Boston Red Sox: Breaking Down the Trade of Jon Lester to the Oakland Athletics

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Boston Red Sox: Breaking Down the Trade of Jon Lester to the Oakland Athletics
Jon Lester's time with the Boston Red Sox ended after being dealt to the Oakland Athletics.

The time has come when we can put away all speculation about the rumors surrounding what will happen with the Boston Red Sox's former No. 1 ace Jon Lester.

No longer will we have to ask ourselves whether or not he'll receive an extension. No longer will we have to ask ourselves whether or not general manager Ben Cherington would deal him. 

We now know the answer.

The Boston Red Sox have sent Lester and outfielder Jonny Gomes to the Oakland Athletics in exchange for power-hitting outfielder Yoenis Cespedes and a competitive balance pick in the 2015 draft.

News of the deal was first confirmed by Jon Heyman of CBS Sports, who made the announcement early on July 31.

With the benefit of hindsight, we can easily see how this transaction was inevitable. But how did it get to this point? What were the various factors that convinced Cherington and the Red Sox's front office to make such a blockbuster deal?

More importantly, what does this mean for Boston moving forward? 

The Red Sox have already traded one of their starting pitchers—Felix Doubront—to the Chicago Cubs, and there also remained a very good chance that veteran starter John Lackey would be on his way out via a trade, per Ken Rosenthal of FOX Sports (h/t CBS Local).

That respective move eventually transpired per Heyman (h/t Mike Axisa of CBS Sports). The Red Sox moved Lackey to the St. Louis Cardinals in exchange for Joe Kelly and Allen Craig.

Talk about shaking up a starting rotation.

Before we get into the nuts and bolts of this blockbuster move, let's try to figure out what led to this situation happening.


Lester was seeking a contract extension at the end of his five-year, $30 million deal.

The Context

Lester was entering the final year of a five-year, $30 million contract in 2014. In the wake of his performance during Boston's 2013 World Series title run, there was plenty of talk surrounding whether or not the Red Sox would grant him an extension.

There were some discussions in this direction, but according to Rosenthal, Boston's offer was far less than what Lester was seeking. He wrote back in April:

The Red Sox's most recent offer to Lester was far below market value -- four years for between $70 million and $80 million, according to sources within the team'€™s clubhouse. 

Lester, who is eligible for free agency at the end of the season, rejected the offer and will not resume negotiations with the club until the offseason, the sources said.

Lester had stated multiple times that he wanted to remain in Boston—an aspect he reiterated strongly before the 2014 season via Gordon Edes of ESPN Boston.

But the two sides remained far apart and with the Red Sox's season floundering, one had to wonder whether or not Lester's immediate future with the team was in doubt.

Approaching the July 31 deadline, talks heated up with a number of teams speculated to be in the mix for Lester's services.

Then came the news that Lester would be scratched from his regularly scheduled start on July 30.

This action was perhaps the biggest indication yet that Lester would be on the move.

As it turned out, we just had to wait one more day.



Slugging outfielder Yoenis Cespedes was the key part to the deal between Boston and Oakland.

The Numbers

As stated above, the Red Sox will receive Cespedes and a 2015 competitive draft pick from the Athletics.

In exchange, the A's add Lester to their starting rotation along with platooning outfielder Jonny Gomes and with cash.

Lester currently owns a 10-7 record on the year with a 2.52 ERA—on pace to be the lowest in his nine-year career. Lester will be added to a star-studded Athletics rotation that already includes All-Stars Jeff Samardzija and Scott Kazmir, along with the promising Sonny Gray, per Edes. 

This move, along with some of their other transactions, puts the A's in an position to remain a favorite playoff contender, perhaps finally being able to push beyond teams like the Detroit Tigers in the postseason—something they have been unable to do in the last two seasons.

But the A's paid a lofty price for Lester, sending away the back-to-back Home Run Derby champion in exchange.

Cespedes had been batting .256 with 17 home runs and 67 RBIs before the trade. This is only his third year in the majors, and there are plenty of reasons to speculate that the 28-year-old has plenty of good years ahead of him.

From the A's perspective, losing Cespedes is a tough pill to swallow. But Cespedes was due to make $10.5 million in 2015—the final season of his four-year, $36 million contract. 

For the mid-market Athletics, whose net payroll is just above $91 million, sending away Cespedes makes sense from a contractual standpoint. Simply put, Boston can afford Cespedes in 2015. The A's cannot.


The A's would have a tough time re-signing Cespedes after the 2015 season.

Gomes is due just over $1.5 million in the final year of his two-year contract. He was batting .234 with six homers and 32 RBIs in 209 at-bats.

