Mark Feinsand and Bill Madden of the New York Daily News reported that the Boston Red Sox are aggressively pursing Toronto Blue Jays’ ace Roy Halladay, hoping to acquire him before the start of the winter meetings on December 7. The Red Sox would likely need to give up pitcher Clay Buchholz as the centerpiece of a deal, as well as top shortstop/pitching prospect Casey Kelly and shortstop Jed Lowrie.
Other teams reported to be interested in Halladay include the New York Yankees, Los Angeles Angels, and Los Angeles Dodgers. The Blue Jays were also reported to have contacted the Chicago Cubs with rumored interest in shortstop prospect Starlin Castro and pitcher Jeff Samardzija, however, the Cubs do not have the financial flexibility to add Halladay.
It appears that if you have a top shortstop prospect and/or top pitching prospects, and the flexibility to add Halladay’s $15.75 million dollar contract for 2010, you will be talking with Jays. Of course, any team trading for Halladay will want to work out a contract extension before a trade, which will probably range in the $17-20 million a year range for 4-5 years.