- Oct. 31 - Declined the 2009 option on Henry Blanco
- Nov. 13 - Acquired Kevin Gregg from the Marlins for Jose Ceda
- Nov. 18 - Re-Signed Ryan Dempster to a four-year contract
- Nov. 19 - Added Mitch Atkins, Justin Berg and Marcos Mateo to the 40-man roster
- Dec. 3 - Signed Chad Fox to a minor league contract with an invitation to Spring Training
- Dec. 11 - The Pirates picked Donald Veal in the Rule 5 Draft
- Dec. 11 - Acquired David Patton from the Reds (Rule 5 Draft) for Cash
- Dec. 12 - Avoided arbitration and agreed to one-year contracts with Chad Gaudin, Neal Cotts and Reed Johnson
- Dec. 16 - Signed Joey Gathright to a one-year deal
- Dec. 31 - Signed Aaron Miles to a two-year contract
- Dec. 31 - Traded Mark DeRosa to the Indians for Jeff Stevens, Chris Archer and John Gaub
- Jan. 5 - Agreed to terms with Milton Bradley
- Jan. 6 - Traded Jason Marquis to the Rockies for Luis Vizcaino
A report from Dugout Central pointed toward desperation as the reason the Cubs have more than just 'tweaked the roster' this winter.
Available Arms
If the Cubs do not attempt to revisit the talks with the Padres over Jake Peavy once the ownership transition is concluded, Jim Hendry will either have to pick from the list below or try to swing a deal with another team. Here is a complete list from Cot's Contracts





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