One of Trump’s most famous pals is the “Queen of All Media,” Oprah Winfrey. The successful businessman had a meaningful friendship with Oprah, as evidenced by the cozy way she’s cuddling up to him in this picture. The pair considered themselves buds… until Trump ran for office, that is.
Oprah was not impressed and Trump called her out via his Twitter account for being “insecure.” This was seven years after he tweeted that he was excited to be a guest on her show. If we’ve learned anything from this walk down Trump’s memory lane it’s this: friendships and politics don’t mix.
Donald And Muhammad Ali
Meaningful moments in sports are not missed by Trump, as evidenced by this photo with the biggest legend of boxing, Muhammad Ali.
Young Donald was shaking hands with Muhammad, joined by Governor Thomas Kean, in Atlantic City. Trump knew well how to win over powerful affiliates.
With The Round Girls
If you think Donald is only fond of having pictures with boxing and wrestling legends, you’re absolutely wrong! In a Tyson vs Spinks fight in Atlantic City, the avid fan of boxing and its stars took time to pose for a photo with the round girls.
It’s hard to say who requested the snap (The Don is, after all, a self-confessed fan of beautiful women), but if we base it on the picture, these ladies were certainly bearing the biggest smiles.
Trump And The King Of Pop
It’s clear that the prince of real estate can’t get enough of the King of Pop. This photo was taken in April 1990, during the grand opening of Taj Mahal casino, originally known as the Trump Taj Mahal.
As the owner, Donald made sure he allowed in only the finest guests to promote his business. The guy sure knows how to market his businesses, we’ll give him that.
Trump, Marla, and Evander Holyfield
Donald may love snagging snaps with his favorite celebrities, but he has a fair share of his own fans as well. In this photo, he is seen signing his book, The Art of Deal, for the professional boxer, Evander Holyfield. Holyfield looks happy receiving his personal copy of Trump’s signed book.
Also, actress Marla Maples is spotted here, waiting in the background to watch the Tyson vs. Williams fight with Trump in Atlantic City. During this time, Trump and Maples were rumored to be having an affair. This was before Trump had finalized his divorce with Ivana.