Being a sore loser made Jon Lester into the ultimate winner

Lester still has hunger to win every fifth day (1:13)

Despite already winning three World Series championships and amassing many personal accolades, Jon Lester discusses his want for another ring. (1:13)

IT OFTEN STARTS with just a stare from the mound.

Then, between innings, some heated words exchanged with his catcher -- or with whomever called the wrong pitch from the dugout.

After a poor performance, his agent might receive some "very dark texts." But no matter which direction Jon Lester's frustration is pointed when he's not winning, the one place he's sure to look is the mirror.

"He's always been that way, from the time he signed as a high school kid," Chicago Cubs president Theo Epstein said recently. "He was always holding himself to a really high standard, always really accountable and always competing with himself in some ways. He loves the competition of the game and beating other lineups, but I see it as he's in competition with himself."

It's a theme repeated over and over by those who know him best. With Lester, the competition is internal. He's accomplished just about everything in the game -- including three World Series titles, four All-Star appearances, three top-five Cy Young finishes and one of the game's richest contracts -- yet he keeps on competing like a rookie trying to make the team for the first time.

And he might just be putting together the best season of his career. He'll take his 9-2 record to the mound Tuesday night against the Los Angeles Dodgers (10 p.m. ET, ESPN/WatchESPN) hoping to end the Cubs' five-game losing streak. He sports a 2.10 ERA and 197 ERA-plus. His ERA in June is a minuscule 0.67. After a down year in 2017, he ranks among the National League's elite again at age 34.

"I want to win," Lester said simply as he sat in the visiting dugout in Cincinnati last Thursday. "I want to continue to win. I don't like to fail. It's those things that keep me going."

But he's not one of those guys who has to win at everything he does -- you won't find Lester slamming a pingpong paddle or flinging a golf club in frustration. His competitiveness is all channeled to one place: the pitching mound. And when things don't go right there, answers need to be found.

From everyone.

"He goes to some dark places when he has a bad inning, let alone when he struggles in a game or two," Cubs game planner Mike Borzello said. "I deal with him all game long and there are certain times I'll get the stare into the dugout on a pitch, maybe we chose to try, that doesn't work. As that ball is hit, on his follow-through, he'll look right at me in the dugout. That probably happens at least twice a game. Maybe once. It's never zero. I want to run into the tunnel."

Lester's response?

"I'm a sore loser," he chuckles. "It's kind of bratty. ... I think that's where the frustration comes in, when you got out there and s--- the bed and really let your team down."

And while Borzello -- or former catcher David Ross -- can get an earful, Lester isn't above admitting he's wrong. It just takes a bit for him to calm down and listen.

"He gives his heart and soul to every pitch," Ross said in a phone interview. "When things don't go right, it's really defeating for him. It's hard for him to climb out of those places sometimes. The role I played was to lift him up and focus him mentally. ... He's broken down to me, in full tears -- this big, giant left-handed human being -- in tears, just wanting to be better than he already is. He wants to be that guy and make everyone happy."

Lester has been described as a pleaser, as well as one of the most generous teammates in the game. His charity work for cancer research and to help families is the standard for any professional athlete, but measuring himself against baseball icons isn't Lester's style on or off the field.

Longtime agent Seth Levinson claims Lester has no idea of his place in the game and he is constantly reminding the ace how good he actually is. Ross agrees that Lester is the type of player who will never appreciate his career until it's over.

"That's 100 percent true," Ross said. "He has no idea how good he is. He feels like he's constantly trying to live up to something."

In an attempt to remind him, Levinson recently sent Lester a Whitey Ford jersey after the Cubs pitcher passed the Hall of Fame hurler in strikeouts. Then came one with Sandy Koufax's name on it, after Lester went by him in wins.

"He kept trying to hammer home all this stuff to me so I just wanted to be a smartass back to him," Lester said after receiving the Ford jersey. "I told him, 'Another dead guy goes down.' He texted back, 'Whitey isn't dead. He's 88 and doing just fine.' The one time I have a response for him, the guy is alive.

