Mark Cuban congratulated Donald Trump for winning the 2024 election. Here's a timeline of their 'love-hate relationship.'

Mark Cuban and Donald Trump are old frenemies.

Dimitrios Kambouris/WireImage/Getty Images

• Mark Cuban said in 2016 that he has a "love-hate relationship" with Donald Trump.
• The two have traded insults and compliments in the press for years.
• Cuban initially supported Trump's campaign, but later became an outspoken critic.

Mark Cuban described his friendship with Donald Trump in a 2016 interview with Rolling Stone as a "love-hate relationship."

Over the years, the two billionaires have cycled through seeing each other as rivals, business partners, friends, and enemies.

Cuban once supported Trump's political aspirations, but later became an outspoken critic and shared what caused him to change his mind. Still, he congratulated Trump this week on winning his second term in the White House.

Here's a look back at Cuban and Trump's complicated friendship.

Mark Cuban and Donald Trump started out as rivals with dueling business-themed reality shows.

Mark Cuban on "The Benefactor."

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Trump's show, "The Apprentice," and Cuban's show, "The Benefactor," both began airing in 2004.

In a 2004 blog post titled "Thank you, Donald," Cuban wrote that he took offense when Trump told the Chicago Sun-Times that "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," Cuban wrote. "The Benefactor is going to be nothing like The Apprentice. Why? Because, Donald, we are not alike in any way."

He recalled meeting Trump at a Super Bowl party at Mar-a-Lago in 1999, after which Trump invited him to meet in New York. Cuban wrote that Trump had covered "every inch of every wall" in his office with photos and magazine covers of himself.

"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 wrote. "I guess our definition of success is just completely different."

After Cuban published his blog post, Trump said that he didn't remember meeting Cuban. Cuban wrote a follow-up blog post titled "Of course you don't remember, Donald."

"The Apprentice" aired for 15 seasons, while "The Benefactor" was canceled after six episodes.

In 2009, they teamed up for an event with Cuban's cable network, HDNet.

Mark Cuban, Donald Trump and UFC Fighter Josh Barnett.

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Cuban's cable network, which he founded in 2001, aired sporting and entertainment events including mixed martial arts.

At a 2009 press conference at Trump Tower, Trump and Donald Trump Jr. joined Cuban to promote an "Affliction: Trilogy" event featuring MMA fighters Josh Barnett and Fedor Emelianenko.

"Donald's amazing," Cuban said at the press conference. "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."

The event ended up getting canceled when Barnett failed a drug test and a replacement could not be found, Sports Illustrated reported.

Cuban criticized Trump's birther conspiracy theories targeting President Barack Obama in 2012.

President Barack Obama released his birth certificate in 2011.

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Following his calls for Obama to release his birth certificate, Trump also offered to donate $5 million to charity if Obama released his college transcripts. In an interview with KDFW Fox 4 in Dallas, Cuban called the offer "one of the dumbest things ever."

"Donald you shave your head, a million dollars to any charity you want," Cuban said.

Cuban was initially supportive of Trump's 2016 campaign, calling him "the best thing to happen to politics in a long, long time."

Donald Trump at a rally.

ROBYN BECK/AFP via Getty Images

"I don't care what his actual positions are," Cuban said of Trump on his Cyber Dust messaging app in July 2015. "I don't care if he says the wrong thing. He says what's on his mind. He gives honest answers rather than prepared answers. This is more important than anything any candidate has done in years."

Cuban praised Trump for upending conventional wisdom about candidates requiring "politically scrubbed" backgrounds, which he said had meant that "smart people who didn't live perfect lives could never run" for president.

"The Donald is changing all of that," Cuban said. "He has changed the game and for that he deserves a lot of credit."

Trump thanked Cuban on X for his "nice words."

But Cuban ended up endorsing Hillary Clinton and speaking out against Trump in 2016.

Hillary Clinton and Mark Cuban at a rally in Pittsburgh.

Gene J. Puskar/AP

At a rally in his hometown of Pittsburgh in July 2016, Cuban ripped into Trump with colorful slang.

"You know what we call a person like that – the screamers, the yellers, the people that try to intimidate you? You know what we call a person like that in Pittsburgh? A jagoff," Cuban said. "Is there any bigger jagoff in the world than Donald Trump?"

Trump responded in a post on X, referring to Cuban as "dopey Mark Cuban of failed Benefactor fame."

Later, in 2024, Cuban would give more insight into what made him change his mind.

As Cuban weighed a 2020 presidential run, Trump wrote on X in 2017 that Cuban was "not smart enough to run for president."

Mark Cuban at the White House.

BRENDAN SMIALOWSKI/Getty Images

"I know Mark Cuban well," Trump wrote. "He backed me big-time but I wasn't interested in taking all of his calls. He's not smart enough to run for president!"

"Isn't it better for all of us that he is tweeting rather than trying to govern?" Cuban responded on X.

Cuban told The Huffington Post that Trump's online outburst was likely tied to a New York Post article naming Cuban as a potential 2020 challenger.

Forbes reported in 2022 that Cuban had, in fact, considered running for president in 2020, even commissioning a national poll before deciding not to enter the race.

After Biden dropped out of the 2024 race, Cuban threw his support behind Vice President Kamala Harris.

Vice President Kamala Harris.

Megan Varner/Getty Images

Cuban was among over 800 venture capitalists who pledged their support for Harris on VCsForKamala.org and one of 88 signatories of a letter from Wall Street and tech executives endorsing Harris.

Cuban also campaigned for Harris in swing states including Arizona, Michigan, and Wisconsin.

Ahead of the 2024 election, Cuban shared more on what changed his mind about supporting Trump.

Mark Cuban.

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Speaking with former Republican presidential candidate Vivek Ramaswamy in August, Cuban said he initially thought Trump was "great" until he "got to know him."

"He's not a typical Stepford candidate," Cuban said. "I thought that was a positive."

He added, "He was unethical then, and he's still unethical."

In an August appearance on "The Daily Show" hosted by Jon Stewart, Cuban shared the interaction with Trump that caused him to revoke his support.

"We were talking about this one debate for CNBC that he wasn't going to be at — I'm like, Donald, why don't you go to a local small business and sit there at the table and show off your business chops and show people you're a businessman," Cuban said. "He goes, 'Mark, Donald Trump and Mark Cuban don't go to people's houses and have dinner, are you kidding me?' That's who he is."

Cuban told Stewart that when he asked Trump about his "ground game," Trump replied, "Well, I got all these religious people who are going to do the work for me."

Cuban also criticized Trump's policies. In September, Cuban called Trump's proposed 200% tariff on John Deere agriculture equipment produced in Mexico "insane" and a "good way to destroy a legendary American company."

In an email to Business Insider in September, Cuban said, "I don't have a problem with Trump the person," adding that Trump, "like anyone, including me, has good and bad traits."

Cuban continued, "I wouldn't want to do business with him, but when I've been around him he is funny and charming. But that doesn't qualify him to be President. I didn't think he did a good job before. I think it would be worse if he got in again."

The Trump campaign did not respond to a request for comment.

After Trump won the 2024 election, Cuban congratulated him in a post on X.

Donald Trump on election night.

Chip Somodevilla/Getty Images

"You won fair and square," Cuban wrote on X in the early hours of the morning after election day.

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