Mark Cuban and Trump have traded insults for years, here's why the billionaires turned against each other

NEW YORK CITY, NEW YORK: With less than a week before Election Day, the animosity between Donald Trump and Mark Cuban is off the charts.

This isn’t just about politics; it’s a long-standing clash of egos with each billionaire throwing jabs that date back decades.

Cuban, best known as the bold 'Shark Tank' investor and former owner of the Dallas Mavericks, hasn’t been holding back, taking digs at Trump and his “circle” of women. And of course, Trump’s not letting that slide.

Mark Cuban calls out Donald Trump’s 'inner circle' on 'The View'

It all kicked off recently when Mark Cuban appeared on 'The View' and made a disparaging comment about the women Donald Trump surrounds himself with. “Donald Trump, you never see him around strong, intelligent women. Ever. It’s just that simple," he declared. 

That was bound to ruffle feathers, especially among Trump’s loyal supporters and former administration women. Trump’s former press secretary Kayleigh McEnany was quick to fire back.

"This is so profoundly offensive," she responded, adding, "I worked for Donald Trump. I consider myself a strong woman. I consider those around me strong women, what about the women who vote for Donald Trump? Are they weak? Are they dumb?"

Cuban later tried to smooth things over, trying to clarify that he wasn’t implying all women who support Trump lack strength or intelligence.

"Let’s clarify something," he began in a post on X. "This is what I said during a conversation about why Nikki Haley was not active in his campaign 'Donald Trump, you never see him around strong, intelligent women. Ever. It’s just that simple. They’re intimidating to him. He doesn’t like to be challenged by them and, you know, Nikki Haley will call him on his nonsense with reproductive rights and how he sees and treats and talks about women. I mean, he just can’t have her around. It wouldn’t work.'"

"I’m happy to clarify that 1. I know many strong, intelligent women voting for Trump. Including in my extended family. I’m certainly not saying female voters are not smart, strong, and intelligent. 2. I know he has worked with strong intelligent women, like Elaine Chao, Kelly Anne, Ivanka, and many others I stand by my opinion that he does not like being challenged publicly," he added.

The decades-old Donald Trump and Mark Cuban feud

The tension between Mark Cuban and Donald Trump didn’t just spring up overnight. Back in 2006, Cuban recalled his first meeting with Trump at a Super Bowl party at Mar-a-Lago, where Trump allegedly dismissed him with a smug, “Someday you’ll be able to sit up there with the rich people,” before walking away.

Cuban was already a successful businessman at the time, having taken his company Broadcast.com public in 1998 — so the comment obviously didn’t sit well with him.

Fast forward a few years, and Cuban’s short-lived reality show The Benefactor hit the airwaves, with 16 contestants competing for $1 million from the billionaire. Unfortunately, it didn’t last and got canceled after just one season—around the same time Trump’s The Apprentice was gaining traction.

Always one for the last word, Trump sent Cuban a hilarious letter congratulating him on the show but with a twist of that classic Trumpian sarcasm.

“Dear Mark: I am truly sorry to hear that your show has been cancelled for lack of ratings," he wrote. "When I initially called you to congratulate you on The Benefactor – little did you or I realize how disastrous and embarrassing it would turn out to be for you.”

He even offered to “lend a helping hand” if Cuban ever tried another show. "If you ever decide to do another show, please call me and I will be happy to lend a helping hand," he added.

And since then, the duo haven’t missed a chance to take shots at each other. In 2014, Trump even threw in a snide remark about Cuban’s failed attempts to buy an MLB team. “Major League Baseball was really smart when they wouldn’t let Mark Cuban buy a team. Was it his financials or the fact that he’s an asshole?” he posted on X (then Twitter).

Election 2024: Mark Cuban becomes Donald Trump’s vocal critic

Mark Cuban has now become one of Donald Trump’s loudest critics in the lead-up to the 2024 presidential election. After Cuban’s comments on 'The View', Trump pulled out all the stops to roast Cuban.

He wrote, “Mark Cuban, a really dumb guy, who thinks he’s 'hot stuff' but he’s absolutely nothing, is now out there saying that I don’t surround myself with strong women. Actually, he is very wrong, I surround myself with the strongest of women – With the understanding that ALL women are great, whether strong or not strong. This guy is such a fool, he’s constantly on Television being critical, and only for the reason that I tuned him out completely while President because he called incessantly. I told him, very pointedly, 'Look Mark, I’ve got a lot of things to do, I just can’t be taking so many pointless calls from you.'"

"In any event, that affected him greatly, because he’s a very insecure guy and a MAJOR LOSER, always has been and always will be! Nobody likes him, nobody respects him, and he’s unattractive both inside and out! He should go back to talk about the person he was forced to support because I didn’t want it, Lyin’ Kamala Harris. Also, he’s got no clubhead speed! I may, in fact, be surrounded by the strongest women in the World, including Heads of Countries, who make Mark look like a “baby!” All strong women, and women in general, should be very angry about this weak man’s statement," Trump added.

Considering, it is probably safe to assume Cuban won't be invited to join the Trump administration if he wins on Tuesday, Whiskey Riff reported.