Trades
- April 3, 2009: Traded Jay Cutler and 2009 5th round pick (140th overall, Johnny Knox) to Bears for Kyle Orton, 2009 1st round pick (18th overall, Robert Ayers), 2009 3rd round pick (84th overall subsequently traded, Mike Wallace) and 2010 1st round pick (11th overall subsequently traded, Anthony Davis)
- April 25, 2009: Traded 2010 1st round pick (14th overall, Earl Thomas) to Seahawks for 2009 2nd round pick (37th overall, Alphonso Smith)
- April 25, 2009: Traded 2009 3rd round pick (79th overall, Kraig Urbik) and 2009 3rd round pick (84th overall, Mike Wallace) to Steelers for 2009 2nd round pick (64th overall, Richard Quinn) and 2009 4th round pick (132nd overall, Seth Olsen)
- April 26, 2009: Traded 2009 5th round pick (149th overall, Davon Drew) and 2009 6th round pick (185th overall, Cedric Peerman) to Ravens for 2009 5th round pick (141st overall, Kenny McKinley)
- April 26, 2009: Traded 2009 7th round pick (235th overall, Zack Follett) and 2010 5th round pick (146th overall subsequently traded, Cam Thomas) to Lions for 2009 6th round pick (174th overall, Tom Brandstater)
- August 17, 2009: Traded 2010 5th round pick (158th overall subsequently traded, Matt Tennant) to Patriots for Le Kevin Smith and 2010 7th round pick (231st overall subsequently traded, Selvish Capers)
- August 25, 2009: Traded an undisclosed 2009 draft pick to Patriots for Russ Hochstein
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