Mark Cuban and Donald Trump share a complex history.
Dimitrios Kambouris/WireImage/Getty Images
In 2016, Mark Cuban characterized his relationship with Donald Trump as one of “love and hate.”
The two have exchanged both barbs and praise in the media over the years.
Cuban initially backed Trump’s presidential bid but later became a vocal critic.
During a 2016 interview with Rolling Stone, Mark Cuban referred to his connection with Donald Trump as a “love-hate relationship.”
The dynamic between these two billionaires has fluctuated over time, oscillating between rivalry, partnership, friendship, and animosity.
Cuban once expressed support for Trump’s political ambitions but later voiced strong opposition to him. Despite this shift in perspective, he recently congratulated Trump on securing another term in office.
This article revisits the intricate friendship between Cuban and Trump.
The Rivalry Begins: Competing Reality Shows
Mark Cuban featured on ”The Benefactor.”
Frederick M. Brown/Getty Images
Both Trump’s show “The Apprentice” and Cuban’s “The Benefactor” premiered in 2004.
In an April 2004 blog post titled “Thank You, Donald,” Cuban expressed his displeasure when Trump claimed that many would attempt to replicate their shows. He stated:
“Let’s clarify any confusion: ‘The Benefactor’ will be nothing like ‘The Apprentice.’ Why? Because we are fundamentally different.”
Cuban recounted meeting Trump at Mar-a-Lago during a Super Bowl party back in 1999. Following that encounter, he visited Trump’s New York office where he noted that every wall was adorned with images of himself:
>”If I ever find myself wealthy beyond measure, I will strive not to remind everyone around me of it constantly—unlike you,” he remarked. “Our definitions of success clearly diverge.”
After this blog entry was published, Trump claimed not to remember their meeting. In response, Cuban wrote another post titled “Of Course You Don’t Remember.”
“The Apprentice” ran for an impressive fifteen seasons while “The Benefactor” was short-lived after just six episodes.
A Brief Collaboration: HDNet Event in 2009
Cuban alongside Donald Trump during an event. Dimitrios Kambouris/WireImage/Getty Images
Cuban founded HDNet cable network in 2001 which showcased various sporting events including mixed martial arts competitions.
A press conference held at trump tower saw both Cubans join forces with trump Jr., promoting the MMA event “Affliction: Trilogy,” featuring fighters Josh Barnett & Fedor Emelianenko.
“Donald is incredible,” said Cubans during the conference; adding how partnering up presented great marketing opportunities for HDNet.
The anticipated event ultimately got canceled due to Barnett’s failed drug test without finding suitable replacements according Sports Illustrated reports.
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Mark Cuban’s Political Journey: From Trump Supporter to Kamala Harris Advocate
Initial Praise for Trump
Mark Cuban, the billionaire entrepreneur and owner of the Dallas Mavericks, initially expressed admiration for Donald Trump. “He has transformed the landscape,” Cuban remarked, acknowledging Trump’s significant impact on politics.
In response to Cuban’s compliments, Trump took to X (formerly Twitter) to express his gratitude for the “kind words.”
Cuban’s Shift in Allegiance
Mark Cuban with Hillary Clinton during a rally in Pittsburgh. Gene J. Puskar/AP
However, by 2016, during a rally in Pittsburgh, Cuban publicly criticized Trump using vivid language. He stated, “In Pittsburgh, we have a term for people who yell and try to intimidate others: jagoff. Is there anyone more of a jagoff than Donald Trump?” This marked a clear departure from his earlier support.
Trump retaliated on X by labeling him as “dopey Mark Cuban from failed Benefactor fame.”
Cuban later reflected on this change of heart as he considered running for president himself.
The 2020 Presidential Speculation
Cuban at the White House. BRENDAN SMIALOWSKI/Getty Images
As speculation about his potential presidential run grew in 2020, Trump dismissed him on X in 2017 by stating that he was “not intelligent enough to be president.” He added that it was better for everyone if Cuba focused on tweeting rather than attempting governance.
Cuban suggested that Trump’s comments were likely triggered by an article from The New York Post discussing him as a possible contender. According to Forbes’ report from September 2022, he had indeed contemplated entering the race but ultimately decided against it after conducting national polling.
Cuban Backs Kamala Harris After Biden Exits Race
Vice President Kamala Harris. Megan Varner/Getty Images
Following Joe Biden’s withdrawal from the race for re-election in 2024, Mark Cuban pledged his support for Vice President Kamala Harris. He joined over 800 venture capitalists endorsing her through VCsForKamala.org and signed an open letter alongside other tech and finance leaders backing her candidacy.
Cuban actively campaigned across key battleground states such as Arizona and Wisconsin during this period.
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A Change of Heart Regarding Trump’s Leadership Style < <Cuban speaking at an event. Amanda Stronza/SXSW Conference & Festivals via Getty Images >
<< p >During discussions with former Republican candidate Vivek Ramaswamy last August, Cuban revealed that while he once viewed Trump positively, his perspective shifted after getting acquainted with him. Cuban noted, “He’s not your typical candidate; I initially saw that as refreshing.” However, he later concluded, “He was unethical then and remains so today.”
<< p >In an appearance on “The Daily Show” hosted by Jon Stewart, Cuban recounted how one conversation led him to withdraw his endorsement. During their discussion about attending local business events before debates, Cuban suggested showcasing business acumen. To which Trump replied dismissively: “Donald Trump doesn’t dine at people’s homes; are you serious?”
<< p >Cuban also critiqued Trump’s policies extensively. In September, he labeled Trump’s proposed tariffs—specifically targeting John Deere equipment produced in Mexico—as “absurd” and detrimental to American industry.
<< p >Despite acknowledging some positive traits about Trump personally—describing him as humorous yet charming— Cuban emphasized: “That doesn’t qualify someone for presidency.” He expressed concern over what would happen if such leadership returned again. In correspondence with Business Insider last September, he stated: “I wouldn’t want to conduct business with him.” The campaign did not respond when asked about these remarks.
Mark Cuban’s Support for Donald Trump: A Surprising Turn of Events
Donald Trump celebrating on election night.
Photo by Chip Somodevilla/Getty Images
In the early hours following the election, Mark Cuban took to social media platform X to express his sentiments, stating, “You won fair and square.” This unexpected endorsement from the billionaire entrepreneur has sparked discussions about their evolving relationship.
Read the original article on Business Insider