Now we can assuredly speculate that Oakland is not planning on re-signing Lester to a lengthy contract extension. It is hard to fathom them having the money to execute such a deal. Thus, Lester fits the mold of a pure two-month rental to help propel the Athletics into—and perhaps through—the postseason.


Cespedes' power, evidenced during the 2014 All-Star Game, will help upgrade Boston's outfield.

Benefit for the Red Sox

Is there any? Is this the deal that Red Sox fans wanted to see happen?

This author will go ahead and let the backlash play itself out. From a public-relations standpoint, dealing Lester will probably come with plenty of negative implications in coming months, but at least we can start shifting our focus to the future and putting this abysmal 2014 season to rest.

In short, Boston is in desperate need of outfield help. Prior to the trade, Boston's crop of outfielders was batting a combined .244 with an OPS of .656.

Anyone who has followed the Red Sox over the course of this season can tell you of the problems this unit has endured. There have been injuries, underwhelming performances and the like.

Cespedes does fill an immediate need and provides an upgrade at the corner outfield positions. The Red Sox don't have a lot of soon-to-debut prospects in their minor league system to supplement this need, so dealing for Cespedes does help considerably.

Ronald Martinez/Getty Images
The Red Sox need power from their outfield. Cespedes now provides that.

We should also consider the numbers Cespedes has put up at Fenway Park, though, it is only a small sample size. In six games and a mere 24 at-bats, Cespedes is hitting only .250 in Boston, but three of his six total hits there have been doubles.

More importantly, we can take into consideration the lofty confines of Fenway in comparison to the relative pitcher-friendly aspects to Oakland's Coliseum.

Thus, it would be a safe bet to assume Cespedes' numbers will increase at Fenway during his stay.

Additionally, the Red Sox can afford the $10-plus million owed to him in 2015. The short-term deal fits right in line with what Cherington likes to do from a contractual perspective. If Cespedes does not work out, the Red Sox are not tied to him for the long run. 


Jared Wickerham/Getty Images
Clay Buchholz is the last remaining starter from Boston's 2013 championship team.

Boston's Future

As stated, there may be plenty of implications surrounding this trade, some of which may last for a while. Who knows what the eventual impacts will be upon Lester's former teammates—guys like David Ortiz and Dustin Pedroia, both of whom have stated they wanted Lester to stay, per Ricky Doyle of

But the business of baseball remains, and those implications will have to play out.

More importantly however, we should take a look at what the immediate ramifications will be upon the Red Sox's pitching staff. The team has already dealt Doubront, and with Lester now on the move—and possibly Lackey as well—how will Boston's starting rotation look moving forward?

It isn't that far off that we may see veteran righty Clay Buchholz as the only remaining starter from Boston's 2013 championship squad. Considering his 5.87 ERA this season, that is a scary thought.

But the Red Sox do have some other immediate options to fill the void. Both Brandon Workman and Allen Webster have major league experience, and Workman filled in for Lester on July 30. Rubby De La Rosa is also a likely candidate to earn some starts.

The Red Sox may also want to see what they have with the recently acquired Kelly regarding the future of their rotation.

However, the major focus will be on what transpires with the Red Sox's rotation next season.

Yes, the Red Sox have a solid group of prospective starters working their way up through the farm system. Guys like Workman, Webster, Henry Owens and Anthony Ranaudo could very well factor into the equation within the next year.

Lefty Henry Owens is the most highly touted pitcher in Boston's farm system.

We also cannot overlook the possibility that Lester returns to Boston during the offseason. As stated, it is hard to think the Athletics will re-sign Lester considering his likely contractual demands. The Red Sox could afford bringing him back.

Of course, there are plenty of other teams that will be seeking his services as well. It may ultimately be up to Lester to decide what the best situation is for him after the 2014 season. Boston could be a favorite landing spot, inciting a reunion of sorts hopefully without any attached hard feelings.

But anything beyond that remains pure speculation at this point.


Was the Lester/Gomes for Cespedes deal worthwhile for Boston?

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This was a blockbuster deal. There isn't any way to get around it. 

Boston sends away its No. 1 ace—a fan favorite and one who has cemented his legacy with the Red Sox already.

Obviously the A's are in much better position to contend for an American League championship. Boston's outfield has immediately been upgraded, too. They needed that help in desperate fashion.

But it is going to be hard to swallow what has just happened. No matter how one views the trade, the short- and long-term ramifications of this deal remain undetermined. 

With the Red Sox now entirely focused on 2015 and beyond, one can only wonder what happens from here.



All statistics, records and accolades courtesy of unless otherwise indicated. Contractual information courtesy of Cot's Baseball Contracts.

Peter Panacy is a featured columnist for Bleacher Report, covering the Boston Red Sox. Be sure to check out his entire archive for Red Sox news, insight and analysis. Follow @PeterMcShots on Twitter.

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