Is Jacoby Ellsbury another Carl Crawford waiting to happen?

Kelley L Cox-USA TODAY Sports

If the Red Sox sign Ellsbury long-term, would they regret it like they did the Crawford contract?

With the Red Sox facing the Dodgers as the one-year anniversary of the Nick Punto trade looms, it's time to think about what that deal meant to Boston. The Red Sox were able to shed significant salary and long-term deals, and that allowed them flexibility that simply didn't exist in Ben Cherington's first off-season as the general manager. That's how they ended up with productive, short-term players like Mike Napoli, Shane Victorino, Stephen Drew, and Koji Uehara, and also how they were able to add Jake Peavy before this year's trade deadline when a need opened up in the rotation. It's a significant reason, if not the reason, that they're in first place in the East and leading the American League in wins.

It's also time to think about what the deal has yet to the mean for the Sox and the building of future squads. More specifically, if failures in the past mean the Red Sox should be avoiding long-term deals in the future, such as with impending free agent outfielder and all-star Jacoby Ellsbury. Even the idea of a long-term and expensive Ellsbury contract with the Red Sox has some fans reeling, as they simply can't handle risking another Carl Crawford. There are many, many reasons, though, why an Ellsbury deal wouldn't have to be that way.

Just because spending money didn't work with Adrian Gonzalez and Crawford -- and remember, it nearly worked in 2011 -- doesn't mean it's always a poor strategy. It's about what the money is spent on, and leaving yourself room to work once said spending is done. The problem in 2011 wasn't so much that Carl Crawford was hurt, though it certainly played a part: it was that the Red Sox didn't have the financial flexibility to do something about it, or to patch holes elsewhere, like in a rotation that couldn't even afford the duct tape needed to patch it back together.

20130731_kdl_sj7_211Photo credit: Greg M. Cooper-USA TODAY Sports

This was an issue again in the winter of 2011-2012, when the Red Sox had to deal Marco Scutaro to be able to have the financial wiggle room to sign Cody Ross, and made a series of trades to bolster their bullpen after Jonathan Papelbon left for more lucrative pastures. Ben Cherington inherited a situation where he had to have David Ortiz or Papelbon -- two significant contributors on the previous iteration of the Sox -- and couldn't have anything else unless he shifted bodies and money around to compensate. Things wouldn't get any easier until Gonzalez, Crawford, Josh Beckett, and Punto all became Dodgers and freed up more money than anyone has before.

So, why could Ellsbury work where others failed? For one, the Red Sox wouldn't be adding Ellsbury to a roster loaded with long-term deals. Dustin Pedroia is the only player on the team signed past 2015 with guaranteed money, and his average annual value -- the amount that will count against the luxury tax each year -- will be $13.75 million, or just $500,000 more than Ryan Dempster is making right now. The expectation is that Boston will be able to build a significant core over much of the rest of the decade thanks to their farm system, even with the assumed attrition and failure to develop that will inevitably arise for some of the crop. If, as hoped, three-fifths of the rotation in 2016 is occupied by the likes of Anthony Ranaudo, Matt Barnes, Henry Owens, Allen Webster, Rubby De La Rosa, Brian Johnson, or, if you're feeling ambitious, 2013 first-rounder Trey Ball, then that's essentially money that can be pocketed or invested elsewhere, because none of that bunch is going to command much in salary.

That's just the rotation, too: there are also position player prospects and young ones like Jackie Bradley Jr., Will Middlebrooks, Xander Bogaerts, as well as a few who are a little further out but should be around by the time frame we're discussing, like Blake Swihart and Christian Vazquez. There is suddenly going to be a ton of room to spend money, to the point where it's irresponsible to avoid contract discussions with Ellsbury this winter. A lot could happen between now and then, and many of these prospects could falter or be less productive than hoped, forcing the Sox to add players and therefore salary elsewhere, but there should be plenty of financial room for an Ellsbury deal even with that in mind. Hell, the fact that some of these prospects could fail is even more reason to try to secure the services of someone they know is productive.

169926454Jackie Bradley Jr. is a reason to keep Ellsbury, not a reason to let him walk. (Photo credit: Jim Rogash)

Let's think back to what part of the problem with Crawford was. He was expensive, at $142 million over seven years, and he didn't handle his failure well. Whether that's because of the media, the fans, injury, or Crawford almost doesn't matter: what does matter is that his failure was not handled well, and begot additional failure. It's hard to know just how a player is going to react to an environment that they aren't used to, and Crawford is the expensive reminder of this. Ellsbury, though, has been with the Red Sox since the beginning of his professional career. He's already worked back from major injury and disappointment -- twice. He's familiar with the environment, both in terms of fan and media expectations, and has been an integral part of successful Red Sox teams. This is a player the Red Sox know, and one that they are in a far better position to invest in long-term than they were or ever will be with someone like Crawford.

That's one of the reasons Dustin Pedroia has a long-term extension. They know him, they love him, and they want their players to emulate him. They want players to strive to be the next Pedroia, to work hard and embrace Boston and the team. Ellsbury has done his share of working hard, his share of winning, and owner John Henry has even mentioned him as a potential long-term fit despite the club's break from the ways of 2011. It's very likely for this major reason that separates Ellsbury from Crawford: the Sox know what they're getting.

Sure, Ellsbury could get hurt, as he has before. But the roster construction is different than it used to be. The aforementioned Jackie Bradley Jr. is around, and could switch from left field -- where offensive requirements are much lower than they used to be -- to center if Ellsbury is to get hurt. If Ellsbury starts to slow, and his defense slips, he could be swapped to a corner much like current Red Sox right fielder Shane Victorino has successfully been, with Bradley taking over in center. Unless both Bradley and Ellsbury are injured and out, there's a built-in, high-quality backup -- that means no Marlon Byrd, no Scott Podsednik, and no Darnell McDonald roaming center field. Remember, too, that, unlike the last couple of years, the Red Sox would theoretically have the resources available to them to make other compensatory moves on the roster, and it's a lot easier to find a new left fielder than it is a capable center fielder.

What could Ellsbury make? In part, because of deals like Crawford's, likely not as much as the current Dodger and former Sox. Ellsbury could sign a deal that's similar to Pedroia's while still pulling in a huge check each year that satisfies his agent, Scott Boras. Something like six years and $100 million, or seven years at $110 million, would pay Ellsbury significantly more per year than the $9 million he's currently making in his final year of arbitration, while also not overburdening the Red Sox financially either now or in the future. They might have to move around some money to make it fit right in 2014, but remember: they have six starting pitchers under contract, and one of the more expensive ones is likely to be in another uniform to start the season. That kind of deal is fair to Ellsbury, in a world where the inferior B.J. Upton pulls in five years at $75 million, and Michael Bourn has to settle for four years and $48 million. Remember, too, that the luxury tax is going to continually rise, changing both the percentage of what Ellsbury's contract takes up of the soft cap, as well as what the Red Sox have available to spend.

Losing Ellsbury would be no small thing, even with Jackie Bradley Jr. there to slot in. We're entering late-August, Ellsbury's bat didn't even awake until late-May, and he's still pacing the entire Red Sox club with more than five wins over replacement according to Baseball Reference. Banking on Bradley to replicate that out of the gate is unfair and unrealistic, and while they could find other productive uses for the money were they to let Ellsbury walk, if the price is right, it seems like we already know where it should be going.

Ellsbury has his risks, as does any player signing a long-term deal. The Red Sox have the money, the need, and the knowledge of Ellsbury to pull off a deal that satisfies both parties, though, and makes everyone happy. The same cannot be said for Crawford, and comparing the two just doesn't work in the way that many fear it does.

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