Dempster Joins Cubs' Front Office, Hints at Recruiting Lester

Chicago Cubs fans continue to hold their collective breath about the team signing a top-tier free agent pitcher. Ryan Dempster isn't going to start for the team any time soon, but the team signed the hurler to a one-day contract in order to allow him to retire as a Cub.

The veteran pitcher, who suited up for five different teams in his big league career, spent the majority of that career with the Cubs as he lasted nine seasons on the north side. Over that span, he posted a 67-66 record with a 3.74 ERA, 1070 strikeouts in 1182.2 innings, and a WHIP of 1.31. He was both a closer, posting 33 saves in the 2005 season, and a starter, going 17-6 and making an All-Star Game appearance for the 2008 Cubs.

In more recent times, Dempster made his way to the Boston Red Sox in 2013, where he pitched for the eventual World Series champions that year. He opted not to pitch during the 2014 season, and despite some speculation that he might make a major league comeback, he decided to retire on Friday instead.

Even with his retirement, Dempster will still be busy. The Cubs announced Friday that he will serve as a special assistant to GM Jed Hoyer and team president Theo Epstein. In that capacity, the Cubs said in a statement that Dempster will “spend time with the club during spring training, visit the club’s minor-league affiliates during the season, evaluate amateur players leading up to the draft and perform professional scouting assignments.”

One of the side benefits for the Cubs is that Dempster pitched on the 2013 Red Sox team with Jon Lester, who the team has reported offered a six-year contract worth around $140 million. There has been a surge of late interest from several other teams, including the Los Angeles Dodgers, but Dempster has been beating Chicago’s drum in conversations with the free agent pitcher.

“Jon (Lester) and I have talked about how great it is to play here,” Dempster said. “He knows that. He’s got an extremely tough decision. Hopefully it’s here with the Chicago Cubs, because he won’t be disappointed.”

Contact Us