BOSTON (CBS) — In terms of playing the “What If?” game, there may be no singular moment with a greater impact on baseball history in the 21st century than the failed acquisition by Alex Rodriguez by the Boston Red Sox in 2003.

Had MLBPA director Donald Fehr allowed A-Rod to take a substantial pay cut while moving from Texas to Boston, then 2004 World Series MVP Manny Ramirez would’ve never helped break the curse, two-time Red Sox World Series winner Jon Lester would have never played a game for Boston, and A-Rod would have become Boston’s big-name star instead of New York’s.

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Of course, Red Sox fans are quite happy with the way things worked out after that trade got shut down. And while it’s all ancient history now, Rodriguez discussed that moment in a podcast appearance with Buster Olney this week. Rodriguez said that he felt crushed when the deal was officially dead, and he — and his stomach — did not handle it particularly well.

“It was a backbreaker,” Rodriguez said. “I remember going out with my buddies in New York, and Cynthia [his former wife], and we all went out to [a club]. We were out all night. I’m not a drinker; I got bombed that night. And literally, we used to use limos at that time, and like at 4 or 5 in the morning, I threw up on the streets of New York from, like, disappointment. It was like two months of just like, ‘Ugh!’ I’ll never forget that night.”

Rodriguez said that he very badly wanted to become a member of the Red Sox.

“It was like one of the biggest disappointments of something that I worked so hard at, with Cynthia, with John Henry, and it fell apart in the ninth inning with two outs,” Rodriguez said.

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Rodriguez ended up moving to third base after going to the Yankees — after Aaron Boone blew out his knee in a pickup basketball game, following his Game 7 ALCS homer vs. Tim Wakefield. But prior to that, he said he pictured a tremendous rivalry involving himself as Boston’s shortstop and Derek Jeter as the Yankees’ shortstop.

“I knew that it would have set up a great story line for baseball when you think about — I mentioned Larry Bird vs. Magic Johnson. I thought two shortstops, Jeter and I going up against each other would have been not only good for New England and New York, but for all of baseball,” Rodriguez said.

Olney also asked Rodriguez about the infamous brawl that broke out in 2004, with A-Rod and Jason Varitek at the center of it all. Rodriguez said those Red Sox-Yankees games at the time had a “college football atmosphere,” where every game was “really, really important.”

“That was a game where I think they were struggling, I was hitting the ball well. They kept pushing me back, pushing me back, pushing me back, and hitting me. And at some point I’m like, ‘All right, enough is enough guys. Throw the ball over the f—ing plate. Uncle,'” Rodriguez shared. “I said a few things to the pitcher [Bronson Arroyo], Jason doing what he’s supposed to do, protecting his pitcher, he got heated. He wasn’t gonna back down, I wasn’t gonna back down. And we just went at it.”

A-Rod also shared the fascinating nugget that he tried to recruit David Ortiz to Texas prior to the 2003 season, when Ortiz ultimately ended up in Boston, where he became one of the most significant players in franchise history.

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Alex Rodriguez, David Ortiz (Photo by Jerritt Clark/Getty Images)

The sequence of events — involving things that did happen as well as things that didn’t — from 2003 into 2004 was obviously significant in shaping baseball history. While A-Rod and the Red Sox likely weren’t happy at the time, Red Sox fans are surely happy with the way everything turned out in the end.

CBSBoston.com Staff