Tomase: As Jon Lester retires, a reminder of where Red Sox went wrong


John Henry has called it the biggest mistake of his Red Sox tenure, and he'll get no argument from me.

It's not Carl Crawford or Bobby Valentine or Adrian Gonzalez or David Price or Theo Epstein's gorilla suit. It's Jon Lester, the homegrown left-hander who should've spent his entire career in a Red Sox uniform, but instead threw his last pitch at Fenway Park nearly eight years ago.

On Wednesday, Lester announced his retirement to ESPN at age 38 after 16 years, 200 wins, five All-Star appearances, and three World Series titles between a pair of formerly star-crossed franchises.

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While Red Sox fans reflect fondly on Lester's career, regret tinges their memories, too. He never should've left, never should've won a ring somewhere else. He was born to play in Boston, embraced it, embodied the characteristics we admire in our athletes, and then he was gone.

If the idea of playing 16 years for the same franchise sounds antiquated and unrealistic in the modern era of what-have-you-done-for-me-lately analytics, let the record show that Lester did not walk out the door. He was pushed.

When the Red Sox lowballed him at the start of 2014 with a four-year, $70 million offer, they jumped to the end of the story. He was traded to the A's at the deadline as part of the great hangover purge, and I remember flying to Kansas City to talk to him before a late-season start, still nonplussed by the sight of him in yellow and green. Even then, he expressed a willingness to return to the Red Sox, but they compounded their mistake by failing to offer market value in free agency.


He instead signed with the last-place Cubs for $155 million, a rate that would prove to be a bargain not only when Lester won 77 games with the exact same winning percentage (.636) and ERA (3.64) he had compiled in Boston, but more importantly, when he led the Cubs to the 2016 World Series after being named MVP of the NLCS.

The Red Sox, meanwhile, spent a couple of years adrift without a leader atop their rotation. Then Dave Dombrowski arrived and signed Price to a record $217 million contract that the moody left-hander salvaged with an inspired run in October of 2018.

There's no reason Lester couldn't have done the exact same thing, especially given his postseason track record. Had David Ortiz not been impossible to retire during the 2013 World Series, Lester would've been the easy choice for MVP after going 2-0 with a 0.59 ERA. He won nine playoff games in his career with a 2.51 ERA, joining former teammate Curt Schilling and Giants ace Madison Bumgarner on the short list of best postseason pitchers of the last 30 years.

He also legitimately loved pitching here, a city and market that aren't for everyone. After beating cancer in 2007, Lester won the clinching game of the World Series in Colorado. He won another title in 2013 and in between experienced every emotion from joy to bitter disappointment, blossoming from a youngster in a supporting role to an unquestioned leader.

Whatever his missteps, no one ever questioned Lester's character. I experienced this firsthand after writing about the club's pitchers drinking beer in the clubhouse during games in 2011. For months, the rotation froze me out, and it carried into the following spring training, where ace Josh Beckett was consumed with finding "the snitch."

The two conducted diametrically opposed interview sessions on the same day in Fort Myers. Beckett played the predictable role of defiant hardhead with his stubborn I-don't-owe-you-bleep demeanor. Lester, by contrast, owned up to his lapse and vowed it would never happen again.

He was born to play in Boston, embraced it, embodied the characteristics we admire in our athletes, and then he was gone.

John Tomase on Jon Lester

Beckett clearly preferred the starters never speak to me again. Lester ignored him, because he knew that he had screwed up, not me. By the end of that spring, I was on speaking terms with Clay Buchholz and even John Lackey again, too. (Beckett, not so much.)

By the end of August, Beckett would be gone and Lester would be the ace of the staff, a role in which he excelled.

You'd have to be a Pollyanna to expect that to last forever, but it surely shouldn't have ended in 2014, not after Lester went 10-7 through July with a 2.52 ERA and made his third All-Star team. But with the Red Sox in freefall and Lester sure to test free agency anyway, the Red Sox shipped him west for outfielder Yoenis Cespedes, a deal that would've been a disaster except GM Ben Cherington turned Cespedes into future Cy Young Award winner Rick Porcello that winter.


Following his six years in Chicago, Lester finished with stops in Washington and St. Louis. His stuff had been steadily deteriorating by the time the Cardinals acquired him last July for the stretch run, but he found one last way to turn back the clock, going 4-1 and beating the Brewers for the 200th and final win of his career

By that point, the Red Sox had shown zero interest in reuniting with him despite opportunities to do so via free agency or the trade market. But it was probably just as well. Some mistakes can't be undone.