It was February 1984. The American Music Awards, the most watched music event of the year. Michael Jackson was at the absolute peak of his fame. Thriller had already sold tens of millions of copies, and he was about to walk away with a record eight awards in a single night. And then Diana Ross did something that stunned the entire room.
She walked up to him on stage. She took his face in her hands. And she kissed him on the mouth in front of the cameras, in front of the world. Not a peck. Not a friendly greeting. A kiss. And as she held his face, her hand was clearly visible. On her finger was a ring. A ring that Michael Jackson had given her.
The audience saw it. The cameras caught it. And within hours, the speculation that had been building for years, the whispers, the rumors, the tabloid headlines, suddenly felt like something else entirely. Something real. A few months later, Diana Ross announced her engagement to Arne Naess Jr., a Norwegian shipping magnate she had recently met.
Michael Jackson was not mentioned. The ring disappeared. And Michael Jackson, by every account from everyone who knew him, was devastated. But the most shocking part, you still haven’t heard it. 25 years after that night at the American Music Awards, 18 years after Diana married someone else, 15 years after Michael’s heart had broken and healed, and broken again in ways the world only partially understood, Michael Jackson sat down and wrote his will.
He was 50 years old. He was preparing for the greatest comeback of his career. 50 concerts at London’s O2 Arena. He had three children he loved more than anything in the world. And when he thought about what would happen to those children if something happened to him. When he thought about who in the world he trusted enough to raise them if his mother could not.
There was only one name. Diana Ross. She was named the secondary guardian of Prince, Paris, and Blanket Jackson. If Katherine Jackson were ever unable or unwilling to serve in that role. Diana Ross would take her place. Diana Ross reportedly did not know this until after Michael died. Think about what that means.
A man who had loved this woman since he was 9 years old. Who had been hurt by her. Who had written a song about her that his own producer begged him to tone down. Because it was too raw. Too personal. Too angry. Who had spent years trying to move forward and never quite managing it. That man at the end of his life.
Still trusted her more than almost anyone else on Earth. He chose her for the most important thing he had ever been given. And she found out when he was already gone. But the most shocking part. You still haven’t heard it. To understand what that moment meant. You have to go back to the beginning. Back to 1969. Back to a 9-year-old boy in a Volkswagen minibus pulling up outside Hitsville USA.
Motown Records headquarters in Detroit. Wearing a little green outfit with a hat. About to audition for the most powerful record label in black music history. Diana Ross was 24 years old. She was the lead singer of the Supremes, the most successful American group of the 1960s. The woman who had broken racial barriers in popular music that no one had thought breakable.
She was elegant, controlled, magnetic, and at the very top of the world she inhabited. Michael Jackson was 9 years old. He was the youngest performing member of his family’s singing group. He had a voice that made grown men stop talking. And he had never been anywhere like this before. The mythology that Diana Ross discovered the Jackson 5 was, by most accounts, a Motown publicity strategy.
It was Gladys Knight and executive Suzanne de Passe who were instrumental in bringing the group to Berry Gordy’s attention. But attaching the Jackson 5 to Diana Ross’s name gave them immediate credibility. Their debut album was even titled Diana Ross presents the Jackson 5. A coronation before they had even entered the room.
What was not manufactured was what happened next. As the Jackson family relocated to California, Michael moved into Diana Ross’s Hollywood home for approximately a year while his family secured permanent housing. He called her mama. He called her his girlfriend and refused to let anyone near her. His mother Katherine would later write that Michael had been in love with Diana ever since he and his brothers had been her houseguests.
He would tease his sisters, La Toya and Janet, telling them they weren’t pretty until they started looking like Diana. He was 9 years old and he had already decided. And now everything changed. Diana took a genuine interest in Michael in those early years. She was warm, disciplined, polished, fiercely ambitious.
A surrogate mother figure for a gifted, hypersensitive child suddenly thrust into an adult world of contracts and cameras and expectations he had never been prepared for. He observed and absorbed everything. Her stage presence, her authority, how she commanded a room, how people rearranged themselves when she entered it.
She was not just a mentor, she was the standard. In 1977, Diana was cast as Dorothy in The Wiz, a big-budget Hollywood adaptation of The Wizard of Oz with an all-black cast. By then, Michael was 19 years old and had left Motown. But Diana reportedly pushed for him to be cast as the Scarecrow, even though the studio had doubts.
