Ryan Dempster has tried to sell Jon Lester on signing with the Cubs


Ryan Dempster officially retired as a member of the Cubs yesterday and accepted a job in the team’s front office. He’s already doing his part to improve the ballclub.

According to Patrick Mooney of CSNChicago.com, Dempster told reporters that he has spoken with free agent left-hander Jon Lester in hopes of luring him to Chicago. Dempster and Lester were teammates with the Red Sox in 2013 when the team won the World Series.

“Jon and I have talked about how great it is to play here,” Dempster said at the team’s Clark Street office building. “He knows that. He’s got an extremely tough decision ahead. But whatever the decision is going to be, hopefully it’s here with the Chicago Cubs, because he won’t be disappointed.

“I know that the city of Chicago would embrace him. He’s just the type of person that can pitch here and do really well here.

“Hopefully, we’re lucky enough to have him with us.”

It’s nice to be able to utilize Lester in that way, but the Cubs also have Theo Epstein and company in-house, so everyone is pretty familiar with each other. Like most situations with free agents, this will come down to how much money the Cubs are willing to commit.

The field for Lester reportedly includes the Cubs, Red Sox, Giants, and Dodgers. He’s not expected to make a decision before next week’s Winter Meetings in San Diego.