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Buy or Sell? Red Sox Have Bright Future Despite 2014 Woes

Trading Jon Lester could be one way the Red Sox build around a promising future. (AP Photo/Charles Krupa)

When the July 31 trading deadline arrives, teams across the landscape of Major League Baseball will be forced to acknowledge the standings, and recognize where they belong in the pennant race. There is plenty of time between now and then for teams like the Boston Red Sox to reverse their poor fortunes and ride momentum towards the stretch run, but there’s also the distinct possibility that consistent success will elude this team leading up to that fateful day.

Imagine it’s July 31, and with two months remaining in the regular season, the Red Sox find themselves about ten games outside of first place and a handful of games outside of the two wild card spots, which truly are wild card spots with the expanded postseason format. If you’re general manager Ben Cherington, you may be making deadline moves to improve the roster of the team beyond 2014.

It would seem that, regardless of the performance of the 2014 club, the future of the Boston Red Sox already exists within the system. From the talented pitching found in Pawtucket to the legend of Mookie Betts, it would seem unlikely that the Red Sox sign many free agents to large contracts in the coming seasons, or at least not as many as they have over the last few years.

The money may best be spent locking up the young talent the Red Sox could develop into the core of a potentially dangerous franchise. That begins by extending Xander Bogaerts, who has shown signs of a blossoming superstar this year. If the Red Sox were to discuss an extension with Bogaerts, they could come to agree upon a potentially team-friendly deal like the seven-year, $41 million deal Anthony Rizzo agreed to with the Chicago Cubs last season.

The Lester Dilemma

A less obvious situation is the dilemma facing Jon Lester and the Red Sox. As it stands today, Lester is the ace of the Red Sox in the middle of an exceptionally strong season, which also happens to be his contract year. At the end of the year, Lester will be on the open market alongside Detroit Tigers pitcher Max Scherzer, who recently turned down a reported six-year, $144 million deal.

Boston could avoid investing in Lester altogether by trading the southpaw before the deadline. Lester would be an extremely appealing arm to clubs in the hunt for the postseason, given his career 2.11 postseason ERA in 76.2 innings. The return for Lester at the deadline would likely be more valuable than losing him in free agency and only receiving draft pick compensation. Losing Lester may ensure that the 2014 season is over, but moving him could bring back a great return to restock the farm system.

The Red Sox have the arms they need to build a strong rotation for years to come, and it’s possible to maintain these pitchers without having to spend a great fortune. This type of flexibility will come in handy if the team does recognize the need for stronger options across the roster, and then they could concede to free agency.

Infusion of Youth for Rotation

In 2014, the Red Sox could use a rotation led by John Lackey, whose unique contract situation should lead to an extension in my opinion. Given Lackey’s success of late, the Red Sox could extend Lackey to a deal that rewrites his 2015 league minimum pay in order to keep the pitcher under team control longer at a cheaper price. I would think that such a contract could be for less than three years (2015, 2016, and 2017) and $27 million.

Beyond Lackey, the Sox will have Clay Buchholz, Felix Doubront, Rubby De La Rosa, Allen Webster, and Anthony Ranaudo, who will likely make his major league debut at some point this season. The strengths of that type of rotation promote long-term success, both because the rotation is so young and because a lack of large contracts means other young pitchers like Matt Barnes and Henry Owens won’t be blocked as they rise through the farm system.

On offense, we’ve already seen glimpses of the future starting nine. Garin Cecchini looked good in his cameo appearance earlier this season, and it’s reasonable to believe that he and Bogaerts will become a dynamic duo on the left side of the Sox infield. Dustin Pedroia isn’t going anywhere, so Mookie Betts may have to learn the outfield, or find himself a part of a trade because his bat belongs in the big leagues.

2014 has been a disaster thus far for the Red Sox. While the championship team last year certainly overachieved, there’s no doubt that Boston should at least be actively competing for the postseason all year long, but if July 31 rolls around and the Sox haven’t climbed the standings yet, it could be much more beneficial for them to pull the plug.

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