Wintrust Financial (WTFC) 8-K Wintrust Financial Corporation to Present at Raymond James and Associates 32nd Annual Institutional Investors Conference

Exhibit 99.2

1 Raymond James & Associates 32nd Annual Institutional Investors Conference March 7, 2011 March 7, 2011 March 7, 2011 March 7, 2011 March 7, 2011

2 FORWARD-LOOKING INFORMATION During the course of our remarks today, we will make certain predictive statements regarding our plans and strategies and anticipated financial effects to assist you better in understanding our company. These forward looking statements about future results are subject to risks and uncertainties. Refer to our periodic reports on file with the SEC and the slides at the end of this presentation regarding forward- looking statements for further detail in this regard.

Today's Presentation Who we are Where we have been-how we got here Where we are going Summary financial results Questions 3

5 Who We Are Nineteen year-old community focused banking organization with approximately $14 billion in assets Fifteen community banks with strong ties to local residents and business leaders in the Chicago and Milwaukee metropolitan markets 9 de novo charters established since 1991 11 bank acquisitions since the 4th qtr 2003, including 4 FDIC-assisted acquisitions in 2010/2011 (some were merged into existing charters) A small branch acquisition completed in October 2010 in Naperville, IL. Total deposits acquired were approximately $23 million 87 existing banking locations In our early years and by design, the vast majority of customers don't even know Wintrust exist -- as you will see later, this is changing

6 Who We Are - Company Overview Community Banking Specialty Finance Wealth Management Fifteen community banks Chicago and Milwaukee metropolitan markets 87 locations Full product suite - home equity, home mortgage, consumer, real estate and commercial loans, safe deposit facilities, ATMs, & internet banking Wintrust Mortgage Corporation National mortgage production capabilities with focus on Chicago metropolitan area Two finance companies - premium finance and account receivables Loan production to optimize banks' balance sheets First Insurance Funding P&C Life Insurance Tricom- Temporary help industry processing and financing Other niches (including airplanes, housing associations, franchise lending, mortgage warehouse lending - to name a few) Restarting the indirect auto lending program Wayne Hummer acquired in 2002, and 2 subsequent acquisitions $9 bn in AUM Brokerage, asset management and trust capabilities Commercial Banking HAVE IT ALL - Big Bank Resources, Community Bank Service Chicago and Milwaukee downtown lending offices All community banks Full product suite - commercial loans, treasury management, lock box services, international Focus on middle- market C&I Added over 50 new lenders since the beginning of 2009.

7 1991 1992 1993 1994 1995 1996 1997 1998 1999 2000 2001 2002 2003 2004 2005 2006 2007 2008 2009 2010 7 40 Internal Growth 52 83 189 354 471 706 1053 1348 1650 2074 2676 3619 4450 5399 6456 7363 7098 8387 9945 10966 Acquired Growth 29 29 29 103 297 1020 1721 2209 2271 2271 2271 3014 Asset Growth - Internal / Acquired (in millions)

8 Banking Locations

Wintrust Locations Banking Wealth Management Mortgage

10 Chicago and Milwaukee metropolitan markets Initially focused on high net worth areas. Have since moved into broader market Flexibility to continue to profitably penetrate broader market Downtown Chicago focusing on corporate and commercial customers Positioned as local alternatives to the "Big Banks" We know our communities extremely well Personalized service, creative marketing and employee involvement Have taken advantage of big-bank consolidation and market dislocation to grow quickly Vigorously defend and grow market share Who We Are - Core Strategy Good Markets Consistent strategy for nineteen plus years Community Focused Market Share Growth

11 Funding Assets Who We Are - Operating Strategy Loan-to-deposit ratio 85% - 90% Generate ~ two-thirds of loan volume from banks Remaining loan volume from niche businesses First Insurance Funding Tricom Other (including housing associations, franchise lending, mortgage warehouse lending, indirect auto -- to name a few) Consistent, conservative credit standards Manage risk through portfolio diversification and decentralized structure Minimal "nuisance fees", if at all Same or better products and delivery - differentiate with service Technology as the great equalizer Strong, diversified funding base Recent markets have proven the value of that approach Franchise is built on core deposit funding 87% of total funding Substantially all deposits are customer generated Approximately 5% traditional brokered deposits Goal is to be top two in both deposit market share and household penetration in each banks' local market area

