The moment Jon Lester credits as a turning point in his Cubs tenure
Jon Lester’s legacy in a Cubs uniform will last as long as the franchise is around.
His impact on the clubhouse and his performance on the mound was a driving force behind the Cubs ending a 108-year championship drought and hoisting the World Series trophy in 2016.
So it’s easy to look back on his six years with the Cubs as an overwhelming positive, but he didn’t get off to the start he envisioned in Chicago.
When asked what he would tell his younger self entering the new chapter of his life at Wrigley Field, Lester paused for a moment but knew right where he wanted to go with the topic.
“I would probably slow down,” Lester said. “To go back, in spring training, you come in the new guy, you get this awesome contract and all this hype and you want to pitch a no-hitter from Day 1. I would say, ‘slow down, be you, take your time and it will all fall into place.'”
Lester got the ball for Opening Day in that 2015 season and made 4 starts in April with an 0-2 record and 6.23 ERA. From May 1 on, he went 11-10 with a 2.99 ERA.
He remembered back to a conversation he had with David Ross early in the 2015 season where the now-manager gave him the same advice to slow down.
“He pulled me aside at the hotel one day — we were on the road — and he goes, ‘hey, I need to talk to you real fast,'” Lester recalled. “He goes, ‘you just need to be you. Quit worrying about trying so hard to get everybody out before the game starts. Just pitch your game and everything will fall into place.’
“From there, I felt a lot more comfortable and slowed down a little bit. But I think I didn’t slow down enough for a while. We all know time goes by so fast. Like I said in my press conference last year when it was my last start at Wrigley, I didn’t know six years could go by so fast. That’s 100% — you turn around and it’s six years. That’s a long time but it goes by in a blink of an eye.
“Looking back at that, had so many good times there that I wish I could’ve just slowed down a little bit and enjoyed them, sat back a little bit and enjoyed it a little bit more.”
Lester had signed the biggest deal in Cubs history prior to the 2015 season — a $155 million pact.
Ross also recalls that conversation six years ago and how his good friend dealt with the lofty expectations that came with the free-agent hype.
“I remember the pressure he put on himself to live up to the contract early on,” Ross said. “He just wasn’t himself coming out of spring, trying to do so much. He was a pretty darn good guy before he got here and then he was trying to live up to a number that’s impossible that I think is just natural for a lot of people to do. I’ve never been in that spot but I’ve been around a lot of players that do that.
“When starting and trying to be so perfect, we were talking about getting back to just competing. Stop thinking so much in the middle of games and trying to make the perfect pitch and why this goes on, why that goes wrong. At the end of the day, you just go out there.”
Of course, that’s exactly the type of advice and insight that earned Ross the position of Lester’s personal catcher.
Their bond has been strong even after Ross retired in 2016 and joined the Cubs front office and eventually the coaching staff.
When Ross got to see Lester for the first time as a Washington National Monday afternoon, he embraced his good friend in the Wrigley Field concourse with a big hug.
“I love that freaking guy,” Ross said. “I told him, ‘good luck tomorrow.’ I told him I would tell him ‘good luck,’ but I wouldn’t mean it.”
As for the weight of expectations about his contract, Lester quickly made peace with that. Winning made things quite a bit easier in that regard.
The Cubs won 97 games in 2015 and advanced to the National League Championship Series. In 2016, Lester finished 2nd in Cy Young voting and posted a 2.44 ERA with 19 victories.
“When we lost in ‘15, everybody knew, ‘I can’t wait to get in spring training ‘cause we’re gonna win next year,'” Lester recalled. “And it was just a mindset, something we talked about, something that really nobody shied away from.
“It was nice to win in the first two years. For me personally, I think it took a lot of pressure off of me. It was kinda like ‘we fulfilled the contract’ type of thing. Then I was just able to go out and pitch after that.”