<p class="ingestion featured-caption">Mark Cuban and Donald Trump are old frenemies.Dimitrios Kambouris/WireImage/Getty Images</p><ul class="summary-list"><li>Mark Cuban said in 2016 that he has a "love-hate relationship" with Donald Trump.</li><li>The two have traded insults and compliments in the press for years.</li></ul><p>In a 2016 interview with Rolling Stone, <a target="_blank" class href="https://www.businessinsider.com/mark-cuban-net-worth-2018-9">Mark Cuban</a> described his friendship with <a target="_blank" class href="https://www.businessinsider.com/mar-a-lago-photos-before-donald-trump-2024-9">Donald Trump</a> as a "love-hate relationship."</p><p>Over the years, the two <a target="_blank" class href="https://www.businessinsider.com/wealth-billionaires-musk-bezos-zuckerberg-net-worth-jensen-huang-waltoans-2024-8">billionaires</a> have cycled through seeing each other as rivals, business partners, friends, and enemies.</p><p>Cuban once supported Trump's political aspirations, but has since become an outspoken critic and shared what caused him to change his mind.</p><p>Here's a look back at Cuban and Trump's complicated friendship.</p>