12 Deposit Market Share-Chicago MSA As of June 30, 2010 and 2009 At June 30, 2009 At June 30, 2010 In-market Deposit In-market Deposit 2010 Deposit Market Deposit Market Rank Bank Holding Company Dollars Share % Dollars Share % JP Morgan Chase & Co. ** $ 45.0 BB 15.8% $49.2 BB 17.4% Bank of America ** $ 33.2 BB 11.7 % $32.0 BB 11.3% Bank of Montreal ** $ 24.4 BB 8.6 % $26.7 BB 9.4% PNC Financial Services Group** $ 11.3 BB 4.0 % $12.9 BB 4.6% Northern Trust Corporation $ 13.3 BB 4.7 % $12.7 BB 4.5% Wintrust Financial Corp. $ 8.7 BB 3.1 % $10.2 BB 3.6% PrivateBancorp, Inc. $ 7.5 BB 2.7 % $ 9.0 BB 3.2% Fifth Third Bancorp ** $ 8.6 BB 3.0 % $ 8.9 BB 3.1% Source: FDIC Website - Summary of Deposits as of June 30, 2010 and 2009 Market share data is for the Chicago Metropolitan Statistical Area ** - Corporate Headquarters is out-of-state A Leading Chicago bank

How We Got Here 13

14 Consistent Strategy - Changing Tactics (1991-2005) (2010-11) (2008) (2009) (2006-07) Organic & Acquisition Growth 7 traditional bank acquisitions since 2003 9 de novo charters since 1991 "Rope - A - Dope" Slowed growth Maintained extremely conservative underwriting Reduced relative cost of funds Controlled expenses "Off the Ropes" Life insurance premium finance acquisition PMP acquisition (in late Dec '08) Over 50 new lenders hired since Jan '09 Loans a $2.3 bn since 12/31/08 (includes $334 mm of covered loans from FDIC-assisted deals) Deposits a $2.4 bn since 12/31/08 Organic & Acquisition Growth Take advantage of "dislocation" Consistent loan growth 4 FDIC-assisted transactions Acquired 1 branch in Naperville, IL Raised capital-RETIRED TARP WINTRUST TACTICS CREDIT CYCLE Capital & TARP-CPP Focused on minimizing dilution to shareholders Q3'08 - raised $50 mm of convertible preferred Dec. '08 - $250 mm TARP-CPP Healthy Restrained Recovery The Perfect Storm Stabilization Storm Clouds Gather Warning signs 1Q'06 Disadvantageous yield curve Loosened credit standards Credit spreads moved to unacceptable levels Compound Annual Growth Rates

15 Compound Annual Growth Rates Through 2005 (Years ended December 31, 2005) 1 year 2 year 3 year 4 year 5 year Revenues 27.6% 26.8 25.0% 31.8% 31.4% Net Income 30.5 32.6 34.0 38.1 43.1 EPS (diluted) 17.5 17.9 19.8 21.3 27.1 Assets 27.4 31.2 30.0 31.9 31.2 Loans 19.9 25.7 26.8 26.8 27.5 Deposits 31.8 31.8 29.6 30.6 29.8

16 Storm Clouds and What We Expected Storm Clouds Gather in 2006 Disadvantageous yield curve Loosened credit standards Credit spreads moved to unacceptable levels Opportunities for those with dry powder Lending opportunities Acquisition opportunities for bruised banks and asset generators Need to be first out ^ cannot be burdened by a troubled loan portfolio, lack of funding or capital "It's times like this where money returns to its rightful owners"

