AP Photo/Matt Rourke
The recording, which was picked up by a hot mic and published by The Washington Post on Friday, came from an interaction between Trump and television personality Billy Bush.
"Donald Trump's actions have made any Trump [employee] who doesn't quit immediately, toxic and unemployable by anyone else," the owner of the NBA's Dallas Mavericks and star of ABC's "Shark Tank" posted. "Expect a mass exodus."
"Every single @realDonaldTrump hotel and golf course is toast," he continued. "Done. Over. Bernie Madoff now has a better brand."
Trump addressed the matter again in a late-night video address, offering a brief apology and saying he looked forward to the Sunday night presidential debate.
Almost immediately, Trump came under fire from those on both sides of the aisle - as many top Republicans either strongly condemned the comments or unendorsed the Manhattan billionaire altogether.
Cuban has been a Clinton supporter since he endorsed the Democratic nominee at a Pittsburgh rally in July, and he has ripped Trump repeatedly on social media and in interviews, calling him the most "dangerous" presidential candidate he could imagine during a recent interview with Business Insider. Cuban recently offered Trump $10 million to hold a four-hour policy debate with him.
Earlier in the cycle, Cuban was more sympathetic about the prospect of a Trump presidency, but he later soured following the conclusion of the Republican primary race. At various points during the campaign, he offered to serve as either Trump's or Clinton's running mate.