Weathering a Storm: The Mental Strength of Jon Lester

I heard someone I respect and admire say recently that life is largely about the storms that come our way and how we handle them when they do. We are always either in a storm, coming out of one, or one is coming. It’s a harsh and inevitable reality that adversity will come, and we prove and shape ourselves in how we face it. So much of how and whether or not we are able to address the storms comes from not just what’s between our ears but also the support system that’s around us. And some people meet their storms, weather them, and move on, while others seem to live nearly their whole lives in one. In the early and mid 2000s, there were two players making their way up the ranks of their respective minor league systems. One was on every prospect list, and the other didn’t appear on any of them. Today, the first has been out of baseball for several years, and the second has won the World Series twice and is on a team that is arguably well suited for him to win a third.

It’s tricky to illustrate the precise difference between what made Elijah Dukes struggle so much while Jon Lester has thrived after Dukes dominated so much of the prospect hype at the time. About twelve years ago, there were a few red flags attached to Dukes, but if you had to guess who of these two would be garnering more attention today, I am not sure that Lester would have been the obvious choice. Why this has turned out the way that it has probably has much to do with not only the storms these two have faced, but what it took to weather them.

The importance of a player’s mental makeup has been a popular focus of attention on this site in recent weeks, and with good reason, as it is increasingly clear that the Cubs as an organization are clearly more invested in this side of the profile than perhaps they were in years past. After all, baseball’s history is rife with examples of guys who have just never made it, in spite of seeming to have the right pedigree. The overlooked problem might be the importance of the mental aspect of a player, even when there are what appear to be can’t-miss physical skills (think Billy Beane). Sometimes, though, there’s still an element of the intangible in what makes one player make it or not, and that can often manifest itself in fighting through something that goes beyond just what happens on the field.

Lester was forced to face an incredibly difficult struggle very early in his baseball career when he learned late in the 2006 season that he had a form of lymphoma, and he’d be spending his offseason going through treatments in hopes of returning for the 2007 season. He was 22 at the time. It was a relatively innocuous diagnosis in the world of cancer, but it was still cancer, and for player just at the beginnings of his career and barely old enough to buy a round for his friends, this is a daunting way to spend your first offseason as a major leaguer. Prior to his debut in June of 2006, Lester wasn’t particularly heavy on anyone’s radar. In 2005, he wasn’t on Baseball America’s Top 100 list and he didn’t even get an honorable mention on the Baseball Prospectus Top 50 in February of that year. He had finished three seasons of minor league ball by then, and while he was rising steadily through the system, Lester wasn’t catching a lot of eyes just yet. His debut season ten years ago was perfectly pleasant, but his stat line in that year isn’t one that will pop out off of the page.

Then, cancer. Lester himself took to describing his journey through it in 2013, emphasizing the positive changes that the experience brought into his life. Not everyone faces these storms this way, however. To try and get a glimpse into the Jon Lester of those years before he was a major leaguer, I reached out via email to Gary Rasjich, who is now the director of scouting for the Baltimore Orioles, but in the early 2000s, he was scouting for the Boston Red Sox, and he described how Lester first came to his attention: “I first heard about Jon Lester from a Connie Mack coach in the Seattle area during Jon’s sophomore year in high school and first saw him pitch in a game the next summer. He was ‘what they look like’, tall, strong, and athletic.” Rasjich went on to point out that Lester’s parents were at each of his games, and that his mom was even the official scorer for his high school team, a team that he left an impression on that his high school coach says is still etched firmly in place.

Lester came out of that experience to return to the Red Sox in the middle of the 2007 season to what was ultimately a rather respectable campaign, even without considering that he had just recovered from cancer. Most noteworthy about his return that year, though, is what he did after the regular season ended. In the Sox’s second World Series championship since breaking their own curse in 2004, Lester was given the ball in Game Four. True, the Red Sox were already up three games to none over the Rockies, but his introduction to the playoffs hadn’t been pretty when he’d had a rough relief appearance in Game Two of the ALCS against the Indians. He went on to relieve Tim Wakefield for three innings in game four of that series, and pitched brilliantly with four Ks and just one hit.

