Debate marks latest bump in Mark Cuban and Donald Trump’s roller-coaster relationship

Donald Trump and Mark Cuban’s on-again, off-again relationship is set to reach its nadir at Monday night’s presidential debate at Hofstra University in Hempstead, N.Y., where Cuban will apparently try to rattle Trump by sitting in the front row.

Cuban, now a vocal supporter of Hillary Clinton, tweeted last week that he had received a ticket to watch the first debate. The Dallas Mavericks owner declared her first face-off with Trump would be the “Humbling at Hofstra.” He added: “It Is On!” Clinton’s campaign confirmed Monday that Cuban was still set to attend.

Trump replied in force, calling Cuban “dopey” and threatening to invite a former mistress of his Democratic foe’s husband. The woman, Gennifer Flowers, publicly accepted the invitation to join Cuban in the debate audience’s front row, but Trump’s campaign manager walked back the idea Sunday.

“Donald. Remember when you told me on the phone we were ‘Bobbsie Twins’ and I laughed?” Cuban fired back at Trump.

The two celebrity billionaires have feuded for years. Among other things, Trump has taunted Cuban’s golf game, his “physically weak” body, his intelligence, his wealth, his looks and the ratings of his shows, such as “Shark Tank” and “The Benefactor.” Trump has also tweeted that “nobody loves” Cuban, who took plenty more jabs at Trump.

However, they reached a détente in the summer of 2015, when Cuban publicly praised Trump’s freewheeling campaign, not long after it was launched. In July last year, Cuban described Trump’s White House bid as “probably the best thing to happen to politics in a long long time.”

“I don’t care what his actual positions are,” Cuban wrote then on his Cyber Dust social-media app. “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.”

“Thank you @mcuban for your nice words. I am rapidly becoming a @dallasmavs fan!” responded Trump, who had previously said he loved watching the Mavericks lose.

The back-and-forth praise continued. During the primary, Trump held a Dallas, Texas, rally in the Mavericks arena and thanked Cuban afterwards. Cuban even said he’d consider being Trump’s vice president if he were asked to join the Republican ticket.

But their relationship soured again over time. Cuban endorsed Clinton and appeared at a rally with her. And he trolls Trump constantly on Twitter. In one particularly notable stunt earlier this month, Cuban offered Trump $10 million for a charity of his choice, in exchange for a four-hour policy interview. Cuban, who has said he doesn’t believe Trump is a billionaire, added: “If you need it, I’ll write you the check and you can keep the money rather than give it to charity.”

Cuban also recently predicted that the stock market would tank if Trump wins the presidential race.

“I know Mark. And the problem with Mark, he’s not smart enough to understand what we’re doing. He’s really not smart enough, in my opinion, to understand what’s going on,” Trump said in response, speaking on Fox Business, hours before Cuban offered $10 million to him.

“I’ve known him for a long time. He tweets me all the time. He sends me so many tweets.”

Additional reporting by Liz Goodwin.