It seems odd to think of the Pirates as players in any trade situation, however, they are currently tied with the Cincinnati Reds atop the National League Central division.
It would certainly behoove the Red Sox to have serious conversations with the Bucs, as they have significant pitching depth at the major and minor league levels that could benefit the Red Sox tremendously.
It is safe to assume that the Sox would stay away from Eric Bedard and A.J. Burnett.
Other than those two names, the Pirates could offer the services of right-hand pitcher James McDonald, who sits on a 5-2 record with a 2.39 ERA in 2012.
McDonald is just 27 years old and is a product of the Los Angeles Dodgers organization. He is 23-23 lifetime with a 3.72 ERA. His ERA is skewed from a four-game stretch in 2010 while in Los Angeles where he posted an 8.23 ERA before being traded to the Pirates.
His sample size against American League batters (3.26 ERA) is limited, as he has only played in five interleague games in his career.
Should the Pirates decide that they would like to retain McDonald, they have plenty of solid arms in their farm system to entice the Red Sox.
Heading in to the 2012 season, Baseball America had right-hand pitcher's Gerrit Cole and Jameson Taillon as the top two overall prospects in the Pirates' system. You can bet the Sox would seek one of those players in any deal for Youk if they don't receive a big-league-ready pitcher in any potential deal.
For the right package, the team could also consider left-hand pitcher Jeff Locke or right-hand pitcher's Luis Heredia or Kyle McPherson.
The problem the Red Sox face in any deal with the Bucs is the affordability of Youk versus LaHair or Headley. Youk is the best option on the Pirates' radar offensively and defensively. The only question is: How serious is Pittsburgh when it comes to competing in the NL Central?