I just had to give my two cents on this signing. Now, a lot like former Twins reporter Jim Caple, I'm not upset because he left Boston. To me, Boston isn't much worse than the Evil Empire. They, after all, have the second biggest payroll, so its Boras had to be the big reason for this. Whatever he told Damon to get him to sign with New York (and betray the good legacy he had in Boston), it worked the way it did with A-Rod in 2000.
Damon isn't going to work out for the Yankees, though, for a few reasons. For one, he does address the center fielder issue, yes, but he is a highly overrated defender. He's got speed, yes, but he's like getting Bernie Williams circa 2000 or 2001. Some speed out there, but no arm and in Yankee Stadium, that could get ugly again.
More than that, he's displacing Derek Jeter as leadoff hitter on that team, or so the stories say. This is not a good idea. To begin, Damon is a worse leadoff hitter than Jeter. Now, in many ways, this isn't such a bad thing, because Damon is still a very good one on his own, but he isn't the future Hall-of-Famer Jeter is. For example, to look at a few key stats Jeter beats Damon on. For one, its known that Jeter performs better in that spot. He scores more runs then Damon (122 to 117 last year, 1154 to 1041 since 1996, including 2003 when Jeter was out for a time), more power (169 HR to 127 HR in that same time frame, although Damon has hit a few more doubles and nearly twice the triples), has posted a higher OPS (.847 to .784), and hits for a higher average (.314 to .290). All in all, Jeter has the edge in nearly all categories. Damon has slightly better speed, has stolen 59 more bases in that period, and has the edge in triples and doubles (albeit, by only seven).
But no one can take away Jeter's obvious leadership qualities. As many have already pointed out, Damon doesn't fit in with the New York crowd. The minute he shaves his beard, cuts his hair, and kills his personality, he'll end up much the same way Jason Giambi has. He won't be the same player. Sure, he'll be productive and its not to say he can't handle New York, but he won't the way Jeter does.
If the Yankees want Damon to really help their cause (and, based on their moves thus far, they still need a 1B and a lot more pitching), he needs to move to the second spot in front of A-Rod, Sheffield, Giambi, Matsui, Posoda, Cano, and whomever else. Damon will begin to regress and I think he'll lose his better aspects a lot quicker than Jeter will.
I don't love Derek Jeter and I certainly don't love the Yankees. But its clear that he is the superior leadoff hitter and leader on that Yankees team. He has to be number one in the order and to his teammates. After all, A-Rod and his $252 million contract didn't take his position away, so why should some "idiot" come in and take it from him?