Over the years, billionaire investor Mark Cuban and former President Donald Trump have shared a multifaceted relationship. Their complicated and rather chaotic history started as being TV rivals.
What Happened: In 2004, Cuban’s “The Benefactor” and Trump’s “The Apprentice” began airing. While The Apprentice ran for 15 seasons, Cuban’s The Benefactor was canceled after just six episodes.
At the time, in a blog post titled “Thank you, Donald,” Cuban expressed his frustration after Trump told the Chicago Sun-Times, “You’ll have 100 people trying to do shows a little bit like us.”
“Let's get some things cleared up in case anyone is confused. The Benefactor is going to be nothing like The Apprentice. Why? Because, Donald, we are not alike in any way,” the “Shark Tank” star stated.
In the same blog post, Cuban reminisced about meeting Trump at a 1999 Super Bowl party at Mar-a-Lago, after which Trump invited him to meet in New York.
According to the billionaire, the former President’s office walls were completely covered with photos and magazine covers featuring him.
See Also: Shaq Called Trump ‘A Straight-Up Guy’ Before Presidency, ‘I Think He Just Says It Wrong’
“After leaving your office, I promised myself that if I ever got liquid and had an obscene amount of money in the bank, I would make a point not to remind myself and everyone else around me of it every minute of every day unlike you,” he said, adding, “I guess our definition of success is just completely different.”
Following Cuban’s blog post, Trump stated he didn’t recall meeting him. In response, Cuban wrote a follow-up post titled “Of course you don’t remember, Donald.”
Five years later, in 2009, Cuban praised Trump for his marketing nous. “Donald’s amazing. He sets the standard for marketing and promotion and to get him involved in MMA and to partner with him is an amazing opportunity for HDNet,” he said.
Why It Matters: Despite their rivalry, Cuban initially supported Trump’s political aspirations but later became a vocal critic due to their differing views on success and the Republican nominee’s incessant self-promotion.
The duo also collaborated in 2009 to promote a mixed martial arts (MMA) event through Cuban’s HDNet network.
In 2017, Trump also retaliated against Cuban, saying the billionaire wasn’t smart enough to run for president.
Last week, Cuban admitted to supporting Trump in 2016 but said that a conversation with his running mate JD Vance led to a change of heart.
Earlier this month, the billionaire also said, “I truly don't hate him [Trump] at all. I just think he was and would be a lousy president.”
In August while speaking with Vivek Ramaswamy, Cuban said, “I actually started off supporting Donald and then I got to know him better. I was like, ‘He's great, he's not a typical Stepford candidate.' I thought that was a positive, and then I got to know him.”
He added, “He was unethical then, and he’s still unethical.”
Cuban has been openly supporting Vice President Kamala Harris, the Democratic candidate for the 2024 presidential election.
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Disclaimer: This content was partially produced with the help of AI tools and was reviewed and published by Benzinga editors.
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