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.
Donald and Oprah
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.
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 Doing Blue Steel Before It Was Cool
You’ve witnessed several photos of Donald Trump in his youth that revealed his softer side, from his cute baby photos to his doting parent role with his children. But we cannot ignore the fact that Trump was rocking the blue steel look well before Zoolander made it a thing.
Think of the countless times he’s made false statements. Now imagine him doing it with this look on his face. Suddenly believable, right?
Best Friends Forever
As a public figure, even prior to his position in the White House, Trump was already famous thanks to his successful business ventures and TV appearances. His notoriety was only bolstered by his frequent appearances at major sports events, like his all-time favorite: the WWE.
Here he is seen taking yet another photo op with an impressively huge champion wrestler, Hulk Hogan. The two are known to have been pals for a long time and Hogan was one friend who remained a staunch supporter of Trump after he was elected president.