Bitcoin News Today: James Wynn's 40x Short Defies Bitcoin's Bullish Momentum

James Wynn, a high-profile crypto trader known for his aggressive leveraged bets, has once again positioned himself against the bullish momentum in the cryptocurrency market. On October 27, 2025, Wynn opened a 40x leveraged short position on Bitcoin (BTC) via Hyperliquid, a decentralized derivatives platform, betting that the recent price surge would reverse. The trade, worth $110,000 at entry, currently holds an unrealized profit of $661.38, with a liquidation price of $117,468, according to Yahoo Finance. This move follows a broader market rally driven by easing inflation data and anticipation of a Federal Reserve rate cut, which pushed Bitcoin above $115,000, the same Yahoo Finance piece reports.

Wynn's strategy contrasts with the bullish sentiment dominating the market. Crypto whales and institutional investors have been accumulating long positions in BTC and Ethereum (ETH), anticipating further gains. However, Wynn's history of high-risk trading—marked by over $22 million in cumulative losses—has drawn scrutiny. Despite this, sources close to him claim he has generated $250 million in profits recently through undisclosed strategies, though his win rate remains at 33.33%, the Yahoo Finance article adds. His latest trade also includes a cryptic reference to a "new account" under which he has been operating, adding to the enigma surrounding his tactics.

The risks of leveraged shorting in crypto markets are starkly illustrated by another whale's recent struggles. A trader identified by wallet "0xdDc" faced a $4 million floating loss after opening a 40x short on Bitcoin prior to an unexpected Trump-related market event. To avoid liquidation, the whale added $1 million in USDC collateral, reducing their net profit from $8.6 million to $4.6 million, as reported by Phemex. This underscores the fragility of highly leveraged positions in volatile markets, where even minor price movements can trigger cascading losses.

Wynn's actions echo a broader trend of large-scale shorting in decentralized finance (DeFi). Earlier in October, an anonymous wallet (0xb317) executed a $208-million cross-margin short on Hyperliquid with 20x leverage, earning $190 million in profits during a market crash triggered by U.S. tariff announcements, according to TradingView. That trade exacerbated liquidations, with over $1.23 billion in losses recorded across exchanges, the TradingView piece notes. While some view such strategies as skillful market timing, others argue they amplify systemic risks by deepening sell-offs through margin calls and auto-deleverage mechanisms.

The crypto community remains divided on whether Wynn's success stems from expertise or luck. His timing of the October 27 short—just as Bitcoin approached $117,000—raises questions about potential insights into macroeconomic catalysts, such as the Fed's rate decision or U.S.-China trade developments, the Yahoo Finance article observes. Meanwhile, critics highlight the ethical and regulatory challenges of anonymous, high-leverage trading. In traditional markets, such activity would face strict compliance checks, but DeFi platforms like Hyperliquid lack comparable safeguards, critics argue.

As Bitcoin's price fluctuates amid mixed signals, Wynn's latest gamble will test whether his contrarian approach can yield redemption or repeat past failures. For now, the market watches closely, aware that a single price rebound could erase his modest gains—or trigger another high-profile collapse.