In 2019, A Kentucky Volleyball Referee Started Buying Call Options For An Unloved Stock With 90% Short Interest. He Lost Money For Over A Year. In January 2021, Mike McCaskill Made The Biggest Bet Of His Life On GameStop. He Walked Away With Over $25 Million.
A volleyball referee in Louisville spent over a year losing money on GameStop options before a single month in early 2021 changed everything. What he understood about the stock and what he did when the moment arrived separates his outcome…
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A Louisville Referee Spotted GameStop’s Short Interest Early
In 2019, a 45-year-old volleyball referee in Louisville, Kentucky, noticed GameStop (NYSE:GME | GME Price Prediction) carried about 90% short interest, The Ringer reported. He had years of experience trading penny stocks and options.
He bought weekly call options at 5 to 10 cents per contract, according. A call option gives the right to buy a stock at a set price. Weekly calls that cheap expire within days and pay nothing unless the stock rises sharply before then.
Over more than a year, his trades mostly lost money. He was right about short interest but wrong on timing.
Pennies Turned Into the Biggest Trade of His Life
In August 2020, Ryan Cohen, co-founder of Chewy (NYSE:CHWY), bought a 10% GameStop stake, and the stock rose from $4 to $10, according to The Ringer. After Cohen’s board appointment on January 11, 2021, McCaskill loaded up, according to The Ringer. On January 13, 2021, a prominent TV host posted about the squeeze potential.
On January 19, 2021, he bought 750 short-term $60 calls, The Ringer reported. In late January 2021, he sold most of his position as the stock neared $347, booking approximately $25 million in profits.
He kept about 2,500 shares, The Ringer reported, hoping to sell them at $1,000. GameStop has never reached that level. Two accounts he opened for his children, ages 4 and 6, each cleared $1.5 million.
Most GameStop Buyers Never Got His Exit
This is a survival story. We know McCaskill’s name because his timing worked.
GameStop split its stock 4-for-1 in July 2022, so his sale price can’t be compared with today’s quote. Here are the split-adjusted figures:
- Current price: $24.70 (delayed after-hours quote, 4:49 PM ET, October 2, 2026)
- 1-year: GameStop down 9.26%; S&P 500 up 14.95%
- 5-year: GameStop down 44.15%; S&P 500 up 77.16%
- 10-year: GameStop up 354.53%; S&P 500 up 258.34%
What To Take From McCaskill’s Story
If you keep buying cheap weekly calls, expect to lose money. McCaskill had three things most imitators lacked: years of options experience, conviction to hold through continued losses, and discipline to sell into the spike. That last one is rarest.
He found a specific condition he could measure, kept early positions small enough to survive being early, and took the money when it came. I’d read this more about a story with an unusual result, and less a case for buying options or hunting heavily shorted stocks.
The sizing and exit rules that keep a trade like McCaskill’s from wrecking an account are the whole point of our free speculation playbook, which fences off the fun money with real rules.
Contact [email protected] for any questions or corrections.
AJ spent 10 years writing about financial markets at The Motley Fool. His coverage centers on technology stocks and the broader macroeconomic trends, from interest rates to geopolitics, that shape where markets are headed next. AJ is drawn to the stories where big-picture economics and individual companies collide.
