Strategy’s Tightrope Act: Selling Bitcoin, Buying Stock, and Building a $2.55 Billion Cushion

Strategy has torn up the rulebook that made it the corporate world’s most dogged Bitcoin accumulator. The board has authorised the sale of up to $1.25 billion in cryptocurrency, a first for a company that had previously treated its holdings as sacrosanct. The move marks a sea change: the software firm now sits on a mountain of 847,363 Bitcoin — roughly 4% of all coins ever mined — but is ready to monetise a slice of that trove for the first time.

Flanking the sales permission is a $2 billion share buyback programme, split evenly between common stock and the preferred securities known as STRK and STRC. The preferreds will see their dividend jump to an annual 12% starting in July 2026, a move designed to lower future payout costs and shore up credit quality. Simultaneously, the company has built a dollar reserve of $2.55 billion in cash, which management says will cover operating expenses for the next 17 months.

The company hasn’t abandoned its buying habit entirely. It recently added another 1,550 Bitcoin to its coffers, bringing total acquisition costs to around $64.1 billion. That still leaves Strategy as one of the largest corporate holders of the digital asset, but the new flexibility means it can now pivot between hoarding, selling, and repurchasing its own equity — a balancing act that analysts view very differently.

Should investors sell immediately? Or is it worth buying Strategy?

Wall Street is split. JPMorgan strategists warn that any meaningful Bitcoin sales from Strategy could distort supply and demand dynamics in the crypto market, potentially ending the company’s reign as the dominant institutional buyer. Others are more bullish: Cantor Fitzgerald has a buy rating and a $212 price target, Citi sees $130, and BTIG goes as far as $250.

The stock has swung wildly in response. On Friday it edged up to €89.20, leaving it with a weekly gain of roughly 23% — though that bounce does little to erase a year-to-date loss of about 34%. At its peak the shares traded near €392; now they are a fraction of that, and the annualised volatility stands at a staggering 89%.

Strategy’s new playbook is a bet that a cash buffer, selective share repurchases, and a much higher preferred dividend can restore investor confidence before the July 2026 payout deadline. Whether the market buys the story will depend on how deftly the company walks the line between tapping its Bitcoin vault and keeping its long-term accumulation narrative intact.