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Forward-Looking StatementForward-Looking Statement

This presentation contains certain forward-looking statements within the meaning of the

Private Securities Litigation Reform Act of 1995. Forward-looking statements include

expressions such as “may,” “expect,” “anticipate,” “intend,” “believe,” “could,” and

“should,” and reflect our current expectations and projections about future events.

Actual results could materially differ from those presented due to a variety of internal

and external factors. Except as required by the SEC, we undertake no obligation to

release revisions or report events or circumstances after the date of this presentation.

Additional information concerning factors that could cause actual results to differ

materially from those in the forward-looking statements is contained from time to time in

our SEC filings, including, but not limited to, our report on Form 10-K; our reports on

Form 10-Q; and other filings. Copies of these filings may be obtained on our website at

www.taylorcapitalgroup.com or the SEC’s website at www.sec.gov.

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Who is Taylor Capital Group?Who is Taylor Capital Group?

• Holding company for Cole Taylor Bank– 9th Largest bank based

in Chicago area*

• Celebrating 80th anniversary in 2009

*Ranked by assets as of 3/31/08

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Who is Taylor Capital Group?Who is Taylor Capital Group?

• Commercial banking is our sole focus– Serving Chicago

metropolitan area

– Owner-operated businesses

– Sales from $5 million to $250 million

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Key FinancialsKey Financials

Nasdaq: TAYC Snapshot at 6/30/2008

Share price on 8/18/2008…………………$10.93

Shares outstanding……...11 Million

Market Cap………….. $120 Million

Ownership……...49% Insider/ESOP 51% Public

Total Assets………….…..$3.7 Billion

Total Equity……………..$221 Million

Total equity to assets….……10.26%

Tangible equity to assets……8.63%

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Key DevelopmentsKey Developments

• First half results– C&I first half loan growth 46% (annualized)

– First half loss of $29 million vs. net income of $12.5 million for first half last year

– Loss attributable to $61 million provision for loan losses in 1H08

• Plans to raise additional capital– Working with investment bank for 2008 capital augmentation

• $50 million convertible preferred stock at holding company

• $50 million in bank subordinated debt

– Signed Letter of Intent

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Key DevelopmentsKey Developments

• CTB President and CEO: Mark Hoppe– More than 27 years in commercial banking with LaSalle

Bank, N.A.• CEO, LaSalle Midwest Bank in Michigan

• Vice chairman, LaSalle National Leasing Company

• New Director: Hill Hammock– Chief administrative officer, Chicago Public Schools

– COO, ABN AMRO North America, Inc.

– More than 30 years with LaSalle Bank, N.A.• COO

• Chief credit officer

• Chief risk officer

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Residential ConstructionResidential Construction

• Problem facing banks across the region and the country

• Unprecedented drop-off in new home sales

• Portfolio is in our market

• Long time Chicago-based homebuilders

• Reducing residential construction as % of overall portfolio

Issues Cole Taylor Bank’s Position

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864

516

824

504

850

493

879

456

1,045

423

$0

$200

$400

$600

$800

$1,000

$1,200

Commercial Residential Construction

Q207 Q307 Q407 Q108 Q208

Improving Loan MixImproving Loan MixMillions

+20.8% Y/Y

–18.1% Y/Y

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Strategic GrowthStrategic Growth

• Made choice to invest in growth, not fall behind

• Developed growth strategy to take advantage of disruption

• Doubled commercial lending team

• New bank and commercial lending leadership

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Chicago Middle Market BankingChicago Middle Market Banking

• Chicago area market share*– Top two banks 58%

– Top five banks 83%

– Cole Taylor Bank 2%

*Of companies with $10 - $500 million in annual sales

Top 5 Banks, 83%

Cole Taylor Bank, 2%

Other Banks, 15%

Our Opportunity

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Chicago Middle Market BankingChicago Middle Market Banking

• Large and diverse market

• Strong base of owner operated business

• Market potential >15,000 firms

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Chicago Middle Market BankingChicago Middle Market Banking

• Primary competition is:– MB Bank

– Fifth Third Bank

– Bank of America

– PrivateBank

– WinTrust

– National City

• Singular focus on small-middle market gives us great upside

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Strategic Growth InitiativeStrategic Growth Initiative

• Recognized opportunity to take advantage of market disruption in 2007

• Strategy developed• Committed substantial resources to core

commercial banking • Brought in new bank and commercial

banking leadership • Doubled commercial lending team

– Exploit growth opportunity in market disruption– Navigate industry downturn

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Talent Investment to Facilitate Growth Strategy…Talent Investment to Facilitate Growth Strategy…

Acquired Category Leaders– Larry Ryan, Chief Lending Officer

– Mike Morton, Chief Credit Officer

– Mike Sharkey, Head of Asset Based Lending

Acquired 40 accomplished Chicago-area bankers– 25 commercial lenders averaging more than 13

years of experience

– Experience managing larger portfolios

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Cole Taylor’s Plan Focused On Market PotentialCole Taylor’s Plan Focused On Market Potential

Top priorities:– Leverage existing relationships during market

disruption

– Enhance effectiveness of staff

– Expand non-credit product offerings

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Representative New ClientsRepresentative New Clients

• Plastic container manufacturer – $29 million in sales– $12 million in credit, derivatives, treasury management

• Seasonal goods importer – $225 million in sales– $25 million in credit, derivatives, treasury management,

foreign exchange, letters of credit

• Specialty metal products manufacturer - $25 million in sales– $13 million credit, treasury management

• Bank holding company - $500 million in assets– $25 million credit, DDA/Cash letter/Fed Funds, letters of credit

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Early Results PositiveEarly Results Positive

• First 90 days– $300 million in new commitments since 3/31

– $214 million in total new loans (up 34% annualized) since 3/31

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…and Superior Credit Support…and Superior Credit Support

Added senior credit, loan review, workout teams

– Augmented staff

– Enhanced controls and monitoring

– Infrastructure in place to manage larger, more complex book of business

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SummarySummary

• TAYC is a stock with significant upside

• Portfolio is being managed and minimized

• Team in place to build and manage a significantly larger organization

• Adding capital to support growth: the future of the bank

• 2Q loan and relationship growth confirms strategy

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QuestionsQuestions

??

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Thank youThank you