He didn't have a chance to come here then because the Tigers had an up-and-coming center field prospect named Curtis Granderson. Now, Damon is going to be part of the Tigers' effort to replace him, and the Tigers are very comfortable inserting him near the top of their lineup.
"Today, it makes us more competitive than we were yesterday," manager Jim Leyland said. "This isn't some signing. This is a guy who has substance and a track record. ... Primarily this ended up a presence move, an offensive move, and I think it's a huge presence."
It wasn't a move the Tigers or Damon were anticipating this offseason, not even after the holidays passed. The 36-year-old outfielder was a key member of the Yankees' World Series championship club, batting .282 with 107 runs, 36 doubles, 24 home runs and 82 RBIs out of the second spot in the lineup.
Damon had expressed interest in returning to New York, but after completing a four-year, $52 million contract, he was reportedly hoping for at least a two-year, $22 million deal from the Yankees. The closest New York would get was two years at $14 million.
Damon disputed reports that he wasn't willing to take a pay cut, saying all he wanted from the Yankees was a two-year contract.
"Unless it comes from my mouth, don't believe it, I guess," Damon said.
He conceded, though, that the market played out differently than he would've expected.
"No one really could have anticipated what this market was going to be," Damon said. "I mean, I'm very happy with the deal we eventually signed. The bottom line is it's a tough market. Players like Jermaine Dye and Felipe Lopez are still out there."
Once the Yankees moved on, Damon said, he turned his attention to the Tigers. It was an odd attraction for someone who had spent about half his career in Boston and New York, but he said it was a place he had eyed in the past.
"I don't know. I knew five years ago, playing against the team," Damon said. "They had lost a whole lot of games in 2003, but I just saw how they developed a year later, and they kept developing. And I thought, 'Man, this team is going to be tough to beat.' Sure enough, in 2006, they were good enough to get to the World Series.
"I feel like we have someone who can win the Cy Young Award, someone who can win the MVP Award. But most importantly, [it's] a team where, if things go well, we can win a lot of games."
He also said he knew many of the players here, having talked with them during Spring Training over the past four years during the many Yankees-Tigers matchups.
For things to go well enough to get him to Detroit, though, it took another long journey, this one a negotiation with Boras that lasted nearly six weeks.
"We've been negotiating for about 25 years together or so," Tigers president/general manager Dave Dombrowski said, "and I can say I've never had an easy negotiation with Scott. That's not good or bad. That's the fact."
He's also never had a lengthier negotiation on a free agent -- not with Boras, not with anybody.
Dombrowski said they received a call from Boras about Damon, but that it didn't go far. That was around the time Dombrowski told reporters they had not expressed interest in Damon, which he said in hindsight was because they had reached their budget.
Nothing progressed until owner Mike Ilitch talked with Dombrowski and gave them the payroll flexibility to pursue a deal. Damon said they wanted a two-year contract, and briefly discussed it, but that it wasn't going to happen.
"That was the hangup early," Damon said. "We were trying to work it out to be a two-year contract, because of the fact that I wanted to be here and lay down some roots, because I didn't feel like I was at the point in my career going year to year."
Once talks lingered, Damon said, that's when other teams became interested, including the White Sox. Rumors swirled that Damon's wife preferred Chicago to Detroit and wanted her husband to sign there, but Damon said that wasn't the case.
"I think everything was perfect about playing in Detroit, and my wife agreed," he said. "She's going to go out there and support me, no matter what team I play for."
The final steps to complete the deal apparently were messages of support from Leyland and one of Damon's new teammates -- Dontrelle Willis.
The call with Leyland was set up by Dombrowski and Boras, to give Damon a chance to hear where he fit on the club.
"He wanted to assure him how much we wanted him," Dombrowski said.
The call with Willis was Damon's idea. He knew the left-hander from their time on Team USA for the 2006 World Baseball Classic and had kept in touch since, and Damon wanted to ask someone on the club how players and fans would react to his arrival.
"After I got off the phone with him, I was like, 'This is going to work,'" Damon said. "And we're expecting bigger things from him. He's obviously going to battle to get back to form. And even he said, 'This is a great place to play, you're going to enjoy it.' Said all the right things to me, and I was like, 'Wow.'
"Scott called me about two minutes after that and asked if we were good to go. And I said, 'Absolutely.'"
With that, the saga was over, and with it, the Tigers' search for help around the top of their lineup is over. They're finished making moves, Dombrowski said, but they're hoping the last one is the one that gets their offense going.
"I'm sure he was anxious to get here," Leyland said. "We were anxious to get him here."