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Should the Red Sox Consider Signing Roy Oswalt?

(Photo Courtesy of Greg Fiume/Getty Images)

With the Red Sox looking to fill 40% of their starting rotation, names such as Jeff Francis, Bruce Chen, and Erik Bedard are being thrown around. If those guys doen’t sound particularly appealing to you, then you’re not alone. Short of CJ Wilson, the general consensus seems to be that the free agent market for starting pitching is weak.

But what if a pitcher with three All-Star appearances, two 20-win seasons, and a career ERA of 3.21 was available? It just so happens that free agent Roy Oswalt fits that criteria perfectly! If Boston is intelligent serious about fixing their rotation, Oswalt is the man to sign.

The Pros

You don’t need to be a stat geek to see that Oswalt has good stuff. The former Houston ace has a decade of elite seasons to back that up. His 159 career wins are the 11th most among active players and his career ERA (3.21) is 4th best. If he hadn’t been playing in the pit that is the Houston Astros for the majority of his career, Oswalt would have more wins, national recognition, and that much more respect. Additionally, he’s pitched in the World Series and just recently was a member of the Philadelphia super staff. Simply put, the guy knows what it takes to win and has the numbers to support it.

Additionally, on a team where behavior is a concern (Yes, I’m referring to the Boston Red Sox and not a 4th grade little league team), Oswalt has the reputation of being a consummate professional. On a team of beer drinking thugs, his leadership alone would be a great addition. Furthermore, his agent, Bob Garber, is on record saying that Oswalt has already made his money and is looking to finally win a ring. Who doesn’t want a respected and talented veteran looking to win a championship?

And of course, the Yankees are presumably interested in Oswalt as well. Nothing is more satisfying than snatching away one New York’s targets.

The Cons

While statistics are a fantastic way to analyze the past, they don’t always shed clear light onto the future. Oswalt is 34 and he spent time on the disabled list last season. Do the Red Sox really need an extra injury riddled player? 34 isn’t exactly 25 either, so Boston probably doesn’t want to dish out a huge contract to another aging veteran.

Before he was traded to the Phillies, I was always under the impression that Oswalt was a Southern/Midwest kind of guy and wasn’t fond of big, obnoxious East Coast markets. He did waive his no trade clause to go to Philadelphia, however, so he obviously will play for a team that puts him in a position to compete for a World Series. Despite their gaping holes, the Red Sox still meet those requirements.


Boston should absolutely pursue Oswalt as long as the price tag isn’t unreasonable. A two-year deal for around $12 MM a year would be fair for a starting pitcher of his caliber. I’d even tack on a third year option, but only because I’m a sucker for past performances. A hypothetical third year of rebuilding is unacceptable for the Red Sox, and the Red Sox can afford to spend the money. Oswalt is the perfect win-now move to get fans excited and prove themselves to not be reputation-smearing cheapskates.

Of course, the Red Sox can not depend on just a Roy Oswalt to fix their rotation. The only things that are certain in life are death, taxes, and overpaid baseball players being put on the 15-day disabled list from time to time. Oswalt should be the best of several starting pitchers the Red Sox sign to strengthen the rotation and look to compete in 2012.

About Josh Segal

Josh Segal is a professional shock artist and trash talker. He also occasionally writes opinion pieces about the Red Sox, Patriots, Celtics, and their respective leagues at large. Segal is currently a junior at Kenyon College where he plans to double major in drama and political science. Apparently he also writes his own biographies in the third person.

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One comment for “Should the Red Sox Consider Signing Roy Oswalt?”

  1. Don’t trust anybody from the national league to be able to put up the same numbers in the AL. He might not be as bad as Smoltz and Penny etc but Oswalt would most likely be league avarege and expensive.

    Posted by Martin | November 18, 2011, 12:43 am

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