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Ryan Dempster For Two Years Means Pressure Is On The Prospects For 2015

Boston's current rotation means the organization is betting heavy on the future for their future


The Red Sox now have five starters set for the 2013 rotation with the signing of Ryan Dempster, as well as depth for the foreseeable future in the bullpen and at Pawtucket. Dempster signed for just two seasons, but a three-year deal for a free agent pitcher could have been justified fairly easily. After all, the rotation of the Red Sox is going to be far different heading into 2015 than it is today, and things aren't guaranteed to be anywhere near as packed.

These are the assumed rotations for the next three seasons, without any kind of trade or promotion: it's who is locked in, at present, over this time frame:

2013 Contract 2014 Contract 2015 Contract
Jon Lester $11.6M Jon Lester $13M opt. Clay Buchholz $12.3M
Clay Buchholz $5.8M Clay Buchholz $8M Felix Doubront Arb. Year 1
Ryan Dempster $13.3M Ryan Dempster $13.3M

John Lackey $16M John Lackey $16M

Felix Doubront Pre-Arb Felix Doubront Pre-Arb

Easy enough in 2013, and in 2014, Jon Lester's affordable option is likely to be picked up even if he's just average in this upcoming campaign. After that, though, things clear out a bit. Lester is a free agent, Dempster's new contract has ended, and unless Lackey's league-minimum option for 2015 is picked up, all that's there is Buchholz and Doubront.

Lackey's option might be picked up -- roughly $500,000, even if he's basically a little below-average at that stage, is a huge bargain. But that all depends on whether his elbow injury that resulted in Tommy John surgery fits the language specified in his contract. Until the Red Sox actually pick up the option, it's hard to tell if that's the case, as there has been no confirmation of such by either party at this stage. For the sake of clarity, let's assume he's not involved, but the ideas past this point still have merit even if the option is put into play. Likewise, Lester could be re-signed, but if he rebounds, the cost could be prohibitive -- again, for simplicity, he's not available.

One thing that's becoming apparent about free agency is that the very best pitchers don't often make it that far. Cole Hamels signed an extension before he could become a free agent, Jered Weaver was taken off the market before he ever got there -- signing your homegrown aces is becoming the thing to do, especially with money flowing throughout much of the game. That's why it's hard to rely on game-changing pitchers like Justin Verlander, Felix Hernandez, and Clayton Kershaw -- all free agents after the 2014 season -- to be available by the time their contracts are, as of now, set to end.

All three come from markets large enough to support a lucrative extension, and even if they didn't, the Red Sox have never been big on overly long-term contracts for starters. It's likely, going forward, they're going to be more comfortable with the two-, three-, and four-year deals out there, rather than diving into five and beyond, as all of those pitchers listed are near-guaranteed to pull in, whether they sign now or for 2015. Risk is reduced, flexibility remains, and the chances of stumbling into another Lackey contract or Josh Beckett extension are reduced.

All of this is a long way of saying that the Red Sox are going to have to lean heavily on developing their own starting pitching from within in order to successfully build a rotation from year-to-year. The reason Lester and Buchholz are at such bargain prices for Boston, now and going forward, is because they came up through the system, and the Red Sox were able to promise them more money than they had ever seen, years before they were set to hit free agency. Sometimes, you can get burned that way, but the dollar amounts are far lower than those that are paid on the market. Dan Haren, who struggled with injuries and was overall unimpressive in 2012, was just paid $13 million by the Nationals -- the same amount Lester, who at the time was looking like a future ace, agreed to for his 2014 salary, the largest on his extension. And that amount wasn't even guaranteed to him.

The Red Sox have pitching depth in the minors now, as well as the hope that Doubront develops into a mid-rotation starter that they can similarly lock-up at prices that look like bargains compared to what that kind of arm costs on the open market. Matt Barnes, Rubby De La Rosa, Allen Webster, and Doubront are all considered in Boston's top-10 most-talented players under 25 years old -- all in the top eight, even -- but prospects are about potential, so at best, this group is penciled lightly into the 2015 rotation.

Boston could hit on all four of these pitchers, with Doubront emerging as a strong four or a three, and Barnes, De La Rosa, and Webster all landing as mid-rotation guys, or maybe even number two starters. They could also see Doubront fail to ever be efficient enough to be more than a five, Barnes fail to use his curve and change enough -- or effectively enough -- to be more than a four with an elite fastball, and one or both of De La Rosa and Webster ending up in the bullpen thanks to command issues that keep them from starting effectively. That's a huge range of possibilities, with the extremes in consideration as well as middle-of-the-road scenarios, where Boston ends up with a pair of productive starters as well as some useful relief options.

There are more pitchers behind this group, but those have the highest ceiling. Brandon Workman and Chris Hernandez are still at the stage where they are possibly more likely to not work out than they are to be big-league starters. The same goes for Drake Britton, Stolmy Pimentel, Anthony Ranaudo, and all the way down the line. There's a very good chance the Red Sox end up with enough productive, cost-controlled arms to fill out the 2015 rotation, but it's not a guarantee by a long shot.

With all of these holes in the 2015 rotation right now, though, it's clear Boston's emphasis is on attempting to get back into that process of developing from within, and signing that homegrown pitching to what are relatively inexpensive, but long-term, deals. They aren't wrong for doing so, either, as the collection of pitching talent they have assembled, especially post-Nick Punto trade, is impressive and deep. It's a risk, though, just like with anything else, but with the free agent market for starting pitching in flux, it might be the path of least resistance to success.