WASHINGTON, D.C. — 47th President Donald J. Trump has reportedly been caught blatantly cheating during a friendly—but increasingly hostile—game of Monopoly with several of his top officials. Participants in the now-infamous game night included Speaker of the House Mike Johnson, Senator Ted Cruz, Health Secretary Robert F. Kennedy Jr., White House Press Secretary Karoline Leavitt, and Defense Secretary Pete Hegseth.
According to multiple witnesses—and an unfortunately still-live Truth Social stream—the game began normally, until Trump unilaterally declared that “going to jail” applied to everyone except the President, citing “Article 7 of the Monopoly Constitution,” which Hasbro scholars later confirmed does not exist. “Presidential immunity,” Trump insisted, “means I don’t go to jail. Only Democrats go to jail. That’s how the game works. Read the rules, folks. I know the rules better than a man with a monocle that looks like he could be the uncle of the Pringles guy.”
Trouble escalated when Trump began collecting rent on properties he didn’t own, including Boardwalk, which he insisted “has always been Trump property” and renamed “Mar-a-Walk.” He also reportedly changed the rules mid-game, requiring every other player to pay him a “Trump Toll” every turn or risk going directly to jail—a move Senator Cruz called “innovative,” while Karoline Leavitt nervously laughed and asked if this counted as an executive order.
Health Secretary RFK Jr. allegedly attempted to challenge the rule change but was overruled by Trump who then demanded Kennedy prove his vaccine status before being allowed to roll the dice.
This Monopoly debacle mirrors Trump’s long, storied history of less-than-creative rule-bending. A man who has filed bankruptcy in real life more times than he’s claimed if Ivanka weren’t his daughter, they would be dating (at least six times), Trump declared Chapter 11 mid-game a total of twenty-four times, each one strategically used to avoid paying rent, fines, or debts to other players whose skin looked any shade darker than Trump’s. “That’s called winning,” Trump shouted. “It’s what smart businessmen do. I’m the best at business. No one’s ever done business better than me.”
Trump then abruptly swapped out a handful of Deal Action Cards with a suspiciously well-preserved stack of Jeffrey Epstein’s old business cards, claiming they could be used as a “special Get Out of Jail Free” mechanic. According to his newly invented rule, players could have their token “commit suicide under mysterious circumstances,” instantly escaping jail but forfeiting all their properties—which, naturally, would be seized by Trump as part of his “executive liquidation package.”
This Monopoly fiasco follows a leaked video from Scotland, where Trump was caught (once again) cheating at golf—his one true sport of choice—when his caddy was seen dropping a ball in a better position, just feet from Trump himself. “The wind moved it,” Trump claimed later, despite the wind’s well-documented lack of opposable thumbs.
Trump’s history of cheating at games is so extensive it’s practically a sport of its own. He famously plays checkers like it’s chess, declaring his pieces “kinged” as soon as they hit the board, and moving in whatever direction his ego demands. In Connect Four, he’s been known to scream “I WIN!” when only three red chips are aligned, insisting the fourth one is “on its way” and that “counting is a liberal conspiracy.”
This pattern of rule-breaker and fantasy economics earned him the nickname “Commander in Cheat”, a title immortalized on the cover of a book by author Rick Reilly and frequently referenced by celebrities such as Samuel L. Jackson, who both publicly accused Trump of cheating during golf matches.
In the final moments of the Monopoly match—despite draining the bank reserves to fund his never-profitable empire, logging two dozen bankruptcies, and still somehow holding zero dollars—Trump “accidentally” knocked over the entire board and triumphantly declared the game a draw.
“Look,” he said, gesturing to Ted Cruz to clean up the mess, “I’m the best businessman here. Everyone knows it. I was just about to win—you all saw it. People are saying it. A lot of people. But I’m not the kind of guy who needs to win every time, even though I could. And I do a lot of winning. Too much, in fact. But I’m a good guy. Some say the best. I don’t say that—others say that. But sometimes it’s better to call it a draw than to win while everyone else loses. Like the democrats. They have got to be sick of losing by now. They do a lot of losing.”
At press time, White House Press Secretary Karoline Leavitt attempted to make sense of Trump’s words but cut the press meeting short by kicking out the Wall Street Journal and telling those who remained that Trump will be selling a special Mar-a-Lago Collector’s Edition of Monopoly on the official White House website. This “special” edition of the classic board game comes with gold-plated tokens of the classic shoe and top hat, and replaces the original 28 original property cards with 27 Mar-a-Lago cards and 1 Little Saint James property foil card.
