It was actually sort of shocking last week when the Red Sox traded Stephen Drew to the Yankees for Kelly Johnson (and cash!).
Granted, it was just Kelly Johnson and Stephen Drew (and cash!). But this was the first time the two clubs had exchanged players since 1997. That 17-year gap is the longest in American League history, rivaled only by the 14-year period after the Red Sox traded Sparky Lyle for Danny Cater in 1972 (which significantly changed the course of baseball history).
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:
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.