Now, the idea has become improbable. Considering the New York Post report this week that indicated the Yankees were unwilling to go over budget in order to sign Damon, the odds of him ending his career in the Bronx appear slim. For once, a strict budget appears to be just that.
"I do have a number that we're working under," general manager Brian Cashman said last month, after trading away Cabrera in exchange for Javier Vazquez. "We will be at that number, and it will be less than last year. It's as simple as that."
The Yankees are approaching that number, though, and so they set a limit: no more than $2 million annually for a left-field upgrade, according to the Post.
New York hardly seems to be bluffing with Damon. It has All-Star-caliber players at nearly every other position, making left field a secondary priority. And the Yanks know that Damon, now 36 years old, will need both regular rest and regular time as a designated hitter. He does not possess the versatility that manager Joe Girardi craves.
Forgetting Damon, however, does not mean that the Yankees will necessarily default the job to Brett Gardner. Free agents such as Xavier Nady, Marcus Thames, Rocco Baldelli and Jerry Hairston Jr. -- whom the Yankees were reportedly closing in on last weekend -- could all potentially be had for less than $2 million annually. Any of those four, all right-handed hitters, could form a passable platoon with the left-handed-hitting Gardner.
And that much suits the Yankees just fine. A rather telling passage in last weekend's Post report recalled a situation last July, in which the Yankees had all but completed a trade to acquire outfielder Mike Cameron from the Brewers. But Hal Steinbrenner, the club's control person, refused to add the $5.5 million in salary it would take to bring in Cameron, and so New York instead stood pat.
Those types of worries, so foreign in the past around the Bronx, are suddenly cropping up on a regular basis -- not out of necessity, but out of a desire to create a more cost-efficient machine. Damon was a cog from the old system, in which the Yankees spent in the moment and worried about the consequences later. He is a casualty of the new system.
According to SI.com, Damon has received offers from both the Giants and Braves, though it's unclear whether San Francisco remains interested after signing first baseman Aubrey Huff, a move that will shift fellow free-agent acquisition Mark DeRosa to the outfield. No other teams have been rumored to have shown serious interest in Damon.
With the market so shallow, Damon well may reduce his contract demands -- down already from $13 million annually at the start of the offseason -- to something more attractive to the Yankees. Even so, a budget is a budget, and New York has taken a hard line thus far this offseason.
Damon, throughout last summer, spoke of his desire to return to the Yankees and his hope that the two sides could strike a deal.
"I've loved my time here," he said last month. "Hopefully, it's not over, but we just have to wait and see what New York comes to offer. We're listening to anybody out there."
With each passing day, however, the chances of Damon returning to the Yankees seem to crumble that much more.
Anthony DiComo is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.