Donald Trump’s Best Moments In WWE, Ranked

Hamish Woodward

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Former US President Donald Trump is in the news for his exploits fairly regularly, but he should be more known for his time in the WWE.

He has been in the public eye for decades, and is most famous as the host of “The Apprentice” (before his ill-fated spell as the most powerful leader in the free world).

Donald Trump appeared in the WWE for decades, always being in the background of some of the company’s grandest moments.

In this article, we’ll detail all the best moments from Donald Trump’s WWE career, letting you in on some of the biggest secrets of his WWE career.

Donald Trump vs Rosie O’Donnell

In 2007, WWE booked a match between Donald Trump and Rosie O’Donnell…sort of.

While this sounds utterly bizarre – it is! Vince McMahon had the genius idea to hire two indie wrestlers to dress up as the two TV personalities, and have them duke it out live on Raw.

The two TV stars were locked in a feud since 1993, since O’Donnell attended Turmp’s wedding to his then-wife Marla Maples.

The pair fired off over TV and in newspapers over the decades, until two wrestlers playing dress up finally settled the score in the ring.

It was awful and everybody hated it. This didn’t stop WWE from doing the exact same one year later, with Hillary Clinton vs Barack Obama.

Donald Trump Buys Raw

In 2009, Donald Trump shocked the world (and WWE investors) by purchasing Monday Night Raw.

He appeared on Raw, announced by Vince McMahon as the new owner of an “independently run” Monday Night Raw, although the show would still feature the famous WWE stars.

The next week, he promised a three-hour Raw show with no commercials, leaving fans incredingly happy with Donald Trump’s new ties with the WWE.

The show turned out great, and was among Donald Trump’s best moments in the WWE.

However, WWE shareholders were confused by the angle, and demanded McMahon “buy back” Raw a week later, ruining the storyline completely.

WrestleMania IV

Donald Trump is a huge part of the history of WrestleMania, actually hosting two of the early events.

After the huge success of Andre the Giant vs Hulk Hogan at WrestleMania III, everyone was excited to see what was next for the WWE.

Venues were queuing up to host the next year’s event, but it was Donald J. Trump who won the bid for WrestleMania IV.

Both WrestleMania IV and V were sponsored by Donald Trump, with matches like Hulk Hogan vs Andre The Giant II, and Randy Savage vs Ric Flair taking place under his watch.

The events were promoted as taking place at Trump Plaza, although that was a classic WWE lie. Boardwalk Hall in Atlantic City hosted the events, although Donald Trump’s impact on WWE history is still as huge as ever.

WWE Hall of Fame

While his current politics have soured Donald Trump on a lot of people, it is hard to say he did not deserve to be inducted into the WWE Hall of Fame.

Donald Trump was the celebrity inductee during the 2013 ceremony, joining a list of celebs like Arnold Schwarzenegger and Mr T in being honored by WWE.

They pointed to his help in putting on WrestleMania V, the time he bought Raw and his part in the “Battle of the Billionaires” (more on that next) as the reason why Donald Trump is a WWE Hall of Fame inductee.

Battle of the Billionaires

Donald Trump’s best moment in the WWE has to be his involvement in the “Battle of the Billionaires” at WrestleMania 23.

After a confrontation on Monday Night Raw between Trump and Vince McMahon, they placed a friendly wager – the loser of their match had to have their head shaved.

However, both men were at an age where wrestling was not on the cards (plus, Trump has never been in any athletic shape).

To get around this, they each chose a champion to represent them, so the match at WrestleMania 23 was Bobby Lashley (Trump) vs Umaga (Vince).

The match at WrestleMania 23 saw Steve Austin as the special guest referee, and all five men got involved in the match – including Trump hitting a clothesline on Vince, before eating a “Stone Cold Stunner”.

The Battle of the Billionaires ended when Bobby Lashley pinned Umaga, which led to Trump, Austin and Lashley shaving Vince McMahon bald, live at WrestleMania.

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