Four Chicago Cubs players have filed for free agency on the first day that players could file. Ryan Dempster, Jim Edmonds, Bob Howry, and Chad Fox all filed. Out of the four players I really only expect Jim Hendry and management to look into resigning Dempster and Howry.

All Cubs fans are hoping that Dempster won’t require a ton of money to stay with the Cubs. I would expect Howry to not demand as much money the way that he threw the ball in 08. I’d be willing to give Howry a one year deal to see if he turns things arounds and Dempster a three year deal.

Dempster went 17-6 with a 2.96 ERA in 33 starts, striking out 187 in his first full season as a starter after trying to be the Cubs closer. Dempster’s last contract was for three years at $15.5 million. I say offer him a nice raise and pay him around $21-$24million for a three year contract.

I’d expect Fox and Edmonds to not resign with the Cubs as both of them could be on the verge of retiring.

I should also mention that the Cubs lost Casey McGeehee as the Milwaukee Brewers claimed him off waivers. McGeehee is a pretty good player but was never going to much time at his natural poistion which is third base. McGeehee was a 10th round pick by the Cubs back in the 2003 draft.