Trump On Trump: Gambling USA 2025, It’s Going To Be A Bigly Year


SPECIAL REPORT: On the eve of Donald Trump's inauguration as POTUS 47, iGF Editor-in-Chief André Dubronski explores the likelihood of a Clash of Trump Titans over the legalisation and future of American gaming

Before the presidency, before “The Apprentice”, there was gambling and Donald Trump’s controversial Atlantic City casino empire: The Trump Plaza Casino and Tower, the Trump Marina Hotel Casino, the Trump Taj Mahal. All today demolished, sold on, renamed or ruined.

So given the controversy and chequered history–when is there never controversy concerning the Great Disruptor–it’s fair to assume that Donald Trump knows a thing or two about the success and travails of gambling — even if it’s only how to crash and burn and still walk away with paper billions.

Now, in what may turn out to be a gripping sidebar to Trump 2.0, father, U.S. president 45 and 47, and son, heir presumptive Donald Trump Jnr. are set to go head-to-head over the future spread of American gambling.

At least that’s the plausible conundrum at the heart of Regulus Partners’ latest outlook for the 2025 gambling market in the USA.

For while Donald Trump Jnr. (pictured, left), fresh off the plane from Greenland, has been appointed as an “Adviser” for markets and elections predictions betting site KalshiEx, Regulus–the leading gambling, sports and leisure data-driven analysts–say his father’s new administration is all set to reel-in the more exotic hybrids of the nation’s iGaming firmament — be they DFS 2.0, CFD’s, sweepstakes casinos or quasi-legal prediction sites like Kalshi and Polymarket, who also take wagers on the bond market, currency fluctuations, the rise and fall of cryptocurrency, et cetera.

For those confused or confounded by this plethora of acronyms, DFS represents Daily Fantasy Sports, as pioneered by DraftKings and Flutter’s FanDuel; while CFD means Contract For Difference, being a short-term financial contract that pays the difference between the opening and closing price of a trade.

Anti-woke Crusader

Kalshi, headed by Co-founder Tarek Mansour, and similar so-called “grey area” betting operators have long-been in the eye of the federal Commodity Futures Trading Commission (CFTC), who have been waging a long battle on trying to ban this form of betting on elections, sporting contests, award shows et al.

The issue has been extensively covered in these pages by iGamingFuture.

Kalshi, for example, won an important legal injunction in the run-up to the recent Trump-Harris presidential and wider elections, which allowed them to accept around US$100 million (£81.96m) in wagers on outcomes.

KalshiEx, again under scrutiny, was one of several prediction markets who went for a Trump win
Donald Trump Jnr. has since confirmed that he used “Kalshi on election night to track our victory in real time.”

“It was obvious,” crowed the president’s heir, “that prediction markets were going to upend mainstream media.

“I’m thrilled to be joining them.”

But the self-avowed anti-woke crusader and MAGA acolyte, who sits on a clutch of conservative business boards, is now on course to clash with his father’s administration, if not the man himself.

Power Broker

The CFTC has in no way caved in its fight with Kalshi and battle to bring the wider prediction market to federal heel.

Under the 2010 Dodd-Frank Wall Street Reform and Consumer Protection Act, the U.S. Congress prohibited “contracts tied to terrorism, assassination, war, gaming or activities banned by federal or state law”.

And the specifics of what contracts are covered by the ban were left in the power and determination of the CFTC.

They argue that Kalshi has transformed its futures exchange “into an online casino”.

Kalshi’s latest punts concern which power brokers will attend President Trump’s inauguration and the odds of the U.S. fulfilling his ambition to buy Greenland, the Danish autonomous territory so recently visited by his son and namesake.

“We believe that 2025 has started with a critical mass of U.S. legal workarounds for quasi online gambling products reaching a tipping point that is overwhelming the state-by-state solution,” Regulus warned in their start-of-the-year overview.

“The generally pro-gambling nature of the incoming administration actually increases the likelihood of action, in our view, because gambling stakeholders will be listened to.

White Knight

“Initially, the federal government might just seek to clarify what is not allowed, but governments rarely stop there; even right-wing governments that want to be small.

“If the Feds do start to intervene, and we believe that they have been left with little choice, then 2025 could be a defining year for US gambling.”

Defining and quite possibly a year of definitions because at the moment CFDs are subject to a different legal framework than traditional retail casinos, online sports books and iCasino operators.

And this makes it much more difficult to stop licenced CFD operators, such as Kalshi and off-shore Polymarket from offering sports-related products and thus negates the regulatory powers of individual U.S. states to control–and tax–betting in their territory.

Undoubtedly, sweeping new legislation and a White Knight are needed to clean-up the labyrinthine legal mess of American gambling.

But that knight is unlikely to be Donald J. Trump Jnr., like his father a Lord of Disruption, who revels in the grey zone of uncertainty and encumbent opportunity.

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