The fact that Bitcoin briefly broke below $60,000 for the first time since October 2024 before recovering above that level is less revealing than what happened in the options market while it did: two of the largest single trades by dollar amount on Monday landed in Strategy (MSTR) and Coinbase (COIN), and they pointed in opposite directions. The differing positions may reflect varying views among market participants regarding the outlook for crypto-related equities.
Tyler Bailey’s reporting for CNBC published Tuesday morning captures the numbers behind both trades, and they’re worth unpacking carefully — because the structure of each position, not just the dollar size, may provide insight into how some institutional market participants are positioning themselves.
Strategy’s $56 Million Bear Lean
In MSTR, one trader sold 29,425 of the 125/180-call diagonals, collecting roughly $56 million in premium. The mechanics: short the 125-strike calls expiring August 21, long the 180-calls expiring June 18. The position is most profitable if Strategy shares stay below $125 through August expiration — ideally both legs expire worthless and the trader pockets the full credit.
The timing matters. Strategy’s recent BTC sales — the company’s first in years, according to CNBC — have rattled investors in both MSTR and the broader crypto space. Michael Saylor built the Strategy thesis on relentless accumulation. Selling, even modestly, breaks the narrative. The structure of the trade may indicate expectations for continued pressure on Strategy shares, although the precise rationale behind the position is not publicly known.
Coinbase’s $21 Million Comeback Bet
The Coinbase trade is structured very differently. One trader sold 10,990 June 18 expiration calls for $4.9 million, and used the proceeds — plus an additional outlay — to buy $26 million worth of August 21 expiration 160-calls. Total net exposure: roughly $21 million long.
This structure is commonly associated with an expectation of higher prices, although options strategies can serve multiple purposes, including hedging and risk management. The June short captures elevated near-term premium (income now, on elevated vol), while the August 160-calls need COIN to trade above $183.40 to be profitable — approximately 13% above where the stock was trading during Monday’s session, per CNBC’s reporting.
Spending $21 million net on August upside, when the stock and the underlying asset have both been hammered year-to-date, may reflect an expectation of improved performance over the coming months. Some market participants may interpret the structure as consistent with expectations for changes in implied volatility.
The Bitcoin Backdrop: 27% Down, 50% Off the All-Time High
Neither trade exists in isolation from what Bitcoin itself has done. The flagship cryptocurrency has shed approximately 27% of its value in 2026 and sits roughly 50% below its all-time high, per CNBC’s data. Friday’s dip below $60,000 was the first breach of that level since October 2024 — a move that coincided with increased activity in crypto-linked equities.
The iShares Bitcoin Trust ETF (IBIT) landed in the top 20 most active options tickers by volume on Monday, which is a useful positioning signal even without knowing the exact call/put split. When IBIT options volume spikes alongside the kind of drawdown Bitcoin has seen, it may reflect increased hedging activity, speculative positioning, or portfolio adjustments.
Tom Lee, FundStrat head of research, offered his read via CNBC:
“In the face of the onslaught of AI narratives undermining trust of traditional systems, bitcoin remains the soundest money, and the resilience of its proof of work architecture has been demonstrated.”
Lee’s framing — Bitcoin as a structural store-of-value despite AI-era competition for the “trust” narrative — is worth noting, though it’s a thesis that has been tested hard this year with BTC down more than a quarter. Lee’s comments represent his personal views and should not be interpreted as forecasts or investment recommendations.
What Could Keep the Bear Case Alive
The MSTR trade is a reminder that the bear case here isn’t just macro. Some investors may view the company’s recent Bitcoin sales as a departure from its historical accumulation strategy. Future performance may be influenced by Bitcoin’s ability to maintain recent price levels and broader market conditions.
The premium that MSTR has historically traded at relative to its net asset value could compress further — dragging the stock independently of Bitcoin’s own price action. COIN faces a different but related problem: exchange revenue is volume-dependent, and a sustained low-volatility, low-price-level environment is worse for Coinbase’s business model than a sharp drawdown that generates trading activity.
The bullish case embedded in that Coinbase August diagonal — COIN above $183.40 by late August — would likely depend on a combination of market, business, and cryptocurrency-related factors. That’s a sequence, not a single catalyst.
What to Watch
The June 18 expiration on both the MSTR and COIN diagonal structures is the first near-term marker. If Bitcoin remains above $60,000 and either name rallies into that date, the short June legs could be tested. Bitcoin’s performance may remain an important factor influencing sentiment toward crypto-related equities, according to CNBC — remains the single most important near-term input for the entire crypto-equity complex.
The August 21 expirations on both trades make the late summer the structural resolution date. Between now and then, any further Strategy BTC sales, shifts in U.S. crypto regulatory posture, or macro risk-off moves that pressure high-beta names could influence the performance of crypto-related equities and associated derivatives positions.
Market relationships in this space are dynamic and may change over time; past correlations between BTC price and crypto-equity performance do not guarantee future results.
Risk Disclaimer: Trading CFDs involves substantial risk and may not be suitable for all investors. CFDs are complex instruments and come with a high risk of losing money rapidly due to leverage. You may lose some or all of your invested capital. You should consider whether you understand how CFDs work and whether you can afford to take the high risk of losing your money. Past performance is not a reliable indicator of future results. This article is provided for general informational and educational purposes only and does not constitute financial, investment, legal, tax, or trading advice, nor a recommendation, solicitation, or offer to buy or sell any financial instrument.