The duo first met in 1993 at a college baseball game between the University of Miami and the University of Michigan, and one year later, they got to know each other while playing in the minor leagues. Though Jeter had been playing since 1992, Rodriguez made his MLB debut first, playing his first game with the Seattle Mariners in 1994.
After Jeter made his New York Yankees debut in 1995, he and his pal quickly became two of the most notable names in baseball, even sharing a cover of Sports Illustrated that proclaimed them as part of “the finest group of shortstops since World War II.”
They weren’t yet teammates, but their friendship was already legendary. In the 2011 biography The Captain: The Journey of Derek Jeter, Yankees and Mariners players recalled teasing the duo about their super tight bond. When the two clubs faced each other in 1998, one of Jeter’s former teammates asked him, “Are you going to your boyfriend’s house?”
In late 2000, however, the cracks in their relationship began forming. Rodriguez had signed a $252 million contract — at the time the biggest in sports history — to join the Texas Rangers, while Jeter signed a $189 million deal to stay with the Yankees. It should have been a celebratory moment for both of them, but things took a turn when Rodriguez was asked who in baseball could possibly break his new record.
“I don’t know who it’s going to be,” the New York City native told ESPN in December 2000. “The 252 is going to be hard to break because of my age and my talent at such a young age. Even a guy like Derek, it’s going to be hard for him to break that because he just doesn’t do the power numbers and defensively he doesn’t do all those things.”
Jeter responded by saying he wasn’t interested in breaking the contract record anyway, but the die was cast. In March 2001, Rodriguez dug the knife in deeper when he told Esquire that the New Jersey native “never had to lead” in his baseball career.
In February 2004, the pair finally became teammates for the first time when Rodriguez was traded to the Yankees. The three-time MVP agreed to switch positions to third baseman as Jeter was already the team’s star shortstop; this also meant that the duo would play side-by-side on the field.
The twosome retired within two years of each other, and their relationship has since remained a popular discussion topic among baseball fans. In September 2018, Rodriguez admitted that he and Jeter have had their share of highs and lows, but he’ll always have love for his ex-teammate.
“Derek and I are friends. I’ve known Derek since we were 15 years old,” he told Cigar Aficionado at the time. “Like all relationships, there’s ups, there’s downs, there’s ups, but where it sits today is where it’s always sat — with respect.”
Keep scrolling for a look back at Jeter and Rodriguez’s friendship over the years.