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The unluckiest CryptoPunk sale in history happened because of a single typo
In November 2021 the owner of CryptoPunk 7557, one of only 55 "Tiara" Punks ever made, tried to list it for 4,444 ETH which was about $19 million at the time
Instead he typed 4.444 ETH and the listing went live for $19,400 which is a 99% discount
A bot sniped it the same second, sent a 3.33 ETH bribe straight to a miner to make sure nobody else could front run it, bought the Punk in the same block and relisted it for 325 ETH a minute later
He sold a Punk worth $1.5 MILLION for the price of a used Toyota and the bot turned his typo into a $1.4 MILLION flip in under 60 seconds