Trading Deadline 2014, Or What the Hell Just Happened?

Jon Lester

In a season of unexpected twists and turns, most of which ended up being blind alleys where the Sox got hit in the head with a pipe, last week’s trading deadline was easily the strangest. With almost a third of the roster exiting over a period of weeks, culminating in Thursday’s bloodletting, there’s a lot for Red Sox fans to process. As Chad Finn notes, the prevailing opinion isn’t as much anger or despair as confusion. Part of that is because the moves by themselves were so unanticipated, but it’s also because they suggest that they were just the beginning. To recap what just happened and reflect upon what might happen next, let’s ask and answer a few questions.

Q: The first and most obvious question is: literally, what the hell just happened?
A: Setting aside the DFA of Pierzynski, which was not particularly surprising, the Red Sox made the following moves:

  • (July 26) Jake Peavy traded to the San Francisco Giants for Edwin Escobar (Giants #2 pitching prospect) and Heath Hembree
  • Felix Doubront traded to the Chicago Cubs for a PTBNL
  • Stephen Drew traded to the New York Yankees for Kelly Johnson
  • Andrew Miller traded to the Baltimore Orioles for Eduardo Rodriguez (Orioles’ #3 pitching prospect)
  • John Lackey traded to the St Louis Cardinals for Allen Craig and Joe Kelly
  • Jon Lester and Jonny Gomes traded to the Oakland A’s for Yoenis Cespedes and the A’s competitive balance draft pick

Q: All of which means what?
A: Most obviously, that the Red Sox have officially thrown in the towel on the 2014 season – as they should have. The math says it isn’t technically impossible – yet – but also that it’s practically impossible. Which means that correct course of action was to use this year as a means to reload for future years.

The interesting thing, however, is that unlike traditional deadline trades, the centerpieces weren’t prospects. Every year the rumored trades are not the actual trades, but it’s usually because the names are wrong. This year, not only were the names wrong the entire type of player was different.

The Red Sox did acquire prospects in the Miller/Peavy deals, it’s true, but their most valuable assets in Lackey and Lester respectively were not used for the likes of the Dodgers’ Joc Pederson or the Pirates’ Josh Bell, but rather for current major league players. The $64,000 question is why.

Q: Is it because the Red Sox are playing for 2015?
A: That’s the most common narrative at this point, and there is a fair amount of evidence to suggest that’s the case. Clearly the Red Sox aren’t going to commit to a full tear down and rebuild, nor should they with the roster of young, controllable talent they have assembled. And virtually every statement from Cherington, Farrell, Hazen or anyone else associated with the team has focused on the importance of 2015.

That being said, the Red Sox are both intelligent and intensely focused on value. It seems unlikely that if a a Top 30 or 40 MLB prospect was made available to them – with the six years of control attached to it – in return for Lackey or Lester the Red Sox would prefer wild cards like the deeply slumping Craig or the big time power but limited on base skills of a Cespedes. Maybe this year with all of the associated growing pains of Bogaerts, Bradley and so on has left them a little gun shy about prospects, but that seems improbable.

Which implies that the Red Sox simply were not offered that type of elite talent. Faced with a list of sub-Addison Russel type prospects who would be years away from helping in a best case scenario, the front office changed their tactics to focus on major league players, in particular what they believe to be a scarce market resource: offense.

Q: Why is offense down?
A: There are many potential explanations, and probably all of them play some role. From better drug testing to defensive shifts to an explosion of high velocity arms, offenses around the league are depressed. Not as much as in Boston, obviously, but there is no question that pitching is currently ascendant.

More problematically for the Red Sox, potential solutions aren’t exactly plentiful on the free agent market. There are decent hitters available, but nearly all come with question marks. Victor Martinez and Hanley Ramirez are old, Melky Cabrera comes with PED questions and so on. There are no true superstar hitters available.

There is, however, a lot of pitching.

Q: What kinds of pitching?
A: All kinds. Excellent starters in Lester, Scherzer and Shields. Pitchers with a few more question marks in De La Rosa, Kuroda, Masterson and McCarthy. Others with options like Anderson, Burnett, Chen (both Bruce and Wei-Yen), Cueto, Gallardo, Happ, Haren and Morrow. And so on.

Q: So the Red Sox appear to be betting that it will be easier to remedy their pitching than their hitting via free agency?
A: Or trade. Apart from Bogaerts and potentially Betts, the Red Sox lack elite talent. Owens is good, but not in the class of the Oriole’s Gausman and pitching prospects go. Swihart and Devers, meanwhile, are potentially elite but not widely regarded as being in that class yet.

All of that being said, in the wake of this week’s trades the system is now absurdly deep. Whether the Red Sox are able to package some of that quantity and return elite talent via trades remains open to question, but that’s certainly an avenue they’ll have to proceed.

Q: Why?
A: First because there are almost too many candidates. Consider the starting pitching candidates: De La Rosa, Escobar, Johnson, Owens, Ranaudo, Rodriguez, Webster, Workman and Wright. For the sake of argument, say two thirds of those fail: the Sox are still left with three potential starters.

