Polymarket bettor loses $650,000 wagering on Iran regime collapse
A pseudonymous trader known as "Cinibengales" has lost more than $650,000 after placing high-stakes bets on the decentralized prediction market Polymarket, wagering on the collapse of the Iranian government and the entry of U.S. forces into the country outcomes that failed to materialize as contract deadlines approached.
On-chain analytics firm Lookonchain flagged the activity on March 30, reporting that Cinibengales created a new cryptocurrency wallet on March 6, withdrew $1.5 million in USDC from the Kraken exchange, and deployed the funds into war-related prediction contracts on Polymarket. The trader took large positions on markets including "Iranian regime falls" and "U.S. forces enter Iran," both carrying short-term expiration dates.
With the "Iranian regime falls by March 31" contract now pricing the "Yes" outcome at virtually zero, Cinibengales' positions appear set to expire worthless. Despite a month of intensive U.S.-Israeli airstrikes on Iranian infrastructure, including the strike that killed Supreme Leader Ali Khamenei on February 28, the Islamic Revolutionary Guard Corps maintained control. The Assembly of Experts swiftly designated Mojtaba Khamenei as successor in early March. Polymarket traders currently place the probability of the regime surviving past the March 31 deadline at 99.5%.
The losses follow a turbulent period for Iran-related Polymarket contracts, which have recorded more than $500 million in total trading volume since the U.S.-Israeli strikes began, according to estimates cited by the BBC. In late February, another trader operating under the pseudonym "anoin123" lost approximately $6.5 million in a single day after betting against the airstrikes, wiping out months of accumulated profits. A separate wallet named "Roeyha2026" placed a $50,000 bet just 11 hours before the bombing campaign began and nearly doubled its stake, fueling debate about potential insider trading.
The Cinibengales episode illustrates a recurring dynamic on prediction markets: binary contracts can reward patience for weeks before delivering catastrophic losses when a single event fails to occur within a rigid timeframe. As NPR reported, the convergence of military intelligence, anonymous cryptocurrency wallets, and real-money prediction markets has raised fresh questions about whether platforms such as Polymarket and Kalshi require stricter regulatory oversight.
Longer-dated Polymarket contracts suggest the question of Iran's political future remains open. Markets pricing the probability of regime change before the end of 2027 currently show roughly 35% for "Yes," reflecting uncertainty about the Iranian government's durability under sustained military and economic pressure. For Cinibengales, however, the immediate verdict is unambiguous: the regime outlasted the bet.
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