Boston Red Sox Armchair GM, Trade Deadline Edition: Brendan O'Toole

Don't worry, he ain't going nowhere. Mandatory Credit: Scott Rovak/USA TODAY Sports via US PRESSWIRE

Because the All-Star break is incredibly boring, we've decided to dust off the Armchair GM series here at OTM. Over the coming week or so, each of us will be putting on our best Ben Cherington hats to figure out what the Sox should do between now and the non-waiver trading deadline on July 31. Matt Sullivan kicked it off on Tuesday, and Matt Kory followed up yesterday. I'll be keeping the shop today.

So it's my turn to take the reins of the Red Sox franchise and figure out where to take them this year. It's weird, because this requires actual baseball analysis, but then it was this or comment on Jon Lester's little Twitter blowup yesterday, so... Let's trade some guys! (I'll probably still wind up writing about the Lester thing, because I am a masochist.)

Boston's in a truly strange position heading into late July. They've been absolutely hosed by injuries, their play has been maddeningly inconsistent, and they entered the second half with a .500 record. But due to the impressive parity of the American League and the new wild-card format, they're only 2.5 games out of a playoff berth. The Red Sox are about to see Jacoby Ellsbury and Clay Buchholz return to the team; two players probably better than anyone they could pick up via trade. Of the teams ahead of Boston in the wild-card hunt, none are unstoppable, and Boston's actually got a better run differential than all but the Angels. (Boston's at +44, Baltimore's at -36. And the Orioles are 2.5 up. See that lasting?)

Honestly, the Red Sox could probably just stand pat and count on improved luck and health to carry them into at least an interesting September. But that would make for an awfully boring column. Besides, they're currently lousy with extra veteran outfielders and bullpen arms, both of which are pure gold at the trading deadline. A thing to remember about the trading deadline is that fringe contenders, especially the ones that haven't been there in a while, tend to get desperate. As such, there's another angle the Red Sox can take here, and that's the evil Stephen King pawnbroker angle:

"Oh, need a catcher with some pop, do ya? Yeah, I think I saw one of those in the back. Let me just check... What were ya lookin' to pay for that? Only a B-level? Well, ya know, I'll tell ya. Back in aught-nine, fella came in here, hopin' for a long reliever. Young fella, name of... I don't remember his name, but I remember he was young. Had five hundred grand and a washed-up infielder. Well, I had to turn him down. Didn't want to, but I've got a family to feed, know how that goes. Well, his team, they finished two games out. Blew a few late leads, mighta made it if he'd been willing to spend a little more. Not saying that's why he killed himself in the winter, but mayhap it was. So how much were you looking to spend?"

With that in mind:

Boston sends C Kelly Shoppach, P Justin Germano, and RP Vicente Padilla to New York (NL) for P Jeurys Familia.

I'm not sure why when I think "desperate contenders" I instantly think "Mets," but there it is. New York's NL squad is in the hunt for the first time in quite a while, and with an aging top two in the rotation and a perhaps-leaving star third baseman, they're likely to throw resources at a real shot this year. Although I considered trading Padilla to Tampa for a bag of baseballs (he seems like their kind of guy), he shores up New York's bullpen nicely for the stretch run, and oddly is rocking a reverse split this year, throwing better against lefties (.677 OPS) than righties (.818). Germano just spent half a season in Pawtucket carving up the International League, and looked good in relief for Boston against the Yankees, but I just don't see that lasting in the AL East. Heading over to the NL, Germano could serve as a terrific long reliever and swingman for the Mets, especially with Dillon Gee headed to the disabled list.

Shoppach's hitting .269/.358/.527 at present; Mets catchers as a group are hitting .244/.304/.299. Kelly could drop 150 points off his OPS and still be a substantial upgrade. I've heard rumors that veteran catchers are also infused with magical leadership qualities, which I guess could be useful for a team making an unlikely playoff run. Of the Mets' top three pitching prospects, Familia is I think the one they'd be most willing to part with. His stuff projects very well, but he's not as sure a thing as Zach Wheeler or Matt Harvey. Still, if Sandy Alderson hits his head, Wheeler immediately, please.

Boston sends 3B Garin Cecchini, OF Brandon Jacobs, and SP Franklin Morales to Chicago (NL) for SP Matt Garza.

