The King’s Final Vow: How Michael Jackson’s Lifelong Obsession With Diana Ross Defined His Heartbreak and Legacy

When the will of Michael Jackson was unveiled following his untimely death in 2009, one detail—often overlooked amid the spectacle—served as the final, poignant punctuation mark on the most enduring and complicated relationship of his life. Among the legal formalities, the King of Pop designated one person to care for his children should his mother, Katherine, be unable to do so: Diana Ross. It was the ultimate, silent testament to a love that began with an innocent childhood crush and evolved into a tumultuous, decades-long obsession that fueled his creative life, defined his heartbreak, and ultimately remained unrequited. This is the untold story of Michael Jackson and Diana Ross—a powerful, emotional bond that transcended fame, scandal, and even marriage, cementing itself as his “one great love that escaped him.”

The genesis of this fixation traces back to a pivotal moment in music history. Michael Jackson first encountered Diana Ross at the tender age of ten, when he and his four brothers, the Jackson 5, auditioned for Motown Records ([00:44]). Diana, already the label’s most shining star, recently having stepped out of her legendary tenure with The Supremes, represented the zenith of success and glamour. For the young Michael, she was not just a superstar; she was an ethereal figure, a vision of beauty and talent that instantly captivated his young heart.

While the media was fed the narrative that Ross “discovered” the Jackson 5 and used her connections to propel them to stardom ([01:08]), the truer, more intimate dynamic began behind the scenes. When the Jackson family relocated to Los Angeles, Michael moved in with Diana ([01:14]). This arrangement, intended to ease the transition, instead provided the fuel for a powerful, budding infatuation. Michael, even as a small boy, was utterly devoted, teasing his brothers and calling her his “girlfriend,” refusing to let anyone else near her ([01:21]). His brother, Jermaine Jackson, later confirmed this, stating that Michael had “always loved Diana from when he was a small boy” and knew he had to wait until he was an adult to act on his feelings ([00:14]).

This youthful crush matured into a consuming desire as Michael entered his teenage and young adult years. The 13-year age gap—Michael was 13 years her junior—never registered as an obstacle for him, but it would become the critical fault line in their association, casting a permanent shadow that Diana could never overcome ([03:20]).

The relationship took a significant, professional leap in 1977 with the film adaptation of The Wiz ([01:31]). Ross was cast as Dorothy, a controversial choice given that, at 33, she was deemed too old for the role by critics. However, it was widely speculated that Ross’s ability to secure the part was contingent on her pulling a newly-minted teen idol—Michael Jackson—into the project to play the Scarecrow ([01:46]). For Michael, the incentive was less about the role and more about the proximity. His mother, Katherine, would later recall that Michael had “further incentive to land a role in the movie” because he had been in love with her ever since they were houseguests ([02:05], [02:11]).

The filming of The Wiz served as the crucible for the intensifying romantic speculation. Biographer J. Randy Taraborrelli recounted the late-night escapades of Michael and Diana, who would regularly attend parties at infamous New York haunts like Studio 54 ([02:27], [02:35]). The gossip reached a crescendo one morning when an assistant, frantically trying to locate the pair after they failed to show up for filming, was shocked to learn they were together in his apartment, suggesting Ross had spent the night there ([02:42], [02:48]).

Further igniting the firestorm was a comment allegedly overheard by the assistant. Diana was reportedly talking to girlfriends and was heard saying, “Well, I’ll tell you one thing: Michael definitely isn’t gay” ([02:55], [03:01]). When the assistant pressed Michael on whether anything romantic had occurred, the King of Pop offered an evasive, yet telling, response: “You’d have to ask her that” ([03:04], [03:12]). The flirting was wild and public ([00:27]), but the truth remained tantalizingly vague.

Diana Ross, a “fiercely ambitious woman,” was acutely aware of how a public romance with a much younger Michael would impact her public image and, consequently, her career ([03:39]). This professional pragmatism led her to consistently pull back from taking Michael’s affections seriously. Michael’s reaction, however, was pure, unadulterated infatuation. Following a photo session with Ross and photographer Todd Gray, Michael—unable to contain his enthusiasm—ordered two large prints of every single picture, totaling approximately 144 prints ([03:42], [03:51]). “I want one set for myself and one for Diana,” he insisted, calling the work “magic” ([03:59], [04:05]). This obsessive behavior reached its peak when he erected a full-scale shrine dedicated to her in his family home, filled with photographs and mementos—a sanctuary to the object of his unyielding desire ([05:06]).

