CHICAGO — Jon Lester will be associated with the Chicago Cubs forever. The big-game pitcher is one of the greatest free-agent signings in Chicago sports history, a transformational figure from the period when the franchise modernized Wrigley Field and ended a 108-year World Series drought. In retirement, the question lingered more as to how much Lester wanted to be associated with the Cubs.
The answer suddenly appeared Friday afternoon when Lester showed up in the Wrigley Field press box dressed in a suit and tie, beginning a trial run as an analyst for Marquee Sports Network. He will be doing a mixture of studio work and game broadcasts during this homestand, offering insights from his 16 years in the majors.
It was surreal that Lester won his 200th game in a St. Louis Cardinals uniform, an achievement he once hoped to celebrate at the Friendly Confines (until the Cubs decided not to bring him back for the 2021 season). It was noticeable that Lester put on the Boston Red Sox gear again for spring training this year, serving as a guest instructor at their camp in Florida. Lester’s close friendship with former teammate David Ross — the manager fired by Cubs president of baseball operations Jed Hoyer in November — could have frayed the connection to Chicago.
“When it’s your buddy, it’s a little harder to kind of see what’s going on,” Lester said. “But when you kind of step back and look at it as a business aspect, stuff like that happens all the time. You just have to think that the Cubs are trying to do what’s in their best interest. Like I said, when it’s one of your buddies, it’s like, ‘Well, that sucks.’”
It will be interesting to see who shows up when the Cubs hold a 10-year reunion for the 2016 World Series team. Lester doesn’t believe there will be a permanent rift between Ross and the franchise that helped him launch a successful post-playing career.
“I think he understood what was going on,” Lester said. “As far as the 10-year thing, I would imagine that he’ll probably be back in baseball here shortly. I know when I talked to him around New Year’s time, he said he was going to take this year off and kind of see where next year goes. He’s the kind of guy that I believe will stay around baseball in some capacity.”
Lester is the kind of guy who once put his credit card down at four Chicago bars and bought 4,838 Miller Lites one weekend, saying thank you to Cubs fans for their support over the years. It was an all-time walk-off move, but you will be hearing more from him.
‘It’s hard to beat Chicago in the summer’
Lester isn’t looking for a full-time job, but he’s curious about the TV industry and interested in gaining on-air experience. He will work Sunday’s game against the Arizona Diamondbacks with Pat Hughes and Joe Girardi. He will also be in the broadcast booth Monday and Tuesday with Jon Sciambi and Jim Deshaies, analyzing those games against the Milwaukee Brewers.
This Cubs team managed by Craig Counsell is 47-53 after Saturday’s quiet 3-0 loss to the Diamondbacks, making it extremely hard to see Hoyer’s front office buying at the July 30 trade deadline. As a player, Lester was known for his honesty and willingness to answer virtually any question. A TV rookie isn’t going to blast the Cubs on a team-owned network, but Lester’s voice will carry a lot of weight if this is something he decides to pursue.
Lester saw a Morgan Wallen concert at Wrigley Field last year, and he had visited the Cubs while Ross managed the team. He spends most of his time at home in Georgia, shuttling his three children between school, sports and activities.
“I run an Uber service without the stars,” Lester said. “I don’t get any positive comments from them.”
‘The sky’s the limit’ for Justin Steele
Justin Steele has a 3.07 ERA this season. His ERA was 3.06 in 2023. (Nuccio DiNuzzo / Getty Images)
Lester was on a beach vacation with his family in South Carolina when he happened to turn on a Cubs game in 2022 and watch Justin Steele pitch. The left-hander reminded Lester of Lester, so he immediately texted Ross, sending along a few suggestions.
After years of gradual development, Steele has established himself as not only an All-Star but a true top-of-the-rotation starter, an emotional leader and a reason to tune in to a Cubs game.
“When you’re younger, there’s always that kind of older comparison,” Lester said. “For me it’s nice because I do see a lot of similarities in the way he pitches, the way he goes about it, his competitiveness (and) his conviction to each pitch. I see a lot of that. But I think the big thing that people need to see is Justin Steele is his own person.
“Justin Steele is not me. And I wasn’t whoever (you wanted to compare me to). You got to kind of carve your own path. And I think he’s doing that. The sky’s the limit for him. He’s got the stuff. It’s just a matter of being out there and pitching.”
The Hall of Fame question
Lester said he doesn’t think about the Hall of Fame, but this weekend’s Cooperstown ceremonies are a reminder that he could someday have his moment in upstate New York. He will be on the Baseball Writers’ Association of America ballot as part of the class of 2027.
If 200 wins are the new 300, Lester will have a compelling case as a three-time World Series champion with the Cubs and Red Sox who thrived in October, posted up for 2,740 innings and earned five All-Star selections.
“If I get that phone call, obviously, I’ll be the happiest person in the world,” Lester said. “But I’m not counting days down until that day by any means. My big thing is I don’t want to get my hopes up and be disappointed. I’ll take it day by day, and hopefully my name’s on there and there’s a few people that decide to check that box.”
(Top photo of Jon Lester from 2019: Justin K. Aller / Getty Images)
