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Red Sox trade Lester, Lackey to overhaul future lineup with Cespedes, Craig

The steep decline of the Boston Red Sox following their 2013 World Series championship has been shocking. But general manager Ben Cherington isn’t sitting around, scratching his head, wondering where it all went wrong. Instead, he’s doing what he can to make sure next year’s edition of the Red Sox rebounds quickly.

Making what could be the biggest deal of the MLB trade deadline day, Boston sent Jon Lester to Oakland on Thursday, also including outfielder Jonny Gomes in the deal. The surprising return for the Red Sox is outfielder Yoenis Cespedes, the right-handed power hitter that their lineup has been lacking this season.

That’s not the only move Boston made before the 4 p.m. deadline either. John Lackey was another of the Red Sox starting pitchers in demand, especially because he’ll cost only $500,000 for next season as a result of missing all of 2012 after undergoing Tommy John surgery. That probably helped Cherington make an even better trade, dealing Lackey to the Cardinals for outfielder Allen Craig and reliever Joe Kelly.

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Trading Lester would’ve seemed like a crazy idea going into this season. But the Red Sox’s poor performance and Lester’s contract situation obviously changed that scenario. Suddenly, Boston had the starting pitcher most in demand, one who could make the greatest impact for a playoff contender and yield some young talent to help reload for next season and beyond.

Lester wasn’t likely to bring the same return that the Rays’ David Price would, since he’ll be a free agent after the season while Price is under club control for one more season.

Because of that, Boston wasn’t necessarily expected to get a player that could contribute to the major league team right away, though a top prospect probably would have gotten a shot with the Red Sox in August and September. However, Cespedes will obviously make an immediate impact both in the middle of the lineup and left field with his defense.

The 28-year-old Cuban slugger is also signed through next season for $10.5 million. Considering his production and the current market value for right-handed power, that’s relatively inexpensive. Boston will eventually have to deal with the question of whether or not to sign Cespedes to a contract extension. But the team gets him for at least one full season.

If negotiations on a new deal go nowhere, as they did with Lester, and the Red Sox end up out of contention again next year, Cespedes could conceivably be traded again, yielding the prospect or two that Cherington didn’t get in exchange for Lester.

Of course, the expectation is for the Red Sox to compete for a postseason spot and World Series championship again next season. Cespedes can be a big part of that, with potential 30-homer power hitting either in front of or behind David Ortiz. Craig could become a key run producer in the middle of the Red Sox lineup as well.

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The fact that the Cardinals were willing to trade Craig for a mid-rotation starter indicates how far his status had fallen with the team. He’s struggling through a rough season, batting .237 with a .638 OPS. Craig is better suited for first base, but Matt Adams has entrenched himself at that position. And the Cards are loaded with young outfielders that can take over in right field. Craig was expendable, and St. Louis was surely eager to shed the $26.5 million he’s owed through 2017 off its payroll.

However, Craig hit over .300 with an OPS of .830 or above and averaged nearly 20 home runs in each of the past two seasons. If he can bounce back to that form, a $9 million annual salary will seem like a bargain. By trading for him, the Red Sox presumably believe that Craig’s struggles are tied to his foot injury suffered last season and is capable of turning himself around.

Or maybe Cherington has even more dealing in mind. The Red Sox already have Mike Napoli at first base and he’s signed through next season. Designated hitter is obviously manned by Ortiz, who’s under contract for next year and has club options for 2016 and 2017. That leaves Craig to play the outfield, which he doesn’t do particularly well (though advanced metrics say his defense in right field this year is above-average).

Besides, which outfield position would Craig play? Cespedes will presumably play left field, with Jackie Bradley in center and Shane Victorino in right. Cespedes reportedly doesn’t want to play center field and Bradley is an elite defender at the position (though isn’t hitting well). Victorino’s production is down from last season, but hamstring and back injuries have factored into that. Set to be paid $13 million next year, the Red Sox probably don’t want to make him a reserve.

Someone has to move, whether it’s one more deadline deal Cherington makes or an offseason transaction.

On the pitching side, Kelly makes up for some of what the Red Sox have traded away. He’s probably more of a back-end starter, however. A hamstring injury has limited the right-hander to seven starts this year, during which he’s compiled a a 4.37 ERA with 41 hits allowed in 35 innings. He’s also under club control for another four seasons, the sort of lower-cost player that Cherington surely covets as he attempts to retool his pitching staff and decide how to allocate resources toward free-agent starting pitching.

One of those free agents could be Lester. How great would these deals look for the Red Sox if that’s what ends up happening? Boston could re-sign Lester in the offseason, something the left-hander has said he won’t rule out. Of course, that’s not a guarantee as Lester stands to be one of the top starters on the market this winter and may be priced beyond what the Red Sox want to pay.

But if Cherington is able to bring him back after using him and Lackey to stock his future lineup with two impact bats (along with a young arm for the rotation), that would be a brilliant development for the Red Sox. The disappointment of 2013 would quickly be forgotten if circumstances worked out so favorably.

About Ian Casselberry

Ian is an editor for Awful Announcing and The Comeback. He has covered baseball for Yahoo! Sports, MLive.com, Bleacher Report and SB Nation, and provides analysis for several sports talk radio shows each week. He currently lives in Asheville, NC.