Risky trader James Wynn linked to Alameda Research?

The unique trading style of James Wynn keeps gaining attention. Wallet history may also link the trader to Alameda Research. 

The recent risky trading moves of James Wynn attracted more attention to his wallet history. Wynn has previously taken both risky long and short positions, with early investments in meme tokens. 

The trading patterns suggested that Wynn may be linked to Alameda Research, exaggerating the fund’s risky strategies even more with his independent reserves. 

The FTX creditor activist Sunil Kavuri noticed Wynn’s choice of assets. He added that Wynn’s early wallets also received funds from Alameda Research, and there was other evidence of insider tips and a connection as one of the fund’s traders. 

James Wynn trades like Alameda on steroids because he probably was a trader there

Dec 2020: Alameda sent James Wynn around $6,000 in ETH

$1bn (40x leverage) position: Flipped long short long BTC in last 2days
PnL: $87m to $10m in 4days

Bought PEPE when market cap was $600k… pic.twitter.com/VzFoQoT9sY

— Sunil (FTX Creditor Champion) (@sunil_trades) May 27, 2025

The main connection to Alameda is that Wynn received 6,000 ETH in 2020, later allowing him to make high-profile trades and discover meme tokens early. 

Alameda Research was also known for allocating funds to any and all new assets that appeared during the 2021 boom, including memes and NFTs. Wynn extended his streak of meme token investments even during the bear market after the FTX crash, getting involved with BabyPepe and ELON. 

Wynn later rebranded as a Hyperliquid trader, raising the platform’s profile, while also taking multiple high-risk positions. The trader is not a Bitcoin maximalist, and in fact was recently involved with another meme token, MoonPig. He showed true belief in the token, suggesting its price could run into the billions. 

MoonPig rallied from May 22 onward, right after Wynn mentioned the token. The asset peaked above $0.10, later erasing its gains to $0.06. Wynn reportedly acquired 3% of the token’s supply, shilled the asset, then locked in gains by selling at the top. On-chain data shows selling from Wynn’s wallets put downward pressure on MoonPig.

James Wynn is now in the red

The attention on James Wynn increased as the Bitcoin (BTC) rally stalled in the past day. BTC traded around $109,007, but even that price drop was enough to erase Wynn’s gains. Previously, Wynn had closed a position with a $25M gain, but then reopened a 40X leveraged long. 

The position is now marking a $2.4M unrealized loss, and may be liquidated if BTC does not recover. Wynn, however, is still confident in the performance of BTC, as the coin reversed still above his liquidation price. 

Wynn believed the trading activity in the past day was deliberate, an attempt to liquidate his position, which still holds for now. 

The past two days even spawned reverse traders, who took short positions when Wynn went long. According to on-chain data, one trader spent the past three days with a reverse-Wynn strategy. The end result was $5.6M in realized gains. The whale retains reverse positions, which are still in the green with $445K in gains. 

Wynn, on the other hand, is more than $13.2M in unrealized losses for the past 24 hour period.

The end result may reverse if BTC resumes its rally. Wynn continues to keep a high profile on social media, while drawing attention to Hyperliquid. 

One of the theories for Wynn’s high-risk trades is that he was deliberately showing the capabilities of Hyperliquid, pushing its token to new peaks. 

After the recent trades, HYPE stalled just under $40. The token traded at $37.64, with no significant gains in the past day. Hyperliquid expanded its open interest to over $8.9B, aiming to compete with the top centralized derivative exchanges.