I started as a dealer in 1992. Back then, the question I got asked more than any other, at parties, at family dinners, by people who’d just found out what I did for a living, was whether the casino cheated. Not whether gambling was risky. Whether the game itself was rigged. People genuinely believed it. I defended the industry then, and I still defend most of it now, but for reasons that have almost nothing to do with why I defended it in 1992.
Gambling and dishonesty have been walking together since long before either of us showed up. It isn’t because gambling is some special breeding ground for evil. It’s simpler than that. Gambling combines three things that dishonest people have always found irresistible: money, hope, and imperfect information. Crooked wheels. Fake lotteries. Bookmakers who vanished the moment they owed you money instead of the other way around. Organised crime treating casinos as a laundromat, sometimes literally. Match fixing that nobody wanted to admit was happening because admitting it meant the whole sport was compromised. None of this was a phase the industry went through. It was the starting condition.
Governments eventually did something about it, and it’s worth being honest about why, because the polite version of the story, that regulators showed up to protect consumers out of some civic instinct, doesn’t hold up. What actually happened is that governments arrived at three uncomfortable conclusions at more or less the same time. Gambling cannot be prohibited successfully, no matter how hard anyone tries. It generates enormous tax revenue, which nobody in government has ever been able to walk away from for long. And left alone, it attracts exactly the wrong people, every time, without exception. Put those three facts together and regulation stops being a moral choice and becomes the only workable one. Licensing. Standards. Testing. Internal controls. Surveillance in every corner of the floor. It took decades to build something a regulator could actually stand behind, and it worked about as well as anything built by government ever works, which is to say slowly, and only after enough people got hurt that ignoring it stopped being an option. Land-based casinos, properly licensed ones, became probably the most transparently operated gambling product on the planet. A slot machine on a casino floor today is tested, certified, and audited more rigorously than most of the medication in your bathroom cabinet.
And that’s exactly the moment gambling stopped needing a building.
Nobody marked the date. Everybody was too busy talking about technology, about convenience, about a customer who no longer had to drive anywhere to lose money. Almost nobody was talking about enforceability, which turned out to be the only question that mattered.
A land-based casino has an address. It has owners you can name, employees you can interview, regulators who can walk the floor, inspectors who can pull the cameras, assets that can be seized if it comes to that. An online operator might have a company registered in Curacao, servers sitting somewhere else entirely, customers spread across forty jurisdictions, and payments routed through processors who have never seen a gaming license and never will. The regulator who used to walk into a building now has to regulate the internet, and the internet was not built with regulators in mind, or with much of anything in mind beyond moving money quickly.
Here’s the part the industry understood before the regulators did, and understood fast. Technology moves faster than law. Money moves faster than regulation. Jurisdiction moves slower than both of them combined, because jurisdiction requires agreement between governments, and governments agree on almost nothing at the speed money travels. The companies figured this out almost immediately. Some are still enjoying the gap. Regulators, for the most part, are still trying to find where it started.
It’s worth being specific about why the regulator can’t catch up, because it isn’t for lack of trying, and it isn’t really a story about incompetence. A land-based regulator inspects a building that isn’t going anywhere. An online regulator is chasing a company that can reincorporate, rebrand, and relaunch faster than a licensing hearing can be scheduled. The American Gaming Association, hardly a body with an incentive to overstate the problem, estimated last year that unregulated gaming devices, offshore sportsbooks and illegal online casinos generate close to fifty four billion dollars a year in the US alone, costing states more than fifteen billion in tax revenue they’ll never see. That figure comes from the industry’s own trade association, the people who represent the operators paying for licenses, audits and compliance departments, watching a shadow version of their business grow next door with none of the overhead. If the legitimate side of the industry can’t get ahead of it, a regulator with a fixed budget and a annual reporting cycle stands no chance.
