fb-pixel Skip to main content

Luring prodigal pitcher Jon Lester back to Yawkey Way would have been the greatest comeback by the Red Sox since the 2004 American League Championship Series, when they rallied from a three games-to-none deficit to defeat the New York Yankees. But Red Sox general manager Ben Cherington isn’t Dave Roberts. He couldn’t steal Lester’s heart.

The Red Sox’ reunion with Lester, like their series of offers to their erstwhile ace, fell short.

The Sox bungled the Lester negotiations from the beginning and watched him choose another team in the end. Their initial four-year, $70 million offer alienated Lester to the point of no return. It is the reason the man who said the Red Sox would have to rip the jersey off his back is now slipping on a Chicago Cubs uniform, reunited with Cubs president and former Red Sox general manager Theo Epstein.


Lester was like the spurned boyfriend or girlfriend who wanted to take back his old flame but then kept remembering how his feelings had been unrequited the first time. The Red Sox didn’t lose Lester to the Cubs in the wee hours of Wednesday morning. They lost the lefty back in spring training with that first offer.

That the Red Sox somehow charmed their way into the final two teams in the Lester free agent chase speaks to the depth of the bond between Lester, Sox manager John Farrell, and the boys in baseball ops. That’s why it’s all the more frustrating that Lester ended up with the Epstein AC, agreeing to a six-year, $155 million deal with a vesting option that could make the total value seven years and $170 million.

The Sox’ final bid — $135 million over six seasons — was in the ballpark. But if the ballpark were Fenway, their deal was way out by the triangle.


“We were given every chance to get to where we were willing to go,” Cherington said at baseball’s Winter Meetings in San Diego. “We got to where we were willing to go. And then he had a choice to make, and he made it.”

Stopping at $135 million feels like the Sox let off the gas just as the checkered flag was approaching. Once you’ve smashed your own idealistic, short-lived, slightly conceited tenet about not offering long-term, lucrative deals to players over 30 to bits, what’s another $15 million-$20 million to bring Lester, who turns 31 next month, home?

The Sox pulled out all the stops when it came to tugging on Lester’s heartstrings, sending Red Sox principal owner John Henry (also the owner of the Globe) to meet with him in Atlanta last Friday. But they stopped short of the number they needed to erase the aftertaste of the $70 million offer.

Contract negotiations are an art, not a science. The Sox honestly believed back in spring training they were laying the groundwork for the hometown discount Lester had indicated he was eager to take when they made their ill-fated initial offer, which was significantly below market value for a pitcher of Lester’s pedigree.

Somehow they miscalculated the pride and resolve of a player who had been in their organization since he was 18 years old and hadn’t backed down from cancer, World Series games, or his role in the chicken and beer fiasco of 2011.


Yes, Lester had declared his fondness for all things Boston from Sam Adams beer to the Prudential building at the Boston baseball writers’ dinner in January, but he had also stated that “you never want to be the guy that takes the market backward.”

The offer estranged Lester. Whether it should have is debatable.

The same stubborn streak that made Lester so good on the mound worked against him off it if he wanted to stay in Boston. He refused to re-engage in negotiations with the Red Sox during the season, much to the team’s chagrin. He never gave a firm, in-season asking price that could have staved off the July 31 trade that sent him to Billy Beane and the Oakland A’s.

He never, you know, negotiated.

So, he was shipped off to Oakland, where he continued a brilliant season that saw him finish 16-11 with a career-best 2.46 earned run average. Lester tied for the fourth-highest WAR (wins above replacement) among pitchers last season at 6.1, according to Fangraphs WAR calculation, the same number as David Price and better than fellow free agent Max Scherzer.

“We hadn’t been able to have any kind of constructive dialogue with him to that point,” said Cherington. “If we had been in first or second place or in the playoffs, obviously we wouldn’t be trading him. But we weren’t, so we had to act rationally.”

The Sox will survive without Lester. They were already planning on it.

They have money to spend and might even pry Cherington’s death grip off a few prospects.


But the crucible of Boston baseball isn’t for everybody. We’ve seen that with players from Jose Offerman to Carl Crawford.

The Sox should put a premium and be willing to pay one for players who have proven they can thrive in the harsh hardball environment of the Hub.

This place might not be for Johnny Cueto or James Shields.

Lester isn’t the first ace to spurn the Sox, frustrated, for greener pastures. He won’t be the last. Roger Clemens left after the 1996 season to be closer to home . . . in Toronto. After the 2004 season, the Sox let Pedro Martinez go to the New York Mets.

The previous regime was wrong about Clemens. This regime was right to let Pedro go. Petey tore his rotator cuff two seasons into a four-year deal.

Losing Lester could be the right move in the end.

Right now, it feels like the Sox overplayed their hand and lost an ace that should have been in their deck.

Related coverage:

■  Sox close to deal for Arizona lefty Wade Miley

■  On baseball: Sox need new pitching pieces — and have ways to get them

■  Jon Lester chooses Chicago Cubs over Red Sox

■  Jon Lester’s career highlights with Red Sox

■  Notebook: If Red Sox land Cole Hamels, it may be costly

■  Red Sox make offer to pitcher Justin Masterson

Christopher L. Gasper can be reached at cgasper@globe.com. Follow him on Twitter @cgasper.