Sophia Bennett
Crypto Analyst
When Michael Saylor said on Strategy's Q1 2026 earnings call that the company was prepared to sell Bitcoin, markets reacted sharply. The stock dropped. Bitcoin slipped. The crypto community erupted. But buried in the history of the world's largest corporate Bitcoin holder is a story most people forgot.
In December 2022, Strategy sold bitcoin for tax‑loss harvesting purposes, the same rationale the company now appears to be signalling to the market once again.
This is not new territory. It just feels that way.
What Saylor Said on the Q1 Earnings Call
During Strategy's Q1 earnings call on May 5, Saylor said he would not rule out a Bitcoin sale if it served Strategy's interest. He also said the company may use part of its holdings to pay dividends, and that it would tell the market before doing so. His exact words were: "We will probably sell some bitcoin to pay a dividend just to inoculate the market and send the message that we did it."
That is a reversal from the company's longstanding "never sell" strategy. In an interview with CNBC just three months prior, Saylor stated that Strategy would "never sell" Bitcoin.
The about‑face was loud. The context was telling.
The December 2022 Sale Nobody Remembers
On December 22, 2022, Strategy sold 704 bitcoin for approximately $11.8 million at $16,776 per coin, but immediately repurchased 810 bitcoin two days later. The sale was designed to carry back capital losses against previous gains and generate a tax benefit.
MicroStrategy bought 2,395 bitcoin between November 1 and December 21, 2022, before embarking on the tax‑loss harvesting strategy. Ultimately, the transactions resulted in an increase of MicroStrategy's bitcoin holdings by 2,500 BTC.
In other words, the 2022 sale was not a retreat. It was a financial manoeuvre, sell at a loss, book the tax benefit, buy back more. Net result: a larger Bitcoin stack.
Why History Makes the Current Situation Less Alarming
Strategy holds an estimated $2.2 billion in unrealized tax benefits tied to high‑cost‑basis Bitcoin that could be harvested through selective sales. Saylor himself compared the strategy to a real estate developer, buying land cheap, selling expensive, and reinvesting the proceeds.
"Real estate development companies literally exist to buy land cheap and sell it expensively," he said. "We're like a bitcoin development company."
The Real Reason Behind the Signal
Saylor added that a widespread belief that Strategy would never offload its crypto hoard had fuelled a narrative among short‑sellers that the company, if faced with a loan repayment, would invariably sell stock rather than Bitcoin. "If you want to defeat that, you have to basically show that you'll trade the Bitcoin back for the stock, or trade the Bitcoin to meet the liabilities," Saylor said.
The admission was partly strategic. By putting selling on the table publicly, Saylor removes the short‑sellers' ammunition.
Where Strategy Stands Today
Strategy reported a massive $12.54 billion net loss for Q1 2026, almost entirely driven by a $14.46 billion unrealized loss as Bitcoin price crashed to $62,000 during the quarter. Despite this, the company still bought 89,599 BTC, doubling down on its long‑term conviction.
Strategy currently holds over 818,000 BTC. The company faces about $1.5 billion in annual dividend and debt obligations, with roughly 18 months of coverage in reserves.
The numbers are large. The obligations are real. And the 2022 playbook, sell a little, harvest the benefit, buy back more, may be exactly what plays out again. For Strategy, selling Bitcoin has never meant abandoning Bitcoin. It has always meant managing it smarter.