"After he gave me the Koufax jersey, he made sure to tell me he wasn't dead," Lester said, laughing. "I knew that.

"Seriously, to have my name next to them is incredible. If you would have told me that when I was 18 years old, I would have laughed at you."

At 18, Lester was a rookie in the Red Sox organization. By 22, he was in the majors -- when the unthinkable happened. Lester was diagnosed with anaplastic large-cell lymphoma, but by early 2007, he had beaten cancer and was back on the mound that spring. He's been on a mission ever since, to help people less fortunate and to make the most of his career. The commitment on the field led him to two World Series championships with the Boston Red Sox. But after getting traded midseason to Oakland in 2014, it set the table for his arrival in Chicago, and for the second portion of his career, as a different kind of pitcher.

'Coming here and possibly being able to do that was a huge part'

THE REIGNING WORLD SERIES champion San Francisco Giants were coming after Lester hard in the winter of 2014-15. The Red Sox wanted him back as well. Both teams had a lot to offer -- particularly the Giants, who threw a lot of money at Lester while boasting a pitcher-friendly ballpark and an immediate contender. What did the Cubs have? Some 108 years of heartbreak -- oh, and Epstein, Lester's former boss in Boston.

"The arrogance, in a good way, that Theo had," Lester says of what helped bring him to the Cubs. "The belief in the young guys. It was just a good feeling. Anytime someone would argue against the Cubs, I would always go back to the Cubs. At the end of the conversation they would say, 'Oh, sounds like your decision is made.'"

He claims his decision wasn't made, but that lure to end the 108-year drought was too much to pass up.

"That was a big thing for me, not being a part of 2004 with the Red Sox," Lester said. "Coming here and possibly being able to do that was a huge part."

Saying so long to his Boston family wasn't easy. All Lester had ever known was the Red Sox way. Not once, but twice, he had to say goodbye: after the trade, and when he signed with the Cubs.

"I told him, I'll see you in a few months," good friend Dustin Pedroia said of Lester's trade to Oakland. "He was a free agent and I thought he was coming back. He called me right before he signed with the Cubs. It was a pretty emotional phone call. That was the first time I realized it was a business. We're kind of naïve because you think you're going to play together your entire career."

"He gives his heart and soul to every pitch. When things don't go right it's really defeating for him. It's hard for him to climb out of those places sometimes. ... He's broken down to me, in full tears -- this big, giant left-handed human being -- in tears, just wanting to be better than he already is. He wants to be that guy and make everyone happy." Former catcher David Ross on Jon Lester

Lester took that leap, signing a six-year, $155 million contract with the Cubs, but he got off to a rough start. Injured in spring training, he pushed himself to be ready for Opening Day -- he wanted to please his new team and fan base -- but it was a mistake. His ERA his first month as a Cub was 6.23, and he entered that dark place, feeling the weight of the world on him because of the contract he had just signed.

"My agent was really good at breaking it down for me," Lester said. "My dad was a police officer. My mom worked on the county road and drove dump trucks. I never did without, but they grinded for everything that we had.

"'Look at your parents, look at teachers, look at doctors, look at people that actually save lives,' my agent said. "'You can't live up to them, so why try and live up to this?'

"As long as I'm always chasing that, trying to live up to [the contract] I'll never be happy. That was about two to three months into my season in 2015, and I said, 'Screw it, I can't control what anyone else thinks about me and what I'm doing between my starts and on my start days.' ... I feel the same way now. I'm just trying to fulfill my years, not let anyone down."'

But his stuff wasn't quite as good as it was when he was younger, and the Cubs, led by Borzello, wanted him to try some new things, mostly pitching more to a hitter's weaknesses. Lester pushed back for more than a year.

"Borzello is a brash personality and when it doesn't go his way, he's like me, a sore loser," Lester said. "I'm getting my ass kicked, he's grinding with you, and we finally had it out one day. Ever since then it's been a great relationship."

Yet Borzello still remembers the game plan needed to get a proud veteran pitcher to buy into a new way of thinking.

