"The good thing is Jacoby brought two World Series championships to Boston, and he's a heck of a player," said Johnny Damon in a phone interview with MLB.com. "It just seems like he's finding a way to stay healthy, and he's going to be awesome for New York. Unfortunately for Boston fans, this is kind of what happens sometimes."
Ellsbury's deal with the Yankees, which is pending a physical, is a stunning $153 million over seven years, MLB.com has reported. It comes just a month after Ellsbury won his second World Series with the Red Sox, this time in six games against the St. Louis Cardinals.
It was eight years ago that Damon, a poster child for the 2004 "Idiots" that snapped an 86-year-old championship drought, took a four-year, $52 million deal and fled the Sox for the Yanks.
"As much as your heart belonged to Boston and everything, it comes down to being a business," Damon said. "Unfortunately, we're part of that. I wish him the best and, yeah, it's pretty crazy."
In Damon's case, following the 2005 season, the Red Sox were at least willing to match the four-year offer, but they offered $12 million less in the total value of the deal.
The Red Sox were all but certain to avoid giving the 30-year-old Ellsbury a seven-year contract. Boston felt it was a mistake signing Carl Crawford for seven years and $142 million three years ago.
In fact, general manager Ben Cherington was grateful when the Dodgers took not only that contract, but also Adrian Gonzalez's long-term pact off the Red Sox's hands in a blockbuster trade on Aug. 25, 2012.
Ellsbury, assuming the deal goes through, will join a long list of star players who played with the Yankees after having success with the Red Sox. Babe Ruth, Wade Boggs, Roger Clemens and Damon are among those who tested those waters. And all of them tasted World Series glory in the Bronx.
That type of history could leave Red Sox fans feeling ornery when Ellsbury and the Yanks make their first visit to Fenway Park on April 22.
Damon, who was 32 when he left the Red Sox, certainly remembers the boos he got on May 1, 2006, in his first trip back to Fenway. He hopes the fact that the Sox are fresh off a World Series this time, compared to a year removed in his case, will make the atmosphere lighter for Ellsbury.
"I think it depends on what people make of it," Damon said. "Jacoby just helped the team win another World Series. They're going to be grateful for that. But the Boston fans are notoriously hateful to Yankee players. The way that Jacoby plays, he's still going to have the respect throughout the league. The fact is, he hustled and that's what Boston wanted -- somebody who cares about the game and somebody who would run into walls and who would take accountability, and that's the guy.
"Yeah, it's going to be tough at times, but he's a good enough player that the fans are still going to respect what he gave to Boston and what he's going to give to New York."
What Ellsbury should give more of to the Yankees is power. The new Yankee Stadium is heaven for left-handed hitters with power to right-center. Fenway, on the other hand, is 380 feet to straightaway right.
In four seasons with New York, Damon hit 77 homers. In his four years with Boston, he hit 56.
"Oh, I think it's going to play great for his swing," said Damon, who last played in the Majors in 2012. "He has power and still has a lot of good years left in him. And the thing is, New York needed to do it. They weren't looked at as one of the elite teams. With that signing, it puts them right back into the race again."
It remains to be seen what the Red Sox will do to offset the departure of Ellsbury. They could go with prospect Jackie Bradley Jr., but the jury is still out on whether he is ready offensively.
Another option would be to move Shane Victorino back to his natural position of center field and trade for or sign a corner outfielder. Carlos Beltran is the most prominent corner outfielder on the free-agent market.
As for the culture shock Ellsbury might feel when he goes from Boston to New York, Damon was actually surprised by what the transition was like for him.
"I actually thought going to New York was easier to deal with, just because there's so much going on," said Damon. "Baseball isn't the New Yorkers' everything. They've got so many sports teams to follow, they've got Broadway, they've got actors and actresses, Wall Street, all that stuff. Everybody can kind of do their thing."
It is somehow fitting that Ellsbury appears to be following a similar route as Damon.
When the Red Sox drafted Ellsbury in 2005, he was immediately compared to Damon, the man who was in his final season in Boston that year.
"I feel like I was part of the Jacoby Ellsbury business," Damon said. "If they re-signed me, maybe they would have traded Jacoby. Or Jacoby may not have gotten that shot in Boston. Things work out for a reason. Unfortunately, some fans don't see it that way. Jacoby has always been compared to me, in a way, since he was signed. So this is just another comparison. And hopefully, he enjoys both places as much as I have."