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Cubs Pitchers Make Sense For Red Sox

Ryan Dempster pitched very well on Friday, shutting the Red Sox offense out over seven innings. It was the third straight start in which he tossed at least seven shutout innings, reducing his ERA to 2.11 in the process. With his typically strong peripherals, Dempster has already tallied 1.9 WAR in 81 innings, putting him on pace for his highest total since posting 5.2 WAR with the 2008 Cubs. However, given his contractual status and the Cubs futility this season, Dempster is likely to find himself finishing the season in another uniform.

While a few contenders — the Yankees and Dodgers, mostly — have already inquired on his availability, the team Dempster just recently blanked could and should have interest. The Red Sox interest in Cubs pitching doesn’t have to stop there, either, as Matt Garza is conceivably available as well. Both righties would help solidify the Red Sox starting rotation and help them get back into the running for a very obtainable playoff berth.

Neither pitcher would come cheap, but the Red Sox have a solid system and the front office familiarity — Theo Epstein and Jed Hoyer run the Cubs now after having served together with the Red Sox for many years — could certainly help matters. The Red Sox might not instantly appear to be natural trade partners for the Cubs pitchers, but they stand to make up some ground as offensive contributors regress to the mean and return from injuries. Adding a 4-5 WAR pitcher to the mix could take them even farther.

The Red Sox rotation currently ranks in the middle of the American League with 4.8 cumulative WAR. However, the group has the third highest ERA behind the Twins and Royals without an abnormally high batting average on balls in play. The rotation isn’t the main reason the team is currently 31-33, 7.5 games out of first place and five games behind the Rays for the second wild card spot, but it certainly isn’t a team strength.

In terms of space available for Dempster or Garza, the mainstays are Josh Beckett, Jon Lester and Felix Doubront. Daisuke Matsuzaka recently returned from surgery, and it isn’t clear how much he’ll provide or even how often he’ll pitch. Clay Buchholz has been one of the most disappointing pitchers in baseball this season. And the Daniel Bard conversion hasn’t gone well, with the reliever-turned-starter recently getting demoted to Pawtucket. There is room in the rotation for an all-star caliber pitcher.

Dempster would cost less than Garza given their respective ages and contract statuses, but the Red Sox have enough in the system to appease Epstein’s requests from the Cubs side. He might have his eye on pitchers like Brandon Workman, Henry Owens or Drake Britton. A half-season of Dempster isn’t worth all three, but this type of prospect — almost major league ready but not considered top talent — would represent a solid return.

Workman projects more as a reliever but he could end up sticking as a starter. Britton was a former top prospect that has fallen off recently. Owens has high upside and might be a tough sell to Ben Cherington in a Dempster deal. On the other hand, Epstein could gamble on Britton’s upside instead of other prospects that might look more like sure things, albeit with less overall talent.

When it comes to Matt Garza, it’s tough to envision a scenario in which Epstein doesn’t instantly request pitching prospect Matt Barnes. He could also target Xander Bogaerts, who is quickly climbing up the Top 100 prospect lists. Jose Iglesias has been attached to the Cubs before, as Epstein values shortstop defense above many other roster aspects. He could look to acquire Iglesias and shift Starlin Castro to second base, third base or even the outfield. The Cubs could also look at impact hitting talent like Bryce Brentz and Brandon Jacobs. The latter is more of a project than the former but both would greatly upgrade the hitting in the Cubs system.

A deal sending Barnes, Brentz and maybe Workman to the Cubs would seem reasonable to acquire Garza, while selections from the lesser tier of Red Sox prospects would satisfy the Cubs’ requirements for a Dempster move. The bottom line remains that the Cubs are motivated to sell and the Red Sox, while seemingly out of the playoff picture now, should still consider themselves buyers.

Internal improvements such as offensive players regressing and contributors returning from injuries are on the horizon and an upgrade in the rotation could really get them over the hump and back into seriously contending for not just a playoff berth, but the AL East division itself.