MW Strategy's stock drops after rare bitcoin sale tests 'never sell' narrative
By Frances Yue
Bitcoin sinks to a two-month low after Strategy sells for the first time in nearly four years
Michael Saylor, executive chair of Strategy, has long been one of the most prominent advocates for bitcoin.
Strategy's stock dropped Monday after the company disclosed a rare bitcoin sale, rattling investors who have long treated the company as a one-way bet on the cryptocurrency.
While Strategy sold a relatively small number of bitcoins, the first sale by the company in nearly four years raises the question of whether the "HODL" strategy - "hold on for dear life" - that Executive Chair Michael Saylor has been a big promoter of has ended.
Shares of Strategy (MSTR), the company formerly known as MicroStrategy and one that is often seen as a leveraged bitcoin vehicle, fell 6.2% toward a six-week low in recent midday trading.
The company said it sold 32 bitcoin (BTCUSD) from May 26 to May 31 for $2.5 million, at an average price of $77,135 per bitcoin, according to a Monday filing. Strategy said proceeds from the sale are expected to be used to fund distributions on its preferred stock.
The sale is small compared with Strategy's overall bitcoin hoard. As of May 31, the company held 843,706 bitcoin, worth roughly $60 billion based on bitcoin's price Monday morning. But the move carries symbolic weight for investors, because Strategy has long been viewed as the most aggressive corporate buyer of bitcoin, with Saylor previously embracing a never-sell posture.
That stance had already started to soften. During Strategy's first-quarter earnings call in May, Saylor said the company would "probably sell some bitcoin to fund a dividend just to inoculate the market, just to send the message that we did it."
During the same call, Phong Le, Strategy's president and CEO, added: "Our ability to sell bitcoin either to buy U.S. dollars or sell bitcoin to buy debt, if it is accretive to bitcoin per share, is something that we would consider doing going forward."
The sale also came as bitcoin has been under pressure. Bitcoin fell 3.8% on Monday to below $71,000, leaving it down 19.2% year to date and 44% below its record high of $126,272.76, reached on Oct. 6, 2025, according to Dow Jones Market Data.
While Strategy's latest bitcoin sale may be too small to move bitcoin prices in the near term, the bigger risk is what it signals over time - that Strategy may no longer be the predictable, steady buyer that has helped support bitcoin demand, according to Louis LaValle, co-founder and chief executive at Frontier, a crypto investment firm.
"The more investors hear about these very large holders selling, the more people say, I see an asset that's trading down, I can go trade Micron stock, or I can go and trade other [artificial intelligence] stocks and make an exorbitant amount of money. Why would I hold bitcoin?" LaValle said in a call.
Still, some analysts said the sale could help reset how investors view Strategy's bitcoin holdings.
The move may actually benefit Strategy, according to Mark Palmer, equity research analyst at the Benchmark Company.
"The market has been discounting or ignoring the value of its bitcoin reserve, based on the assumption that it was effectively untouchable because the company had said it would never sell bitcoin," Palmer said in a phone interview.
"Now we think investors should view Strategy's bitcoin holdings as providing a backstop for the funding of preferred dividends, but not the primary means of doing so," he added.
Palmer said he still expects Strategy's main sources of funding to be its cash reserve, which the company should continue to replenish primarily through sales of common equity.
Strategy last sold bitcoin in December 2022, when it unloaded about 704 bitcoin for $11.8 million, at an average price of $16,776 per bitcoin. At the time, the company said it planned to carry back the capital losses from the sale against previous capital gains, which could generate a tax benefit.
-Frances Yue
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(END) Dow Jones Newswires
June 01, 2026 12:31 ET (16:31 GMT)
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