On a public stage, their chemistry was undeniable. In Diana Ross’s 1981 television special, Michael Jackson was featured heavily, performing with her three times and receiving his own solo performance spot ([04:05], [04:13]). Ross introduced him as “my baby,” and the two hugged and flirted openly, exchanging compliments that read like love notes ([04:20], [04:27]). That same year, she told Ebony magazine, “I’m crazy about Michael and I love him a lot. He’s been my inspiration… his aura is only about love” ([04:34], [04:42]). While Diana’s vivacious and flirty character was part of her infectious public persona, Michael, in his “naive mind,” took these public displays as confirmation that they were, indeed, in a relationship and that they would ultimately be together ([04:51], [05:33], [05:40]). In a 1983 interview, he publicly affirmed his devotion: “Diana Ross is everything you could wish for. I love her. I hope she marries me” ([05:47]).

Despite Michael’s steadfast belief, Diana attempted to manage his expectations and gently let him down. She frequently hinted at the maternal nature of their bond, a narrative the public often accepted. Most famously, on the red carpet at the 1981 Oscars, she jokingly referred to him as her son ([05:19], [05:26]). The age-gap taboo was too strong, and she worried about the career repercussions of a scandalous public romance, leaving Michael’s hopes perpetually unfulfilled.

The full force of heartbreak arrived in 1985 when Diana met Norwegian shipping magnate Arne Naess Jr., whom she married the following year ([06:04]). For Michael, the news was devastating. Though he stated he was happy for her, acknowledging, “I wanted her to be happy,” he confessed the immense personal toll: “I have to admit that I was a bit hurt and a little jealous” ([06:17], [06:22]). His pain was so profound that he cancelled his attendance at her public wedding at the last minute ([06:11]).

The emotional impact of her marriage was vividly displayed at the 1986 American Music Awards. Michael, visibly cold and upset towards Ross, arrived halfway through the show with a conspicuous replacement on his arm: his new close friend, the legendary actress Elizabeth Taylor ([06:32], [06:38]). It was a powerful, if reluctant, public declaration of his pain.

The emotional fallout of this turning point in his life poured directly into his music. While recording material for his Bad and Dangerous albums, Michael penned several songs about Diana and their complex relationship ([06:54]). His brother, Jermaine, later confirmed that the 1992 hit “Remember the Time” was, as Michael had told him, “written with Diana Ross and mind—the one great love that as far as he was concerned escaped him” ([07:03], [07:10]). Even the controversial 1987 track “Dirty Diana” was speculated by many fans to be a “dig at Diana Ross” while he was still angry at her for marrying another man, a testament to his raw, turbulent emotions ([07:17], [07:25]).

Despite her unhappy marriage, which was challenged by the couple living on separate continents—Diana preferring the US for her career and family while Arne was in Norway—Michael remained under her spell ([07:33], [07:41], [07:48], [08:02]). The bond was so potent that Diana secretly saw him, even during her pregnancies ([07:54]). Michael committed his unwavering feelings to print in his autobiography, Moonwalk, writing, “I’ve always loved Diana and I always will” .

As the years passed and Michael’s globe-trotting career grew, their interactions became less frequent . Ross publicly expressed a sense of loss and confusion in 1991, telling The Rock Hill Herald, “When he wants to see me, he sees me. When he doesn’t, he kind of closes the door… he’s just this elusive love out there” .

But the undeniable power of their connection flashed back dramatically in 1995. When Michael was hospitalized, Ross rushed to his side. The intensity of his lingering feelings was made clear when he called her his “world” and, in an astonishing act, had his then-wife, Lisa Marie Presley, “literally thrown out” of his room in preparation for Diana’s arrival, whom he then lavished with gifts and affection .

This final, dramatic assertion of their bond spoke volumes about the unique, lifelong space Diana Ross occupied in Michael Jackson’s life. It was a space that no other person, including his wives, could ever truly inhabit. His ultimate wish, expressed in his will years later, was a final acknowledgment of their lasting friendship and the great mother she had been to her own children, confirming that she was the one he trusted implicitly to guide his own—a last reminder of the special place she always had in his heart ([09:01], [09:06], [09:12], [09:19]). The love story of Michael Jackson and Diana Ross was never a fairytale, but rather a profoundly human epic of devotion, ambition, and heartbreak—the story of a King who, despite conquering the world, could never quite capture the heart of his queen.