Jon Lester remains one of the only great pitchers the Red Sox have ever developed, and his story is remarkable.
Less than two months after making his MLB debut in June 2006, Lester was diagnosed with lymphoma. He spent the offseason undergoing chemotherapy and his cancer went into remission that winter.
By July 2007, he was back with the big-league club. A few months later, in the first postseason start of his career, he pitched the Sox to victory in Game 4 of the World Series. He threw a no-hitter the following May.
Lester was crucial to the Sox’ 2013 championship run, their first postseason since 2009. He started Game 1 of the ALDS, ALCS, and World Series.
In the final season with the Sox, they traded him to the Oakland A’s at the deadline. That fall, he signed a six-year deal with the Chicago Cubs, and in 2016, he helped them win their first World Series in 108 years. When he became a free agent after the 2020 season, he signed a one-year deal with the Washington Nationals, who then traded him to the St. Louis Cardinals at the deadline. When the season ended, he announced his retirement.
Lester remains one of the current Sox ownership’s biggest mistakes. When Lester made it known that he was open to a team-friendly deal, the ownership got greedy. They famously lowballed him in the negotiations, and he rightfully declined their embarrassing four-year, $70M offer, as ‘team-friendly’ should not have meant ‘well below market value.’ The negotiations stalled from there, and they traded him at that summer’s deadline.
The Sox tried again when he became a free agent that winter, but by then, it was too late. Lester has maintained for years that he would have accepted six years in the $120M range, significantly less than what the Cubs ended up giving him. Instead, the Sox went out and gave David Price the biggest pitching contract in MLB history, and came away from the experience underwhelmed.
Even principal owner John Henry admitted years later that they’d made a huge mistake, saying “we blew the Jon Lester signing.”
And with all the overcorrections they made in the years following, they never found a way to correct that mistake.