Johnny Damon Tells Curt Schilling He Never Thought Red Sox Would Let Him Leave For Yankees

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It was almost unfathomable.

A star Boston Red Sox player would be allowed to head to the New York Yankees. Surely, the Sox remembered one of the other times they allowed that to happen with a man named George Herman (For the youngsters out there, you may know him as The Great Bambino… Babe Ruth) .

And although Johnny Damon was nothing like the Babe, the fact of the matter is that in the early and mid 2000’s, the Red Sox – Yankees rivalry was as heated as it’s ever been. Both teams and their fan bases hated each other, which is why it was even crazier to think that the Red Sox actually let Damon walk.

In a new interview on The Curt Schilling Baseball Show, Johnny Damon himself couldn’t believe it happened either.

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“A controversial aspect about you… you went from Boston to New York and not a lot of guys made that move for all the obvious reasons,” Schilling told Damon before admitting that he was one of the few players that it actually worked out for.

“I wanted baseball to remain important and what I had on the table was $52 million from the Yankees or $0 at the time from the Red Sox, before finally getting an offer from the Red Sox after I agreed with the Yankees. I didn’t think they [the Red Sox] would let me walk,” Damon said.

“I bought a house in Boston because they said I would be there for a long time. I understand the business side looking back, Jacoby Ellsbury’s a year away, they still have Manny Rodriguez under contract for a number of years. I’m sure they wanted me for one year and see what happens, but unfortunately I can’t leave a three year contract I was given,” Damon continued.

“At the end of the day it stunk for the fans because I was a favorite, but I made the most of it.”

Johnny Damon left the Boston Red Sox for the New York Yankees. (Photo by Paul Bereswill/Getty Images)


Schilling went on to mention that during that time period he would tell people that he didn’t think it was going to happen – he didn’t think the Sox would let Damon walk over $12 million, and definitely not to their biggest rival. There was also that ‘neatness policy’ thing which meant that Damon would have to cut his long hair and shave that bushy beard…something he was willing to do for an extra $50 million.

Hell, as a Yankees fan I thought Damon was a damn spy. I didn’t trust him or want him on the team at all. It took at least a full season for me to open up to him. Here was Damon, a guy I was relentlessly booing from the Yankees’ outfield bleachers, now in pinstripes.

This is the Yankees – Red Sox century-old rivalry we’re talking about.

However, as Damon says, the move did work out in his favor. That first season with the Yankees in 2006 he hit a career-high 24 home runs. The, in 2009. he won a World Series Championship.

Johnny Damon won a World Series with both the Red Sox and the Yankees. (Photo by Focus on Sport/Getty Images)


Enough time has passed since Damon left Fenway to go to the Bronx and for the most part it seems Red Sox fans have let that animosity die down. Afterall, Damon did break the curse and help the Sox win the 2004 World Series after sweeping the Yankees in four-straight games in the ALCS.

But would he do it again today?

There might be some hesitancy.

“New York is a fantastic city… or was, a fantastic city… hopefully they can get it back.”

You hear that Mayor Adams? Even a former World Series winner knows just how bad the city has fallen, not only on the field with the Yankees, but with the rise of crime and chaos.

Written by Mike Gunzelman

Mike “Gunz” Gunzelman has been involved in the sports and media industry for over a decade. He’s also a risk taker - the first time he ever had sushi was from a Duane Reade in Penn Station in NYC.

One Comment

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  1. As a Sox fan, I was surprised Theo let him leave for the Yankees. He was a solid player and one of the core “glue” players of that team. But again, it was Theo running the show, who allegedly used numbers over emotion (until he signed Carl Crawford) so its not all that surprising.

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