Donald Trump has spent the better part of 40 years mastering a single, ruthless skill: making other people absorb his losses. He perfected it in Atlantic City, where, as Fortune‘s Shawn Tully reported, his casino empire lost a total of $1.1 billion, twice declared bankruptcy, and wrote down or restructured $1.8 billion in debt, as Trump paid himself roughly $82 million.
Trump also refined his methods in bankruptcy courts over the decades, filing for Chapter 11 protection six times across his business empire and walking away from each implosion with his name still on the marquee. He brought the same instinct to international diplomacy—renegotiating NATO funding commitments, tearing up the original Iran nuclear deal, brandishing tariffs until trading partners blinked. The playbook never changed: manufacture chaos, make everyone else desperate for a way out, then collect.
Now, on the third week of an active shooting war with Iran, Trump has run headlong into something his entire operating philosophy was never designed to handle: a 21-mile-wide chokepoint at the mouth of the Persian Gulf that has no CEO to bully, no bondholder to threaten, and no shareholders to absorb the loss. The Strait of Hormuz carries roughly 20% to 25% of the world’s oil supply every single day. It cannot be restructured. It cannot be taken into bankruptcy. And right now, it is effectively closed.
