X0303 4 2009-12-14 0000814184 TCF FINANCIAL CORP TCB 0001204874 BROWN NEIL W 200 LAKE STREET EAST WAYZATA MN 55391-1693 0 1 0 0 President and COO Common Stock 20000 I By TCF Express Trade - IRA Common Stock 24872.344 I By SERP Trust as of 11/30/09 Common Stock 50000 I By Spouse Common Stock 6804.693 I By KSOP as of 11/30/09 Common Stock 4000 I By Children Common Stock 2009-12-14 4 A 0 18882 A 155232 D Option (right to buy) 15.75 2018-01-21 Common Stock 282000 282000 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 directly 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. Stock award from TCF Financial. One-third vests on or before April 1, 2011, 2012 and 2013. Vesting is based on achievement of ROE goal. Price is not applicable. Neil W. Brown By POA Gregory J. Pulles 2009-12-16