It’s been a rough stretch for Strategy Inc. The Nasdaq-listed company, best known for betting its entire corporate identity on Bitcoin, has watched its stock bleed and its crypto holdings lose billions in value. And yet, if you ask the people actually putting money on the line, most of them still don’t think the company is going under — at least not this year.
Polymarket, a crypto-native prediction platform built on Polygon, currently puts the odds of Strategy filing for bankruptcy in 2026 at around 10%. That’s actually a slight improvement from January, when the number sat at 12%. More than $162,000 has been wagered on the question, which isn’t massive, but it’s enough to be a meaningful signal of where trader sentiment stands.
The general logic behind the optimism is straightforward: Strategy still holds an enormous pile of Bitcoin, has about a billion dollars in cash, and doesn’t face any serious debt deadlines until 2028. By some estimates, the company has enough runway to keep covering its dividend and interest payments for the next two and a half years without making any dramatic moves. That kind of cushion tends to calm nerves.
The Bitcoin Sale Nobody Expected
What rattled investors recently wasn’t a debt crisis or a failed fundraising round — it was a simple announcement that Strategy had sold some of its Bitcoin.
For a company that has made “never sell” almost a founding principle, the disclosure landed hard. Bitcoin briefly dipped below $60,000 — its lowest point since late 2024 — and Strategy’s stock dropped roughly 40% in the week that followed. The unrealized losses on its Bitcoin holdings now stand at around $12 billion, a number that becomes harder to brush aside the longer prices stay depressed.
Chairman Michael Saylor has tried to keep spirits up. His argument, roughly, is that even a modest long-term rise in Bitcoin’s price is enough to cover the company’s preferred-share obligations and still leave something on the table for shareholders. It’s a case for patience, essentially — which is either reassuring or frustrating depending on how long you’ve been watching the stock fall.
The Critics Aren’t Staying Quiet
Not everyone is buying the patient investor narrative. Peter Schiff, who has long been skeptical of both Bitcoin and Strategy’s approach to it, has renewed his warnings that the model may eventually collapse under its own weight.
More notable, perhaps, is the growing unease from institutional voices. Zach Pandl, head of research at Grayscale — not exactly a Bitcoin skeptic — recently suggested that Strategy’s leveraged structure is creating pressure not just for the company itself, but potentially for the broader Bitcoin market.
At the time of writing, Bitcoin was trading near $61,430, down a couple of percent on the day. Strategy shares closed 8% lower, then dipped further after hours. Year-to-date, the stock is down about 23%.
So where does that leave things? Confidence is fragile, the numbers are uncomfortable, and the easy optimism of a year ago has definitely faded. But most traders still seem to believe Strategy has enough in reserve to avoid the worst. Whether that belief holds up depends, as it always has, on what Bitcoin does next.
