MLB Trade Deadline: Boston Red Sox in enviable position

It’s the end of an era in Boston, at least for the next few months.

Jon Lester, who produced a 3-0 record and a 0.43 ERA in three World Series starts that contributed to championships for the Red Sox in 2007 and 2013, was traded today to Oakland to hoist the A’s on his back for what Billy Beane hopes will be that club’s first World Series title in his tenure.

The Red Sox could re-sign their ace in the off-season when he becomes eligible for free agency, which is one of the many decisions Red Sox general manager Ben Cherington and the team’s ownership group face. They took advantage of the MLB trade deadline in a big way.

Not long after dealing Lester, Boston dealt John Lackey to St. Louis for right-handed pitcher Joe Kelly and outfielder/first baseman Allen Craig. Andrew Miller was shipped to Baltimore for 21-year-old left-hander Eduardo Rodriguez (who was No. 65 on Baseball America’s top 100 prospect list entering the 2014 campaign) and Stephen Drew was traded to the New York Yankees, clearing the way for Xander Bogaerts to return to shortstop and Will Middlebrooks to get another look at third base.

This has been a surprisingly lean year for the Boston Red Sox. Not even a year after capturing their World Series title in 10 years, the Sox find themselves in the American League East basement, 12 games under .500 and 13 games behind first place Baltimore. Yet there is reason for extreme optimism in Boston.

Though the return of Yoenis Cespedes from the A’s in the Lester/Jonny Gomes trade eases the sting, Cherington is taking a verbal beating across New England, but he knows – and baseball minds around the league are aware – that the Red Sox are well-positioned to build a formidable World Series contender in 2015 and beyond.

First, take a look at Boston’s payroll commitments for the short term and long term. David Ortiz ($16 million), Dustin Pedroia ($12.5 million), Clay Buchholz ($12 million), Mike Napoli ($16 million), Shane Victorino ($13 million) and now Cespedes ($10.5 million) and Craig ($5.5 million) are the only veteran players under contract next year.

Napoli and Victorino will be in the final year of their respective deals. Veteran right-handed reliever Edward Mujica is owed $4.75 million next year, but the Red Sox will not likely bring him back, even if they have to eat his remaining salary.

For a general manager, that presents a chance to construct a roster with a mostly clean blackboard. Cherington built the roster that cultivated a magical run to winning the World Series in 2013. That team was crafted for that year. The opportunity he has this offseason is to serve as the architect of a club that can contend for the long term.

With substantial payroll flexibility, an abundance of highly regarded prospects and an ownership group that is willing to spend, the Red Sox will undoubtedly be active in the free agent and trade markets this offseason.

Whether the 2015 rotation will once again include Lester remains a question. He will be 31 in January, and likely he is interested in a new contract that spans six or seven years. The Red Sox have shown that they are not comfortable with a deal of that length for a player who will be north of 35 in the final years. Jacoby Ellsbury is a prime example.

That philosophy is understandable, especially considering the predicament that the New York Yankees face with CC Sabathia. Now 34, Sabathia is on the decline and is out for the season with a knee injury. He is receiving $23 million this year and is set to get $23 million in 2015, $25 million in 2016 and a potential $25 million vesting option for 2017.

Red Sox owners insist that they will not exceed the luxury tax threshold, and a cumbersome contract for a pitcher who is on the decline in his mid-30s would have a negative impact on the club’s depth. This is why Boston will not likely bring back Lester unless he would agree to a five-year deal.

Since the Red Sox have an abundance of premium prospects, they could pry left-hander Cole Hamels from Philadelphia. Hamels is appealing to Boston because he will be 31 in December but is already signed to a contract that expires in 2019 (when he will be 35). A proven frontline starter, Hamels is set to get $22.5 million a year through 2018 and a potential $24 million vesting option for 2019 (or a $20 team option is the vesting option is not triggered).

If they do not bring back Lester, who would likely only cost a draft pick since the A’s will seemingly at least make him a qualifying offer, the Red Sox will aggressively pursue Lester or another top of the rotation arm.

Boston will fill some roster spots internally. Christian Vazquez is poised to claim the starting catcher’s role next season. Blake Swihart, also one of the top catching prospects in baseball, will likely open 2015 at Triple-A Pawtucket, and he has the athleticism to make a position change, though he is considered an above average signal caller.

The Red Sox have a logjam on the right side of the infield with Xander Bogaerts, Will Middlebrooks, Brock Holt, Garin Cecchini and Deven Marrero. Bogaerts is likely destined for shortstop or third base, and Marrero is regarded as a plus defensive shortstop. Middlebrooks or Cecchini – or even both – could switch to left field or first base. The versatile Holt can play multiple positions.

Even with the acquisition of Cespedes, the Red Sox could go after an impact bat like Miami’s Giancarlo Stanton or Colorado’s Troy Tulowitzki in the off-season. One or two of the aforementioned infielders would likely be part of a blockbuster trade package.

Boston has enviable starting pitching depth with promising young arms like Rubby De La Rosa, Brandon Workman and Allen Webster at the Major League level and top prospects including Anthony Ranaudo and Matt Barnes at Triple-A Pawtucket, and Henry Owens and Brian Johnson at Double-A Portland. Edwin Escobar, who was recently acquired from San Francisco in the Jake Peavy deal, is a left-hander whose future could be in the rotation or as a late-inning reliever. Rodriguez is another left-hander who could serve as a starter or late-inning reliever in the future.

Considering that World Series titles are not won with youth, the Red Sox will likely fill some spots with their prospects and use some of them as trade chips to acquire difference-making veterans. Cherington has a plethora of top prospects and substantial payroll flexibility to construct the roster for 2015 and beyond. Because of this, the future for the Red Sox is encouraging.