This week has been one of the busiest on the sports calendar, from the Georgia Bulldogs knocking off perennial power Alabama in the College Football Playoff title game in college football to Black Monday and the start of playoff football in the NFL to some marquee matchups in the NBA and college basketball. In comparison, it’s been mostly crickets from the MLB, which is enduring the early stages of a lockout with no end or agreement in sight.
Still, the MLB was the league that shook up my week in sports the most when ESPN announced that Red Sox and Cubs ace pitcher Jon Lester was retiring at 38 years old after 16 seasons and three World Series championships. The retirement marked the end of an era for not only Jon, but for me as well. Jon was my favorite player in all of sports and was the only professional player to which I am related (a fact I have relayed to other sports fans maybe a million times). This background provided me a unique angle into baseball as a young fan — one in which my rooting interest was primarily in a player rather than a team. And boy, have those 15 years been great ones, filled with monster starts, October success and historic performances.
There’s a lot of ways I could go in writing a blog tribute to the powerful lefty, so I’ll go a route that spans his pro career as well as mine as a baseball fan, and specifically where those intersect. I’m picking my nine favorite memories of watching him play or following his career, all the way from his Game 4 victory in the 2007 World Series to his last ride with, of all teams, the St. Louis Cardinals. Jon Lester made the MLB better, and, for me anyway, it won’t be the same without him.
INNING ONE: Rookie Jon Lester starts in Red Sox’ sweep of the Colorado Rockies in 2007 World Series
The first sports game I can remember watching came in October 2007, when my dad told me on the way back from school that his second cousin was pitching in the World Series. I wasn’t a sports enthusiast at all but recognized the terms “World Series” and “Red Sox,” and I picked up the terminology and eccentricities of the sport as the game progressed (one being Lester having to hit since the game was hosted by the National League’s Rockies). Back then, Lester was a fresh-faced rookie and cancer survivor, but that night established a theme that would persist through his career — a top-notch playoff performer. I didn’t watch the whole game, but I still felt the joy of victory the next day when I found out that the Red Sox had finished off the rookie Lester’s start with their fourth and final win of the series.
INNING TWO: Jon Lester no-hits the Kansas City Royals
A World Series trophy was evidence of playing for a great team and evidence of making it big time. Then Jon Lester no-hit the Kansas City Royals on May 19, 2008 (just several months after the big World Series win), making history and the grandest of statements of individual dominance. For a couple days, he was at the center of the baseball world and a burgeoning star in one of America’s top markets. I dejectedly watched the Tampa Bay Rays knock Jon off his perch in the ALCS later that fall, but Number 31 had most certainly arrived.
INNING THREE: Sports Illustrated Kids baseball previews and trading cards
As my interest in sports shot up exponentially, I devoured every bit of sports content I could find. The Sports Illustrated Kids magazines were my favorites, and within that medium I couldn’t get enough of each league’s annual preview section. When the baseball previews landed in my mailbox, I’d run down to the edge of the street, snatch the paper copy of the magazine and burst into my house and onto a couch to pore through the pages. I’d immediately flip to the AL East and look to see if Jon Lester was mentioned in the write-up for the Red Sox, and more often than not, his name was right there in bold print (along with an ERA or record for good measure). His likeness was also the holy grail in the baseball cards I would buy from the local target, though sometimes I opted for the team packs just to guarantee a Jon Lester card. And my friends knew better than to pick Jon in fantasy baseball drafts or when we were making our own pretend rosters — he was always my first round pick. Another treasured memory was making the trip out to Camden Yards to see him make a start against the Baltimore Orioles.
INNING FOUR: Jon Lester shuts down the Cardinals in 2013 World Series
By the early 2010s, I was tracking all of the Red Sox games each summer and knew the lineups and rotations from the Washington Post Sunday sports section. But there weren’t all that many wins in the 2012 season, when Boston tumbled to the bottom of the standings because of an awful manager, Bobby Valentine. The roster and talent was in place, I was certain, but the results didn’t show it. The following spring training, I was insistent the Red Sox were going all the way. Fast forward to October and the Red Sox did exactly that. David Ortiz’s bat caught fire in ALCS and World Series contests against the Detroit Tigers and St. Louis Cardinals, respectively, but Lester was a superstar on the mound, proving to be every bit the playoff ace he teased in his first few trips to the postseason. I couldn’t stay up for all the World Series games that year, but I was living and dying on each result and wearing my Red Sox Lester player tee to school every day the Sox were playing. When I woke up one morning to find that Boston had closed out the Cards to win the Series in six games — just months after my Ravens won the Super Bowl — I was ecstatic, even more than the 2007 title that came in my early days as a fan.
INNING FIVE: Boston Red Sox lowball Jon Lester, trade him to Oakland Athletics
In those early years as a fan, I rooted for the Red Sox almost as much as I was emotionally invested in Lester’s career (I’d still get mad when they moved his spot in the rotation or if he didn’t earn the win after a strong start). I thought — and I’m sure Jon did too — that he would be on the Red Sox for life. Instead, Boston gave him a contract that was insultingly low, hesitant to commit big dollars to a pitcher in his 30s. That led to prolonged drama throughout the season, culminating in Jon Lester becoming July’s big trade target at the trade deadline. As angry as I was to hear that Jon could be leaving Boston, I was excited to embrace a new team, even drawing and coloring his name and number to imagine what his jersey would look like for other teams, including the nearby Orioles and his hometown Mariners. At around noon, ESPN updated with a winner of the Lester sweepstakes — the Oakland A’s.
