Sydney Said No to Trump Over ‘Mafia Connections’ - New Jersey Said Yes

In 1987, Aussie regulators said Trump was too mobbed-up for Sydney. The U.S.? They gave him a license and looked the other way

G’ Day! Wanna hear another CRAZY story about Donald Trump?

My Australian readers are gonna love this one! What a bunch of losers!

Back in 1987, while Trump was busy collecting headlines as New York’s golden-haired real estate prince, something interesting happened on the other side of the world. Australia took one look at his casino application and said “absolutely not.”

I came across a story about the declassified documents from New South Wales - which are brutal in their directness. No diplomatic hedging or bureaucratic soft-pedaling - just a flat declaration that Trump’s “mafia connections” made him too dangerous for their casino industry. The police board didn’t mince words: “Atlantic City would be a dubious model for Sydney and in our judgment, the Trump Mafia connections should exclude the Kern/Trump consortium.”

This was 1987, mind you. Trump was just 40 years old, only five years after New Jersey licensed him to run casinos. Yet Sydney’s police board had already seen enough to recommend shutting him out of the city’s first casino. The man who’d later brag about his casinos got shut out before he could break ground.

Meanwhile, back in the good old USA, regulators were apparently taking a very different approach. Trump’s Atlantic City operations racked up money laundering violations that would make a mob accountant blush. The Trump Taj Mahal alone broke anti-money laundering rules 106 times in its first year and a half, according to the IRS - earning a $477,700 fine in 1998 that was, at the time, the largest the federal government had ever slapped on a casino.

But wait, there’s more.

In 2015 - years after Trump had given up running it, though his name was still on the building - federal regulators hit the Taj Mahal with another $10 million penalty for “willful and repeated violations” of money laundering laws between 2010 and 2012. That’s not exactly a learning curve - that’s a pattern stretching across decades.

The contrast is hilarious. While Australian officials flagged organized crime connections as disqualifying, American regulators seemed content to issue fines and move on. The Taj Mahal became what federal investigators called the “preferred gambling spot for Russian mobsters living in Brooklyn.”

That quote got me thinking - should I do a deep dive on Trump’s mob connections? Let me know in the comments.

Anyway, Trump Plaza got fined for accommodating Robert LiButti, a gambler barred from casinos over alleged organized crime ties - $450,000 for a car scheme to refund him $1.6 million, and $200,000 for pulling Black and female dealers off his table because he asked. Can you believe it? I can!

Australian authorities weren’t wrong to be suspicious. The warning signs were all there if anyone cared to look. He paid $1.1 million for an Atlantic City lot sold by a pair of hitmen for mob boss Nicky Scarfo. Federal records from those years show the IRS catching the Taj Mahal breaking cash-reporting rules, and FBI reports about payoffs around his Atlantic City land deals.

Yet somehow, Trump kept operating casinos in America while being deemed too risky for Sydney’s first casino. It’s almost as if one country’s regulators were doing their job while the other’s were told to look the other way.

The timing makes this even more damning. This international recognition of criminal ties came decades before Trump’s documented violations reached their peak. If foreign investigators could spot the red flags in 1987, what were American regulators doing all those years?

The Australia rejection reveals something uncomfortable about how regulatory capture actually works in practice. It’s not always dramatic backroom deals or briefcases full of cash - sometimes it’s just institutional blindness to evidence that other countries find completely disqualifying.

Trump eventually assembled a casino empire that went through four bankruptcies and accumulated violations that any reasonable oversight body would find alarming. But he did it all with the blessing of American regulators who somehow missed what Australian investigators spotted immediately.

Oh, and while Trump’s casinos were hemorrhaging money and violating federal laws, he personally made millions through management fees and bonuses. The house always wins, but in this case, the house was Trump himself - not the actual casinos bearing his name.

Anyway - Australia was smart enough to figured all this out in 1987 with a simple background check. Turns out all it took was regulators who weren’t on the payroll - or at least weren’t pretending organized crime connections were just a quirky personality trait. And who knows how many scams Trump may have run on Australians if he had gotten a foothold in their country? Luckily, they saw the writing on the wall and said, “Um, yeah, so it’s gonna be a no from us!”

Correction, October 7th, 2026: The title first said Australia banned Trump - one Australian state, New South Wales, turned down his bid for Sydney’s first casino in 1987, after its police board pointed to his “Mafia connections.” This post also said he was 41 and barely a decade into casinos (he was 40, five years after New Jersey licensed him), that LiButti wagered millions with fake identities and shell accounts (Trump Plaza was fined over a car scheme to refund him and for pulling dealers off his table at his request), and that the 1998 Taj Mahal fine was the largest ever for a casino (it was the largest at the time). Lines about a Trump quote, mob-tied subcontractors, federal files that repeatedly flagged the casinos, and unpaid contractors were cut back to what the record shows.

Update, October 7th, 2026: The line on the 2015 Taj Mahal fine now notes Trump had given up running it by then, and the 106 violations are credited to the IRS.