Ryan Dempster knows how good a pitcher Jon Lester is, and has already talked to the free agent about how fun it is to pitch at Wrigley Field for the Cubs. Whether that helps Lester make a decision remains to be seen. Dempster, who was Lester’s teammate in Boston in 2013, made his recruiting pitch to the left-hander before joining the Cubs front office as a special assistant to Theo Epstein and general manager Jed Hoyer.
“Jon and I have talked about how great it is to play here,” Dempster said at the Cubs offices near Wrigley Field. “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.”
Lester, 30 is weighing offers from at least four teams — the Cubs, Red Sox, Giants and Dodgers — and talks between his agents and those teams were expected to continue into the Winter Meetings.
Epstein would not comment Friday on any specific negotiations, but did say the Cubs were not delaying any other talks with free agents or teams regarding possible trades while waiting for Lester to make a decision.
“We’re working on a lot of fronts,” Epstein said. “When there’s a potential impact player involved, it does shape a little bit the course of your short-term thinking. If you get a player who makes a significant difference in the standings, you prioritize creating a winning roster immediately around that player.
“If the offseason goes in a slightly different direction, you would continue to build more organically and continue to think a little bit longer term,” Epstein said.
Dempster said he was impressed by how prepared Lester is before his starts.
“Here I was, a guy who played 16 years in the league, and I’m supposed to be the veteran leader and I watched him and felt like I wasn’t doing enough,” Dempster said of their days together with the Red Sox. “If we could add him here, he’d step in front of everybody and all the young guys could sit and watch and learn from him. He’s just a tremendous pitcher and a tremendous human being and would be a great addition to any team.”
And now, Dempster said, Lester is seeing the reward of all that hard work by being offered lengthy contracts that will likely top $130 million.
— Carrie Muskat