Strategy CEO Phong Le confirmed on Thursday that the company will "likely sell Bitcoin at some point in time" — the first time a C-suite executive has stated the possibility in those plain terms — as scrutiny mounts over whether the company's $15 billion preferred stock structure can withstand a prolonged Bitcoin downturn.
"We'll likely sell Bitcoin at some point in time, but we will be net increasing our Bitcoin and more importantly, increasing our Bitcoin per share," Le said in a CNBC Fox Business exclusive on Thursday, May 28, 2026. The comment echoes a similar possibility floated by executive chairman Michael Saylor in mid-May, but Le's framing landed with more weight: a sitting CEO, on camera, making the implicit explicit.
Strategy currently holds 843,738 BTC purchased at an aggregate cost of $63.87 billion, or roughly $75,700 per Bitcoin on average. With Bitcoin trading near $73,737 at the time Le spoke — about 16% lower year-to-date — the company's entire position sits underwater on a cost basis.
The preferred stock problem
The immediate pressure is structural, not speculative. Strategy has issued five series of preferred stock — STRK, STRF, STRD, STRC, and STRE — each carrying different dividend terms and seniority within the capital structure. Together, they represent roughly $15 billion in obligations and approximately $1.5 billion in annual dividend commitments.
The model assumed Bitcoin would rise fast enough to fund those obligations indefinitely. At current prices, that assumption is under stress.
Jeff Dorman, chief investment officer at asset manager Arca, put the situation bluntly on X on Thursday, May 28: the Strategy situation has "gotten out of hand." Dorman described the capital structure as a bet that Bitcoin was "about to moon" to justify the dividend load, and said the recent decision to repurchase 2029 maturity bonds was "baffling" given the ongoing preferred stock pressure.
His analysis left only two exits: "sell BTC to pay the prefs" or "stop paying the dividend." Both paths carry direct and asymmetric consequences, Dorman wrote — not just for Strategy's investors but for Bitcoin itself, given that Strategy holds the largest corporate BTC position on the planet.
What Polymarket is pricing
Traders on Polymarket are assigning the following odds that Strategy sells any Bitcoin during 2026:
- ~90% by December 31, 2026
- 71% by June 30, 2026
- 18% by May 31, 2026
The near-term number is low, suggesting the market does not expect forced sales in the immediate term. The year-end figure — 90% — signals widespread conviction that some sale is a matter of when, not if.
Why this matters more than Saylor's earlier comment
Saylor raised the possibility of sales in mid-May. At the time, analysts read it as a hedged disclosure rather than a firm signal. Le's Thursday statement closes that interpretive gap. A CEO confirming likely sales — even with the qualifier that Strategy will remain a net buyer — is a qualitatively different statement from a founder's oblique reference.
The qualifier matters but does not neutralize the headline. "Net increasing our Bitcoin" is compatible with selling a portion to service dividend obligations and simultaneously buying more through equity raises. The structure allows for it. Le confirmed that is the playbook.
Broader market context
Strategy's disclosure lands during an already difficult stretch for Bitcoin. BTC is roughly 16% lower year-to-date as of Le's statement. A record streak of ETF outflows has added to downward pressure, compounding the bear narrative building around the asset class.
Strategy's position — 843,738 BTC at aggregate cost basis of $63.87 billion — means it is not a passive observer of price action. It is the price action. Any actual sale would be a market event; even the confirmed possibility of one is landing as one.
The company bought roughly 170,000 BTC in 2025 alone, steadily increasing its holdings through equity and debt issuances. That accumulation pace, combined with $1.5 billion in annual preferred dividends that now demand servicing, is the core of Dorman's concern: the machine that bought BTC was also creating obligations that BTC prices must cover.
What comes next
Le's statement does not signal imminent liquidation. The qualifier — "net increasing our Bitcoin" — is a direct attempt to frame any future sales as tactical rather than distressed. But the market and its analysts will now be tracking preferred dividend payment dates and BTC price movements through a new lens.
If Bitcoin recovers above the $75,700 average cost basis before any major dividend stress arrives, the preferred stock structure remains manageable. If it does not — and Polymarket is pricing roughly 71% odds of a sale by June 30 — the mechanics Dorman outlined will keep tightening.
The question is no longer whether Strategy might sell. It is when, how much, and whether the price it gets is one that supports or undermines the rest of the capital structure.