And then there’s the question nobody in a regulatory hearing likes to ask out loud, which is whether the political will to fix any of this actually exists. It’s worth remembering how most gambling expansion happens in the first place. States don’t legalise casinos because they’ve had a change of heart about gambling. They do it when the budget is tight and a tax base that doesn’t require raising income or sales tax suddenly looks very attractive. That’s the honest version of the legalisation story, and it explains a great deal about how enforcement gets funded once the ribbon is cut. The gambling industry spent close to fifty million dollars on federal lobbying in 2025 alone, and that’s before you count the state level campaigns, the ballot initiatives, the local commissioners who end up sitting across the table from the same companies they’re meant to be scrutinising. None of this is illegal, and most of it is disclosed. But a regulator whose agency depends on the tax revenue of the industry it’s regulating, in a political environment where that industry is also a major campaign donor, isn’t operating with a great deal of independence, and pretending otherwise doesn’t help anyone.
What you get from all this isn’t one industry. It’s several, wearing the same name, and it’s worth looking at what each one has actually done, not what it says it does.
Take the layer of large licensed operators, the ones with real offices and real audit committees. Mostly compliant. Sometimes pushing right up against the edge of what the license allows. Occasionally treating a fine the way a retailer treats a shoplifting rate, a cost of doing business that gets built into the model rather than something to eliminate. William Hill is a useful case study here, mostly because it managed to get caught doing the same thing twice. In 2018 the UK Gambling Commission fined the company over six million pounds for letting customers deposit hundreds of thousands of pounds with nothing more than a verbal assurance about where the money came from. One customer put through over six hundred thousand pounds without a single source of funds check. Five years later, having presumably had time to reflect, William Hill was fined again, this time north of nineteen million pounds, for what the regulator called widespread and alarming failings. A customer opened an account and spent twenty three thousand pounds in twenty minutes without anyone asking a single question. That isn’t a company that didn’t know the rules. That’s a company that ran the numbers and decided the fine was cheaper than the friction. Call it evolution if you’re feeling generous. I’d call it a business model with a line item for regret.
Evolution Gaming, the live casino supplier that most of the industry’s biggest online brands rely on for their roulette and blackjack streams, offers a stranger version of the same problem, because it isn’t clear which layer it belongs to, and the company itself has spent years insisting the answer is Layer 1. In 2021 an anonymous report accused Evolution of allowing its games to be accessed in sanctioned countries including Iran, Syria and Sudan, along with markets where online gambling is simply illegal, such as Hong Kong and Singapore. The stock lost about three billion dollars in value in a single day. Evolution denied everything, and in 2024 New Jersey’s Division of Gaming Enforcement closed its investigation and found no evidence to support the claims. Case closed, reputation restored, business as usual. Then in 2025, a private intelligence firm filed secretly recorded footage into a New Jersey court, as part of a defamation suit Evolution itself had brought, appearing to show current and former executives describing exactly how the company’s games ended up in those same sanctioned markets, and in China, where gambling is illegal outright. Evolution says the footage is being misrepresented. Maybe it is. But a company doesn’t get investigated, cleared, and then re-accused with its own executives on tape unless the underlying question, whether anyone is actually checking who’s on the other end of a live dealer stream, was never really answered the first time. It was just answered quietly enough that everyone could move on.
Then there’s a layer with no real intention of complying with anything, operating wherever the door is open, closing that door and opening another the moment it isn’t. New domains. Affiliate networks that provide just enough distance for plausible deniability. Mirror sites that reappear within days of being shut down, under a name that means nothing and a license that means less. Crown Resorts, somewhat inconveniently for a company with its own name on two of the largest casinos in Australia, spent years running this playbook while looking, from the outside, like a Layer 1 operator in a nice suit. A public inquiry found the company had facilitated money laundering for organised crime through junket operators for years, and a subsequent royal commission described the conduct in a single word that regulators almost never use in official findings: disgraceful. Crown was eventually fined eighty million Australian dollars over one scheme alone, moving money out of mainland China through disguised card transactions. The company kept its licenses. It always does. Losing them would mean admitting the whole system depends on operators nobody can actually replace, which is a sentence regulators try very hard not to say out loud.
