Mark Cuban and Donald Trump have a relationship that can only be described as a wild ride – full of twists, turns, and the occasional collision. At times, they've seemed like friends, united by their shared status as billionaire business owners who aren't afraid to speak their minds. Other times, though, their relationship has been marked by very public feuds that make it clear these two don't always see eye to eye.
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Back in the early days, Cuban saw something in Trump that many others did – a disruptor who could shake up the status quo in a way that traditional politicians couldn't. Cuban, always the savvy businessman, was intrigued by Trump's outsider approach, and there was a time when the two shared more than just headlines. At one point, Cuban even seemed to support Trump, appreciating the potential he saw in a fellow businessman breaking into politics.
But as time passed, Cuban's view of Trump began to sour. The cracks started to show, particularly around Trump's ethics and business practices. For Cuban, a man who built his fortune on smart investments and forward-thinking, Trump's methods were starting to look less like innovation and more like exploitation.
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One of the more interesting tidbits in their complex relationship is how Trump, despite his bravado, reached out to Cuban for advice on the stock market. In 2019, Cuban shared a story with Kevin Hart, describing how Trump would call him up, asking for his thoughts on the market. "What do you think about the stock market?" Trump would ask. In his signature laid-back style, Cuban recounted how he'd laugh and turn the question back at Trump. It's a small moment, but one that reveals the odd, almost playful dynamic that existed between them.
But the playful exchanges didn't last. As Trump's controversies piled up – think Trump University and the ill-fated Trump SoHo–Cuban's disillusionment grew. He began to see Trump less as a bold outsider and more as a "snake oil salesperson," a term he didn't hesitate to use publicly. Cuban's criticism wasn't just about policy or politics but about how Trump approached business and life. For Cuban, it became clear that Trump was more about self-promotion than the meaningful change he once hoped for.
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The shift in Cuban's stance became even more apparent during the 2020 election. Instead of backing Trump, he supported Joe Biden and Kamala Harris, seeing them as the ethical and stable leaders the country needed. Cuban, who at one point even toyed with the idea of running for president himself, seemed to solidify his position as a critic rather than an ally of Trump.
The Cuban-Trump saga goes beyond just two billionaires butting heads. It's a story of how personal ethics and public ambition can collide, reshaping even the most powerful relationships. With his business acumen and occasional political musings, Cuban has watched – and often challenged – Trump's rise and reign. While Cuban hasn't leapt into presidential politics himself, his interactions with Trump offer a unique window into the complex dance between business, power, and public life in America.
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