"He was pretty set in his ways in how he was going to do what he does," Borzello recalled. "I would sprinkle ideas about how to pitch an opponent, and he was pretty adamant about 'This is who I am, this is what I do.'"

So Borzello waited until a bad game. He knew he needed Lester to come to him. Ross served as the intermediary.

"Ross said screw it," Borzello continued. "Today is the day he's going to make some changes. I'm going to call these pitches that he's apprehensive about and I'm going to force him to do it."

Lester threw a three-hitter against the Giants.

"I remember that was the day we became one unit and it was a working relationship," Borzello said.

'Only fools are satisfied'

THE COMMON THOUGHT in baseball is that long-term contracts for pitchers are a waste near the end of the deal. The hope is to win early and figure out the bloated contract later. Lester and the Cubs did just that, winning the World Series in 2016. Now he's out to be the exception to the latter half of the contract rule.

Lester, admittedly, had a bad year in 2017, with his ERA ballooning to 4.33. Physically, he simply could not recover between starts. The long championship season, combined with the shortest offseason in baseball history, had its effects. The whispers and shouts on social media began. "The second half of Lester's contract will be a waste" and "He's no longer the ace" were common themes.

"Turning it back on three months later was tough, but again he kept on going out there and doing what he could do to help us," Borzello said. "It took its toll. I don't think he wanted to accept that it did, but realistically it did."

Lester's agent saw what it was doing to him.

"It fueled his fire," Levinson said. "For the first time, there were people that questioned him and doubted his ability to be successful in the field."

"The biggest thing is when you don't know how to fix it," Lester explained. "That's the real frustrating part. You're letting your teammates down and that's frustrating. It makes the work that much harder. There are times when you think, 'Why do I work so hard to go out there and do this?'"

He pitched better in the latter half of 2017 and in the playoffs, competing -- like he always does. Then he went back to the drawing board.

"Don't you know only fools are satisfied," Levinson said, quoting Billy Joel. "Jon is no fool. He's as self-critical as any player I've even been around and goes to this really dark place if he's displeased with his performance. He despises, detests, loathes losing. And cannot live with the thought of ever letting his team or teammates down."

Physically, Lester started to feel like himself again last winter. His goal was to be the guy everyone could count on from now until his contract is over.

"You always hear about the guys that fail," Lester said. "You never hear about the guys that have good contracts or live up to them. It's hard to live up to something like that. It's so astronomical. I'm going to keep trying."

'He throws the ball where it needs to be thrown'

SOMETIME AFTER THE Cubs signed Tyler Chatwood and Yu Darvish this past offseason, Epstein pointed out that he had wanted to add more "stuff" to the rotation. More velocity, more spin rate -- more everything. The Cubs' rotation had been very good, but was also the lightest-throwing group in the league. Epstein saw an opportunity to grab raw talent and he took it.

So far, some of that "stuff" has struggled for the Cubs, highlighting even more just how good Lester has been. Chatwood leads the majors in walks while Darvish has been shaky, at best, when healthy.

According to ESPN Stats & Information, Darvish features an average fastball velocity of 93.9 mph. Lester's is only 90.8. Chatwood's spin rate on his cutter is 2,573 rpm. Lester's is 2,339. Kyle Hendricks features a changeup with a spin rate of 2,091 rpm. Lester's changeup measures at 1,771. Yet he's the one likely going to the All-Star Game while the other three will be watching it.

"He's a command pitcher," Borzello explains. "He throws the ball where it needs to be thrown. He's now perfect for our pitching system because he can pitch to a report as good as anybody. He can dissect the hitter because he has command of all his weapons. His command is unlike many in this game. Where he lacks in the present-day sexy categories, he's still an elite pitcher when it comes to throwing a baseball where he wants to."

"He's analyzing every pitch," Ross added. "His recollection is uncanny."

