Ranking the best free agent pitching targets

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5. Justin Masterson

Aug 3, 2014; St. Louis, MO, USA; St. Louis Cardinals starting pitcher

Justin Masterson

(63) talks with starting pitcher

John Lackey

(41) during the seventh inning against the Milwaukee Brewers at Busch Stadium. The Cardinals defeated the Brewers 3-2. Mandatory Credit: Jeff Curry-USA TODAY Sports

Masterson, who started his career in Boston before being traded to the Indians in the Victor Martinez deal, has experienced quite the up-and-down career. As of late, the still young (29) right hander has struggled far more than he has prospered.  His best season to date came in 2011, when the then-25 year old Masterson took the American League by surprise, racking up 14o Ks, a 3.21 ERA, 1.28 WHIP and 3.6 WAR along with his first career shutout.

Unfortunately for the former Indians ace, he was never able to replicate or improve on those numbers, and in two of the three seasons since then he finished with an ERA well above 4.50 (4.93 in 2012, and a downright hideous 5.97 in 2014). He was dumped by the Indians at this year’s trade deadline, as his struggles had reached the point where the former ace was doing far more harm than good. The Cardinals took a flyer on him and, as has been the case with Allen Craig here, it has not exactly panned out. He stunningly put up worse numbers in the National League, and there are serious questions as to whether he will ever be the same pitcher if he couldn’t find a rhythm outside of the hitter-friendly American League.

But as is the case with Clay Buchholz, Masterson is talented and may be worth one more chance. Masterson never achieved the level of success Buchholz did, but beyond that there are few reasons not to give him the same benefit of the doubt. Rob Bradford of WEEI reported that the team only plans on targeting one top-tier free agent pitcher this offseason, but Masterson’s value has plummeted to the point where he will be signed to a low risk, prove-it deal. With his age, his familiarity with Fenway and his talent (however inconsistent) Masterson makes a lot of sense for the Red Sox this offseason. The two pitchers behind him have put up much better numbers, but Masterson seems far likelier than either of them.