“My Bad”: Trump’s Billionaire Rubes Keep Getting Conned

There’s no polite way to say this, so let’s go with the truth: Some of the richest, smartest guys in the room keep getting hustled by the guy who sold steaks at Sharper Image.

Complete transparency: I’ve never been a big fan of Bill Ackman or Jamie Dimon, but for years, Wall Street worshiped these dudes like they were the Doublemint Twins of the Oracle at Delphi. Then, Donald J. Trump walks in sporting his red tie, sizable paunch, and vengeance agenda, and these wizards of finance lose their sight in the blinding light of a fake orange tan.

It took less than 100 days of Trump’s second term to shake the markets and the confidence and reputation of two of the President’s highest-profile billionaire cheerleaders, who are now clutching their pearls on CNBC and Twitter. Pardon me, X.

The punchline? They’re not victims. They’re not even bystanders. They’re rubes. They backed this chaos, wrapped it in corporate speak, and sold it to investors as “business-friendly policy.” Now, they feign surprise when the man who promised tariffs governs the country’s economy like a drunk uncle trying to find his keys at the end of a long night.

Ackman: From MAGA Curious to MEGA Sucker

In late 2024, hedge fund magnate Bill Ackman flirted hard with Trumpism. He went full DEI-deranged, making culture war cameos on X and voicing support for Trump’s delusional economic claims. After the election, he told Bloomberg:

“President Trump understands markets. He knows what drives business confidence.” — Ackman, November 2024

It turns out that Trump doesn’t traffic in that kind of “confidence.”

By April 2025, Trump’s chaotically careening tariff policy made Mr. Toad’s wild ride look like a Sunday drive. The pandemonium sparked global retaliation, and the ensuing panic erased trillions in market value. It appears Ackman didn’t realize the MAGA crew had picked his pocket until after his Pershing Square Holdings lost almost 14 percent of its value.

He wrote:

“We are in the process of destroying confidence in our country as a trading partner, as a place to do business, and as a market to invest capital.” — Ackman on X, April 2025

He snivelingly warned that an “economic nuclear war” was on the horizon and Trump’s trade policy would freeze business investment and consumer spending (Business Insider).

Really? Dude, my retirement account could tell you that.

Dimon: From “Pro-Business” to Amateur Hour

Jamie Dimon, JPMorgan Chase CEO and part-time philosopher king of Davos, also gave Trump the benefit of the doubt last fall. Despite Trump’s first-term record of trade wars and market spasms, Dimon told a room of gullible CEOs:

“We may not agree on everything, but Trump’s pro-business instincts are sound. He gets things done.” — Dimon, October 2024

Fast forward 100 days, and the financial turbulence begins to shake a few of Dimon’s brain cells back to life.

“The potential positives of tax reform and deregulation [are being] outweighed by the negatives of tariffs and trade wars, ongoing sticky inflation, high fiscal deficits, and volatility.” — Dimon’s 2025 Shareholder Letter

Translation? The memories of Trump’s many bankruptcies have turned the “gets things done” energy into a full-blown economic migraine.

Dimon has begun hedging his bets with bipartisan platitudes as it dawns on him that Satan “gets things done” too, but that doesn’t mean he should run the world’s largest economy.

Sucker Punched But Not Surprised

The market’s reaction was swift. After the Trump tariffs went into effect, the S&P 500 took a beating. Analysts estimate that $6 trillion in market value has been wiped out since Trump’s inauguration (The Guardian).

Investors are rattled. Trade partners are retaliating. And thanks to rising import costs, inflation is back on the menu, boys.

Scrambled eggs, anyone?

They Know Better: Greed Made Them Stupid

Here’s what’s maddening: these guys know the facts. They know markets, GDP growth, and corporate profits have historically performed better under Democrats.

• S&P 500 returns have averaged ~10.6% under Democratic presidents, compared to ~4.8% under Republicans (Forbes).
• Job growth, consumer confidence, and corporate earnings are more stable and stronger under Democratic leadership.
• Trump’s first term was marked by chaotic trade policy, ballooning deficits, and attacks on the Fed — not exactly the recipe for long-term growth.

Ackman and Dimon didn’t get conned because they lacked information or knowledge. They got conned because Trump and his crew know the first rule of the con: Feed their greed. Ackman, Dimon, and the other billionaire rubes believed they could beat the house and then ride the volatility and profit on the margins.

They bet Trump would do just enough damage to regulations and taxes without bringing the house down. And now? They look miserably at the rubble, wondering how they got took.

Hindsight ≠ Accountability

With the damage unfolding, the public backpedaling begins: Dimon’s caution, Ackman’s angst, and Elon Musk’s muttering something vaguely libertarian while posting AI-generated memes of Andrew Jackson.

We’ve seen this grift before:

1. Billionaire backs strongman.
2. Strongman torches the rulebook.
3. Billionaire clutches pearls.
4. Repeat.

But we can’t afford this nonsense. This isn’t about earnings reports and investor calls. We’re talking about the big stuff: democracy, economic stability, and trust.

When the billionaires fund the chaos, they don’t get to sweep up and squeal, “Ewww, what a mess!”

To Be a Rube is a Life Choice, Not a Business Decision

To save them some time, I’ve drafted the next step in their redemption tour:

“My bad. I got conned — again. I thought a second Trump term would be good for my bottom line. But it wasn’t. He is bad for the markets, worse for global stability, and absolutely disastrous for trust in America’s institutions. I’ll never bet the future of our country on Trump’s three-card Monte ever again. I promise.”

Now, that would be leadership. But I won’t hold my breath. Because in the end, the rubes aren’t just in red hats. Sometimes they’re in custom suits, buying into the huckster’s hustle and believing against all rational thought that they won’t go out like a sucker.