Phillies starter Cole Hamels

Despite additions, Red Sox starting rotation still needs an ace

How important is an ace at the top of a starting rotation for a playoff hopeful or contender? The Boston Red Sox could provide some intriguing answers to that question next season.

The first impulse is to believe that even the Red Sox believe in the importance of an unquestioned No. 1 starter, based on their attempt to re-sign Jon Lester before the left-hander opted to join the Cubs last week. But even that conviction only extended so far, as Boston offered Lester $20 million less than the $155 million that persuaded Lester to move himself to Wrigleyville. Going to a seventh year for a pitcher who will be 31 by the time he reports to spring training was not an option for the Red Sox front office.

But even if general manager Ben Cherington had won the Lester auction, he still would have had at least two spots to fill in the Red Sox rotation with Clay Buchholz and Joe Kelly the only other proven MLB starters on the roster. Calling Kelly a “proven” starter is probably a stretch too, with 48 starts in three seasons on his résumé.

The Red Sox didn’t take long to dwell on losing Lester to the Cubs, however.

One day later, the team acquired Wade Miley from the Diamondbacks in exchange for Rubby De La Rosa and Allen Webster, two prospects who were highly regarded as part of the blockbuster trade that sent Adrian Gonzalez, Carl Crawford and Josh Beckett to the Dodgers in 2012. But neither pitcher followed through on their promise and had fallen off the radar as future Boston stars.

While the 28-year-old left-hander isn’t on Lester’s level, he is a more-than-reliable MLB starter who’s averaged 200 innings over his past three seasons and pitched successfully at Chase Field, one of the most hitter-friendly parks in the majors. That might mitigate some concerns about Miley moving from the NL to the AL.

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Cherington quickly followed up the Miley trade with another deal for starting pitching, peddling Yoenis Cespedes (along with two prospects) to the Tigers for Rick Porcello. Again, Porcello isn’t a No. 1-caliber starter, but soon to be 26 years old, he has plenty of upside and untapped potential that was never fully mined in Detroit. (I’d argue that’s because the Tigers rushed him to the majors at age 20, preventing him from developing a full repertoire in the minors.) The right-hander also has an impressive amount of MLB experience for someone so young, and pitched those innings for a perennial contender.

Both pitchers don’t depend on strikeouts and should benefit from a better defense behind them in Boston. That’s what the Red Sox are banking on, along with their durability.

Staying healthy was an issue for the third starter Boston added last week, signing their former 2006 draft pick Justin Masterson as a free agent. Last season, Masterson was limited to 128.1 innings and 25 starts due to knee, shoulder and oblique injuries in what was a nightmarish season, especially with free agency looming. The right-hander compiled a 5.88 ERA, averaging more than a hit allowed per inning, between the Indians and Cardinals. After he was traded to St. Louis, Masterson quickly rendered himself a non-factor, allowing 24 runs and 35 hits in 30.2 innings and was left off the postseason roster.

Yet several MLB teams saw an opportunity to sign a former top starter to an inexpensive, one-year deal, betting that Masterson would be motivated to bounce back next season and increase his value for another run at free agency a year from now. If you’re of the belief that there’s no such thing as a bad one-year contract, the $9.5 million deal Masterson inked with the Red Sox certainly looks like a savvy, low-risk investment. There is plenty of opportunity for a good return too, as he might be the closest thing to an ace among the three starters Boston added.

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One of the questions about Masterson is whether or not he’s truly a No. 1 starter. Only once among the seasons in which he’s made 25 or more starts has he finished with an ERA below 3.50. And if you’re one of the few who still judges starting pitchers by their win totals, consider that Masterson has never won more than 14 games in a season, and that was for the 2013 Indians who posted 92 victories and earned the AL’s second wild-card bid.


For what it’s worth, Masterson was perceived as Cleveland’s No. 1 starter during his six seasons with the Tribe. If the Red Sox rotation is set, he could arguably be comfortable with that role and the responsibility as staff leader that comes with it. Obviously, Masterson won’t be the ace if he can’t stay healthy, but neither he nor the Red Sox are viewing another injury-riddled season as a possibility.

Can Boston compete in the AL East and wild-card races with the current rotation it’s assembled? Masterson, Buchholz and Kelly can’t be viewed as sure things. Besides, how many teams make it through a 162-game season rotating just five starting pitchers. Prospects Henry Owens, Eduardo Rodriguez and Matt Barnes will surely factor in at various points next year, one reason why De La Rosa and Webster were deemed expendable. So the Red Sox have starting pitching depth, something that could also make the bullpen deeper as the season progresses.

But doesn’t this pitching staff still need that No. 1 guy? Again, if the Red Sox didn’t think so, would they have made such a hard run at Lester? Perhaps this would be an even greater concern if no other options were available.

However, Boston has been one of the teams linked in trade rumors with Cole Hamels for months. Even with the prospects Cherington included in the deals for Miley and Porcello, he has the resources to make an attractive offer to the Phillies. Hamels also carries a four-year commitment, something more in line with the Red Sox philosophy for pitchers over 30 years old. (The left-hander is set to be paid $96 million, unless his $20 million club option for 2019 is picked up. Even then, it would be less than what Lester would have cost financially.)

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Since the Red Sox have shown a willingness to take pitchers one year from free agency, Johnny Cueto, Jordan Zimmermann and Ian Kennedy could also be possibilities. But the Reds, Nationals and Padres are presumably eyeing contention next season and probably aren’t willing to part with top pitchers unless Cherington presents an offer that can’t be refused.

James Shields is another possibility, one who would just cost the Red Sox money instead of top prospects. Boston might once again find itself battling with the Giants for a free agent starting pitcher. He could fill the ace role nicely for the Red Sox. But Shields will be 33 by next spring and isn’t in the same position to demand the same sort of mega-deal that Lester pursued.

Is waiting a year any kind of possibility with the investments that this team has made this season? Pablo Sandoval and Hanley Ramirez were signed with the intentions of getting back to the postseason next year. The same obviously applies to the acquisitions of Miley, Porcello and Masterson. But what if the Red Sox tried to see how next season worked out with a rotation of third and fourth starters, combined with top prospects? If and when that didn’t work out, take a run at next year’s crop of free agent starters, which promises to be even better than this year’s class with David Price, Zack Greinke, Jeff Samardzija, Cueto and Zimmermann and on the top shelf?

If the Red Sox strike out on getting that No. 1 starter before spring training — or even at next season’s trade deadline — that might provide a big hint as to which way the team is leaning. There’s still far too much time remaining in this offseason, with too many top starting pitchers available, to jump to such a conclusion, however.

About Ian Casselberry

Ian is a writer, editor, and podcaster. You can find his work at Awful Announcing and The Comeback. He's written for Sports Illustrated, Yahoo Sports, MLive, Bleacher Report, and SB Nation.