MILWAUKEE – Like all professional athletes, Jon Lester lives in a bubble, flying on private jets and staying in five-star hotels. Part of this is by design, believing that a focus on process and routine creates a sense of calm, something to fall back on during high-stress situations. This is also someone who owns farmland in Georgia and enjoys disappearing into the woods to go hunting.
So while other Cubs have noticed how much their lives have changed since winning the World Series, experienced a different level of celebrity and capitalized on the newfound perks, this is exactly what Lester signed up for when team president Theo Epstein made a $155 million offer he couldn’t refuse.
Except for a quick, in-and-out stop at Cubs Convention in January, Lester hasn’t really been in Chicago since the team’s parade down Lake Shore Drive and Michigan Avenue, the Grant Park rally and the post-championship bender.
The adrenaline will be surging again on Monday night at Wrigley Field, where the Cubs will raise their 2016 banner above the iconic center-field scoreboard before Lester faces the Los Angeles Dodgers on national TV in a National League Championship Series rematch.
“There hasn’t really been a surreal moment,” Lester said before Sunday’s 7-4 win over the Milwaukee Brewers at Miller Park. “For me, it’s always when you get that tangible thing and you have something in your hand or you see that banner go up.
“That’s when it kind of hits home for me. I was a little confused on why we were doing two different days in Chicago for the celebration. (And) now I’m happy we’re doing two days, because then I will get to be a part of the ring stuff on Wednesday. That, for me, will kind of be the surreal moment.”
Lester already owns two World Series rings from his time with the Boston Red Sox, but says he doesn’t show off the championship bling often, except for weddings or other special occasions: “They’re kind of so big and gaudy it’s not really fun to wear it sometimes. It’s kind of almost too big, which is a good thing.”
Lester’s presence helped transform what had been a fifth-place team for five straight seasons, energizing the clubhouse and signaling the Cubs would be serious about winning and move beyond checking minor-league box scores and talking up the future. During his recruiting trip to Chicago the week before Thanksgiving 2014, Lester told Epstein: “They’re going to burn this city down again when we win the World Series.”
“A big part of what we do is for the fans,” manager Joe Maddon said. “They will be out in force. It’s going to be raucous. It’s going to be a party for them. I love it. Our fans deserve it. They waited a long enough time. The reaction has been beyond spectacular.
“Every place you go, more than anything, you hear: ‘Thank you.’”
Lester had enough sense of history to choose No. 34 as a tribute to Kerry Wood, Walter Payton and Nolan Ryan and wanted to be part of something like the epic World Series against the Cleveland Indians that ended the 108-year drought.
“We all saw the stuff this offseason – the different TV programs about our journey and fans and just how much it meant to those people,” Lester said. “The one that hit home was a guy that sat at his dad’s grave for the entire game and listened to (Game 7) on the radio and just his emotions through the whole game. That resonated pretty hard for me.
“That was a pretty cool moment that these fans shared with their family members – who have been through so many years of heartache – to finally win and give these people the championship that the city deserves.”
Even someone who spent nine years in the Fenway Park fishbowl and pitched in 14 playoff series still feels the butterflies. Moving the bullpens to underneath the bleachers means more revenue for the Cubs and tunnel vision for Lester.
“There’s a lot of things going on, a lot of distractions,” Lester said. “But I actually honestly think that the bullpen move is going to help us with all this stuff. You’re kind of separated from things. You’re in a tunnel. You’re away from everybody. You don’t get to really see what’s going on.
“Obviously, when you get out there for first pitch, it’s going to be a little different. But as far as the festivities leading up to that point, I feel like that new bullpen’s going to kind of help combat all those emotions.”