17 The "Rope-a-Dope" Strategy 2006 Through 3rd Quarter 2008 No change in loan underwriting - do not chase the herd!! Slow growth Shrink larger banks (run-off of CD-only customers) Grow newer banks Reduce relative cost of funds Discipline Mix Get paid for making loans - hand out credit with an eye dropper Control expenses Hunker down and ride it out

18 Rope-a-Dope Timing and TARP Capital was always key in the timing as to when to move off of our defensive strategy. In the third quarter of 2008 and in anticipation of moving off of our defensive strategy, we raised $50 million of convertible preferred stock through a private placement. This capital provided us with a cushion to our already well capitalized position as well as the capacity to slowly get back on offense. Immediately after closing, the TARP Capital Purchase Program was announced. We applied and received $250 million in the last weeks of 2008. TARP-Capital Purchase Program funds provided for a head start in our plans.

19 So How Did Wintrust Fare?? Remained profitable throughout the cycle. We have taken advantage of the many opportunities which are always present in adverse credit cycles Dislocated people Dislocated assets Dislocated banks Core Financial Goals Increase core earnings Move bad assets out

20 Consolidated Net Income (before Preferred Dividends, in 000s) 1994 1995 1996 1997 1998 1999 2000 2001 2002 2003 2004 2005 2006 2007 2008 2009 2010 3Q09-YTD 3Q10-YTD -2236 1497 -973 4846 6245 9427 11155 18439 27875 38118 51334 67016 66493 55653 20488 73069 63329 44902 49125 West 31.6 2606 North 43.9

21 Taking Advantage of Dislocations Dislocated People Dislocated Assets Dislocated Banks FIFC purchased a portfolio of domestic life insurance premium finance loans and certain related assets from indirect wholly-owned subsidiaries of AIG Aggregate balance of approximately $1.03 billion Purchase price of $746 million Resulting discount of $287 million Pre-tax bargain purchase price gain of $167 million First purchase: July 28, 2009 Smaller, second purchase: October 2, 2009 Since April 2010, acquired four failed banks from the FDIC - they cover the majority of losses Very disciplined bids- $33 million in Bargain Purchase Gains recorded in 2010 Immediately accretive to earnings Strategic as we moved into contiguous markets not served by us and improved our footprint We intend to assimilate and then aggressively grow these acquisitions to be market leaders Acquired a branch with $23 million in deposits in Naperville, IL in 2010 Set up downtown Chicago office to capture core commercial and industrial (C&I) business Added 50+ lenders since the beginning of 2009 added throughout the organization Adding talented staff in other areas to support our growth and to stay out in front on product delivery systems and regulatory changes.

22 So How Did Wintrust Fare?? - 2009 Report Card Goals Results Concentrate on core earnings Net income of $73 million ($2.18 per share) Record year for earnings Aided by pre-tax bargain purchase gain of $156mm from life insurance premium finance transaction Majority offset by credit expenses Continued improvement in pre-credit earnings Clear "junk" off the balance sheet NPLs declined 43% from Q3 2009 to Q4 2009 NPLs at Q4 2009 were below Q4 2008 levels Net charge-offs $137mm in 2009 to clean balance sheet Scour the market for dislocated assets Purchased life insurance premium finance portfolio & certain CMOs at a material discounts Enhance talent pool Added over fifty new senior lenders and officers since January 2009 Maintain disciplined core growth Balance sheet growth of approximately 15% Selectively look at expansion opportunities Continuously evaluating expansion opportunities, but must be strategic Positioned to start 2010 with strong earnings and clean balance sheet

23 So How Did Wintrust Fare?? - 2010 Report Card Goals Results Concentrate on core earnings Net income of $63 million ($1.02 /diluted share) Aided by pre-tax bargain purchase gains totaling $44mm from FDIC-assisted acquisitions and life insurance premium finance portfolio purchase Majority offset by credit expenses 2010 core pre-tax earnings up 60% from prior year Keep the balance sheet sterile NPLs (excluding covered loans) remain relatively stable in 2010 versus year end 2009 Net charge-offs of $110mm to continue to clear the B/S of stressed credit Credit charge-offs and NPAs are a fraction of peer group and remain at very manageable levels Enhance talent pool Continue to add new senior lenders and officers in 2010 and opened our downtown Chicago commercial lending office Maintain disciplined core growth Balance sheet growth of 14% in 2010 Selectively look at expansion opportunities Acquired three banks in FDIC-assisted deals Acquired a small branch in a strategic community WTFC Has Remained Profitable Throughout The Cycle, with 2009 Being A Record Year For Earnings

