An active trader on Polymarket suffered a staggering $2.36 million loss in just eight days after a string of unsuccessful sports predictions. The losses were highlighted by on-chain analyst Lookonchain, which reviewed detailed trading records tied to the account.
The trader, operating under the pseudonym bossoskil1, placed 53 separate predictions across major U.S. sports leagues and college football during the period. The final tally showed 25 winning bets and 28 losing bets, translating to a 47.2% win rate. Despite nearly breaking even on accuracy, the size of the losing positions ultimately drove the account deep into the red.
Large Stakes Despite Moderate Conviction
Bossoskil1 focused on NFL, NBA, NHL, and NCAA games, settling positions through spread-based prediction contracts. Many contracts were purchased at prices ranging from $0.40 to $0.60, suggesting only moderate confidence in the outcomes.
Even so, the capital committed was enormous. In several cases, individual positions exceeded $200,000, while multiple bets carried exposure well above $1 million.
NFL Bets Delivered the Biggest Hits
One of the largest single losses came from an NFL matchup between the Green Bay Packers and the Chicago Bears. The trader purchased more than 2.5 million shares at $0.54, only for the position to settle at zero—resulting in a loss of over $1.36 million.
Another major loss followed in the Buffalo Bills vs. Jacksonville Jaguars game. Bossoskil1 backed the Jaguars with more than 2.6 million shares, again at $0.54. When the Jaguars lost by three points, the position collapsed, pushing losses to approximately $1.41 million.
Additional NFL misfires included:
a bet on the Eagles over the 49ers, resulting in a $304,000 loss
a smaller position on the Chargers vs. Patriots, which lost roughly $2,700
NHL Exposure and Profitable Bets That Couldn’t Offset Losses
The trader also ventured into NHL markets, where results were mixed. A six-figure bet on the Chicago Blackhawks against the Edmonton Oilers ended with a $8,500 loss, while a position on the Columbus Blue Jackets vs. Vegas Golden Knights resulted in another $2,600 loss.
There were, however, notable winning trades. Some NHL bets delivered returns exceeding 100%, including winning positions involving the Devils, Kraken, and Blackhawks in other matchups. A college football bet on Miami generated more than $500,000 in profit, while a successful NFL bet on the Los Angeles Rams produced gains of over $730,000.
Despite these wins, they were overshadowed by the scale of the losing positions.
Losses May Still Grow
After all settled trades were accounted for, the trader’s net result stood at a $2.36 million loss. At the time of analysis, several positions remained open.
These included:
an NHL bet on the New York Islanders involving roughly 520,000 shares priced at $0.49, representing exposure of about $255,000
a position on Chicago Blackhawks vs. Washington Capitals totaling more than 1.65 million shares, with a combined value of approximately $744,000
A Stark Reminder About Risk Management
The case of bossoskil1 underscores a critical lesson: even a near-50% win rate can result in catastrophic losses when position sizing and risk management are poorly controlled. In prediction markets—where probability, psychology, and volatility intersect—aggressive betting strategies can wipe out multimillion-dollar accounts in a matter of days.
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