Strategy Attracts $58 Million Bearish Option Block Trade Even as Stock Rises: Options Chatter

$Strategy (MSTR.US)$ saw a $58 million bearish block trade of call options Monday, signaling the seller’s skepticism over the world’s largest Bitcoin treasury company's ability to hold on to the share price gains.

The stock advanced about 4% Monday, extending its rebound from the lowest since September 2024, as $Bitcoin (BTC.CC)$ rose, boosting the value of the company’s holdings.

An active seller unloaded call options that give their holder the right to buy 2.4 million shares at $160 each in the next 73 days. The seller collected a premium of $24.20 a share for those call options with the strike price that’s about $2 above the current share price.

The trade was posted after the company disclosed a $17.4 billion unrealized loss on digital assets in the fourth quarter, highlighting the stock’s vulnerability to gyrations in Bitcoin prices. The largest cryptocurrency tumbled almost 24% in the fourth quarter, erasing all of its 2025 gains to end the year down 6.5%.

(Read moomoo AI's summary for Strategy's 8K filing with the SEC here.)

As of Jan. 4, the company held 673,783 Bitcoins. Monday’s 2.6% gain in Bitcoin prices sent the value of those holdings to about $63.2 billion, slightly higher than the company’s enterprise value of $61 billion.

The block trade of $160 call options cited above has a profit probability of about 68% for the seller, based on current prices. Each contract, which covers 100 shares, has a maximum profit potential of $2,265. However, should the stock price climb above the breakeven level of $182.65, the maximum loss potential for the seller could be unlimited.

That multi-leg transaction came with the purchase of call options that give their holder the right to buy the same number of Strategy shares at $300 each in 11 days. That lottery ticket was bought at 10 cents per share, for a total premium of $240,000. That bullish leg of the trade currently has a zero percent profit probability.

Still, at current prices, the trade’s maximum potential loss is $7.50 per contract. Strategy’s share price will need to climb above the breakeven level of $300.075, from its current level of $164 before the end of next week for its buyer to see any gain from the transaction.

Share your thoughts on Strategy in the comments section. Can Strategy climb above $300? Will this lottery ticket pay off for the buyer? Let your voice be heard by voting below. And if you want to read more options columns like this one on TSMC, or this one on Berkshire Hathaway, follow me here, where you can also find my earnings stories on some of the biggest stocks.

Disclaimer: Options trading entails significant risk and is not appropriate for all customers. It is important that investors read the Characteristics and Risks of Standardized Options before engaging in any options trading strategies. Opening new options positions close to or on their expiration date comes with substantial risk of losses for reasons that include potential volatility of the underlying security and limited time to expiration. Options transactions are often complex and may involve the potential of losing the entire investment in a relatively short period. Certain complex option strategies carry additional risk, including potential losses that may exceed the original investment amount. If applicable, supporting documentation for any claims will be furnished upon request.

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