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Red Sox opportunity would appeal to Roy Oswalt

11.16.11 at 2:26 pm ET

MILWAUKEE — There have been instances when the idea of Roy Oswalt pitching in a Red Sox uniform was very real. On multiple occasions, the Sox have taken runs at the right-hander in the trade market, most notably in 2006, when the Sox believed they were close to acquiring Oswalt from the Astros at the trade deadline.

How close were they?

“Close,” said Oswalt’s agent, Bob Garber. “Very close.”

A deal never transpired in the trade market, but as the Red Sox look to address the back of their rotation, Oswalt does fit the profile of a pitcher who would represent an obvious target for Boston. And the Sox, given the fact that the opportunity to contend, would likewise be a team that would interest Oswalt, Garber said, despite the fact that it would require the career-long National Leaguer to jump to the junior circuit.

The 11-year veteran, whose resume includes three All-Star games and six top-six finishes in Cy Young balloting, has a career 159-93 record and 3.21 ERA. Until back injuries limited him to 23 starts in 2011, the right-hander had seven straight years of at least 30 starts, establishing himself as one of the most durable and effective pitchers in the game for the Astros and then, following a trade in the middle of the 2010 season, with the Phillies.

Now, in a free-agent class that is light on elite starting options, Oswalt will carry significant interest for a number of teams, likely including the Red Sox. After left-handers C.J. Wilson (another Garber client) and Mark Buehrle, Oswalt — based on track record — is likely the next best starter available, and the top right-hander this winter.

Moreover, whereas Wilson appears likely to secure a deal of at least five years and Buehrle reportedly could seek a four-year deal, Oswalt — coming off an injury season — would likely not be in line to seek such long-term commitments. That said, Garber noted, he will be seeking a multi-year commitment.

That might seem a bit of a question mark given that back issues limited Oswalt to 23 starts last year, during which he went 9-10 with a 3.69 ERA for the Phillies. Perhaps more notably, his fastball velocity dropped to a career-low average of 91.4 mph, and his strikeout rate likewise dipped to a career-low 6.0 per nine innings. It was a season that looked like that of a pitcher past his prime, and so it is unlikely that he will command the same sort of years — and, perhaps, the same sort of dollars — as Wilson and Buehrle.

That said, Oswalt had a strong finish to the season after he had a successful injection (after a previous unsuccessful injection) to allow him to pitch effectively over the last two months. He had a 3.59 ERA in his last 10 starts, and his strikeout rate ticked up to 6.8 per nine innings and his walk rate was a svelte 2.0 per nine innings.

While the Sox have already invested heavily in their rotation (thanks, in no small part, to the commitments to injured starters John Lackey and Daisuke Matsuzaka), if the Sox are confident in his health, Oswalt could represent a pitcher who would fit the profile of the sort of free agents whom the Sox will realistically target this winter.

‘€œThere’€™s guys that are coming off injuries. There’€™s guys that are coming off bad performance. There’€™s guys that are getting unlucky, or whatever,’€ said Sox GM Ben Cherington. ‘€œThere’€™s pitching out there, not an abundance of impact free-agent starters.’€

A couple years ago, the Sox invested in multiple veteran buy-low options coming off of injuries, signing Brad Penny and John Smoltz to one-year deals. Both returned to health, but nonetheless flopped in Boston; both, ultimately, were released before the end of the year, finishing the season with other clubs.

That said, the idea of minimizing risk while getting a pitcher who potentially could have a significant impact could take the Sox to pitchers like Oswalt. The right-hander is expected to see how the market for his services takes shape once Wilson and Buehrle sign. At that time, the degree to which the Sox are interested in making yet another at Oswalt — this time, as a free agent — will become clearer.

Read More: bob garber, C.J. Wilson, mark buehrle, Roy Oswalt
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