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By Nathan Guttman October 27, 2016

Sitting on CNN’s set on the sidelines of the last presidential debate in Las Vegas, Mark Cuban engaged in one of the toughest exchanges seen in this election cycle, with former New York mayor Rudy Giuliani.

This pre-debate shouting match epitomized the Dallas-based Jewish billionaire’s transformation from celebrity billionaire to one of Hillary Clinton’s most valuable political surrogates. Because Cuban is a kind of mirror image of Trump — a brash, self-billed billionaire who became a household name on reality TV — he could take Clinton’s war against him onto Trump territory.

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Cuban fought Trump on Twitter, he fought him on Fox, he fought him from the debate audience, and like Trump, he never surrenders. Indeed, the Clinton campaign put him in the front row at the debates: They saw Cuban as a useful red flag to wave in the face of the bull on stage.

Cuban had publicly flirted with the idea of his own political career. Now he says Trump has despoiled that path for every other entrepreneur who wants to trade on his or her “outsider” status to win elections. A self-declared independent who prides himself of being a pragmatic with a libertarian streak, Cuban cherishes some liberal political principles. He supported football player Colin Kaepernick’s refusal to stand during the national anthem in protest of the treatment of African-Americans by police and promised to black players of his own team if they choose to join the protest. In 2014, after referring to Trayvon Martin as “a black kid in a hoodie,” Cuban apologized to the family and made clear he acknowledges his own prejudices, and other white people should, as well.

Cuban, who believes government should have a big enough role that it could create jobs, wouldn’t be the first public figure to deny having political aspirations and end up in politics, but for now, at least, he insists that he sees himself observing from the sidelines, without entering the court.

Growing up in a suburb of Pittsburgh, Cuban was never shy about speaking his mind and getting his way. When his Jewish parents, an auto worker and a housewife, told young Mark it was time to prepare for his bar mitzvah, he replied that he’d rather spend his time at football practice. And so it was.

Cuban declined to comment for this article, explaining in an email that he is tied up in preparation for the opening of the NBA basketball season.

As is the case with any business legend, Cuban has his own entrepreneurial origin story, which he shared with Business Insider. He was 12 years old and wanted an expensive pair of basketball shoes. One of his father’s poker friends suggested he try selling garbage bags door to door. Cuban earned enough to reach his goal, and moved on to the next enterprise – selling Cleveland newspapers in Pittsburgh while the local paper was on strike. He was 16 at the time.

It was this spirit that guided Cuban throughout his career. He opened his own bar while still under drinking age. He offered disco lessons in college. He made money off chain letters in business school.

But his big break didn’t come until he moved to Dallas and got into the budding software industry in 1982. He started a company and sold it for $6 million, which he used to start broadcast.com, a webcasting enterprise. Then he sold that to Yahoo! for $5.7 billion.

Having secured his spot on the Forbes list of wealthiest Americans, Cuban moved into the entertainment business, established AXS TV satellite network, and then made his most high-profile purchase, buying the Dallas Mavericks, the beloved basketball team of his adopted hometown, in 2000 from Ross Perot.

Rich? Check. Famous? Next. On Dancing with the Stars in 2007, he showed off his disco skills only to get eliminated in the middle of the tournament. From there, he joined fellow billionaires on the cast of Shark Tank, where aspiring business owners make their pitch in the hope of winning a hefty investment from sharks such as Cuban.

Outspoken about politics, sports and business, Cuban is quieter about his Jewish life. “It’s personal. You recognize that you’re part of a long, long history. And you want that history to continue, and your family becomes a part of it,” he said in a 2011 interview with BallNRoll, an online NBA magazine.

His grandparents emigrated from Russia and changed their name from Chabenisky to Cuban, to better assimilate in the new country. He grew up in Mount Lebanon, a Pittsburgh suburb that’s comfortable, but much closer to downtown than the heavily Jewish, and affluent, Squirrel Hill. Cuban was one of only two Jewish students in his high school, and had little contact with the Jewish community. He did, however, go to Jewish summer camp, the Emma Kauffman Camp in West Virginia, which he attended thanks to a stipend from the Pittsburgh Jewish community.

He’s come far from his days as a Mount Lebanon garbage bag peddler. Last year, Cuban made it to what could easily be seen as the Jewish organized community’s A-list, when he got invited to Vice President Biden’s annual Rosh Hashanah reception.

He now donates regularly to his childhood summer camp. And he contributes an annual gift of $50,000 to the Jewish Federation of Dallas, according to a source involved in the national Jewish communal world.

But it’s impossible to know the truth about Cuban’s — or Trump’s — philanthropy. Trump has bucked more than forty years of presidential precedent by refusing to disclose his tax returns. Cuban, of course is under no obligation to do so. And he says he gives only in the way most honored by Jewish tradition: anonymously.

“I don’t want to do a mitzvah (a good deed) so people know I did it, I want to do it because it’s the right thing to do,” he said in the 2011 interview.

Back in the day, the two men, so similar in some ways, were more friendly. Before morphing into Trump’s nemesis, Cuban viewed his fellow billionaire favorably. He thought Trump’s entry into politics offered a fresh approach and praised the Donald last year for giving “honest answers rather than prepared answers” and for not being a seasoned politician. Cuban saw Trump as “probably the best thing to happen to politics in a long, long time.”

But then the bromance soured. Cuban began communicating with Trump by phone and email and found him ill-equipped and unready for the job. “What I didn’t realize he was missing at the time was a complete and utter lack of preparation, knowledge, and common sense,” he said.

When Trump won the Republican nomination, Cuban hoped Trump would change and bring on a team of professional to shape policies. But that never happened, and Cuban moved to support Clinton, in the only way he knows — blunt and provocative. “It’s rare when you see somebody get stupider before your eyes, but he’s really working at it,” Cuban said of Trump.

Trump responded in kind.

Cuban stepped into the role of Clinton’s defender and attack dog. His Twitter war with Trump even led to death threats.

As Cuban creeps closer to the political epicenter, reporters keep asking him if he’s going to get into the game as a candidate. Back in May, he was willing to entertain the idea of running for the highest office, crediting Trump’s run as an opening for others from outside politics interested in giving politics a shot. “Well, it’s certainly more of a consideration than it was,” he told NBC’s “Meet the Press.” “You don’t have to be the perfect Stepford candidate like you would’ve been in the past.”

But as the election cycle grew uglier, Cuban changed his view on possibly running for office, and on the idea that Trump had somehow helped people like him enter the ring. “There is no possible way. There’s just no way,” he said in late September, adding last week in an interview that Trump’s campaign for presidency has “made it harder for a qualified business person to run for the office.”

Contact Nathan Guttman at guttman@forward.com or on Twitter @nathanguttman

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