24 Annual "Core Pre-tax Earnings" (in 000s) (* - Annualized) "Core Pre-tax Earnings" are calculated by removing from reported Pre-tax earnings the following categories: Provision for Credit Losses; OREO Related Costs; Mortgage Recourse Obligations on Loans Previously Sold; Bargain Purchase Gains; Trading Gains or Losses; and Securities Gains or Losses. Further information regarding the calculation methodology is available in our news release filed on Form 8-K dated January 24, 2011 under the section titled "Supplemental Financial Measures/Ratios".

LOAN GROWTH (excluding Loans Held for Sale) 25 (in millions) 5 year CAGR = 13.8%

26 Non-Performing Asset Ratio Wintrust vs. Peer Group 2003 2004 2005 2006 2007 2008 2009 Wintrust 0.0051 0.0029 0.0034 0.0039 0.0081 0.0158 0.0174 Peer 0.0058 0.0045 0.0042 0.0043 0.008 0.0194 0.03 Peer Group Data is per the Federal Reserve's Bank Holding Company Performance Report

27 Net Charge-offs Ratio Wintrust vs. Peer Group 2003 2004 2005 2006 2007 2008 2009 Wintrust 0.0018 0.0007 0.001 0.0009 0.0016 0.0051 0.0165 Peer Group 0.0033 0.0021 0.0018 0.0015 0.0027 0.011 0.0228 Peer Group Data is per the Federal Reserve's Bank Holding Company Performance Report

28 2010 Capital Activity Enhance and maintain strong capital ratios 12/31/09 3/31/10 6/30/10 9/30/10 12/31/10 Tier 1 Risk-based capital 11.0% 13.4% 13.0% 12.7% 12.5% Total capital ratio 12.4% 14.9% 14.3% 14.1% 13.8% Leverage ratio 9.3% 10.8% 10.2% 10.0% 10.1% Tangible common equity ratio 4.7% 6.3% 6.0% 5.9% 8.0% Provide flexibility for growth Organic growth & lending opportunities Portfolio and business acquisitions 2010 Capital Activity March 2010 - Sale of Common Stock (+$210 mm) December 2010- Sale of Common Stock and TEUs (+$327 mm) Repaid TARP-CPP in December 2010 (-$250 mm)

29 Financial Overview - Wintrust Has Consistently Grown Book Value Per Share Through Cycles Common Book Value Per Share 1996 1997 1998 1999 2000 2001 2002 2003 2004 2005 2006 2007 2008 2009 2010 BV per share 5.65 6.15 7.06 7.92 9.72 13.19 17.43 21.81 26.23 30.38 31.56 33.03 35.27 32.73 TEU at Minumum 0 0 0 0 0 0 0 0 0 0 0 0 0 1.1 * Proforma assuming tangible equity units convert at a maximum price of $37.50

Financial Overview - Wintrust Has Consistently Grown Tangible Book Value Per Share Through Cycles Tangible Common Book Value Per Share $26.66* * Proforma assuming tangible equity units convert at a maximum price of $37.50

31 1991 1992 1993 1994 1995 1996 1997 1998 1999 2000 2001 2002 2003 2004 2005 2006 2007 2008 2009 2010 Capital Growth 14583 11291 17227 25366 40487 42620 68790 75205 92947 102276 141278 227002 349837 473912 627911 773346 739555 784699 853815 1387089 Preferred 0 0 0 0 0 0 0 0 0 0 281873 284824 49460 Trust Pfd 31050 31050 51050 51050 50894 96050 204489 230458 249828 249662 249515 249493 249493 Sub Debt 25000 50000 50000 50000 75000 75000 70000 60000 50000 Financial Overview - Capital Components (in millions) - Common Shareholders Equity - Trust Preferred Securities - Subordinated Debt - Preferred Securities

