"I started trading contracts in March, and before that, I had never traded contracts. In fact, I had never really traded (any derivatives) before, I was just trading MEME."
"Within a month, I turned about $3 million into $100 million, and then lost everything in a week on HyperLiquid."
"I was just doing my own thing, but people started to notice me, my account went viral, with hundreds of thousands of followers, because all of this is traceable on-chain."
"In any case, with all this new attention, trading got out of control. I was basically gambling, just trying to recover lost gains, while not wanting to look like an idiot for having made $100 million and then losing it. I became greedy. I didn't take the numbers on the screen seriously."
On June 6, James Wynn changed his avatar to a McDonald's version of Wojak. In other words, I lost and rejoined the army. By this point, James Wynn had lost over $20 million in principal.
Position and Tweet Timeline Review
The super "gambling dog" James Wynn comments on every single contract, so every open and close on HLP with his publicly visible address reveals James Wynn's, the current "market's first gambling dog", mental journey.
On May 30, James Wynn entered "sage mode" after massive losses.
After losing over $96 million in a week and an overall account loss of $14.03 million, he posted on social media: "Being a contract gambler is very interesting, not regretting at all. Turning $4 million into $100 million, then dropping to $13 million, it's truly exciting. Most people don't dare or can't do such trades. They can't do it, don't have the money, and don't have the courage to publicly bear such risks. Maybe next time I'll try to earn $1 billion, I'll be back."
Regarding this, crypto KOL scooter, who previously leaked LIBRA token insider information, directly mocked: "James Wynn is a typical example, explaining why most scammers and ruggers ultimately lose everything. They never experienced the value of honest money-making, and never truly understood the effort required to earn money. Easy come, easy go." Trading expert Eugene Ng Ah Sio also expressed a similar view in his personal TG channel, "When you use excessive leverage, easy come easy go."
On May 31, James Wynn aggregated $3.25 million through multiple addresses and went long on BTC and PEPE. After multiple liquidations and stop-losses, his actual position value was only $800,000. James Wynn stated on social platforms, "I will make a comeback, I love this game. Money is essentially a mindset. I'm still richer than 99.9% of crypto Twitter users. I placed a huge and well-considered bet, aiming to earn billions. My passive income monthly is more than what most of you earn in a year."
On the same day, James Wynn also posted, "$100 million is not much. For those with shackled thinking, maybe it is. But for a free soul, anything is possible, this amount is negligible. Just $100 million, a drop in the ocean of money. It's laughable how many people have never seen or even heard of this number. Free will is more important than poor thinking."
On June 1, James Wynn again posted about making a comeback, passionately saying: "Some of you act like gods, thinking you would cash out at $100 million. Have you ever considered that I never intended to secure profits at $100 million? Why cash out? For me, it's either win everything or lose everything." Currently, James Wynn holds no positions and has a total loss of $17.72 million.
Subsequently, James Wynn directly posted that multiple CEXs banned his accounts without reason, claiming it was due to his anti-corruption and pro-decentralization stance. He emphasized that he never participated in selling pressure, his funds are clean, and he has long focused on on-chain meme coins and HyperLiquid trading, without accepting token promotion fees or participating in pump schemes. James Wynn stated that if his accounts continue to be banned, he will consider collaborating with Moonpig team to launch a new platform to fight centralized manipulation: "I was born for war, lawyers are ready, I will publicly fight this."
On June 2, James Wynn, who waves the flag of crypto freedom and transparency, announced on social media that he would temporarily suspend contract trading.
But shortly after announcing the suspension, the gambler placed his bet again. Within 4 hours, James Wynn posted his Bitcoin long position chart and directly pointed at Wintermute. He tagged Wintermute's official account, saying, "I'm back".
However, in this trade, James Wynn's long position was once underwater by over $1.35 million.
James Wynn seemed somewhat "heated", raising his arms and shouting, "If you want to support this cause/fight corruption, buy BTC now. I just went long and was instantly sniped. There must be some conspiracy here, I don't know what. It can't be just because of my long position, maybe because I'm a small fish playing in the whale's game, or because I drew attention to HyperLiquid. Anyway, try to support by buying BTC!"
As BTC price continued to drop, whale James Wynn clearly panicked. He urgently posted on social media, "If you want to fight market makers and support me, please transfer USDC to this specific on-chain address. Assuming I win, everyone will get their money back at a 1:1 ratio. Let's defeat them. I need your help." Subsequently, James Wynn deposited the 39,345.11 USDC accumulated from donations into Hyperliquid, lowering his liquidation price.
This zero-cost fundraising tweet instantly sparked discussion. Is the most trafficked man in the crypto market now "begging"? In fact, James Wynn, who used to open positions with over $1 billion in high leverage, has fallen from the "version son" pedestal, losing about $100 million in the past week and additionally losing about $17.5 million in profits.
BitMEX co-founder Arthur Hayes commented, "I'm starting to think this (whale James Wynn's attempt at zero-cost fundraising) might become one of the most successful trading platform marketing campaigns in crypto history. HYPE will prevail. Also, this guy is likely hedging on another anonymous address, specifically to farm the next HyperLiquid airdrop."
On June 3, after James Wynn turned his approximately $100 million BTC long position from loss to profit, he quietly deleted the "begging" tweet he publicly shared at 22:00 the previous day. Currently, his long position is profitable by over $400,000. During the most critical moment last night, Bitcoin's price was only $20 away from his long position's liquidation price, with an underwater position of over $1.35 million.
Eventually, Lady Luck smiled upon him, and his long position turned profitable. James Wynn's gambling career continued. But not for long, as after a "spat" between Trump and Musk, he lost everything overnight.
However, James Wynn has gone through ups and downs, with his wallet swelling and emptying. Who became the biggest winner? The continuously hitting new historical highs of the HYPE token price may have already explained everything. Previously named by James Wynn, Wintermute's founder wishful_cynic wrote, "Overall, I think 'wynn' is just a very well-executed HL (Hyperliquid) marketing campaign, well done. He is excellent. His tweets are also great." In fact, James Wynn mentions Hyperliquid in one out of every three tweet posts, constantly emphasizing decentralization, anti-corruption, and anti-manipulation, and vaguely referring to unconfirmed "account banning" scandals of other centralized exchanges. From a communication perspective, James Wynn has achieved the biggest success in the crypto market this year.
Whether the openly transparent James Wynn has hedged his massive public positions through anonymous addresses, and whether Hyperliquid has direct interests with James Wynn, all these black boxes remain unknown. Behind the tragic tweets, James Wynn does not forget to promote Hyperliquid, "In any case, if you want to gamble and trade contracts like an idiot, then at least use the link below (which will save you trading fees), and use the code 'WYNN'."
