Michael Jackson once called Diana Ross his “mother, lover, and friend,” but the true nature of their relationship has long been shrouded in mystery.

Their connection, which began when Michael was just a child entering the Motown universe, would become one of the most complex and talked-about bonds in music history.

In 1969, an 11-year-old Michael Jackson was introduced to the world through Motown, with Diana Ross—then the label’s biggest star—presented as the Jackson 5’s discoverer.

This was a calculated PR move by Motown boss Berry Gordy, designed to boost the group’s fame by linking them to Ross’s star power.

Although Diana didn’t actually discover the Jackson 5, Michael genuinely idolized her, seeing her as a mother figure, mentor, and even an ideal of feminine perfection. For a time, Michael even lived with Diana in Los Angeles, escaping his strict family environment and immersing himself in her glamorous world.

As Michael grew up, so did the rumors about their relationship. In 1977, they starred together in “The Wiz,” and their closeness on set fueled speculation of a deeper bond.

Although Diana was 14 years older, their chemistry was undeniable, with some crew members insisting Diana spent nights at Michael’s apartment. Diana herself would later joke about Michael’s s3xuality, adding fuel to the fire. Despite the rumors, neither ever confirmed a romance, maintaining an ambiguous public front.

Diana’s departure from Motown in 1981 hit Michael hard. She signed a massive deal with RCA, and Michael’s admiration for her seemed to intensify, becoming almost obsessive.

He reportedly kept a shrine to Diana in his home, complete with photos, statues, and candles burning around the clock. Songs like “Dirty Diana” were widely believed to be about her, and Michael’s public gestures—like leaving Diana as a guardian of his children in his will—underscored her importance in his life.

Their relationship was not without complications. Michael’s mother, Katherine, disapproved, calling Diana a “cradle robber.” Rumors swirled that Michael proposed to Diana twice, both times being rejected.

When Diana married Norwegian businessman Arne Næss in 1985, Michael was said to be devastated, channeling his heartbreak into his music.

In later years, as both faced personal struggles—Diana with addiction and Michael with legal battles—their bond was tested but never completely broken.

Diana was one of the few who supported Michael during his darkest times, including the abuse allegations that rocked his legacy. After Michael’s death in 2009, it was revealed that he had named Diana as his children’s backup guardian, a testament to his lifelong trust in her.

When “Leaving Neverland” reignited controversy in 2019, Diana publicly defended Michael, urging fans to “stop in the name of love.” Her loyalty divided public opinion but reinforced the deep, complicated connection they shared.

In the end, Michael and Diana’s relationship defied easy labels. They were not simply friends or lovers, but two icons forever linked by admiration, loyalty, heartbreak, and a mutual understanding that transcended the ordinary—a bond that, for Michael, lasted a lifetime and beyond.