X0303 4 2009-01-20 0000814184 TCF FINANCIAL CORP TCB 0001204870 BAILEY TIMOTHY P 200 LAKE STREET EAST WAYZATA 55391-1693 0 1 0 0 Vice Chair/Signif Subsidiary Common Stock 2009-01-20 4 A 0 25000 A 299416 D Common Stock 24820.662 I By KSOP as of 12/31/08 Common Stock 18364.589 I By SERP Trust as of 12/31/08 Option (right to buy) 15.75 2018-01-21 Common Stock 68000 68000 D The filing of this statement shall not be construed as an admission that the undersigned is, for the purpose of Section 16 of the Securities and Exchange Act of 1934, the beneficial owner of any equity securities covered by this statement other than those owned by the undersigned. The shares noted are derivative securities based on the Reporting Person's benefits under a non-qualified plan. The option vests in 2 installments: 50% on January 1, 2011; the remaining 50% on January 1, 2012. Price is not appliable. Stock award from TCF Financial. One-third vests on January 1, 2010, 2011, and 2012. Timothy P. Bailey By POA Gregory J. Pulles 2009-01-22