When pop legend Michael Jackson and former First Lady Melania Trump crossed paths, they shared a moment of playful intrigue that almost led to a kiss—all in the name of stirring up a little jealousy. Michael Jackson, known for his charm as well as his music, suggested the cheeky idea to Melania Trump, adding a touch of Hollywood-style drama to the dinner they shared with Donald Trump. The story recently resurfaced, reminding fans of Jackson’s mischievous personality and his unexpected friendship with the Trump family.
Michael Jackson and Donald Trump: A Friendship Among the Rich and Famous
During the 1980s and 90s, Michael Jackson and Donald Trump became friends, bonded by their high-profile lives and mutual admiration. Trump was one of the few celebrities who publicly stood by Jackson amidst controversies and accusations. Even after Jackson’s passing, Trump praised the artist, describing him as “misunderstood.” This defense only solidified their bond in the public eye, with Trump later sharing on Twitter that Michael was a “great talent.”
“Michael was very misunderstood—a great talent,”
But while Trump took to social media to speak on Jackson’s behalf, Jackson and Trump shared many personal moments that remain a part of pop culture lore, including one memorable evening involving Melania Trump.
A Dinner Date at the Pierre Hotel
In the early 2000s, Jackson and Trump’s paths crossed again—this time with Melania Trump, who was still new to the social scene. Melania’s encounter with the King of Pop was surreal, and Jackson’s playful suggestion only added to the unforgettable evening. In a recent interview with DuJour, Melania recalled the amusing dinner at the Pierre Hotel in New York.
The evening started simply enough with Jackson inviting Donald and Melania to the exclusive hotel. After dinner, Donald excused himself to view an art collection in another room, leaving Melania and Jackson to chat. It was then that Jackson leaned over with a sly grin and suggested, “Hey, when Trump comes back, let’s start kissing so he will be jealous!”
Melania’s Reaction to Jackson’s Playful Suggestion
Melania laughed off Jackson’s mischievous idea, admitting they didn’t follow through. Reflecting on the moment, she shared,
“No, no, no. But we were laughing so hard.”
The idea of making Trump jealous may have been just a joke, but it gave insight into Jackson’s fun-loving nature and his unique dynamic with the Trumps.
The moment also hints at Jackson’s complex personality, which often merged playfulness with an underlying sensitivity. It’s not known how Donald Trump would have reacted if he had walked in on a kiss, but Melania’s laughter suggests that Jackson’s humor left a lasting impression.
Michael Jackson and Lisa Marie Presley: A Romance Kindled at Mar-a-Lago
Jackson’s connection to Donald Trump extended beyond their friendship. According to Trump, Jackson and Lisa Marie Presley shared pivotal moments at his Mar-a-Lago estate in Palm Beach, Florida. As Trump recounted in his book The Art of the Comeback, Mar-a-Lago became a romantic backdrop for Jackson and Presley’s relationship.
“I was there, and the magic of Mar-a-Lago brought it out,”
Trump wrote, hinting at a temporary spark in their relationship. According to Trump, they
“were really getting it on”
during their time there, but the relationship faded after they left.
The couple also spent considerable time at Trump Tower, which served as a retreat for Jackson before his marriage to Presley. This part of Jackson’s life connected the artist even more deeply to Trump’s world, creating a layered relationship between the music icon and the business mogul.
Donald Trump on Jackson’s Legacy and the Complexities of Fame
Even after Jackson’s untimely passing in 2009, Trump continued to discuss his friend’s life and challenges. In 2016, during a CNN town hall, Trump opened up about Jackson’s struggle with self-esteem, which he believed stemmed from
“bad, bad, bad surgery.”
Trump’s comments hinted at how Jackson’s pursuit of perfection may have led to health challenges that eroded his confidence.
Jackson’s family, however, was not pleased with Trump’s theories. Jermaine Jackson, Michael’s brother, expressed frustration with Trump’s comments, tweeting,
“Friends don’t pay tribute by peddling b.s. theories.”
Jermaine’s response highlights the delicate nature of Jackson’s legacy, as friends and family continue to navigate how best to honor his memory.
Despite the tensions, Trump remained firm in his belief that Jackson was unfairly judged.
“He was very misunderstood,”
Trump reiterated, emphasizing the side of Jackson he knew—a talented individual with a generous spirit.
The King of Pop’s Mysterious Bond with the Trump Family
Jackson’s interactions with the Trumps remain one of the more curious chapters in the lives of both the pop star and the former president. His playful suggestion to Melania Trump was emblematic of the humor he brought to those he befriended, offering a lighthearted moment between the worlds of music and high-profile business.
What remains is a legacy of shared memories, controversies, and stories that blend the worlds of entertainment and political fame. Jackson’s relationships were always tinged with a bit of mystery, and his connection to the Trump family is no exception.
Jackson may have joked about kissing Melania to make Trump jealous, but his friendship with Trump extended far beyond dinner table humor. It was a bond that spanned decades, woven through mutual admiration and a shared understanding of life in the public eye.