According to Ken Rosenthal , Ryan Dempster will test the open market. He filed for free agency on Friday and is not expected to sign with the Cubs before their exclusive negotiating period with him expires on Nov. 13. This of course means it will be much harder to retain Dempster. I thought for sure he would sign with the Cubs for a home team discount just like Aram and Zambrano did but obviously that is not the case. On the open market Dempster will get 4-5 year deal worth 60-70 million. The Mets, Yankees, Dodgers, Angels, and Braves are all potential suitors for Ryan. If there becomes a bidding war for Demp, the Cubs will lose that War.
The good news if that if the Cubs do not spend the money on Ryan, they could go out and get another decent pitcher to replace him or more offense so he is not missed as much. A guy like Brad Penny could be of some value if his option is declined. Other guys that maybe low risk, high reward guys like Mark Mulder, Mark Prior, and Matt Clement could be options as well.
Also according to Rosenthal, if Dempster leaves it will make a Jake Peavy trade for the Cubs even more prominent and more likely. If Peavy comes here, I doubt Dempster would be missed that much.
Losing Dempster is not the end of the world for the Cubs but will definitely take a blow to the rotation. Besides the players listed above, here are some more free agent pitchers that the Cubs might look at for one reason or another via trade or free agency-
Brett Myers( rumored avaliable)
Aaron Harang( rumored avaliable)
Not the greatest list in the world but Myers, Harang, Garland, and Willis are some good names. I especially think Rothchild could turn around a guy like Willis and Harang.