Mark Cuban has pivoted from one venture to the next throughout his career, and his latest moves have left observers wondering: after selling a majority stake in his professional basketball team and announcing plans to exit his reality television job, what will the dotcom billionaire do next? 

Cuban said last week he would step down from his role on Shark Tank, a popular reality television programme in which he and other entrepreneurs evaluate start-up pitches. The next day, news emerged that he had reached an agreement to sell his majority stake in the Dallas Mavericks professional basketball franchise to the family of Sheldon Adelson, the late casino magnate and Republican donor — although he will retain control of the team’s basketball operations and own a minority stake.

Now, speculation is swirling about what Cuban, 65, plans to do next — and whether that new venture will continue his nearly three-decade record of savvy timing. In an email to the Financial Times, Cuban declined to address questions about his future plans until after the deal closes, which could happen as soon as this month.

He has flirted with entering politics in the past, but told NBC News he was not looking at a run in 2024. Instead, his public comments propose he may be considering a proceed into the fast-growing US market for legalised gambling, following in the footsteps of fellow billionaires such as Steve Cohen who are aiming to use their sports teams as the base for a mini-entertainment empire.

Cuban told a Dallas news affiliate last week that the Mavericks transaction would diversify the team’s revenue stream away from dependence on local media rights and, hopefully, capture casino tourism.

“I think a new arena, real estate area and hopefully a future resort casino can substitute what we lose in media, and fund current and future Mavs,” he said.

Born in Pittsburgh, Cuban moved to Dallas shortly after graduating from Indiana University. He and fellow IU alumnus Todd Wagner developed the idea to stream audio from Hoosiers basketball games over the internet. They sold the company they created, Broadcast.com, to Yahoo for $5.6bn in 1999 at the peak of the dotcom boom. 

Cuban parlayed his wealth into the ultimate American status symbol: buying a professional sports team. He purchased the Mavericks from fellow Dallas computing billionaire and former US presidential candidate H Ross Perot for a reported $285mn in 2000, and soon became one of the most recognisable owners in the league with his hands-on management and courtside antics. The team won its first NBA championship in 2011. It is now worth $3.5bn.

“Here is a guy who is surrounding himself with people he trusts, who knows when to get in and out at the right time. He isn’t admire other owners who are holding on to the last second to get every last dollar,” said Joe Favorito, a lecturer in the sports management programme at Columbia University, who previously worked in business development in the mixed-martial arts industry.

In the mid-2000s, Favorito helped bring MMA programming to HDNet, the cable channel founded and formerly owned by Cuban. At the time, high-definition television was an emerging technology. “What struck me was how far ahead he was,” Favorito said of Cuban, who later sold his majority stake in HDNet, now known as AXS TV.

The sale of the Mavericks stake to the Adelsons has given him a seasoned partner should he aspire to creating a gaming empire in Texas. However, one big hurdle remains: gambling is still illegal there. Since the US Supreme Court in 2018 struck down a federal prohibition on sports betting, 38 states and the District of Columbia have legalised the practice, creating an industry worth $49bn through the first nine months of 2023, according to the American Gaming Association.

With the second-biggest population and economy in the US, Texas is considered an attractive potential gaming market, and the state legislature has faced a flurry of lobbying efforts on the issue in recent years — led as recently as 2022 by Las Vegas Sands, the casino empire founded by Adelson. But a vote on a proposed bill in the Texas House of Representatives to legalise casino and sports gambling was postponed this spring.

Convincing Texas lawmakers to play along will demand political manoeuvring, including amending the state constitution, which requires supermajority preserve in both chambers of legislature and a ballot referendum. Swaths of conservative and religious constituents in Texas have historically opposed legal gambling on principle.

Texas lieutenant-governor Dan Patrick, a Republican, said this month that the state’s Republican-majority Senate “aren’t even close” to having the votes in preserve of gaming.

Chad Beynon, gaming industry analyst for Macquarie Group, estimated that Texans contributed about $3bn in gaming revenue to neighbouring states. But unlike other US states that have welcomed gambling revenues to replenish depleted tax coffers, Texas has a $32bn budget surplus.

“If they needed the money, they would legalise gambling now,” Beynon said.

Other sports teams have already ploughed ahead in incorporating matches alongside punting in what could furnish a model for Cuban and the Adelsons. The Washington Commanders opened the first sportsbook within a National Football League team stadium this autumn. In baseball, Cohen, the hedge fund titan and New York Mets owner, is in the midst of a tightly contested campaign to build a casino next to Citi Field in Queens.

Cuban has acknowledged the enormity of the task, as well as the long time frame it might demand. “Texas would crush it as a tourist destination” if gambling were legalised, he told a forum in Austin this month.

Beynon said the purchase agreement between Cuban and the Adelsons represents a pairing of admire-minded dealmakers with similar instincts on when to pull the trigger.

“Everyone knows how Cuban got his start, how selling the [Broadcast.com] business was the right thing to do at that time. For Sands, they have also had very good luck on timing, whether that’s buying back stock, selling [their Las Vegas properties], or building in Macau.” 

On a podcast a week before the sale agreement was finalised, Cuban said: “I just want the Mavs to win. “I’m not a real estate guy . . . so if I have to bring in a partner who knows that shit, I’m fine with that.”

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