I've never been much of a gambler. I think it's a waste of time, and I just don't enjoy it. Money has never gotten my pulse up. And if I'm honest, the times I've proverbially thrown the dice, I've always lost.
Every time I've sat down at a table telling myself this is the round I get ahead, I've walked away further behind than when I started. So I quit playing, and I settled on the same line every time I walked out of a casino: "What a chump!"
Turns out that's the same way I feel about this country since it was disclosed that Donald Trump made over $2 billion since his return to the White House. He's making us all feel like chumps.
The irony here is rich, and not in the monetary way. Trump failed in running casinos before (by screwing workers and others, he still made money). Anyone who held Trump Taj Mahal bonds in 1991, or Trump Plaza bonds in 1992, or watched Trump Hotels & Casino Resorts file for bankruptcy protection twice more in the years that followed, lost tons of cash.
By his own later admission, he wasn't a great gambler when the odds were real, the regulators were watching, and the competition could out-market him. Atlantic City chewed him up. The industry made him feel like, well, most likely a chump. However, he was one to begin with.
Now Trump is running a different kind of casino, and he hasn't lost a dime running it out of the Oval Office.
That's the metaphor for what's happening with his family's finances. It's bigger than some in-and-out heist. It's a 24/7 house that never loses, and a casino rigged from the top down.
It's a casino where the one man who owns the building also sets the odds, deals the cards, stops the roulette wheel when he wants, and always comes up with a 21 hand.
He's also the pit boss supposed to catch anyone cheating. He's overseeing himself, ensuring he's never held accountable.
The whole tawdry affair — that word seems far too tame — brings to mind the film Ocean's Eleven, the original with the famed Rat Pack stars Frank Sinatra, Dean Martin, Sammy Davis, Jr., and Peter Lawford.
The gist of that movie is in its attention to detail. A crew studies the vault, maps the cameras, times the guards, and pulls off something audacious against a system built to stop them.
The house is assumed to be an ironclad fortress, and beating it takes genius. That's the fictional version of a casino heist: clever people outsmarting a rigged game, a bunch of chumps who find a way to win.
What we're watching with Trump isn't that. It's the inverted version of the film. There's no vault to crack, because the man walking off with the money built the vault, owns it, and appointed the guy whose job is to guard it, himself and his regulatory lackeys.
There's no elaborate plan required when the institutions meant to say "you're under arrest,” a Republican Congress, a Justice Department under his own thumb, and an IRS permanently barred from auditing him, have already stood down. Danny Ocean needed a genius crew and a getaway plan. Trump's operation needs a Truth Social account and a crypto-coin launch.
That's what should offend every one of us about the billions the Trump family has pulled in since January 2025. It's not just the size of the number, but the fact that it defies the basic shape a con job is supposed to take.
Every heist movie, every grifter story, every dime-novel thriller runs on the same promise: eventually, someone notices and starts investigating. An audit happens. Regulators show up. The crew has to get away with it, which means, narratively, there's the cookie-cutter car chase or the airport run.
With Trump's heist, there's no chasing anyone, because nobody's coming for him. No one is auditing him. No legislation is pending to hold his feet to the fire. And under a recent Supreme Court ruling, Trump now effectively controls the regulatory agencies meant to police him.
The people who'd normally blow the whistle are all, instead, supplicating for him.
Which brings it back to the casino floor. In an actual casino, the house wins on the math, the odds are stacked, but at least they're stacked the same way for everyone who sits down. Or they're supposed to be. I've always felt they were extra-stacked against me, but I digress.
That's still, technically, a game — you versus the house. What Trump has built is a room with no other players, where the chips are meme coins and crypto tokens carrying his name, and ordinary investors buy in and lose while the house, the White House in this caper, cashes out clean every time.
Trump went bankrupt when he had to compete against others. Now he's only competing against himself. And we're all standing around the table like chumps, because his winning streak is preconceived and unstoppable.
Every reporter, news outlet, watchdog organization, and congressional committee has the receipts. What none of them have is the guts to go after him, or a precedent, because there isn't one.
By contrast, in 1952, Vice President Richard Nixon felt compelled to go on national television just to defend a gifted cocker spaniel named Checkers. America was aghast at first, but sympathetic after the “Checkers speech.”
Eight years later, Nixon lost the presidency, but his family still had Checkers. The simplicity and normality of it all.
Today, the Trump family is playing a high-stakes game of checkers, cashing in on a scale that defies reality, and making every American feel like a chump.