The Yankees and their $212 MM payroll, have limited funds to spend in their search for an affordable DH. Call me crazy, but maybe, just maybe, if they didn’t owe someone like Grimmace $92 MM+ over the course of the next five seasons, they’d be able to afford a Johnny Damon, who made $5.25 MM last year as DH for the Rays.
In the case of the Red Sox, they’d have to make some sort of move to free up some money for Roy Oswalt, who’s looking for $9 MM (or less) for a one year contract; a number that, in previous years, would have been a drop in the bucket for the Red Sox. Gee, do you think that maybe the failed John Lackey and Daisuke Matsuzaka experiments came back to bite them in the ass? How about the signing of Carl Crawford, who certainly didn’t play up the the expectation of someone with a $142 MM contract?