Wintrust Strategy for 2011 and Beyond Back to the Future 32

33 Back to the Future Strategy for 2011 and Beyond This cycle isn't over yet so we need to proceed cautiously in all of our endeavors Continue to increase core earnings Continue to expeditiously remove problem assets from the balance sheet Plan is to return to the growth mode experienced in the first 15 years of our existence with an overriding emphasis on achieving superior profitability Organic growth New hires Chicago office Selective, opportunistic acquisitions in all areas of our business Continue to locate "dislocations" in the market and take advantage of them Never take our eye off the major operating tenet that made us successful throughout the years-Service, Service, Service

Expected Core Pre-tax Earnings Improvements Subject to market and other conditions, including interest rate environments, and other factors influencing growth, pre-tax, pre-provision earnings could benefit from the following: 4th Quarter 2010 "core pre-tax earnings" run rate of $235 million Tactics: Continued deposit re-pricing Organic growth Liquidity re-deployment Income from additional acquisitions 34

Organic Growth and Branding Organic Growth-going back to pre Rope-A-Dope model Expect each bank to grow $75 million per year Expect each bank to open a branch every two years Seven new branches budgeted for 2011 The Wintrust Brand By design becoming more prevalent and recognized over the last two years Wintrust Wealth Management, Wintrust Mortgage Co., Wintrust Commercial Banking We will offer full affiliate banking to all of our customers by late summer Each of our banks will take on the sub-brand of "A Wintrust Community Bank" in order to take advantage of our network Will not lose positioning of the local alternative to the big banks Rather, we are a consortium of community banks that give customers the best of all worlds-community banks service with big bank products "Have it All" 35

36 Penetrate new markets with community banking model Within 11/2 hours of Wintrust headquarters Acquired entities with existing management that wish to continue to grow Acquisitions in specialty finance and wealth management Must complement existing franchise, be a strategic new business line, or add/improve customer products and services Evaluating FDIC-assisted and unassisted bank deals Completed four FDIC-assisted transactions since April 2010 Three in Chicago, IL and one in Naperville, IL Acquired a separate branch location in Naperville, IL in October 2010 through an unassisted transaction Focus on earnings accretion and improving franchise value Growth Strategy - Expansion

Why Invest in Wintrust? Managing well through the cycle-consistently profitable with strong core earnings growth Asset quality position is manageable and better than peer group and should allow us to be first out of this cycle Strong capital position-NO TARP overhang Enviable core deposit franchise in market area Differentiated, highly diversified and sustainable business model Well positioned to take advantage of industry consolidation We believe our stock is underpriced relative to current market metrics and relative positioning among local peers 37

38

Supplemental Financial Data

40 Total Assets (in millions)

41 Historical Growth

42 Asset Growth of Banks by Year 1991 1992 1993 1994 1995 1996 1997 1998 1999 2000 2001 2002 2003 2004 2005 2006 2007 2008 2009 2010 Lake Forest 8 49 96 143 195 270 380 441 499 581 667 897 1087 1256 1334 1458 1504 1654 1816 2408 Hinsdale 0 23 67 115 167 223 281 350 401 508 642 746 887 980 1401 1270 1314 1439 1462 North Shore 0 44 105 169 266 294 360 450 563 771 871 938 949 997 943 1065 1333 1487 Libertyville 0 35 76 124 186 219 287 355 479 587 758 844 933 973 1032 1054 1131 Barrington 0 11 72 120 177 241 314 447 553 688 788 876 789 818 1036 1182 Crystal Lake 0 7 53 89 125 184 297 429 479 500 580 555 608 666 692 Northbrook 0 22 86 185 255 572 694 745 668 741 899 1190 Advantage 114 150 230 278 289 327 394 453 504 Village 80 99 173 604 635 564 642 791 789 Beverly 0 84 134 161 162 234 302 356 Wheaton 125 157 310 315 394 447 735 Town 308 396 474 571 644 705 731 SBOTL 502 549 570 573 637 708 733 Old Plank 111 171 227 301 297 St. Charles 54 102 172 239 334 (in millions)

