In this episode we untangle how a single photograph of President Volodymyr Zelenskyy’s black jacket became a $150-million flash-point on Polymarket, the largest crypto prediction exchange.

The platform’s “optimistic oracle,” UMA, stalled three times on the question of whether Zelenskyy had “worn a suit before July,” then looked ready to rule No, even as mainstream outlets ran headlines calling the outfit a suit.

We explain how UMA’s four-code voting system works, why one wallet with 1.3 million UMA tokens could swing a verdict, and how similar whale manoeuvres upended a $7 million Ukraine-minerals wager in March and forced Polymarket to over-ride its own oracle in last year’s Barron-Trump meme-coin dispute.

The episode also charts Polymarket’s meteoric rise, from billions in 2024-election volume to a 2025 funding round that puts the company’s valuation above $1 billion, and asks what happens to “truth on-chain” when the incentives, the rules, and the money all point in different directions.

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00:00 Opening – The Jacket That Launched a $150M Bet
02:15 Act 1: The Bet – A Gold Badge and a Sure Thing
12:30 Act 2: The Oracle – Why UMA Keeps Saying “Too Early”
25:00 Act 3: Precedent Problems – Whales, Flips, and Overrides
35:40 Act 4: Retail Risk – How Clear Rules Could Fix It
43:00 Credits & How to Support the Show