For Michael, it was his first major project outside the Jackson family structure. He was thrilled. Not just because of the role, because of who he would be working with. Filming began in New York. Michael, away from his father’s controlling presence for the first time, began to experience freedoms he had never allowed himself before.
He went to Broadway shows. He visited Studio 54. He formed adult connections in a world beyond performance and family obligation. And throughout all of it, Diana was there. What happened between them during The Wiz shoot has never been fully confirmed. But what is documented is this. One of Diana’s assistants spent an entire morning trying to reach them both for filming.
When he finally got through, he discovered they were together at Michael’s apartment. Diana had apparently spent the night. When the assistant later asked Michael if anything had happened between them, Michael smiled and said, “You’d have to ask her that.” When the assistant asked Diana, she gave exactly the same answer.
“You’d have to ask Michael.” Later, Diana was overheard talking to friends. She said, “Well, I’ll tell you one thing. Michael definitely isn’t gay.” Neither of them ever said more than that. The ambiguity was its own answer. But the most shocking part, you still haven’t heard it. By 1981, Michael had released Off the Wall and established himself as a solo star of the first order.
Diana had left Motown and was building a new chapter of her career. They appeared together on her television special that year. She called him “my baby.” And the chemistry between them was visible to everyone watching. Prolonged eye contact, hand-holding, laughter that felt unrehearsed. During a segment of the special, Diana turned to him and said, “I knew you were going to be a star.
What I didn’t know is that you were going to get so sexy.” Michael blushed. Then he turned to the audience and asked, “Don’t you guys think she’s sexy?” The audience roared. That same year, Diana told Ebony magazine, “I’m crazy about Michael, and I love him a lot. He’s a very gentle, wonderful human being. His aura is only about love.
” In a December 1982 interview, Michael was asked directly about his romantic life. He said Diana Ross. He said he loved her. He said he hoped they would marry. He was not being playful. He was not performing for the cameras. He was completely serious. He doubled down 2 years later telling Focus magazine, “Of course, one of my best friends in the world is Diana Ross.
Sometimes I tell her I’m going to marry her. Our relationship goes on forever.” In his autobiography, he described Diana as his mother, his sister, and his lover, all combined in one. And then came 1984 and the American Music Awards and the ring. Wait. Don’t miss this detail. Michael had given Diana a ring.
She wore it publicly at the Motown 25th Anniversary Special and again at the American Music Awards where she kissed him on the mouth in front of the cameras holding his face in her hands so the world could see it. By some accounts, they had told Katherine Jackson together that they planned to marry. Katherine was furious.
She told Diana she was too old for her son. She contacted the press. Headlines appeared calling Diana a cradle robber, making jokes about the age difference, applying the kind of pressure that the public eye applies to anything it has decided is inappropriate. Diana, faced with that pressure, made a decision. She ended whatever they had been to each other.
She married Arne Naess Jr., a Norwegian shipping magnate she had recently met, and Michael Jackson was not invited. He canceled his attendance at the last minute. In his autobiography, he wrote, “When I heard Diana Ross was getting married, I was happy for her because I knew it would make her very joyous. Still, it was hard for me.
I wanted her to be happy, but I have to admit that I was a bit hurt and a little jealous because I’ve always loved Diana and always will.” There was no playful tone in those words, no performance, just a man describing in his own autobiography being heartbroken. And now everything changed. In 1987, Michael released Bad.
The eighth track was called Dirty Diana. Publicly, Michael said it was a song about obsessive fans, about groupies who pursue musicians. Quincy Jones, who produced the album, encouraged that framing. But the original version of the song had been harsher, more personal, more specific. Quincy had asked Michael to tone it down, to rewrite the second verse, to make it less obviously about a particular person.
Michael agreed, but the first and third verses stayed, and people who knew the full story heard them differently. Diana had been involved with musicians her entire career. Lionel Richie of the Commodores, Barry Gibb of the Bee Gees, Gene Simmons of Kiss. The line, “She likes the boys in the band,” was not an accident.