43 1994 1995 1996 1997 1998 1999 2000 2001 2002 2003 2004 2005 2006 2007 2008 2009 2010 Net Interst Margin 0.0335 0.0296 0.0291 0.0341 0.0343 0.0354 0.0366 0.0349 0.0334 0.032 0.0317 0.0316 0.031 0.0311 0.0281 0.0301 0.0337 Net Interest Margin (fully taxable equivalent)

44 Revenue Growth by Quarter (excluding Bargain Purchase Gains recorded in 3Q09 through 4Q10) 1Q97 2Q97 3Q97 4Q97 1Q98 2Q98 3Q98 4Q98 1Q99 2Q99 3Q99 4Q99 1Q00 2Q00 3Q00 4Q00 1Q01 2Q01 3Q01 4Q01 1Q02 2Q02 3Q02 4Q02 1Q03 2Q03 3Q03 4Q03 1Q04 2Q04 3Q04 4Q04 1Q05 2Q05 3Q05 4Q05 1Q06 2Q06 3Q06 4Q06 1Q07 2Q07 3Q07 4Q07 1Q08 2Q08 3Q08 4Q08 1Q09 2Q09 3Q09 4Q09 1Q10 2Q10 3Q10 4Q10 Net Int Inc 5252 6789 7340 7391 8004 8910 9873 9977 10816 11598 12222 13098 13868 14819 15640 16643 17276 18015 19130 19593 22168 24417 25415 26128 26604 28328 31892 33669 36508 36720 39091 45505 49913 53882 55969 56993 57164 61242 65115 65366 64670 65255 66187 65438 61742 59400 60680 62745 64782 72497 87663 86934 95865 104314 102980 112677 Non-int inc 1592 928 1102 1211 1683 1989 2009 2394 2308 2118 2017 3365 4278 4504 4493 5031 6850 7391 7101 7456 12752 13771 15957 18192 17743 19105 18443 17301 18686 21495 21447 23825 24380 16541 28492 24144 28725 24293 18776 19439 19733 20850 11537 27968 24556 33604 22130 19372 36427 45452 37618 42137 31713 23942 48063 44211 North - Net interest income - Non-interest income (in 000s)

45 EPS Growth 1997 1998 1999 2000 2001 2002 2003 2004 2005 2006 2007 2008 2009 2010 Annual 0.4 0.49 0.73 0.83 1.27 1.6 1.98 2.34 2.75 2.56 2.24 0.76 2.18 1.38 Quarterly 0.07 0.09 0.1 0.13 0.08 0.08 0.17 0.16 0.15 0.18 0.2 0.21 0.23 0.24 0.07 0.29 0.29 0.32 0.33 0.33 0.4 0.37 0.4 0.43 0.45 0.49 0.53 0.52 0.54 0.58 0.6 0.62 0.68 0.53 0.8 0.75 0.76 0.69 0.56 0.57 0.57 0.62 0.4 0.65 0.4 0.47 -0.13 0.02 0.06 0.06 1.07 0.9 0.41 0.25 0.47 0.27 exclude deemed preferred dividend on TARP repay of -0.33 in 4Q10 and -0.36 for full year 2010 Annual Quarterly 4th Quarter and full year 2010 amounts exclude $(0.33) and $(0.36) per diluted common share as a result of the deemed preferred stock dividend resulting from the repurchase of the TARP-CPP preferred stock

46 1994 1995 1996 1997 1998 1999 2000 2001 2002 2003 2004 2005 2006 2007 2008 2009 2010 Net Overhead Ratio 0.0357 0.0201 0.0271 0.026 0.0236 0.02 0.0213 0.0159 0.0141 0.0122 0.013 0.0139 0.0154 0.0172 0.016 0.0023 0.014 Efficiency Ratio 0.8603 0.7975 0.6863 0.7233 0.6366 0.6641 0.6352 0.6445 0.6397 0.6696 0.7106 0.7292 0.5444 0.6377 Net Overhead Ratio & Efficiency Ratio

