"It took some thinking," Damon said, "but when I realized that the organization was not holding me at that level, I understood I needed to go elsewhere."
"It was basically not a raise," Boras said. "It was something that really changed his feelings about Boston. In his mind, that offer put him in a position that was difficult for him. He was surprised by it."
Despite all the talk of a seven-year, $84 million contract, Boras told the Red Sox that he viewed Damon's value somewhere between J.D. Drew's five-year, $55 million contract and Carlos Beltran's seven-year, $119 million deal.
After dealing with the Red Sox for two months, it became clear that they were not prepared to pony up the dollars it would take to keep Damon. Their best offer came in at four years and $40 million, about $12 million less than the Yankees' offer.
"When he got Boston's first offer, he realized that he thought of himself differently than the Red Sox did," Boras said. "He knew then that there was a possibility he may leave, and I don't think that he ever considered leaving prior to that."
Tuesday, the Red Sox gave Damon a deadline of Christmas Eve to accept the $40 million deal, but -- unbeknownst to Boston -- Damon was already well on his way to the rival Yankees by then.
"That was their last offer," Damon said. "It didn't sit well with me. I thought I was more important there."
Yankees general manager Brian Cashman, who had made a standing offer of four years at $46 million earlier in the winter, enlisted manager Joe Torre to reach out to Damon more than a week ago to tell him how interested the Yankees were in his services.
"Johnny was a perfect fit for us," Cashman said. "We had a big-time interest in him."
Then, last weekend, Cashman called Damon himself to get a sense of how real his interest in the Yankees was.
"I felt that, all things being equal, he'd go back to Boston," Cashman said. "As the process went about, reading the newspapers, seeing that their offer was at three or four years, I thought, 'I have to personally talk to Johnny myself.' I thought we had to bring this to a halt, not let this drag out."
When it became obvious that Damon had been turned off by Boston's approach, Cashman realized that the center fielder could be had for the right price.
"He was very honest about the fact that he had a very strong bond with that fan base," Cashman said. "Separating himself from Red Sox Nation was going to be more difficult than getting away from the Red Sox team.
"That was the biggest hurdle," he added. "I knew we were going to pay a premium, that we had to have a separation. If they were at 11.5 [million dollars] for four and we were at 12 for four, we were going to lose."
Cashman believed that Boston was looking to pay about $46 million for Damon, so it would take more than that to land him. Once Rafael Furcal signed for $13 million a year for three years with the Dodgers, he knew that Damon, also a leadoff hitter, would now demand a higher price.
"At the beginning of the process, before the Furcal signing, I wasn't even thinking about 13," admitted Cashman. "We had the 11.5 offer on the table for a while, then Furcal signed at 13 and I knew that was going to cause interference."
Cashman called Boras on Tuesday afternoon and increased the offer to $52 million over four years, a $13 million average.
There was one catch -- he wanted the answer that night. Fortunately for the Yankees, he got the one he wanted, as Damon agreed to trade in his red socks for pinstripes.
"I'm sure it's going to be crushing," Damon said when asked about Red Sox Nation's reaction to his move. "Those are loyal fans, great fans, and they really didn't deserve it."
"He developed a bond up there for a reason," Cashman said. "Their fan base is the same as ours; they appreciate maximum effort, accountability, he's a genuine guy and he lights up a room. I look forward to our fan base developing the same bond he had with that fan base."
There has been a lot of speculation that things may have been different had Theo Epstein remained as Boston's general manager, rather than the current front office structure, which includes two GMs as well as CEO Larry Lucchino.
"I don't think it's an issue of them not being prepared or organized," Boras said. "I think it's an issue of their judgment as to what value they placed on Johnny Damon."
In the end, the Red Sox made enough of an attempt to retain Damon to tell their fans that they tried, but the Yankees simply made Damon feel more appreciated.
"They did try, but these guys tried harder," Damon said. "That's why I'm standing here. I feel like I'm wanted here."