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Boston Red Sox: Where Jon Lester May Land

July 30th, 2014 at 2:45 PM
By Sean Penney

Once the Boston Red Sox decided to scratch Jon Lester from Wednesday's start it became inevitable that the team is on the verge of trading him. Multiple sources have reported that the Red Sox are actively shopping their ace prior to tomorrow afternoon's trade deadline, with at least half a dozen teams showing serious interest.

Keith Allison / Foter / Creative Commons Attribution-ShareAlike 2.0 Generic (CC BY-SA 2.0)

At this point it seems less of a matter of if Lester is traded and more of a matter of where. Here's a list of potential destinations where Lester could conceivably land.

Los Angeles Dodgers
What they have to offer: There had been some talk about a Lester-Matt Kemp swap, with the Dodgers eating a significant amount of Kemp's salary, but those talks seem to have fizzled. Kemp is a shadow of the player he was a few years ago, when he finished second in NL MVP voting. Injuries and inconsistencies have derailed his production, making him too much of a risk – even if the Red Sox aren't forced to pay the majority of his remaining contract.

Instead, Boston will try to pry prospects like outfielder Doc Pederson, shortstop Corey Seager or left-handed pitcher Julio Urias away from them. The Dodgers claim they won't include any of those top prospects in any deal, but as the deadline draws closer they may change their tune with so many other teams involved. The Dodgers are one of the few teams that may be willing to give up more because they may not view him as just a two-month rental, considering they have the funds to potentially outbid anyone else for Lester once he reaches free agency. Having him already in town to end this season would give them a leg up in negotiations. 

St. Louis Cardinals
What they have to offer: Outfielder Oscar Taveras would be at the top of the Sox wish list. He's the second best prospect in all of baseball, according to, which would be a steep price to pay for a two-month rental. However, adding Lester to pair with Adam Wainwright could make them the favorites to win the pennant and they've yet to be able to make a permanent spot in their deep outfield for Taveras. If including him is a deal-breaker for the Cardinals, perhaps outfielder Stephen Piscotty could be an option.

The Cardinals already made a move earlier today to acquire Justin Masterson from the Cleveland Indians, which may make them less inclined to deal for another starting pitcher.

Baltimore Orioles
What they have to offer: The Red Sox don't seem worried about trading Lester within the division (excluding the Yankees of course) considering it would be unlikely a team like Baltimore would be able to re-sign him after the season. This might actually benefit the Red Sox more in that keeping him away from a team Lester might want to re-sign with increases their chances of getting him to come back next year, while also stealing top prospects away from a division rival. A package for Lester would need to include at least one of their top two pitching prospects – Dylan Bundy and Hunter Harvey.

Seattle Mariners
What they have to offer: The M's need a bat much more than an ace pitcher, but there aren't any bats on the market that could make as much of an impact as Lester would, which is why Seattle is reportedly interested. Lester is also a native of Washington, so re-signing with the Mariners to be closer to where he grew up could be appealing, which might entice Seattle to give up more. The conversation would need to start with pitcher Taijuan Walker – the 8th best prospect in baseball per Despite some injury issues that he's battled this year, he still projects as a potential front line starter.

Milwaukee Brewers
What they  have to offer: We've seen them make a bold move for a rent-a-ace in the past, when they traded for C.C. Sabathia in 2008. They are in a three-team dogfight in the NL Central that could motivate them to make a big move like this. Unfortunately, they don't have the type of elite prospects to compare with some of the other teams on this list. Pitcher Jimmy Nelson (ranked 53rd by is their top prospect, so the Red Sox would need more than that unless none of the other interested teams were willing to part with any top prospects. Boston may be better off keeping Lester if that's the best they could get for him.

Pittsburgh Pirates
What they have to offer: What kind of world are we living in where the Red Sox are deadline sellers and the Pirates are looking to buy? Yet that's where we find ourselves, with the Pirates considered a dark horse candidate to acquire Lester. Power hitting outfielder Josh Bell would be the likely trade bait. With other teams hesitant to give up an elite prospect or looking in other directions, the Pirates are quietly emerging as a favorite to land Lester. Then again, give it a few hours and that could always change.

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