The Truth About Mariah Carey's Romance With Derek Jeter

Mariah Carey and Derek Jeter are two unparalleled figures in their respective industries. After a 20 year career with the New York Yankees, Jeter was inducted into the Baseball Hall Of Fame in 2020, becoming one of the small fraction of players who are inducted in their first year of eligibility. As a five-time World Series winner, Jeter has had the kind of career most can only dream of. If there's one person who can understand what that success is like, however, it's Mariah Carey.

Since the early 1990s, Mariah Carey has been a household name. Between an unprecedented string of hits, several highly publicized relationships, a modern-classic Christmas carol, film appearances, and the iconic "I don't know her" meme, there's not much Carey has tried her hand at that hasn't been a success. 

The story was different in 1997, however, as Carey's marriage to Tommy Mottola, then-head of Sony Music, was crumbling. Before the dust had even settled, Derek Jeter was there with shortstop-sized shoulders to cry on.

Before the two had even met, Derek Jeter had his eye out for Mariah Carey. As Jeter began his career with the New York Yankees in the mid-1990s, Carey was already incredibly famous. According to Jeter's locker-mate at the time, Chris Heaps, the rookie Yankee was already a fan, singing Carey's cover of the Jackson 5 classic "I'll Be There" with his Walkman. The music wasn't the only thing Jeter was into, however; he had her image plastered in his locker.

"We were side by side, and, I'll never forget, he had that picture of Mariah Carey," Heaps recalled of his early days playing with Jeter, according to NJ.com. "I think he said 'One day, I'm going to marry her.' That was, you know, a teenage thing to say." Even if it was a teenage thing to say, Jeter got awfully close to his dream two years later. Though they didn't end up married, they did end up enjoying a whirlwind romance.

While Derek Jeter was daydreaming about Mariah Carey, the legendary vocalist's first marriage was coming to an end. According to an interview with Vulture about her upcoming memoir, The Meaning of Mariah Carey, Carey first met Tommy Mottola when she was just 19, and he was 20 years her senior. By the mid-1990s, the marriage was deteriorating. The singer referred to Mottola's house as "Sing Sing," comparing her time in the marriage to being in prison. The couple eventually separated, and before the divorce was finalized, Carey was texting Derek Jeter.

Yes, texting, far ahead of the trend in 1997. But Carey was keeping the flirtation secret, and, after meeting Jeter at a dinner party, began the type of teenage fling that Jeter had dreamed of years before. Carey described the night she met him to Vulture, sneaking up to the roof of his apartment for a clandestine kiss in the rain. "I can never forget that moment," she reminisced. "It happened in a divine way because it helped me get past living there, in Sing Sing, under all those rules and regulations."

This was the beginning of a brief but intense fling, with Carey at one point sneaking to Puerto Rico for a covert getaway with Jeter. And while the relationship was short, it marked the beginning of Carey's post-divorce transformation, and the affair became immortalized through song.

Though Mariah Carey and Derek Jeter were no longer romantically involved by 1998, their affair was immortalized in two of Carey's songs, including one pretty big hit. The first song about their relationship, "The Roof," is from Carey's 1997 album Butterfly. The song is a sensual groove, inspired by the night Carey met Jeter and kissed him on the roof of his apartment. While her fans have long suspected the song was about their fling, Carey finally confirmed the story to Vulture in August 2020.

Carey's second song about the affair, "My All," is an understated, flamenco-influenced track that was inspired by Carey's secret trip to Puerto Rico to meet Jeter. This context adds a special layer to the song, which topped the Billboard Hot 100 in 1998; Carey really was risking it all to spend one night away with Jeter. And while Mariah Carey and Derek Jeter were not meant to be — Jeter is currently married to the model Hannah Davis, and Carey had twins with Nick Cannon before going on to date her backup dancer — their brief affair will always remain an important phase in their lives.