The Most Incredible Crypto Trades in History
Some traders turned thousands into billions. Others lost fortunes in minutes. These are the most extraordinary trades in crypto history and what we can learn.
Crypto markets have produced some of the most extraordinary wealth creation and destruction events in financial history. The stories of legendary trades — some heroic, some cautionary — are part of the culture that makes crypto unique among asset classes.
Greatest Wins
- The Bitcoin pizza trade reverse: In 2010, Laszlo Hanyecz paid 10,000 BTC for two pizzas (worth $44M+ at ATH). The counterparty who received the BTC later claimed to have sold them at $1 each — still turning $0.41 into $10,000
- The ETH ICO investor: A participant in Ethereum's 2014 ICO at $0.31 who held until 2021's ATH of $4,800 turned $310 into $4.8M on a $1,000 investment
- Polymarket 2024 US election: traders who bet on Trump at $0.30 months before the election made 3x on one of the largest political betting events in history
- Bitcoin genesis block to $100k: the first Bitcoin ever mined (January 2009) was worth 0; today 1 BTC is worth $100k+
Most Spectacular Losses
- The Mt Gox trustee liquidation: Nobuaki Kobayashi sold $400M in BTC in 2018 causing a major market crash — then revealed he still had 166,000 BTC to sell
- The Terra/Luna collapse: $40B in value destroyed in 72 hours as UST de-pegged in May 2022
- The $200M DeFi liquidation cascade: in November 2022, a single large position's liquidation triggered $200M in cascading liquidations across DeFi
What Every Trade Teaches
The legendary trades share a common thread: conviction, patience, and risk management. The pizza trade is only regrettable in hindsight — at the time, it was a rational use of an asset with no established value. The cautionary tales involve ignoring risk management and concentration. Steyble's risk tools — stop-losses, portfolio limits, diversification — exist because these lessons cost billions to learn.