The late 1990s and early 2000s constituted a golden era of baseball. Specifically, the Yankees enjoyed a prime spot in the limelight. With four World Series titles in five years, they were next to indestructible. One particular player that helped the team clinch those victories was star shortstop Derek Jeter, who was the backbone of the team. Jeter was a force of nature that couldn’t be stopped. Then, in 2004, Alex Rodriguez joined the Bronx Bombers.

The last time the team won a World Series was in 2000 and A-Rod gave new hope to fans. But it would still be five years before the Yankees could win another title, which was Rodriguez’s only one. And yet, the Yankees almost always made headlines because of who their team employed. Best buddies once upon a time, the Rodriguez-Jeter friendship turned into a saga that is still not over today.

Alex Rodriguez once tried to cut a deal with reporters about Derek Jeter

What can be said about Jeter and Rodriguez that hasn’t already been said before? Oozing raw talent, the duo was rising through the ranks of MLB at around the same time. The hardships brought them together, but the simple fact that they were on different teams changed everything. Jeter was a young talent surrounded by other great Yankee players. Rodriguez was equally skilled but probably stuck on a subpar team.

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While Jeter was already a fan favorite in New York, A-Rod’s comment on the Yankees captain probably did not allow him to surpass Jeter’s legacy in the Big Apple. Notably, there was tension between the two when A-Rod took a dig at Jeter for his contract with the Yanks. Reporters hounded them for years afterward, while the two tried to maintain a semblance of friendship. Rodriguez even tried to smooth things over with them once.

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In 2007, the New York Times reported him saying, “Let’s make a contract. You don’t ask about Derek anymore, and I promise I’ll stop lying to you.” This was a new approach after years of the duo glossing over details to say everything was just fine with them.

The former friends had at least one thing in common

Jeter has always been all about baseball, less about his personal life. He’s more open now that he’s retired, but back in his active days, the Hall of Famer wanted to focus on the game, not himself. Rodriguez wasn’t always forthcoming with information either and in that same New York Times article, he echoed his former pal’s views.

He ensured reporters that while they may not be friends who slept over at each other’s houses anymore, they functioned well as teammates. “We were best of friends about 10, 13 or 14 years ago, and we still get along well,” the former Yankee said. “We have a good working relationship. I cheer very hard for him, and he cheers hard for me, and, more importantly, we’re both trying to win a world championship. We’ll leave it right there.”

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The 2000s were the best of times, and the worst of times, especially for these two.