This is my official "not ready to give up on 2012" trade. The Sox are still (barely) in it, and their major weakness is in the rotation. Garza's an obvious solution to that. He's signed through next year, meaning this isn't just a quick rental, as either Cole Hamels or Zack Greinke would be. We've seen him succeed in the AL before, his peripherals are about where they've always been. There's been a bunch of discussion here along the lines of the Red Sox going forward with a rotation of solid-to-very-good pitchers in the absence of a true ace, and this would be exactly that. Garza's not an ace, but he's reliably good, and that's something Boston sorely needs.

At the same time, Garza's not someone you sell the farm for, and that's exactly what I'm looking to avoid here. Cecchini's got great potential, but he's clearly behind both Will Middlebrooks and Xander Bogaerts on the third base track. Jacobs has tools to spare, by all accounts, but the Red Sox system is very deep in the outfield, and the Cubs can better afford to gamble on tools. As for Morales, I think he might well have figured it out, and will keep pitching well. But I trust Garza more against AL offenses.

Boston sends OF Ryan Sweeney and INF Nick Punto to Pittsburgh for P Kyle McPherson

Back to unexciting roster-clearing. Boston's got too many outfielders, and too much Nick Punto. So off they go to Pittsburgh, where the Pirates are rather surprisingly making a real go of it. Ryan Sweeney gives the Pirates a legitimate third outfielder, and Punto lends that scrappy jack-of-all-trades thing he seems to bring to NL clubs. McPherson's not overly exciting, he's one of those classic safe bet prospects. He won't ever be Pedro Martinez, or even Jon Lester. But he won't be Kyle Weiland or 2011-vintage John Lackey, either. Speaking of which...

Boston sends SP John Lackey and cash to Houston for any prospect who knows which end of the bat to hold.

There isn't actually a pro ballclub in hell, the Astros seemed like the next-best thing. Who knows, maybe Lackey will thrive down there. Lots of open grass, lots of outfielders to gesture angrily at. I think he'll be happy. I know I'll be happier with Lackey pitching anywhere else, and if the Sox are able to save even a few million on the deal, it'll be a win. There is nothing John Lackey offers to a contending ballclub that can't be found on a halfway decent American Legion squad, and there's no point in pretending otherwise. Failing a trade, outright release will do just fine.

Boston sends OF Cody Ross to Philadelphia for SP Cliff Lee.

Because some men aren't interested in logical trades, like Scott Podsednik for Antonio Bastardo. Some men just want to watch the Phillies comment threads burn.

(OK, I'm kidding about that one. Although if adding Ross to the Mets offer snagged Zach Wheeler and an infield prospect, I would sadly say farewell to the Flipper of Bats. And come to think of it, it'd have a similar effect on the Philly comment threads.)

Boston sends RP Matt Albers to St. Louis for cash (maybe a PTBNL if we're greedy)

St. Louis boosts their bullpen a bit for their attempt at a repeat, Boston saves a bit of cash. Most importantly, our dreams are no longer haunted by the uncertainty of which Matt Albers will show up on a given night.

Boston sends 1B Adrian Gonzalez-2012 to the Phantom Zone for 1B Adrian Gonzalez-2011.

This might be the most important trade on the list. Take a look at this guy (using Baseball Prospectus's new hitter profiles, which might be my new favorite toy), then take a look at this guy. The first of those is a middle-of-the-order beast. The second is not. If Adrian Gonzalez can start hitting like he's capable of hitting, the effect is the same as trading for a top-flight slugger. Same goes for Jon Lester on the pitching end of things.

And that ought to do it. Boston clears out a great deal of 40-man roster space, picks up a couple of young pitchers to dream on, and leaves its talented core in place. The farm system stays mostly intact, with enough prospects (along with maybe Buchholz, Ellsbury and/or Doubront) to take a run at someone like Elvis Andrus or Justin Upton if they become available in the offseason (more likely than a rushed deadline trade). This season has neither been encouraging enough to go all-in on a big name nor bad enough to tear everything down and wait for Matt Barnes and Jackie Bradley to save the franchise. Clear out the roster, get a good rotation arm, and see what happens.

(This assumes at least a passable rest of July, of course. If they plummet through the basement floor or Josh Beckett actually murders a reporter, then yeah, maybe it's time to see who's looking for a slightly used Ellsbury.)

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