The Sox got burned in that deal, which probably left such a bitter aftertaste that management just couldn’t countenance another deal with the Yankees for a long time. More recently, I think the issue has been public perception, with both clubs so competitive and the passions so high.
Still, if you think there’s a good deal to be made, shouldn’t you make it? Regardless of public perception? I’ve always thought the general managers were the cowards. I might have been wrong:
GMs for Red Sox and Rays both told by ownership they could trade their elite pitchers anywhere in majors — except to #Yankees.
And according to this report, the Yankees actively pursued both Jon Lester and John Lackey. So don’t blame the GMs. Blame instead timid owners. And don’t hold your breath for a Papi-for-Ellsbury deal next winter.