The Rangers and Red Sox agreed to a trade in 2003, but the Major League Baseball Players Association vetoed the deal since it didn't like Rodriguez would voluntarily be taking a reduction in salary from his contract.
Appearing on Dale & Keefe Wednesday as part of the WEEI/NESN Jimmy Fund Radio Telethon, Rodriguez admitted he's thought about what could have been if he joined the team, and also admitted he was disappointed when the deal broke down.
“Oh my God, yes. I have thought about it a lot," he said. "It was such an exciting time for me. I knew how great the Red Sox were going to be. Could I have forecasted four championships? Probably not, but I knew at least a couple in there. I thought that after spending a lot of time with John Henry down here in Florida at my home in Miami and his home in Boca, I knew that this was someone who had incredible passion and knowledge and knew how to put a winning team around him — on the field and in the front office. After talking with Theo (Epstein) and Jed Hoyer, and now they have Sam Kennedy, he just surrounds himself with incredible people. I just thought the combination between John Henry, who is a hedge fund wizard, Tom Werner, who is the king of Hollywood and putting great shows together, and then a lawyer like Larry Lucchino, I just thought they were a triple threat. And then they had Theo. I said this is a place that I can win and win for a long time.
"And of course it all came down and collapsed really quickly after the union did not allow me to give back tens of millions of dollars because it would set the wrong prescient for the other 749 players. I was completely bummed it collapsed. It was so depressing never knowing that the Yankees were even an option at that point. And of course, a few weeks later I sat next to Brian Cashman in New York collecting my MVP award. … And then a few weeks later I have my press conference in New York."
Rodriguez is now part of ESPN's Sunday Night Baseball broadcast.