His Game Four World Series appearance showcased almost six almost perfect innings to help close out the Sox’s second championship that decade. Ordinarily, that would have been a lot to ask of a pitcher who was still barely more than a rookie, but Lester had already faced stiffer challenges off the field. He went on to pitch in the playoffs in 2008 and 2009, and helped the Red Sox win their third World Series since an 86 year drought in 2013, where he again pitched nearly flawlessly when it counted most, striking out 15 batters in 15 innings in that series and walking just one. The degree to which his personal storms helped him in these high pressure situations doesn’t show up on a stat line, but the impact on his mental makeup is there.

While all of this was happening in Boston, some former Red Sox executives were closing in on the final stages of rebuilding a Chicago franchise that had been in desperately bad shape for much of the preceding decades. A part of that last stage in the rebuild was bringing in a pitcher who had not only demonstrated what he could do in the biggest games of the postseason, but who also had the right fortitude to handle the environment he’d be stepping into. With the help of Rian Watt, I contacted Jason McLeod to help glean some insight into the pursuit of the right free agent and what made Lester stand out at the time.

Here’s what McLeod had to say: “A couple of things come to mind. First and foremost is our evaluation of Jon and the production we felt he was going to provide going forward. Beyond that, our history with him and knowing the expectations he would bring upon himself and his teammates to compete and win–with where we felt we were as a team and organization–aligned for both the Cubs and Jon to make that commitment.” McLeod went on to say that, like any free agent, they have an objective process of course, but their previous relationship with Lester “helped with the trust and comfort of our conversations with he and his advisers for sure.” They knew much of what they were getting, and they knew the value he’d bring to a franchise that was going to need more than just quality innings on the mound.

When it comes to that something more, I asked McLeod what he thought Lester brought most to the team outside of his in game performance, and he shared, “His fiery competitiveness. He is there to win…period. He leads by example with the work ethic and the high expectations he places on himself to go out and put his team in position to win is the most important thing to him.” That’s a quality that was sorely needed on a team that would be so young heading into 2015, and though they didn’t know it at the time, needed when the Cubs returned to the playoffs for the first time in seven years and to the NLCS for the first time in over a decade.

The last thing I asked of McLeod was a look into how he thought Lester’s mental makeup had changed since his time when he first came to Boston years ago, and he said a lot of things you’d probably expect about the effects of maturation and having won championships, but what struck me most was what he finished with, “He’s always been a stand up guy and I felt he handled all of the attention last year in an accountable way.” The large contract, the rough start in April, and the “yips” all meant for a storm in many ways for Lester last season. It’s probably common knowledge that the Chicago sports environment can be more like a maelstrom than anything at times, and Lester was—and still is—well equipped to handle all of that.

Now, after signing one of the largest contracts the Cubs have ever given in December 2014 and pitching under the scrutiny that those dollars bring, Lester has a rather successful 2015 season under his belt, but he is again heading into a storm. Not just the yips about throwing to first base that still pester him, or the bone chip in his throwing elbow, but the storm of expectations. Given the mostly unexpected success of last year, the Cubs have the weight of many years of the unrequited dreams of Cubs fans on their shoulders in a way that hasn’t been with this team in a long time.

That said, Lester and those who take the field with him are not just equipped with the right traditional baseball skills to live up to those expectations, but also the right mental skills. We get glimpses of these every so often, maybe in a fight with cancer that ends up being a shared experience with a teammate, or sometimes, just in a look. Gary Rasjich shared this with me even more succinctly, “I will never forget first meeting him after a game.  It was in his eyes.  He was going to be special.” The storms are inevitable, but I think that Lester and the Cubs are built to weather them.

Lead photo courtesy Joe Camporeale—USA Today Sports.

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2 comments on “Weathering a Storm: The Mental Strength of Jon Lester”


You can tell something about a person by their writing style and I think you’re the type of person I would like to hang out with, Jared. You’ve become one of my favorite writers on this site – definitely top 3, man!

Very insightful and well written article, and I really like the way you looked deeper than the surface on Lester and put it into words.

Jared Wyllys

Thanks, Tommy! I really appreciate the kind words.

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