Ryan Dempster is back with the Cubs in an official capacity. The Cubs and Dempster announced Friday he re-signed with the team, resigned and was added to the front office as a Special Assistant to Theo Epstein and Jed Hoyer.
Ryan Dempster has been pulling for his former teammate to sign with the Cubs and talked about Jon Lester with David Kaplan last month. Dempster indicated then Lester is “truly interested in the Cubs, genuinely loves the city and is seriously considering them.” Lester began asking Dempster about the Cubs in 2013 when it looked like the Red Sox would not be signing him to an extension.
Dempster fielded questions about Lester after he discussed his retirement Friday. And he reiterated he’s been recruiting Lester to sign with the Cubs.
“Jon and I have talked about how great it is to play here. He knows that and he’s got an extremely tough decision ahead. But whatever the decision is, hopefully it’s here with the Chicago Cubs because he won’t be disappointed. I know the city of Chicago would embrace him. He’s the type of person who could pitch here and do well here. Hopefully we’re lucky enough to have him here with us.”
Ryan Dempster told the beat writers, “He would be a guy that we can add here to just step in front of everybody. And all the younger guys can sit there and watch and learn from him. Because he’s a tremendous pitcher and a tremendous human being and would be a great addition to any team.”
The relationship between Jon Lester and the Cubs front office has likely been overblown at this point. But multiple reports have pointed to Lester’s comfort level with a team and situation being more important to him than the dollar figures and years on the contract. Having another familiar face in the front office shouldn’t hurt the Cubs efforts to sign him.