Lester's ability to make those other factors matter more than the number on a radar gun is most evident when the calendar flips to October. In 148 postseason innings, Lester has recorded a remarkable 2.55 ERA, and under the brightest spotlight of all -- in the World Series -- that number drops to 1.77. Is there any doubt why his teammates exhale when they see the ball handed to Lester in Game 1 of any playoff series?

"He's a horse," Pedroia said. "Ever since I've known him, he never shies away from a big game. He's a bulldog out there. And there are no excuses from him."

'Hey, what's Lester's deal?'

LESTER DOESN'T ALWAYS wear his emotions on his sleeve. Get him on the team bus or plane -- or even on his Twitter account -- and he can be the life of the party. But at the field, he's not exactly cracking jokes, at least not until his workday is done.

"When he went to Oakland, I had some friends over there and they were like, 'Hey, what's Lester's deal? He doesn't chat too much?'" Ross said. "You have to get him when he's done with his work. I was able to come to work, hang out and get to know guys. That was part of my thing. That's not what Jonny does. He comes to the field and he's not hanging out with anyone until he gets his work done. I think that's the way he was brought up."

There might not be anyone in the Cubs clubhouse who admires Lester more than Hendricks does. The right-hander -- who won the ERA title in 2016 -- was a puppy in the game when the veteran Lester arrived a year earlier, and he's soaked up everything he can.

"It's not all on the surface," Hendricks said of Lester's emotions. "You don't always see it. ... But just go watch one of his bullpens. Sometimes he gets out there and it's full go. He's getting frustrated, getting angry, getting mad if something isn't going right. He might throw 70-80 pitches on the side. That's where you see him competing with himself. He goes at that every single day. That's easier said than done. ... Then, with the guys, he's busting on everyone. No one is safe."

Epstein added: "He doesn't emote a lot. He keeps a lot of things in. That's almost his ballast, almost. His body language and his demeanor, staying at an even keel. Whether things are going well or not so well, he can always go back to center because of that. Maybe fans don't connect with him in the same way they would somebody who shows more emotion. That can fool some people into thinking there isn't a lot going on. Trust me, intellectually, competitively, emotionally, there is a lot going on in the course of a Jon Lester start."

'I want to decide when I'm done'

LESTER HAS TWO years on his contract after this one, then an option year if he happens to pitch 200 innings in 2020 or a combined 400 in 2019-20. After that, he's unsure what he will do. Not surprisingly, he won't just hang on to extend his career. There will have to be a good reason.

"I don't want to play for numbers or be the guy throwing doo-doo, holding on, not giving his team a chance to win," Lester said. "I want to decide when I'm done. I don't want someone deciding for me. That's a huge thing for me. That's an arrogance.

"I'm hoping it's three more years, regardless. And then we'll see where we're at."

At that point, "we" might be looking at a Hall of Fame career. He's well aware the criteria will have to change, because 300 wins can no longer be the benchmark considering where the game is going. Either way, that's not his ultimate goal -- but it would be nice.

"If I'm ever lucky enough to be mentioned in that vein, it's a complete honor," said Lester, who entered Tuesday with a career record of 168-94. "Getting in is going to have to change in terms of that whole aspect of it. ... If it's a possibility, then, 'Wow.' It's humbling to be referenced in that conversation."

Before getting up from the dugout, the conversation turns back to that dark place Lester enters when things don't go right. He was told a long time ago to let it wash away in the shower and not bring it home. But while that uniform is still on, he won't apologize for caring so much.

"I don't know if dark place is the right way to describe it," he said. "I'm just that sore loser, like I said before. The biggest thing for me is just letting everybody down. ... I like to call it that irrational moment where you kind of black out and nobody can talk to you because you're right."

Lester paused.

"I'm not always right."

He's been more right than wrong in his career, and as he continues his second act for the Cubs, he won't back down from the challenges of the game. It doesn't matter who's in the batter's box; Lester is constantly in a fight with the man staring back at him in the mirror after a long day at the office. Nothing will change that.

"There are times when you hate the game, hate this lifestyle, hate the job, but when you step on that mound, you love to compete. And win. I like that."