47 Loan Portfolio Composition As of December 31, 2010 - $9.9 Billion (excludes loans held for sale) CRE Comm'l Other Comm'l. Niches Premium Finance-Comml Premium Finance-Life Ins. Other Res. Real Estate Home Equity Covered Loans Loan comp 0.34 0.17 0.04 0.13 0.15 0.02 0.03 0.09 0.03 Commercial and Industrial Premium Finance - Life Insurance Res. R/E Home Equity Other Other Commercial Niches Commercial Real Estate Premium Finance - Commercial Covered Loans

48 Ending Loan-to-Deposit/Secured Borrowing Ratio* (excludes loans held for sale) 1996 2001 2002 2003 2004 2005 2006 2007 2008 2009 2010 BV per share 0.872 0.827 0.851 0.852 0.775 0.826 0.91 0.91 0.848 0.8711 *Includes $600 million of secured borrowing related to the commercial premium finance loan securitization for which the related loans are recorded on the balance sheet beginning in 2010.

49 Non-Performing Assets to Total Assets (NPAs include NPLs and OREO and exclude covered loans) 1994 1995 1996 1997 1998 1999 2000 2001 2002 2003 2004 2005 2006 2007 2008 2009 2010 Core NPA/TA 0 0.0017 0.0007 0.0016 0.0021 0.0016 0.000676 0.001402 0.0013 0.003 0.0011 0.0019 0.0025 0.0059 0.0138 0.0218 NPA/TA 0.0001 0.0041 0.0025 0.004 0.0045 0.0041 0.0046 0.0048 0.0034 0.0051 0.0029 0.0034 0.0039 0.0081 0.0158 0.0174 0.0153 Total Assets 354 471 706 1053 1348 1679 2103 2705 3722 4747 6419 8177 9572 9369 10658 12216 13968 Assets in millions Peer Group-2003 = 0.58% Peer Group-2004 = 0.45% Peer Group-2005 = 0.42% Peer Group-2006 = 0.43% Peer Group-2007 = 0.80% Peer Group-2008 = 1.94% Peer Group-2009 = 3.00% Peer Group Data is per the Federal Reserve's Bank Holding Company Performance Report

50 Net Charge-offs to Total Average Loans 1994 1995 1996 1997 1998 1999 2000 2001 2002 2003 2004 2005 2006 2007 2008 2009 2010 Net Charge-offs/Average Loans 0.0018 0.002 0.0031 0.0031 0.0028 0.0019 0.0024 0.0026 0.0024 0.0018 0.0007 0.001 0.0009 0.0016 0.0051 0.0165 0.0113 Total Loans 194 258 493 713 992 1278 1558 2061 2556 3298 4348 5214 6496 6802 7621 8412 9934 Loans In millions Peer Group-2003 = 0.33% Peer Group-2004 = 0.21% Peer Group-2005 = 0.18% Peer Group-2006 = 0.15% Peer Group-2007 = 0.27% Peer Group-2008 = 1.10% Peer Group-2009 = 2.28% 0.31% Peer Group Data is per the Federal Reserve's Bank Holding Company Performance Report annualized