And there’s a third layer, the cleverest one, that doesn’t need to worry about most of this because it has stopped calling itself gambling in the first place, and right now it’s the layer worth watching most closely. Kalshi is the clearest example running. It offers what it calls event contracts, essentially a yes or no bet on whether something will happen, including, since early 2025, sports outcomes. Whether the New York Jets beat the New England Patriots on Thursday is, depending entirely on which regulator you ask, either a federally regulated derivative or a straightforward sports bet dressed up in different paperwork. Kalshi holds a designation from the Commodity Futures Trading Commission as a contract market, and argues that gives the CFTC exclusive jurisdiction, leaving individual states with no say at all. Nevada, New Jersey, Massachusetts, Connecticut, New Mexico and New York have all disagreed, loudly, and the results in court have been a genuine mess. Federal judges in Nevada and New Jersey have sided with Kalshi. A federal court in Maryland was unconvinced. A Massachusetts state court called Kalshi’s position overly broad and moved to block it, only for an appeals court to pause that ruling pending further argument. New York’s Attorney General is currently pursuing a thirty six billion dollar enforcement action, while the CFTC itself has gone to court to stop New York from enforcing its own gambling law against a company the state considers to be running unlicensed sports betting for anyone with a smartphone. The CFTC’s chairman has publicly described state efforts to apply gambling law here as an attempt to nullify decades of precedent. Forty four state attorneys general have written back saying, in effect, that the CFTC has no business regulating this at all. Nobody currently agrees on which regulator, if any, is actually in charge, and Kalshi has kept operating sports contracts in most of the country while the argument plays out. The product doesn’t change depending on which building you’re standing in when you place it. Only the label does, and right now the label is winning most of the arguments that matter.
None of this happened in a vacuum, and I don’t think it’s fair to lay it entirely at the industry’s door. Society’s tolerance for being lied to has changed since 1992, and it’s changed a great deal. Companies lie and absorb the consequences as a line item, which is exactly what William Hill did, twice. Governments lie and the news cycle moves on before anyone can hold the thread. Apologies have become a genre of public relations rather than an admission of anything, and Crown’s own statement about its “historical failings” is a small masterpiece of the form, since it manages to describe money laundering for organised crime the same way a company might describe an outdated logo. Fines have become a modelling exercise, run through a spreadsheet before the violation even happens, to see whether it’s cheaper to comply or to pay. Reputation, which used to take years to rebuild, now seems to reset itself every eighteen months or so, once the news cycle finds something newer to be outraged about. The gambling industry didn’t invent any of this. It’s simply operating inside it, and in some corners, reflecting it back with unusual clarity.
Which brings me to the question I actually can’t answer comfortably, and the one the industry talks around constantly without quite landing on. AML. KYC. Integrity programmes. Responsible gambling messaging plastered across every website and every advertisement. All of it necessary. None of it in question. But somewhere underneath the acronyms sits a harder question than any of them are designed to answer. Are we becoming a more honest industry, or have we simply become far more skilled at discussing honesty, in the language regulators want to hear, while a live casino supplier gets cleared of one sanctions investigation only to be caught on tape describing the exact thing it was cleared of, and a company offering sports bets under a different name spends its energy suing the regulators trying to stop it rather than answering the underlying question of what it’s actually selling.
Thirty years ago, people asked me whether casinos cheated, and at the time I thought the answer was fairly straightforward. I still think most properly regulated land-based casinos deserve a great deal more credit than the public gives them, and I’ll defend that position anywhere. What I’m far less certain of is whether the same can still be said of the gambling industry as a whole, in every form it now takes, under every name it now operates under, and under every label its lawyers have decided this year is the one that keeps a regulator out of the building.
Those stopped being the same question a while ago. I’m not sure enough people have noticed yet.
