The New York Yankees-Boston Red Sox rivalry ran its hottest in the early-2000s when the foundation of the last great Yankees dynasty was still intact, and New York was baseball's hottest free-agent destination. The Red Sox tried to play up that they were the foil to the Yankees' Goliath by pegging themselves as the little guy.
A prime example came back in 2002, when the two clubs duked it out to land then-coveted Cuban defector Jose Contreras. New York won the bidding, leading to then-Red Sox CEO Larry Lucchino to christen the Yankees as "the Evil Empire." The implication was that the Yankees had only gotten to where they were by stepping on the backs of the poor also-rans of the league, a brush he tried to paint Boston with.
But was that really the case? Did the Red Sox truly get to become the biggest thorn in the Yankees' side by being the scrappy underdog? Boston might like to portray itself as something similar to the Billy Beane-era Oakland Athletics, but as the great Mariano Rivera made it be known during his chat with Boomer Esiason last month, nothing could be further from the truth.
Mariano Rivera says loyalty to a team has been lost in today's MLB, and reveals the biggest offer he ever got was from Boston😳@MLB @mlbstorenyc pic.twitter.com/DW8qzkIcXQ
— WFAN Sports Radio (@WFAN660) May 15, 2026
Asked by Esiason if he could ever imagine pitching for another team, Rivera said, "No, I never imagined that. I never wanted to imagine that either. Yes, I got offers [from other teams], but for me, everything wasn't about money. It was about loyalty. It was about something that my family and I [thought] was better for us, and for the New York Yankees, obviously, and for the fans. I mean, I don't wanna imagine that after 10 years wearing the pinstripes and then all of a sudden I'm going to Boston."
Rivera was subsequently asked what team gave him the biggest offer. With a wry smile, Rivera responded, "It was the Boston Red Sox."
The Red Sox weren't the poor underdog they tried to play up in contrast to the Yankees
The Red Sox of that era played up their homegrown players like Dustin Pedroia and Kevin Youkilis, as well as savvy moves for undervalued and/or underdeveloped players like Kevin Millar and David Ortiz. They annoyingly dubbed themselves "The Idiots," comparing themselves to an unwitting band of merrymen falling backwards into baseball victories.
Except if that were the case, they wouldn't have offered Mariano Rivera more money than the Yankees did. They wouldn't have made a serious play for Bernie Williams, either. They wouldn't have traded for Alex Rodriguez and his then-record $252 million contract until the MLBPA raised enough of a stink that the deal was voided.
A poor small-market club wouldn't have been able to sign Johnny Damon away from an actual, poor small-market team, the Oakland Athletics. It wouldn't pull off blockbuster trades for Curt Schilling or Josh Beckett. It certainly wouldn't have been able to give Manny Ramirez $160 million in 2000s money.
The Red Sox of the new millennium were never underdogs. They never lacked resources. They never operated the way they preferred to be portrayed. They never had a real, come-out-of-nowhere upset.
You know who did fit that bill, though? The 1996 Yankees, who felled the Atlanta Braves in the World Series with a bunch of upstart young players, like the Core Five, plus a misfit collection of discarded names like Paul O'Neill and Tino Martinez.
The Red Sox never managed that. Sure, they won the 2004 World Series and broke the Curse of the Bambino, but they were never true underdogs. They spent big money very often, and when they lost out, it was either because they were the runner-up or, like Rivera, the player valued loyalty over money.
