Crazy Rich Insider Traders
By Neil Rose, CFA
The rules stopped applying.
I don’t know what’s more surprising about the current surge in insider trading: the volume, the brazenness, or the transparency of it all.
Donald Trump and his family (and some new allies and friends) have raked in billions since the 2024 election. Self-dealings and conflicts of interest don’t apply, apparently. Foreign policy favors and presidential pardons have come with huge windfalls for the real estate, investment, and crypto operations of the Trump Organization.
Two years ago, and in the face of a $500 million civil penalty, Donald Trump claimed he was running out of cash. He argued in a court filing that if his penalty wasn’t reduced to $100 million, he’d have to sell off his real estate assets.
Presidents used to avoid conflicts of interest. George W. Bush sold his ownership of the Texas Rangers before becoming president. Jimmy Carter put his peanut farm in a blind trust. Different times.
Less obvious are the big gains from insider trading in and around the White House. While nothing has been pinned just yet (strange given the Securities and Exchange Commission and the Commodity Futures Trading Commission know who trades what), knowledge of Trump’s imminent actions—including specific policy announcements, military developments, and even words Trump will or won’t utter, to name a few—has been used to place big, profitable bets in stock futures, oil futures, and the online prediction markets, Kalshi and Polymarket.
(Yes, you can bet on whether certain words will be mentioned during a specified event or time period by politicians, celebrities, sports broadcasters, etc.)
In March 2026, roughly $580 million in oil futures changed hands in a single minute, about fifteen minutes before President Trump posted to Truth Social that the U.S. and Iran had held productive talks and that military strikes were being paused. S&P 500 futures saw a simultaneous surge of over $2 billion in notional value. Oil tumbled. Stocks rallied. Exactly who was behind the trades is knowable but no one has been outed—or even seriously investigated.
Public outrage hasn’t risen above a simmer. This kind of stuff isn’t shocking anymore. And why protest when you can just download an app and join?
While the new era of insider trading has accelerated since the 2024 election, it started years before. For years, members of Congress have increasingly profited from their access to privileged information. Apparently, they are immune from insider trading laws; their only obligation is to disclose trades within 45 days. Their portfolio returns have been staggering to the extent one compelling explanation stands out: insider trading.
The internet has noticed. Numerous tracking websites, apps, and ETFs have emerged, allowing investors to follow specific members of Congress (albeit with a 45-day lag).
Among the biggest following belongs to one of Congress’s most successful traders: Nancy Pelosi and her husband Paul. Autopilot’s Nancy Pelosi strategy alone has over $500 million today.
Meanwhile, who gets in trouble? The Special Forces soldier betting $33,000 over a dozen trades on a Polymarket contract on Nicolás Maduro’s removal from power in Venezuela. His trades reportedly paid out $400,000.
The new era of insider trading only adds to the precarious state of a historically expensive stock market. Market tops have always been marked by an increase in financial shenanigans and fraud. Could the current bull market end with an insider trading wave on top of an online gambling and sports betting epidemic?
But the real danger and risks might be more structural and longer term. A major contributor—the major contributor—to the strength of U.S. markets and the dollar over the years has been a long-term, compounded trust in the U.S., one rooted in America’s strong and consistent rule of law. To a person, business, or country, growth and success over the long term only comes if it is deserved.
I think about this a lot lately. The adage keeps coming to mind: it takes years to earn trust and seconds to lose it.
America and market-based economies are not bulletproof. If the U.S. loses enough trust, it could be deemed undeserving—as a destination for investment, as home of the world’s reserve currency, as a trade partner, as a reliable ally.
I wish those in power would think about this, too, instead of finding ways to tap into America’s credit for personal gain.
This material is for informational purposes only and does not constitute investment, tax, or legal advice. The views expressed are those of the author and not necessarily those of Regency Capital Management.
About the Author
Neil Rose, CFA, is the founder and CEO of Regency Capital Management.
