Saylor abandons the “never sell”: Strategy considers tactical Bitcoin sales to optimize its taxation

Long presented as an unwavering holder of Bitcoin, Strategy Inc. has just reached a historic milestone. Michael Saylor’s company now plans to sell part of its BTC strategically, not out of necessity, but to gain a colossal tax advantage.

Strategy switches to active management of its BTC

On May 5, 2026, during its first quarter earnings call, Strategy Inc. (formerly MicroStrategy, Nasdaq: MSTR) dropped a quiet but significant bombshell.

The company, the world’s largest institutional holder of Bitcoin, has officially opened the door to tactical BTC sales. A first in the company’s history, known for its “never sell” doctrine.

Michael Saylor, executive chairman, was direct: “We will probably sell some of our Bitcoins to fund a dividend, to stimulate the market.” 

CEO Phong Le reinforced this message: “We will not sit idly by saying we will never sell. We want to increase our total BTC, but especially our Bitcoin per share.“

On the accounting side, the quarter was difficult. Strategy recorded a net loss of $12.54 billion, mainly due to an unrealized loss of $14.46 billion in fair value on its digital assets. Bitcoin had dropped from around $87,000 to $68,000 between January and the end of March. These losses remain purely accounting, with no real cash impact.

The software business, meanwhile, remains strong: $124.3 million in revenue (+12% year-over-year), with a solid gross margin of 67.1%. Available cash stands at $2.21 billion.

$2.2 billion reasons to sell… without abandoning Bitcoin

Behind this change of stance lies a ruthlessly efficient tax engineering strategy. Strategy has built its BTC reserves at very variable prices, from initial low-cost purchases to recent acquisitions around $80,000 to $100,000. By selling lots bought at a high price, the company can realize significant capital losses.

The calculation is clear:

• $7.6 billion of potentially realizable unrealized losses.
• An applied tax rate of 29% generates approximately $2.2 billion of recoverable tax assets.
• These losses offset gains realized elsewhere, reduce exposure to the corporate alternative minimum tax (CAMT), and create valuable tax shields.

An additional asset: the IRS regards Bitcoin as property, not a security. The anti-abuse rules on wash sales therefore do not apply. Strategy can sell… then repurchase immediately if it wishes.

These funds would also be used to repurchase MSTR shares when they trade below 1.22 times net asset value, an operation modeled during the presentation at one billion dollars, showing an additional yield of +636 basis points at 0.5 times NAV. Enough to reduce dilution, trap short sellers, and enhance shareholder value.

Bitcoin is no longer just a passive store of value in Strategy’s vaults. It becomes a tool for tax optimization, capital management, and shareholder value creation. This might well be the model that other BTC holders eventually adopt, and Strategy has just paved the way.