The Cubs brought back Kerry Wood and Greg Maddox before they ended their careers. It is something about Chicago that makes a player miss the city. Ryan Dempster only lived down the street from Wrigley Field. For all we know he probably still owns the place.
Ryan Dempster reportedly turned down the Red Sox on a 2 year $25 million contract. He also has had offers from the Royals and the Brewers. The rumor is that he is looking for a 3 year deal but a 2 year deal with the Red Sox seems close enough to negotiate.
There are no strong signs that the Cubs have turned on the after burners to try and get Ryan Dempster but it would appear that they may have the best opportunity. The Cubs are looking for someone with his capabilities and consistency to fill the rotation. He also brings the comedy and chemistry the pitching staff needs to relax and play well.
It is known that Ryan enjoyed his time playing with the Cubs and he would most likely want to finish his career in Chicago. His time in Texas was obviously uncomfortable as he struggled to get settled in. Ryan knows his time is getting short as a pitcher. He will most likely want a deal with a team that he comfortable with that he can play out the rest of his career.