Summary

  • Donald Trump stole a gossip columnist's girlfriend, leading to a heated argument on The Howard Stern Show.
  • Trump admitted to stealing the girlfriend.
  • The argument escalated with personal attacks and Trump bragging about his relationships.

From the moment that Donald Trump first rose to fame, he has been a master of garnering the world's attention. For proof of that fact, all anyone has to do is look at Trump's presidency and the fact that he made cameo appearances in so many movies and shows.

Of course, one of the aspects of Trump's personal life that has often been in the spotlight is his love life. After all, fans want to know about Trump's marriages, his girlfriends, and if he got along with his ex-wife's other husbands. With that in mind, it is amazing that very few of Trump's fans know he once threatened to steal a gossip columnist's girlfriends during a heated interview with former friend turned mortal enemy Howard Stern.

Donald Trump Got Into A Bitter Fight With A Gossip Columnist On The Howard Stern Show

Many years ago, a writer by the name of A.J. Benza penned pieces for Newsday and the New York Daily News. According to Benza, that job put him in consistent contact with Donald Trump who would feed him gossip. Benza and Trump's relationship later changed when the future President stole Benza's girlfriend.

Donald Trump Often Walked In On Undressed Underage Pageant Candidates
Donald Trump hosting Satuday Night Live
Via: NBC

After Trump came between Benza and his former girlfriend, the two men had a bitter argument on The Howard Stern Show.

The situation began when Benza went on Stern's show to be interviewed and called Trump out for stealing his girlfriend. As anyone who has followed Trump's life will know, the former President is a master of getting attention. With that in mind, it shouldn't surprise anyone that Trump called into Stern's show, so he could respond to Benza.

According to The Daily Beast's article about what happened next, Trump didn't dispute Benza's claim about him at all. Instead, Trump agreed that he stole Benza's girlfriend, but he claimed he didn't know they were involved at the time.

Based on that alone, it may have at first seemed like Trump wanted to put the drama behind them. However, Trump then quickly began boasting about taking Benza's girlfriend, Kara Young, from him.

“I stole his girlfriend, but I didn’t know I was stealing your girlfriend...I’ve been successful with your girlfriend, I’ll tell you that...A.J., I won your girlfriend. You know it, she knows it, and everybody knows it.”

AJ Benza paparazzi photo
A.J. Benza leaving a restaurant
Via: Instar

Unsurprisingly, Trump's comments made Benza furious, to say the least. That resulted in Benza taking shots at Trump as he claimed to know inside information that Kara Young shared with him.

“[Kara] tells me you cut your own hair. You’ve got [hair] plugs, does the world know that?”

Donald Trump AJ Benza  Interview With Howard Stern
Donald Trump old-school interview with Howard Stern 
Via: Deposit/Howard Stern Show Youtube 

During a 2016 episode of his radio show, Howard Stern explained why he wouldn't replay any of Donald Trump's controversial old appearances. "I feel Donald Trump did the show in an effort to be entertaining and have fun with us and I feel like it would be a betrayal to any of our guests if I sat there and played them now where people are attacking him.”

As their argument continued, Benza went on to make a claim about Trump and Russia. Keep in mind, this argument took place in 2003, many years before stories about Trump and Russia dominated the political landscape. According to Benza, Trump used to boast to him about how he should go to Russia since women there "have no morals".

Never one to back down from a fight, Trump came out swinging at Benza at that point. Trump did this by claiming that Kara Young never loved Benza while insulting the columnist.

“Trust me, A.J.—she didn’t love you. I’m doing you a favor, A.J., she didn’t love you. A.J. doesn’t like Trump for one reason: I stole his girlfriend. I took her away like he was a dog.”

Howard Stern Roasted Donald Trump's Relationship With His Daughter Ivanka After Their 'Woke' 1
Howard Stern relationship with former president Donald Trump
Via: TheThings

Trump also bragged about Young being with him without Benza knowing it. From there, Benza claimed that he was going to get involved with Ivanka Trump once she was old enough. At first, Trump responded that Benza would never have a chance with Ivanka Trump. Trump then threatened to steal any woman Benza got involved with.

"Hey, A.J., I guarantee you have zero chance. A.J., any girl you have, I can take from you—if I want. Any girl you have, I can take from you. You’re full of s**t. So any girl you have, I can take. That I guarantee. And that was proven before.”

A.J. Benza Revealed What It's Like To Date Donald Trump

After Donald Trump and A.J. Benza got into their epic fight on Howard Stern's show, the idea of them making peace seemed virtually impossible. While there is no indication that happened, Benza was incredibly positive about Trump in a later interview.

In 2016, a writer for The Atlantic reached out to A.J. Benza and interviewed him through a series of emails. During one of their exchanges, Benza revealed what Kara Young once revealed to him about what it was like to date Trump.

How long did Kara "Mary" Young date Donald Trump and A.J. Benza, according to Who's Dated Who?

Relationship:

When They Started Dating:

When They Broke Up:

A.J. Benza and Kara Young

1995

May 2001

Donald Trump and Kara Young

2001

2001

As Benza explained, he expected Young to talk about Trump throwing around his wealth and power. Instead, according to Benza, Young revealed the sweet side of Trump that very few people know about.

Donald Trump and Kara Young when they were young
Donald Trump and Kara Young on the red carpet
Via: Instar

"What stood out for her were silly moments or sweet gestures. She told me about the time he took her backstage in Atlantic City to see James Brown and how he put on a cape and danced with the man, or the fact that her mother is still alive today because of the top-notch medical care he organized and went into his pocket for. Or the time he had a stretch limo pull up to her West Village apartment so that she and her little boy could go to the Natural History Museum. And how startled she was when, exiting the car, she turned to thank the black-cap wearing, mustachioed driver, only to see it was The Donald in disguise."