Boston Red Sox's Guide to the 2014-2015 Free-Agent Pitching Market

The Boston Red Sox need to acquire starting pitching help this offseason if they want to compete in 2015, and they need to acquire a lot of it.

Fortunately, according to WEEI.com’s Alex Speier, the Red Sox should have around $52 million to spend this winter and spring, should they so desire. They may need to allocate some resources to third base and the bullpen, but most of that money should go toward fixing up their rotation.

On Tuesday, we took a look at five potential trade candidates for the Red Sox to pursue in order to improve their rotation. Here, we’ll look at five free-agent additions the Sox could chase in an attempt to compete again in 2015.

There are a few notable omissions here. For one, it’s tough to see the Red Sox pursuing Max Scherzer after neglecting to sign Jon Lester to an extension, so he’s not listed. We’re also omitting players like Edinson Volquez and Francisco Liriano, because the role of staff enigma already goes to Clay Buchholz.

The Sox are also likely to take a gamble on one lower-tier arm, like a Gavin Floyd, Wandy Rodriguez or Aaron Harang. But for now, let’s focus on legitimate, middle- or top-of-the-rotation starters whom  Boston can acquire in the coming months.

5. Ervin Santana, RHP

Todd Kirkland/Associated Press

At this time last year, Santana looked primed for a massive contract. The then-30-year-old pitcher was coming off the second-best season of his career, and as Fox Sports’ Ken Rosenthal and others reported, he was looking for a five-year, $100 million contract.

Unfortunately, Santana’s market was depressed by the compensation pick attached to his name. And after a less impressive season (at least by ERA) with the Braves in 2014, his asking price figures to be a little more modest this time around.

Santana has had a fairly turbulent career, reaching a peak of 6.0 fWAR in 2008 and hitting a low of minus-1.1 fWAR in 2012, according to FanGraphs. He’s been all over the place in between those two numbers in every other season, settling in as a little worse than a three-WAR pitcher over the past two years.

He’s an attractive option for the Red Sox because he’s reliably made at least 30 starts every year since 2009, and he’s solved some of the walk issues that plagued him early in his career. He’s also capable of bouts of dominance.

The Sox will want to be a little leery, though, as his fly-ball profile doesn’t fit well with Fenway Park and he’s likely to require at least a three-year investment. Still, Boston could do worse than to anchor the middle of its rotation with Santana, even if he doesn’t project as a value play.

4. Justin Masterson, RHP

H. Rumph Jr/Associated Press

Masterson likely cost himself a good chunk of money with his lackluster 2014 season. The 29-year-old put in the worst full season of his career, allowing a 5.88 ERA in 128.2 innings with the Cleveland Indians and St. Louis Cardinals.

Part of Masterson’s struggles likely stemmed from a knee injury that he missed time with and seemed to battle all year long. But the right-hander also walked far too many batters (69) and saw a marked decline in velocity, and those aren’t terms you want attached to your name when heading into free agency.

It’s tough to predict the type of contract Masterson will get thanks to his poor 2014 season. On the one hand, he could still be in line for a two- or even three-year deal, given his overall track record. On the other, he might want to head to a pitcher-friendly ballpark on a one-year deal and try to re-establish some value.

Either way, expect the Red Sox to show some interest in their former prospect. Masterson isn’t a top-of-the-rotation arm, but he can ably fit as a No. 3 starter, and he’s still likely to be death on right-handed hitters.

He’s the sort of moderate-risk, high-reward pitcher who’d make a great complement to the signing of a bona fide ace. Given his familiarity with John Farrell, this is a move that would make plenty of sense.

3. Brandon McCarthy, RHP

Patrick Semansky/Associated Press

McCarthy figures to be one of the more heavily sought-after mid-tier arms on the market this offseason. The 31-year-old right-hander finally threw more than 200 innings in 2014, and while his 4.05 ERA doesn’t look particularly enticing, his FIP was down at 3.55, according to FanGraphs, and he was much better as a Yankee than he was as a Diamondback.

There are plenty of risks associated with McCarthy, to be sure. For one, he’s had trouble staying on the mound, and while some of his injuries have stemmed from freak accidents, some have come as a result of arm trouble, too. McCarthy is also fairly homer-prone, and while Chase Field and Yankee Stadium are two extreme homer-friendly ballparks, Fenway isn’t exactly a pitcher’s haven, either.

But McCarthy has the potential to serve as a terrific No. 3 starter, and his floor is probably as a low No. 4. He doesn’t figure to command a huge contract, given his spotty track record of success, and he showed an impressive ability to induce ground balls at a more frequent clip in 2014.

Because there won’t be any draft-pick compensation attached to his name, it’s entirely possible that the bidding for McCarthy gets a little silly. But if he can be acquired at a reasonable price, he’s a worthy gamble for Boston.

2. James Shields, RHP

David J. Phillip/Associated Press

Yes, the “Big Game” nickname is becoming a bit ironic. And yes, Shields has struggled this postseason. But don’t let recency bias or a small sample size delude you into thinking Shields isn’t a very good pitcher.

Shields has thrown at least 200 innings every year since 2007 and has produced at least 3.5 fWAR during every one of those campaigns save one, according to FanGraphs. He doesn’t walk a lot of people, induces a healthy amount of ground balls and isn’t particularly prone to giving up the long ball. Yes, he’s 32, but Shields has been the model of stability during his career.

There are real reasons not to want to give a pitcher his age a five-year contract, and that’s probably what Shields is looking at after dominating in Kansas City over the past two years. And it’s true that Shields isn’t quite as good as the other two premier options on the market, Jon Lester and Max Scherzer.

While you can prefer that the Red Sox take another route, you can’t deny that Shields would make them a much better team. The Kansas City Star’s Andy McCullough recently reported that Red Sox are the favorites to land Shields this offseason, so expect to hear plenty more rumors as the offseason progresses.

1. Jon Lester, LHP

Charlie Riedel/Associated Press

At this point, the situation with Lester and the Red Sox needs no further rehashing. It’s clear that he’s the best or second-best arm on the market, in competition with Max Scherzer, and it’s clear that the Red Sox have the financial resources to secure Lester’s services for a long time, if they choose to do so.

As Rob Bradford of WEEI.com reported in September, though, the Red Sox don’t intend on signing two high-profile pitchers. That means their choice likely boils down to Lester or Shields, and while Lester is clearly the better pitcher, he might not be so much better that the Sox can justify doling out an additional $50-plus million and two contract years.

Earlier this offseason, we broke down the various advantages and disadvantages to signing Lester or Shields, and despite the more significant cost, Lester still came out on top. Re-signing him gives the Red Sox a legitimate top-of-the-rotation arm who we know can succeed in Fenway Park, and acquiring Lester for his age-31 and age-32 seasons is an enticing proposition.

For those reasons and many more, Lester should be the Red Sox’s No. 1 free-agent target this offseason. Pairing him with a player like McCarthy, Masterson or Santana, or an arm acquired via trade, would go a long way toward rebuilding a rotation that also figures to feature Buchholz and Joe Kelly. Lester could give the Sox a chance to legitimately compete once more in 2015.