Jon Lester Trade Could Lead the Red Sox to Plenty of Regret

Anthony WitradoFeatured ColumnistAugust 27, 2014

ATLANTA, GA - AUGUST 17: Jon Lester #31 of the Oakland Athletics throws a first inning pitch against the Atlanta Braves at Turner Field on August 17, 2014 in Atlanta, Georgia. (Photo by Scott Cunningham/Getty Images)
Scott Cunningham/Getty Images

It’s right about now, preparing to enter the final month of the regular season, that seller’s remorse sets in for the Boston Red Sox.

The Jon Lester-for-Yoenis Cespedes trade that happened between the Red Sox and Oakland A’s at the July non-waiver deadline looked like a win-win when it first happened. The A’s were going for it in October to erase the nightmares of autumns passed, and the Red Sox were getting a threatening power bat for a free-agent-to-be pitcher while they were one of the worst teams in the American League.

Win, win. 

Both the Red Sox and A’s had a ton to be excited about swapping Jon Lester & Yoenis Cespedes:

— SB Nation (@SBNation) August 1, 2014

Or so we all thought at that time.

While the A’s are having their share of issues with the trade, mainly that the art of scoring runs has been lost on them since the trade, theirs is a short-term problem and one they were bound to encounter next season anyway.

Cespedes will be a free agent after next summer, and the A’s are going to be priced out of his services, leading general manager Billy Beane to strike at an opportune time. Meaning the A’s have a real shot to reach the World Series with another stud pitcher, this one a tried-and-true ace.

So you can see their side of this deal, for now and later. They are a small-market, low-payroll team that has to jump through closing windows of opportunity whenever they encounter them.

The Red Sox don’t have that problem. They are big market, huge payroll. They pry open windows, never hoping they can catch one before it shuts. They have the resources to get what they need when they need it, price tag be damned. 

So the notion that they could trade away a legitimate ace, Lester, in his walk year, and still be the frontrunner to acquire his services this winter was not only reasonable, it was the safe bet based on comments Lester had made in the recent past. 

“At the end of the season, it’s not going to change my mind about going back there if they are aggressive and competitive and do the things they say they’re going to do,” Lester told John Tomase of the Boston Herald. “Boston is definitely a place I would go.”

Then again…

Lester told WEEI in Boston just a couple days later, “I don’t need to go to the highest bidder if that isn’t going to make me happy. I make decisions based on me and my family and is this place – whether it’s Boston or one of the other 29 teams – is this place going to be good for me and my family?”

Baseball executives have their doubts about Lester returning to Boston. According to Jon Heyman of, executives are using words like “long shot” when it comes to the chances of a Red Sox-Lester reunion.  

Then there is the reality that the Red Sox attempted to sign Lester to an extension, but it was seen as a low-ball deal by the market and possibly by the player. 

None of this truly knocks Boston out of the running, but it is far from a ringing endorsement and miles away from the assumption that Lester was bound to re-sign with the Red Sox. The formality in that has evaporated, and the Red Sox are on the verge of starting the 2015 season without anything that remotely resembles a frontline starting pitcher.

Aside from Lester in the free-agent pool of starters, the aces are so few and far between that every team that is interested in Lester is likely to also be in on Max Scherzer and James Shields. If that is the case, the Red Sox might have to break their stance on not offering pitchers over the age of 30 long-term, big-money deals. It’s that or risk having a patchwork rotation in the heavy-hitting American League East.

That alone might be enough to regret the Lester-for-Cespedes trade.

Except there is more to this. Boston faces a similar free-agent problem with power-hitting Cespedes, who, like Lester, will have plenty of attention and plenty of cash thrown at his feet after next season. However, unlike Lester, there is no Beantown pull for the Cuban star.

If Boston can’t land a big-time starter this winter, then they are bound to be at the bottom rungs of their division for another season, because Cespedes alone is not enough to transform the Red Sox into a winner. And eight months of losing baseball won’t tug at any of Cespedes’ heartstrings, which will be worth lots of millions of dollars when he hits the open market.

It is safe to assume Boston will make a qualifying offer to Cespedes, and if he signs elsewhere it will mean all Boston got out of this trade is a draft pick that may or may not realize expectations and make it to the big leagues.

BOSTON, MA - OCTOBER 29: Executive Vice President and General Manager of the Boston Red Sox, Ben Cherington, watches as the team warms up during the team workout Fenway Park on October 29, 2013 in Boston, Massachusetts.  (Photo by Jared Wickerham/Getty Im
Jared Wickerham/Getty Images

That is a truly mangled effort by general manager Ben Cherington and his front office. While the A’s are at least getting something out of the dealthe chance to have an ace during a World Series runthe Red Sox could come out of this with absolutely nothing to show, including hope.