Cubs manager David Ross said he’s “optimistic” of a possible reunion between the club and free agent starting pitcher Jon Lester this winter.
“I hold out hope. I'm a glass-half-full kind of guy, so I keep my fingers crossed,” Ross told reporters on Wednesday.
After six seasons on the North Side, Lester hit the open market in late October when the Cubs bought out his $25 million option for the 2021 season. But he and the club have expressed mutual interest in extending their partnership on numerous occasions, dating back to the end of the 2020 regular season.
New team president Jed Hoyer said last week the club has been in touch with Lester’s representatives this winter and will continue to be, adding they’ve expressed their desire to work something out with the veteran lefty.
“If things could work out, we’d love to have him back,” Hoyer said. “We have to figure some things out first. That kind of goes without saying, because otherwise, something would be done by now.”
Ross has stayed in touch with Lester this winter, among other Cubs, but has checked in more as a friend rather than as their manager. Ross told Lester he wished he was in Chicago when Lester bought nearly $50,000 worth of beer for fans to offer his gratitude upon hitting the open market.
"I’ve had plenty on his bill, that’s for sure," Ross said. "I thought that was really cool."