Michael knew her history. He had watched from a position of helpless closeness as she moved through relationships with other men while keeping him at a carefully managed distance. The Gene Simmons connection became particularly bitter. According to accounts from that period, Diana and Gene were involved, and at some point during that involvement, Diana apparently mentioned Michael Jackson by name in a way that reached Gene’s ears.
Gene blamed Michael. The two men developed a hostility toward each other that lasted for years. And while all of this was happening, while Michael was recording Dirty Diana and trying to channel his heartbreak into music, Diana was doing something that Michael found maddening and irresistible in equal measure. She kept appearing.
This is what no headline ever captured. Whenever Michael moved on, or tried to, Diana materialized. When he was photographed with Madonna, Diana appeared at the same event and sat on his lap, reclaiming the spotlight. When Elizabeth Taylor, his dear friend and emotional anchor, stepped on stage at an award ceremony to stand beside him, Diana moved between them, holding his arm, inserting herself into the frame.
When Brooke Shields escorted him to public events, Diana found ways to pull his attention back. Michael said it himself in recorded conversations. She would come along whenever he tried to build a connection with someone else. She didn’t want to commit, but she didn’t want him to move on, either. In 1993, during his famous interview with Oprah Winfrey, Michael said, “I never said this, but I always had a crush on Diana Ross.
” By then, he had reframed it as something youthful, something past. But the private recordings told a different story. In conversations with his spiritual advisor, Michael spoke about the years it had taken him to get over Diana. He said, when asked directly, “Years, a hell of a long time. I loved her so much.
” He also said something else in those recordings, something that reveals how the years of distance and hurt had settled into something more honest. “I thought I was with Diana. It was just in my own mind. I haven’t had a real relationship.” You still haven’t seen the biggest surprise. In 1995, while Michael was hospitalized during a period of extreme stress, Diana came to visit him.
According to accounts from that period, Michael had his then wife, Lisa Marie Presley, leave before Diana arrived. He lavished Diana with attention and gifts during the visit. Whatever the precise truth of that account, the pattern it describes fits everything that is documented. Even years after her marriage, even during his own marriage, even after Dirty Diana and the heartbreak and the long stretches of distance, his attachment to her had not dissolved.
That same year, while recording material for the HIStory album, Michael reportedly worked on an unfinished track simply titled Diana Ross. Its lyrics and musical content remain unknown. Its existence alone says everything that needs to be said. In 1997, at the Rock and Roll Hall of Fame induction ceremony, Diana hosted the event.
On stage, Michael told her, “I’m crazy about you.” She spoke about him with genuine warmth. The language between them, even then, even after everything, was the language of people who share something that cannot be easily named. At the 1996 World Music Awards, Diana walked into the audience during her performance and sat on Michael Jackson’s lap, serenading him.
He held her tightly, visibly shy, almost embarrassed. But he held her. I can’t believe this, either, but keep watching. In 2002, Michael signed his will. He named Diana Ross as secondary guardian of his children. A decision she reportedly did not know about until after his death. When the news became public, Diana said this.
Michael wanted me to be there for his children, and I will be there if they ever need me. Not I am surprised. Not I had no idea. Just I will be there. As if it was the most natural thing in the world. As if being chosen by Michael Jackson, even from beyond his death, was something she understood completely. Michael Jackson died on June 25th, 2009.
Diana issued a statement. She said, “I can’t stop crying. This is too sudden and shocking. I am unable to imagine this. My heart is hurting. I am in prayer for his kids and the family.” She did not attend the memorial service at the Staples Center. Instead, she released a separate statement that she addressed to Michael directly.
She said, “I am not there at the Staples Center. I am there in my heart. I’ve decided to pause and be silent. This feels right for me. Michael was a personal love of mine, a treasured part of my world, part of the fabric of my life in a way that I can’t seem to find words to express. A personal love. Not a colleague, not a dear friend, not a protege, a personal love.
Ask yourself this. What does it mean to love someone from the age of nine until the day they die? To be held at a distance by that person for 50 years, never quite let in, and never quite let go. To write songs about them and shrines for them and keep candles burning in their honor. To put their name in your will for the most sacred responsibility you can imagine.
And what does it mean to be Diana Ross in this story? To have loved someone genuinely in your own complicated way. And to have always known that what he felt for you was something you could not fully return. Could not fully accept. Could not fully walk away from either. Diana never fully explained. She has maintained across decades the same careful silence that she maintained in 1977 when her assistant asked what had happened and she said, “You’d have to ask Michael.
