Tony Massarotti

After Flurry of Moves, Questions Abound for the Red Sox


At least give the Red Sox credit for this much: they were ready to move. If and when the Red Sox lost out on Jon Lester, the Red Sox were positioned to execute a series of alternatives, whether you love the moves or hate them.

Within roughly 36 hours of learning that Lester would be accepting a six-year, $155 million offer from the Chicago Cubs, the Red Sox completed trades for left-hander Wade Miley and right-hander Rick Porcello, then signed righty Justin Masterson to a one-year contract. Boston certainly seems to have cornered the market on No. 3 starters, and the flurry of pitching moves leads to a series of important question about the 2015 Red Sox, starting with the most obvious:

1. Are they done maneuvering?

With the bigger stuff, the answer is probably yes.

But let’s hope not.

With the trades, Boston’s rotation consists of, in no particular order, Clay Buchholz, Rick Porcello, Wade Miley, Justin Masterson and Joe Kelly. All are groundball pitchers. All but Miley are right-handed. Red Sox general manager Ben Cherington suggested the Sox already have a “strong” rotation with this group, but we all know the Sox lack a true front-end starter.

In what has become an offensively-challenged game post-steroids, can the Sox compete with this group in the watered-down American League East? Sure. But a true championship contender would likely require them to have at least one starter in the rotation far closer to elite. Maybe one will emerge from the group mentioned above or from the minor-league system – Henry Owens? – but everybody would feel much better with something far more certain.

A couple of things to note: First, estimating the cost for arbitration, the Sox’ payroll commitments currently rest at $180-$185 million. The luxury tax threshold is at $189 million. Owner John Henry already has indicated that the Sox are willing to eclipse the $189 million barrier, but it’s hard to imagine the Sox going much beyond, say, $200 million. Ideally, they also need the financial room to add players during the season.

Second, while Masterson cannot be included in any deal until after June 15 – rules require free agents to remain with their new teams until then – either Miley or Porcello could be dealt at any time. Cherington noted that, in his mind, the Sox were “early” in the offseason and that the club would be open to “what comes to us.” Given that Miley, in particular, is not eligible for free agency until after the 2017 season, he could be an appealing option for a team like the Washington Nationals, who thus far have been unable to sign Jordan Zimmerman to a new deal beyond 2015.

Zimmerman, who is 45-22 with a 2.96 ERA over the last three seasons, is a front-end starter the Sox lack. Might the Sox be willing to give him – or someone like him – much of the money they were willing to give Lester in what effectively amounts to a trade-and-sign? It’s worth considering.

2. Should Justin Masterson really be a starter?

According to reports, Masterson’s deal will pay him a base salary of $9.5 million with incentives of $500,000 each for 185, 190, 195, 200 and 205 innings. If Masterson ends up in the rotation and makes his turns, that would make him a $12 million pitcher, which places him in the middle of the rotation.

Presumably, Masterson’s incentives are there for health reasons. But what if they’re not? Masterson has had dominating stints as a reliever during his big league career and he might be most valuable and effective as a multiple-inning reliever in the middle of the game. An annual salary of $9.5 million is in line with what the New York Yankees just paid Andrew Miller, who, while left-handed, will almost certainly be used exclusively as a reliever.

Here’s the point: with the Sox possessing a mediocre rotation – with or without Masterson – he may be far more valuable and effective in a bullpen that still needs to be bolstered. As a reliever, Masterson has a career 3.01 ERA with a 3.14 strikeout-to-walk ratio, 8.8 strikeouts per nine innings pitched and a batting average against of .225 (with a .626 OPS). As a starter, those numbers worsen to 4.35, 1.95, 7.4 and .260 (.719).

Translation: Masterson is a mediocre starter, even when durable. He has the chance to be a dominating reliever who could give manager John Farrell 100+ innings out of the bullpen, which could be enormously valuable.

In fact, even if the Sox don’t make a deal for a front-end starter, they might be better off giving one of the rotation spots to a youngster – Anthony Ranaudo, Owens, etc. – and adding Masterson to their relief corps.

One final thing: part of the reason Masterson would be better in the bullpen is because he gets mauled by left-handed batters. Last season, lefties batted .320 against him with a .914 OPS. Given that Masterson will be 30 in the spring, it’s hard to imagine that he will suddenly develop a changeup or cut fastball to augment the sinker and slider that make him so dominating against right-handed batters. (He also has something close to a sidearm delivery.) Putting him in the bullpen would allow Farrell to more carefully pick spots.