In that instant, I became a devoted A’s fan. I re-read Moneyball and predicted that the A’s would go all the way and win the World Series on my blog “Professor Sports.” Lester performed well, but Oakland started to decline as the season progressed and eventually had to play in the do-or-die single elimination AL Wild Card game against Kansas City. Though Jon started off well, the story of the game quickly became his inability to pick off baserunners — the start of a years-long battle with the yips that would be brought up by every announcer calling his games. The Royals pulled away in the final innings, crushing me and ending Jon’s short tenure wearing the green and yellow of the Athletics.
INNING SIX: Chicago Cubs win the Jon Lester lottery, transform into contenders
Once it became clear Jon Lester was heading to another destination, I fixated on each article that popped up on my MLB app to see all of the contenders. The hot stove was quiet throughout November, with Lester and fellow pitcher Max Scherzer as the top options on the market. In the final days before the decision, the contestants narrowed down to three: the Boston Red Sox (who were offering more this time around), the San Francisco Giants (who were offering the most) and the Chicago Cubs.
I hated the Giants and felt indifferent on the Red Sox, but the idea of Jon Lester in Wrigley Field excited me. On Chicago’s North Side, he’d have a chance to end the Curse of the Billy Goat and wear the pinstripes that Henry Rowengarner wore in Rookie of the Year, while joining a young and talented roster with names like Anthony Rizzo and Starlin Castro. Thankfully, Jon felt the same way, signing for six years and 155 million to join the Cubs. One of my stocking stuffer presents that year was an issue of Sports Illustrated with Jon Lester gracing the cover (my first-ever copy of the adult Sports Illustrated magazine), announcing that the Cubs were contenders. Indeed, they were.
INNING SEVEN: Jon Lester endures yips, batting woes to stay a top ace
Following Jon Lester’s career was different from following any other All Star like, say, Bryce Harper. While he found his footing and lit it up in the National League, his game had eccentricities (or weaknesses, as some would say). The issues throwing to first base became a regular topic of conversation for the broadcasters, while his struggles at the plate were historic. Jon started his career batting 0-for-66, the worst mark ever, before finally landing his first hit in June 2015. Following baseball through the lens of a single player was dramatically different than rooting for the Ravens and Cowboys in the NFL with roster turnover and new faces each season, and there were both ups and downs to the experience.
INNING EIGHT: Jon Lester pitches in historic Chicago Cubs Game 7 Victory
Similar to my prediction in 2013 with the Red Sox, I prophesied a Chicago Cubs victory in the World Series during Spring Training 2016. The Cubs that year were a juggernaut, tearing through the National League with MVP Kris Bryant and reigning Cy Young winner Jake Arrieta, among others. When it came playoff time, I was in all the way, watching the Cubs take down the Giants and Dodgers to reach their first World Series in decades (with Jon sharing NLCS MVP honors).
Then came the World Series against the team now known as the Cleveland Guardians. The powerful Cubs lost their spark, starting the series in a 3-1 hole. I was certain the Cubs could shock the world and comeback, but time was running out. Then Chicago won its next two games to force a decisive Game 7, and it was all set up for a landmark victory. The Cubs pounced early and often in Game 7, pulling away from Cleveland twice and using all of their big name pitchers, Lester included. But with the game seemingly sealed, closer Aroldis Chapman blew the game and let Cleveland tie the score. A rain delay ensued, and high school John had to go to sleep before the regional cross country championships the next day.
We all know how the game ended — Ben Zobrist scored the go-ahead run and the Cubs held off Cleveland for an 8-7 classic and their first World Series win since 1908. Once again, history.
INNING NINE: Jon Lester finishes career in the playoffs with the St. Louis Cardinals
In his final years, Jon’s skills were in sharp decline as the Cubs faded out of title contention. Chicago was frisky every couple of years, with No. 34 even appearing in an NL Wild Card game against the Colorado Rockies, but the North Side provided few opportunities to boost one of the greatest playoff resumes of this generation. COVID prevented fans (myself included) from seeing the NL playoff match between the Cubs and Marlins, although any chance at a Lester finale in Wrigley was dashed by the Marlins’ 2-0 sweep.
The next season turned out to be Jon Lester’s last in the big leagues, one spent in the unfamiliar reds of the Washington Nationals and St. Louis Cardinals. I found out both developments from my friend Joe Pohoryles, and the situation brought up a conundrum — do I root for two ballclubs that I absolutely despise? For Jon, I did, even seeing his return to Wrigley Field in May 2021 and rostering him on my league-winning Washingtonian Web Gems fantasy baseball team in the stretch run. Jon wasn’t the same pitcher that he was half a decade earlier, but he battled to end the season on a solid stretch and was a part of the Cardinals’ historic 17-game win streak. I’d say that was a good ending to a prolific career, one characterized by resiliency and dominance against all odds.
EXTRAS: Where now? For Jon Lester, I sure hope he’ll get into the Baseball Hall of Fame. His postseason statistics are elite and his durability puts him among the top names of the 21st century, though it might take a couple go-arounds for the notoriously unreliable HOF voters to give him his spot. I’m sure Jon will have no shortage of ways to fill the time, whether it’s his family, hunting or media appearances.
For me, I’m somewhat of a baseball free agent. But as the best do, I’m narrowing down my options and weighing the pros and cons. Baseball won’t mean as much to me as it meant when Jon Lester was out there on the mound. Still, Jon Lester helped instill in me a love for sports and a love for America’s pastime, and for that I’m truly grateful.