That kind of depth is an asset, of course, but it also presents substantial roster construction challenges, as the Red Sox were reminded this year.

Q: What do you mean?
A: One of the inviolable rules of player development is that it is non-linear. Some players succeed immediately only to stumble later, others struggle for years before putting it all together. The best example of this currently playing is Mike Trout; the widely accepted best player in the game pancaked when first hitting the majors.

What this means for the Red Sox is that they’re probably not going to want to trust too high a percentage of their rotation or lineup to rookies. Youth will be an important, indispensable part of the Red Sox strategy now and moving forward, but you’re not likely to see them roll out a lineup of six rookies with four in the rotation next year.

Far more likely is that some of these assets are converted to talent with a more predictable major league performance track record.

Q: Such as?
Q: That’s the question, and it’s far too early to say. But let’s say that you offered a team a “Pick 5″ such as the club reportedly did with Seattle once upon a time:

  1. Cechinni
  2. Webster
  3. Marrero
  4. Vazquez
  5. Johnson
  6. Rodriguez
  7. Escobar
  8. Barnes
  9. De La Rosa
  10. Middlebrooks

A lower payroll team could miss on two of the five and still solve three roster spots with eighteen combined years of control attached. That’s a return everyone would have to at least think about.

Q: So how should Cherington be graded on his deadline moves?
A: It’s hard to assign anything but an incomplete. It was strange, for example, for a pitcher of Lester’s caliber – even granting the fact that he’s a rental, especially for a lower budget club like the A’s – moved for a player who A) doesn’t get on base particularly well and B) is only under contract for one more year.

But we don’t know what was available. And we certainly don’t know how Cherington plans to use the potential minor league surplus in the offseason.

At the very least, however, Cherington gets points for doing something.

Q: Meaning what?
A: Imagine being a Philadelphia fan, were Amaro Jr essentially stood pat with a club that is worse than the 2014 Red Sox, has far less prospect depth and two pitchers making north of $20M a year – one of whom may now be out for the season with an elbow injury.

While it was nice to see the brief bounce the Red Sox received coming out of the All Star break, the subsequent five game losing streak at least made the front office’s job simpler. Instead of sitting on the fence until the last minute, they were able to shift into sell mode with a week to spare. Cherington needed to take advantage of what will hopefully be a rare opportunity to sell, and he did.

How he fared is a subject we’ll likely be debating for years.

Q: What’s next?
Q: The rest of the season, obviously, will serve as an audition of sorts for Betts, Bradley, Middlebrooks, Webster et al. Bogaerts, his horrific midseason slump notwithstanding, isn’t going anywhere. But pretty much everyone else could be. Two months of at bats, particularly given that one of them will include September call ups, won’t make for a definitive evaluation, but it will at least give the major league coaching staff the chance to make their own assessments of players up close.

Entering the offseason, then, the Red Sox need to figure out what to do with their logjam of outfielders. Nava, Cespedes, Bradley, Betts, Victorino and Craig can’t all play at once. Who goes? Who stays?

The most important task, however, is figuring out the rotation. Given that it’s extremely unlikely that the Red Sox are going to roll out Clay Buchholz and four pitchers with an average of a year of service time per, where are the additional starters going to come from? Free agency? Trade? The return of Lester?

Q: Isn’t it “fanciful” that Lester returns to the Red Sox?
A: He probably doesn’t end up here, no. If they were going to retain him, wouldn’t they have already? Didn’t John Henry pretty explicitly say that the Red Sox weren’t signing big money deals for players over thirty? And when was the last time a player traded resigned with the team that traded him – apart from Cliff Lee, that is? Probably, yes, and I can’t remember.

But how many players would say, as they’re about to be traded away to another team, that they wouldn’t resign wherever they landed because their first preference would be to come back? Maybe it’s all just a clever public relations effort on the part of Lester’s agent, but the pitcher doesn’t strike me as the kind of guy who’s going to read from a PR flack’s script. Which means that what he’s said before the season, during the season and after being traded might actually be true: he might really want to come back.

Which brings us to John Henry’s statement. Everyone seems to be assuming that if the Red Sox were unwilling to give him a hundred plus million dollars before the season, they’d be unwilling to do so after. In other words, they have a rule and that rule is never broken. What if, however, it’s more of a guideline than a rule. And what if one of the reasons they wanted to wait was to see if Lester got hurt or underperformed, or whether one of their minor league arms like De La Rosa or Webster took a big step forward? If that’s the case, then the variables in their equation have changed as Lester’s pitched brilliantly while the would be replacements have underwhelmed. And what if “The Monster” gets involved, as Lester’s PR importance and popularity increase his perceived value? And what if ownership looks at it not as Lester but Lester + Cespedes?

What if, what if, what if. That many in a row tells you everything you need to know about how likely it is that Lester returns. But the tea leaves say the chances aren’t zero, either, which in and of itself is remarkable.

Even if Lester were to miraculously return, however, Cherington has to replace Lackey as well. Which is why, even if the club is right and the pitching market is robust, he’ll have his work cut out for him.

In the meantime, I’ll sit back and see how he reassembles the pieces he’s acquired. Should be fun to watch.

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