Lester was a truly special player once October rolled around
Over the last year, two pivotal players in Boston Red Sox World Series wins have announced their retirements.
Dustin Pedroia, after dealing with lingering knee pain, called it a career last year. And on Wednesday morning, Jon Lester announced his retirement from baseball after a 16-year run that began in Boston.
Lester won World Series with the Sox in 2007 and 2013. At 23-years-old, he started the clinching Game 4 against the Colorado Rockies in the 2007 Fall Classic, while also tossing five largely lights-out showings in the 2013 postseason, two of which were in the World Series against the St. Louis Cardinals, the team he finished his career with.
The Red Sox traded Lester ahead of the 2014 trade deadline to the Oakland Athletics, and he later joined the Chicago Cubs in free agency, where he won his third and final World Series in 2016. He signed with the Washington Nationals for the 2021 season but was moved to the Cardinals at the trade deadline to try to chase a fourth World Series.
“Any time he had the ball, it was a different feeling as a teammate,” Pedroia told ESPN’s Jesse Rodgers about Lester. “The power, the way he worked, the will to win. He had great stuff, but his best gift was he found a way to win. That’s something you can’t teach, you can’t coach. It’s a special player that has that. There’s not many.”
Lester was a five-time All-Star who had at least a 60% win/loss percentage in 10 of his big-league seasons. He’ll perhaps, and deservedly, be best remembered for his unflappability in the postseason, which helped two teams that had their share of postseason horror stories win World Series.