Trump had a sporadic relationship with World Wrestling Entertainment in the late 1980s; in 1988 and 1989, WrestleMania IV and V, which took place at the Atlantic City Convention Hall, was billed as taking place at the nearby Trump Plaza.
During the lead-up to WrestleMania 23, Trump was challenged by Vince McMahon in a "Battle of the Billionaires," which in turn became a hair versus hair match (where the loser would have to be shaved bald). For the match, both Trump and McMahon each chose a superstar to represent them in the match; McMahon chose Umaga and Trump chose Bobby Lashley. At the event, Lashley was able to defeat Umaga. During the match, Trump got physical and attacked McMahon at ringside. After the win, Trump, with the aid of Lashley and special guest referee Stone Cold Steve Austin, shaved McMahon bald.
Two years later, in 2009, Trump "bought" Monday Night Raw from Vince McMahon. The following week, he ran the first-ever "commercial-free" broadcast of Raw, and helped to implement the addition of a celebrity guest host on the show, which lasted a year after. Not long after he became the owner of Raw, however, Trump would "sell" the show back to McMahon.
In 2013, he was inducted into the WWE Hall of Fame as part of the weekend festivities surrounding WrestleMania 29.