3. Is the lineup really as good as we think it is?

With the game having gone back to the pitchers, it’s easy to understand how the Red Sox have been thinking this offseason. In the absence of Lester, they have decided to spend the bulk of their money on offense – Pablo Sandoval ($95 million) and Hanley Ramirez ($88 million) – while spending mid-level dollars on the rotation. Maybe that’s smart. Maybe it isn’t. Time will certainly tell.

At the moment, depending on your opinion, the Sox’ lineup likely looks something like this:

Mookie Betts, RF
Dustin Pedroia, 2B
David Ortiz, DH
Hanley Ramirez, LF
Pablo Sandoval, 3B
Mike Napoli, 1B
Xander Bogaerts, SS
Ramon Vazquez, C
Rusney Castillo, CF

Obviously, there is some room to maneuver here. This lineup assumes that Betts will play over Shane Victorino. And while Vazquez would likely hit ninth, it might make more sense to have the speedier Castillo in front of Betts. Whatever the case, the Sox lineup is heavy on right-handed batters – in this regard, Ramirez’ ability to hit right-handed pitching makes him a better fit than Yoenis Cespedes – and still poses some questions.

Do we know for certain that Betts can play? What about Bogaerts? Vazquez? Castillo? The core of the lineup seems strong, which is something the Sox lacked last season. But there are still questions at the top and bottom with young and/or unproven players who have no real track record of success in the big leagues. The development of those players – particularly Bogaerts and Betts – remains of utmost important for the longer-term success of the team.

4. Is Xander Bogaerts a good fit for this roster?

After his promising showing at the end of the 2013 championship season, Bogaerts – along with Will Middlebrooks and Jackie Bradley, for that matter – was counted on for some level of production and growth in 2014. All of them subsequently struggled. In retrospect, the inability to really develop any of those players was the greatest failing of 2014 because the future of the franchise remained, at best, at a standstill.

For the moment, let’s stay focused on Bogaerts, whom the Sox have seemingly resisted including in a trade for a front-end starter based largely on his potential as a hitter. Defensively, there always have been questions. Now the Sox have assembled a starting rotation of groundball pitchers, which seems to place an emphasis on infield defense. And yet, at the most important defensive infield position, they have a player whom many regard to be, well, unorthodox.

That doesn’t seem to make a whole lot of sense, does it?

Last year, the Sox started Bogaerts at shortstop. For whatever reason, they then panicked following his early-season struggles, re-signed Stephen Drew and bumped Bogaerts to third. Then they dealt Drew and moved Bogaerts back. Given all of the question surrounding Bogaerts’ ultimate landing spot when the player was in the minors, this type of reactionary behavior was downright short-sighted and stupid.

Defensively, Bogaerts probably lost something close to a full year of development. It was bad enough that he struggled. But the Sox also messed with his head.

With their kind of pitching staff, the Sox really should have a gifted defensive shortstop. Assuming Bogaerts plays there, they don’t (and won’t). Bogaerts’ defense is a potential weak spot and bears watching. If he can’t play the position well enough – and that doesn’t have to be at a Gold Glove level – it could undermine much of what the Sox are trying to do.

5. Why is Allen Craig still here?

A career .306 hitter prior to last season, Craig was a train wreck with the Red Sox. In 29 games, he had 12 hits and 36 strikeouts in 94 at-bats, batting .128. Between Boston and St. Louis, he hit .215 for the season. Craig forged a reputation as something close to an everyday player with St. Louis in 2012-13, and he is signed for the next three seasons at salaries of $5.5 million, $9 million and $11 million.

For luxury tax purposes Craig counts only $6.2 million against a team’s payroll. But in actual cash outlay, the number over the next three years is $8.5 million per year, which makes trading Craig a little more complicated.

Generally speaking, Craig seemingly falls into the same class as someone like Kendrys Morales or Billy Butler, who just signed respective deals for $8.5 million annually and $10 million annually with the Kansas City Royals and Oakland A’s. He can play some first base. He can certainly serve as a designated hitter in the right market. The Red Sox may have to eat some money, but they can likely include Craig in a deal for pitching, be it in tandem with something else (for a starter) or straight up (for a reliever).

Again, remember that the Sox are at about $180-$185 million in committed payroll already. Depending on whether the Sox have to eat money, Craig could save them up to $6.2 million on their luxury tax payroll. Given the presence of Daniel Nava and Brock Holt, among others, Craig doesn’t seem to fit on a roster stacked with right-handed hitters.

Given his poor performance last year, Craig might not be a candidate for trade until spring training – if and when another team suffers an injury. Certainly, his situation bears watching. At the very least, his presence gives the Sox the ability to tweak their roster – from the starting rotation to the bullpen – and fortifies the notion that the last two days were not the end of the Red Sox offseason.

It might have been the beginning.

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