5 Things I Would Do if the Red Sox Decide to Sell

As I write this before Sunday’s game has been played, the Red Sox are 10 games in back of the Blue Jays for the division. That’s bad. We’re also five back from a wild card berth, with all of the Royals, Twins, White Sox ahead of us in that race. That’s worse. If you’re looking for the bright side, well, we’re a game up on the Atros in the wild card race.

Which means that, yes, even the good news is bad.

All of that being said, it is, as I asserted to Chad Finn above, too early to write the 2014 Red Sox season off as a lost cause. Fangraphs, in fact, has the Sox’ odds of a playoff berth at 18.9%, which are actually better than they’re giving the Yankees (18.7%) who are a mere six games out. As much because the rest of the division has problems of their own as anything else – the Blue Jays are still the only team in the East with a positive run differential – the Red Sox are, improbably, not out of this thing. Which means that if you’re Cherington, you probably have to give them a few weeks yet to sink or swim.

But for the sake of argument, if they did decide to sell, how might they proceed? Finn tackled that question here, and his approach makes sense: don’t trade any real assets for duct tape and bailing wire, don’t trade John Lackey, and if you find a buyer who’s all in on Johnny Gomes’ intangibles, sell high. We differ on one important idea, but more on that shortly. Here are five things I would do if the Red Sox were to shift into sell mode.

Move Minor League Pitching

There isn’t much debate at this point, his walk rate notwithstanding, that Henry Owens is ready for Triple A. The problem is that there isn’t anywhere to put him, with that rotation to be fully stocked with Webster, Ranaudo, Barnes, maybe Wright – and soon enough, De La Rosa and Workman. Unless you think that a) all of those pitchers will end up in a major league rotation and b) you’re willing to live through their growing pains at the major league level simultaneously – much as the Braves once did, some of those arms should be moved. As to which ones, I would generally defer to the front office, but an arm like Workman would seem to have some value to other clubs, particularly in the National League. He throws strikes and has had major league success, which makes him potentially valuable. But he has never been particularly dominating, at least not in the way that Barnes, De La Rosa, Webster or, more recently, Owens have been at times. So while you can never have enough pitching, it might be time to begin converting that surplus into usable parts. The first team I’d call up, by the way, would be the Cubs. They’ve got positional prospects, but they’re light on higher end pitching talent. And Cherington does happen to know their President and General Manager.

Trade Jon Lester

This is where I break with Chad, and I do so with one big caveat. If the Red Sox are ultimately willing to extend themselves sufficiently to retain Lester – let’s say in the $120 million range, conservatively – they should do so now. If, on the other hand, their reported $70 million borderline slap-in-the-face initial offer is within hailing distance of their threshold, then they shouldn’t waste any time and find him a new home as soon as possible. The fact that he’s a pending free agent limits his value, of course, but I’d be surprised if a contending club didn’t offer value above the single pick that the Red Sox would receive in return for his departure. In short, if the club decides that a) they’re not going anywhere this season and b) that they are not in a position to sign him (regardless of whether we think they should), then the only logical outcome to me is c) trade him.

Trade a Reliever (or Two)

Of all of the asset classes that get moved at the trading deadline, none is so disproportionately valued as relievers. Clubs that feel that they’re a mere piece or two away will and do overpay for relievers who might be worth 30 innings down the stretch. Given that the bullpen, with the odd exception here or there, has been an area of strength for the club this year, this is a logical place to deal from. Add in the fact that, as discussed above, the Red Sox have something of a surplus of arms near the majors, moving a bullpen piece like Badenhop, Breslow or Miller for an outsized return while simultaneously creating an opportunity for one of the young arms to work their way into the majors seems like a no brainer.

Do Not Trade John Lackey

John Lackey has had his ups and downs over his career with the Red Sox, and as Jackie MacMullan intimated in an interview earlier this season, his personality hasn’t changed with his performance: even pitching well, he’s still prickly and ornery. But that’s not the important part. The important part is the “pitching well” bit. Fresh off his remarkable 2013 comeback campaign, Lackey has looked much like he did with the Angels: not a true ace, but durable, occasionally brilliant, and capable of delivering quality innings. Also? He’s scheduled to make $500,000 next year. To trade him, then, you’d have to receive not only the value for the type of pitcher he is at present, which is a very good one, but also for the savings he will represent next season – which is easily into the eight figures. Young stars are rarely moved these days because they represent such a unique combination of ability and a low price tag; that’s Lackey next season. So unless you get absolutely blown away, which is unlikely given his age, you’re not going to get comparable value for him. Trading Lackey, therefore, would be foolish. And that’s without even getting into the wider context, which is that – assuming Lester is not retained – a trade of Lackey would leave Buchholz and Doubront as your only major league starters under contract for next year.

Trade Stephen Drew

Somewhere Finn is shaking his fists at this notion, but I am no Drew hater. I would have him playing third instead Bogaerts, but I applauded the signing when it was announced. It’s no secret that I’ve never been much of a believer in Middlebrooks, and Drew does two things well that this team needed (and still needs): he’s solid on defense and he can hit right-handed pitching. Adding him was, in that respect, a no brainer. But he is also gone after this season, as the left side of our infield is getting crowded with potential candidates, from Bogaerts and Middlebrooks who we’ve seen to Cecchini and Marrero who we have not (or in the former’s case, seen little of). Which means that, again assuming the season comes to be regarded as a lost cause, you might as well maximize your return on assets while you’re able. What kind of package might the Tigers put together, for example, to extract both a high leverage bullpen arm and a tier one starting shortstop from us, for example? Such a move would address their two most glaring weaknesses, and could propel them to the title their owner is so desperate to achieve he’s signing Monopoly-money contracts. If you’re in the hunt, I agree that you don’t want to strengthen a rival, but if you’re not you’d hope they’ll extract every bit of value they can. Which means moving Drew.