Jim Caple has a good column on this over on ESPN's Page 2:
He makes a compelling case that Damon is in for a less-than-stellar fit with the Yankees. OK, so they paid him more cash... but seriously, is he cut out to be part of straight-laced, overly corporate Evil Empire? Giambi has looked horribly out of place the entire time he has spent in NY and I can see the same thing with Damon.
Plus... it's the f-ing Yankees. Maybe $12M can make someone think differently, but I don't get it. You spend the last few seasons with them as your most hated rivals and then you just flip a switch and it's all "We are the team to beat..." and the "we" is NY?
I am still amazed by that kind of thing with pro athletes, even though I shouldn't be.