” Michael cannot be asked anymore. In 2019, when the documentary Leaving Neverland sparked controversy and many in the entertainment world stayed silent, Diana Ross spoke. She posted on social media defending Michael saying she believed and trusted that he was a magnificent and incredible force. She ended with a reference to her own most famous song, “Stop in the name of love.
Stop in the name of love.” It was her plea. It was also perhaps something else entirely. The words of a woman who had once accepted a ring and then given it back. Who had kept candles burning in a man’s private room without ever knowing they were there. Who had been chosen in death to be the mother of his children. This is what no headline ever captured.
The real story of Michael Jackson and Diana Ross is not a love story that succeeded or failed. It is something more complicated and more human than that. It is the story of a 9-year-old boy who decided in a room in Detroit in 1969 that this woman was everything he would ever want to be and everyone he would ever want to love.
And who never entirely revised that decision no matter what the years brought. Diana Ross was 14 years older than Michael Jackson. She was his mentor, his surrogate mother, his professional inspiration. She was the woman who had helped launch him into the world, who had stayed beside him through decades of fame and chaos and heartbreak.
Who had been named in his will for the most sacred responsibility he could bestow. She was also by his own repeated and public account the love of his life. Whether she loved him in the same way, she never said. Not once in 50 years. And Michael Jackson, who said everything in his music, who poured every private feeling into lyrics and productions and performances that the world still listens to seemed to understand at some level that this was how it would always be.
He still put her name in his will. He still kept the candles burning. And in the end that is the truest thing about this story. Not what Diana Ross felt or didn’t feel. Not what happened or didn’t happen in a New York apartment in 1977. Not what the ring meant or what the kiss meant or what the name on an unfinished song meant.
The truest thing is simply this. Michael Jackson loved Diana Ross for his entire life. And love like that, unrequited or returned, completed or unfinished, leaves a mark on everything it touches. Listen to the music. You can still hear it. There is one more detail that belongs in this story. One that almost no one mentions when they talk about Michael Jackson and Diana Ross.
In 1981, during the television special where Diana called him my baby and they flirted openly on stage, a journalist asked Diana about a possible collaboration. She said she would love that. She said Michael was doing extraordinary things. She said he was supposed to be coming to town soon. And then she said this.
Michael and I, we’re in love and there’s nothing to do about it. There’s nothing to say. She said it lightly, with a laugh, in the way that public figures say true things and then retreat behind the laughter so no one can hold them to it. But she said it. We’re in love and there’s nothing to do about it. Perhaps that was the truest description of everything that passed between them for 50 years.
Not a romance that succeeded or failed. Not a love story with a beginning and middle and end. Just two people in a specific and irreducible situation. In love and with nothing to do about it. Michael Jackson understood this in his own way by the end. In those private recordings with his spiritual advisor, he said, “I thought I was with Diana.
It was just in my own mind. I haven’t had a real relationship.” He had made peace of a kind with the gap between what he had felt and what had actually existed between them. He acknowledged that some of what he experienced was his own creation, his own projection onto a woman who cared for him deeply, but could not be what he needed her to be.
And yet, he still put her name in his will. He still, in the last legal document of his life, reached for the woman he had loved since he was 9 years old and asked her, without telling her, without giving her the chance to say yes or no, to be there for his children if his mother could not. It was the most Michael Jackson gesture imaginable, private, unilateral, full of trust that had survived everything.
Diana Ross, when she learned of it, did not hesitate. She said she would be there if the children ever needed her. She said it simply and without qualification. Katherine Jackson remained healthy. The contingency never activated. Prince and Paris and Blanket grew up in the care of their grandmother, and Diana Ross remained at the edges of their story, present when needed, graceful in her distance.
But Michael had chosen her one last time for the last thing that mattered. And that choice tells you everything you need to know about what Diana Ross meant to Michael Jackson. Not the ring, not the kiss, not the shrine full of candles and photographs, not Dirty Diana, not Remember the Time, not the unfinished song that only had her name.
Just his signature on a document. Her name beside the names of his children. That was the last word. And it was entirely, unmistakably his.
