Are The Red Sox Being Too Conservative? The Value And Risk Of Long Deals

The first priority for the Red Sox this offseason, above winning in 2013, has been to avoid digging the team into new holes with long-term contracts that will stick with the team for years to come. In essence, to dodge the Crawford problem.

As a result, the Sox are running as fast as possible from the idea of the megadeal in general. That's why we haven't heard anything from them on Greinke, and it wasn't until Josh Hamilton's market seemed to shrink that they started to be seen as serious players. And for the most part we Sox fans have been relieved that this is the case.

But is there room for a little bit of bad?

The problem with the team in recent years hasn't been one thing. Carl Crawford, for instance, wasn't just bad as a long-term contract. He was an absolute disaster from day one. Even with Crawford's terribleness in 2011, it took a dramatic collapse by the pitching staff to spell the end to Boston's postseason hopes. Only in 2012, between the awful atmosphere that had sprung up around the collapse, a series of poor performances from typically reliable players, an unusually competitive American League (see: Orioles, Athletics), and a decent helping of injuries did the whole show really collapse, resulting in a terrible 69-93 record (helped along though it was by the Punto trade).

Really, the situation wouldn't have been so bad if it weren't for the fact that the Red Sox had also seen their farm system dry up. The Adrian Gonzalez trade sent out prospects for high-priced production, Lars busted, the 2009 draft was largely a flop, Jed Lowrie and Ryan Kalish couldn't stay healthy, and in the end Ben Cherington was left with such a small budget for 2012 that, in an attempt to get creative and meet high demands, he ened up shipping off the one guy who actually ended up producing last year.

Consider the 2007-2009 period which, aside from one short meltdown by the game's second best offense in the '09 ALDS, was a pretty great period. The Sox were paying Julio Lugo $9 million a year. Daisuke was getting the same, Jason Varitek was pulling in $10.5 million to hit .220/.313/.359 in 2008, J.D. Drew didn't pull his weight in 2007, nor did David Ortiz in 2009. Mike Lowell was in at $12.5 million to provide a mediocre 2008 season and an awful 2009 season.

Seriously, let's take the 2009 season by itself. For all that it ended with a disappointing postseason sweep by the Angels, the Sox won 95 games that year. That year the Red Sox got a total of 1.2 fWAR from David Ortiz, Mike Lowell, Julio Lugo, and Daisuke Matsuzaka. They paid those players a total of about $43 million, more than a third of the team's $122 million payroll for the season.

How did they do it? Simple:

Jason Bay - $7.75 million, 4.9 fWAR

Kevin Youkilis - $6.25 million, 5.9 fWAR

Dustin Pedroia - $1.75 million, 5.0 fWAR

Jon Lester - $1 million, 6.4 fWAR

Jacoby Ellsbury - $0.45 million, 2.4 fWAR

As much as it's a bad thing to bury a payroll under heavy contracts, it's also not realistic to completely avoid top-dollar deals. Ever since the game wizened up to things like OBP and defense, it's become increasingly difficult to find really good deals on the market. Sure, you can make a few smart moves, especially if you've got a home park that plays to extremes--a fly-ball pitcher in Petco, or a righty pull-hitter in Fenway, for instance. But you're not going to stumble upon guys that have always been really good but nobody noticed.

That leaves only a few routes to get top talent: pay top dollar, grow them yourself, or ship off top prospects. And no matter which path a team goes down, in the end they're going to need the farm system to produce. After all, if they're buying up top guys, they're going to need production from the rest of the roster at a cheap price. The only difference is that, in that scenario, a farm system producing decent role players might be enough.

These days the difficulty is increasingly going to be about finding the middle ground between buying the big guys and keeping the farm system rolling now that buying big players costs a draft pick. For the Red Sox, though, this may be the last year for them to make that big move on the open market without losing their first rounder.

Think about what the 2015 or 2016 roster might look like with the burden of a bad contract. If the youth movement works as we hope it does, and we've got a bunch of roster spots filled with average-or-better players under team control, how much will we really be lamenting the weight of, say, Anibal Sanchez if they were to sign him and have him decline rapidly?

As is, the Red Sox have some $40 million left to spend on their 2013 team even with the burden of John Lackey making $16 million sitting above the rest. Their youth movement from before has largely evaporated. If Will Middlebrooks is still on the minimum and Clay Buchholz is in the early stages of his long-term deal, Youkilis and Bay and their cheap contracts are no more, Lester and Pedroia are each making eight digits (though technically their CBT implications remain the same), and Ellsbury's arbitration deal will likely be pretty big as well. And because the farm system hasn't given them a new batch of youth players, this is just a questionable team that could be good if the Sox hit on some of their gambles.

But in 2015, what if we're slotting Jackie Bradley in for Shane Victorino? Xander Bogaerts, two of the Rubby De La Rosa/Matt Barnes/Allen Webster trio, one of Bryce Brentz, Garin Cecchini, and Jose Iglesias manage to contribute. We find one or two more guys in Boston's impressive depth, be it Brandon Workman providing a solid back-end workhorse arm, or one of the wavering pitchers in Drake Britton, Stolmy Pimentel, and Anthony Ranaudo managed to make something of themselves. Perhaps Deven Marrero has a good couple of years and the Sox swing him and some other mid-level guys for a solid player with 2-3 years of team control left.

Even if the Sox only add three guys to Will Middlebrooks over the next few years, that still leaves a ton of money to spend on just 21 roster spots, especially considering how many of those are dedicated to bullpen arms and bench bats. The Sox shouldn't be throwing money around with no real thought, and there's something to be said for the idea of saving up all their bullets for the years where they'll have the absolute best chance to win. But looking at 2013, they have some very definite needs, and there do appear to be players available who could fill those needs for the right price. Unless the free agency pool in 2015 and 2016 are going to be the best ever, the Sox might only be stockpiling money they'll never end up having a use for if they go too conservative over the next couple of months.