FORWARD-LOOKING STATEMENTS This document contains, and the documents into which it may be incorporated by reference may contain, forward-looking statements within the meaning of federal securities laws. Forward-looking information can be identified through the use of words such as "intend," "plan," "project," "expect," "anticipate," "believe," "estimate," "contemplate," "possible," "point," "will," "may," "should," "would" and "could." Forward-looking statements and information are not historical facts, are premised on many factors and assumptions, and represent only management's expectations, estimates and projections regarding future events. Similarly, these statements are not guarantees of future performance and involve certain risks and uncertainties that are difficult to predict, which may include, but are not limited to, those listed below and the Risk Factors discussed under Item 1A of the Company's 2009 Annual Report on Form 10-K and Part II, Item 1A of this Quarterly Report on Form 10-Q and in any of the Company's subsequent SEC filings. The Company intends such forward-looking statements to be covered by the safe harbor provisions for forward-looking statements contained in the Private Securities Litigation Reform Act of 1995, and is including this statement for purposes of invoking these safe harbor provisions. Such forward-looking statements may be deemed to include, among other things, statements relating to the Company's future financial performance, the performance of its loan portfolio, the expected amount of future credit reserves and charge-offs, delinquency trends, growth plans, regulatory developments, securities that the Company may offer from time to time, and management's long-term performance goals, as well as statements relating to the anticipated effects on financial condition and results of operations from expected developments or events, the Company's business and growth strategies, including future acquisitions of banks, specialty finance or wealth management businesses, internal growth and plans to form additional de novo banks or branch offices. Actual results could differ materially from those addressed in the forward-looking statements as a result of numerous factors, including the following: 51

52 FORWARD-LOOKING STATEMENTS (cont.) --negative economic conditions that adversely affect the economy, housing prices, the job market and other factors that may affect the Company's liquidity and the performance of its loan portfolios, particularly in the markets in which it operates; -- the extent of defaults and losses on the Company's loan portfolio, which may require further increases in its allowance for credit losses; -- estimates of fair value of certain of the Company's assets and liabilities, which could change in value significantly from period to period; -- changes in the level and volatility of interest rates, the capital markets and other market indices that may affect, among other things, the Company's liquidity and the value of its assets and liabilities; -- a decrease in the Company's regulatory capital ratios, including as a result of further declines in the value of its loan portfolios, or otherwise; -- effects resulting from the Company's prior participation in the Capital Purchase Program; -- increased costs of compliance, heightened regulatory capital requirements and other risks associated with changes in regulation and the current regulatory environment, including the requirements of the Basel II and III capital regimes and the Dodd-Frank Wall Street Reform and Consumer Protection Act; -- legislative or regulatory changes, particularly changes in regulation of financial services companies and/or the products and services offered by financial services companies; -- increases in the Company's FDIC insurance premiums, or the collection of special assessments by the FDIC; -- competitive pressures in the financial services business which may affect the pricing of the Company's loan and deposit products as well as its services (including wealth management services); -- delinquencies or fraud with respect to the Company's premium finance business; -- the Company's ability to comply with covenants under its securitization facility and credit facility;

53 FORWARD-LOOKING STATEMENTS (cont.) -- credit downgrades among commercial and life insurance providers that could negatively affect the value of collateral securing the Company's premium finance loans; -- any negative perception of the Company's reputation or financial strength; -- the loss of customers as a result of technological changes allowing consumers to complete their financial transactions without the use of a bank; -- the ability of the Company to attract and retain senior management experienced in the banking and financial services industries; -- failure to identify and complete favorable acquisitions in the future, or unexpected difficulties or developments related to the integration of recent or future acquisitions, including with respect to any FDIC-assisted acquisitions; -- unexpected difficulties or unanticipated developments related to the Company's strategy of de novo bank formations and openings, which typically require over 13 months of operations before becoming profitable due to the impact of organizational and overhead expenses, the startup phase of generating deposits and the time lag typically involved in redeploying deposits into attractively priced loans and other higher yielding earning assets; -- changes in accounting standards, rules and interpretations and the impact on the Corporation's financial statements; -- significant litigation involving the Company; and -- the ability of the Company to receive dividends from its subsidiaries. Therefore, there can be no assurances that future actual results will correspond to these forward-looking statements. The reader is cautioned not to place undue reliance on any forward-looking statement made by or on behalf of Wintrust. Any such statement speaks only as of the date the statement was made or as of such date that may be referenced within the statement. The Company undertakes no obligation to release revisions to these forward- looking statements or reflect events or circumstances after the date of this press release. Persons are advised, however, to consult further disclosures management makes on related subjects in its reports filed with the Securities and Exchange Commission and in its press releases.

54 Questions