It has been widely reported that Damon offered to accept a 2 yr, $20M contract from the Yankees. By then, the Johnson deal was almost finalized, which meant that almost $6M of the $20M they had budgeted for Damon (presumably) was now wrapped up in Johnson, so they countered with 2 yrs, $14M. Considering Damon hardly wanted to take a pay cut, he wasn't going to play 2 years for $1M more than he made in one year on his previous contract. Thus ends the Johnny Damon era for the Yankees.
By all accounts, Damon wanted to return to the Yankees. His willingness to go from $13M a year for 3-4 years to $20M for 2 years shows that. But by all accounts, the Yankees never valued Damon above a 2 year, $20M contract to begin with. If you were willing to play for that, and you wanted to play for the Yankees, why did you dick around so long, only changing course when it was clear the Yanks had moved on (don't think that leak of the Johnson negotiations was an accident)? Had you said, "Yeah, I'm old, I'm rich, I can take a $3M pay cut and still feed my family," you'd be on the Yankees, your desired destination right now.
But here's the problem, you're a Boras client. And Boras never takes into account his clients' desires to be on a contender, or the actual facts of what his clients bring to the table versus what a team should pay them, he pretty much operates on the assumption that his clients only care how high his commission is. He misplayed the A-Rod opt-out badly, and ended his relationship with the slugger (though, thanks to Hank, it worked; though after this past postseason, I'm not complaining). He now has made Damon this season's Abreu, a player who will almost certainly end up playing for far less than he's worth had his agent not been a douche (granted, Abreu's agent wasn't his problem last year). Only Damon won't be as lucky as Abreu was last year because he won't be playing for a contender.
Let's consider the options. New York is obviously out, and Boston currently has Elsbury and Cameron, so the AL East is out. The Angels just signed Matsui, and don't need a half-time DH type outfielder, they're out. Seattle just traded for Bradley, they're out. The Tigers are shedding payroll, and its questionable whether they'll be competitive next year anyway, so they're out. Minnesota likes younger players generally, and as far as anyone knows are looking for neither a DH or outfielder. That's the American League. We'll do the NL quickly. The Phillies don't need him, no one else in that division matters (sorry Mets fans). St. Louis will resign Holliday unless Boras does to him what he did to Damon. That's the central, (sorry Reds fans). In the West, the Dodgers are irrelevant because of the McCourt divorce, the Giants might take him but won't pay him much and frankly, still won't be competitive (sorry Damon fans, he's not putting anybody over the top) and as far as I know the Rockies aren't interested. That leaves no real contenders or teams with money (save maybe the Mets) who might be interested in Damon. The Mets will almost certainly come to terms with Bay, whom no one else wants (coincidentally, that's the same reason St. Louis will keep Holliday).
At this point, if any of these teams decided they did need a bat/outfielder not named Holliday, they'd look to Bay before Damon. So all this just to say that Damon will probably not be on a contender or playing for anywhere near $13M. Had Boras, at the winter meetings, communicated Damon's willingness to play for 2yrs/$20M, Damon would be a Yankee, making bank, looking at a chance to repeat. Instead, Boras talked about Damon's DNA and talked Damon right out of any chance of having the sort of salary he probably is still worth. Good job, Super Agent, good job.