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The rivalry between the Boston Red Sox vs the New York Yankees is a tale as old as time. Both are strong teams, both with some hot-headed young men playing for the pride of their cities. Although, and this is said very casually, the rivalry has cooled somewhat in recent years, some games are worth looking back at. The 2004 World Series is arguably one of the most legendary. It messed with the Yankees badly, particularly captain Derek Jeter.

When the Red Sox ended their 86-year World Series title drought, fans rejoiced like never before. They had finally won, and that too after eliminating the heavyweights like the Yankees in the ALCS. The ‘Curse of the Bambino‘ was at last broken. While Boston went deep into celebrations, the Yankees fell into a hole of despair. Jeter took it especially badly, and it rankles him to this day. Because not only was his team defeated, a Red Sox player publicly made a mockery of him.

Manny Ramirez’s 2004 World Series sign made Derek Jeter ‘sick

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Flashback to November 2004 – the streets of Boston were filled with the sounds of people celebrating the Red Sox win. The Yankees, of course, were safely inside their homes, participating in the parade through their television screens. Or perhaps not watching it at all. Derek Jeter certainly wasn’t. But one piece of information still made its way to the former captain – Red Sox’s outfielder Ramirez was holding a sign with his name. It read, “Jeter is playing golf today. This is better!” A fan had made it originally, but Ramirez liked it so much that he held it up himself.

Talking about the painful ALCS defeat and BoSox’s World Series win and its aftermath in episode 5 of his docuseries, The Captain, Jeter said, “It’s misery, you know. Sick to my stomach. Got out of New York, went back home, Boston won the World Series.” The retired shortstop continued, “Manny Ramirez had a sign saying ‘Jeter is playing golf right now’ during the parade. Someone had sent it to me. Um … so yeah that made me sick.”

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The docuseries premiered in 2022, and it seems like even almost two decades later, the Red Sox win still bothers Jeter. And he’s not alone.

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Most Yankees lost sleep after losing to the Red Sox…

… except maybe then-manager Joe Torre. It was certainly a surprising outcome. The Bronx Bombers were in a 3-0 lead and it was almost assured that they would win yet another championship title. But when the Red Sox managed a comeback from those scores, it left everyone shocked.

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Yankees’ catcher Jorge Posada shared in The Captain, “I didn’t sleep for a while.” And while most players had similar responses, Torre had something different to say. “It was one postseason that you wish hadn’t happened, but I don’t think I ever lost sleep saying ‘I wish I had done this instead of that,'” he shared.

In the years since, the Yankees have won one World Series in 2009, while the Red Sox have won three more. In this legendary rivalry, which side are you rooting for?