by performance factor at vesting	33,950		40.99		—		—		—		—
Vested and issued	(128,238	)	41.00		(82,307	)	44.39		(68,712	)	46.85
Forfeited or canceled	(12,875	)	75.08		(14,414	)	60.05		(16,125	)	52.98
Outstanding at end of year	465,515		$	74.37	396,855		$	67.71	359,196		$	54.37
Vested, but deferred at year end	33,828		$	43.01	21,530		$	43.54	108,143		$	44.16

The actual tax benefit realized upon the vesting 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 of restricted shares and performance-based stock in 2019, 2018 and 2017 was $870,000, $994,000 and $975,000, respectively, 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, 2019, there was $10.5 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, 2019, 2018 and 2017 was $9.8 million, $8.0 million and $8.9 million, respectively.

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 2019, 2018 and 2017, and no awards were paid in those years. There were no outstanding awards under this plan at December 31, 2019.

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. Generally, participants completing 501 hours of service 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 $12.3 million in 2019, $10.4 million in 2018, and $8.9 million in 2017.

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 2019, 2018 and 2017, 43,386, 33,977 and 35,022, respectively, shares of common stock 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 2018, increased the shares authorized under the ESPP by 200,000 shares. At December 31, 2019, the Company had an obligation to issue 10,523 shares of common stock to participants and had 172,677 shares available for future grants under the ESPP.

As a result of the Company's acquisition of HPK Financial Corporation (“HPK”) in December 2012, the Company assumed the obligations of a noncontributory pension plan. The HPK Plan was frozen as of December 31, 2006, with no additional credit earned for service or compensation paid after that date. Similarly, in connection with the Company's acquisition of Diamond Bancorp, Inc. ("Diamond") in October 2013, the Company assumed the obligation of Diamond's pension plan. The Diamond Plan was frozen as of December 31, 2004, and only service and compensation prior to this date is considered in determining benefits. In 2019, both of these plans were terminated and participant account balances were distributed. The Company recorded expense (income) of $487,000, ($38,000) and $1.2 million in 2019, 2018 and 2017, respectively, related to these plans.

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 2019, 2018 and 2017, a total of 18,577 shares, 18,856 shares and 27,508 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, 2019, the Company has an obligation to issue 295,228 shares of common stock to directors and has 42,311 shares available for future grants under the DDFS Plan.