Investor James Wynn faced over $110 million in losses after his 1044 BTC position liquidated following a Bitcoin drop. Despite this, he still holds a long position of 1591 BTC with 40x leverage, valuing at approximately $167.5 million. Wynn's aggressive trading style in cryptocurrencies, including meme coins like PEPE, has earned him a reputation in the crypto community. The initial expectation of Bitcoin rising above $105,000 failed as the price fell due to various factors, including statements by former US President Donald Trump and deteriorating relations with China. Wynn highlighted the corrupt nature of the markets and suggested opting to buy Bitcoin and store it securely.