Strategy, the largest corporate crypto hoarder, sold $216 million of Bitcoin last week – a sign that it is abandoning co-founder Michael Saylor’s “Never sell your Bitcoin” mantra as a slumping digital asset market hits its own shares.
It marked the company’s largest Bitcoin sale since it started building up its massive holdings in 2020, and only its third sale overall as it makes a hard pivot to a more flexible investment strategy – treating the token as just another source of liquidity.
Bitcoin ticked up 0.4% Monday to $63,870.52 – still far below the firm’s average purchase price of approximately $75,000 per token.
Lacie Zhang, research analyst at Bitget Wallet, said the sale doesn’t come as a complete surprise since Strategy had previously signaled that Bitcoin sales were a possibility if needed.
“What matters more is that each actual sale weakens the ‘never sell’ perception around the Bitcoin treasury model and brings capital structure pressure back into focus,” Zhang told The Post.
Formerly known as MicroStrategy, the firm has followed an intense buying strategy focused on raising capital, buying Bitcoin and holding onto it — earning it a reputation as the leading so-called “crypto-treasury” company.
Under Saylor, who stepped down as CEO in 2022, that “crypto-treasury” model encouraged crypto bulls to buy shares of the firm in hopes that Bitcoin would continue to rise and their winnings would be multiplied.
But instead, the volatile market has taken a turn for the worse – sending Strategy’s stock down 75% over the past year.
“The market is finally forcing these companies to choose between holding their digital assets or keeping their investors happy with cash. They chose cash,” William Stern, founder and chief executive of financial firm Cardiff, told The Post.
In the latest quarter, as Bitcoin fell 14%, Strategy suffered an $8.32 billion loss on digital assets.
The company is now worth roughly $35 billion – a sharp drop from its peak of around $128 billion last year.
Big-name investors like Peter Thiel, who backed multiple crypto-treasury companies, have also been hit hard by the sell-off.
June marked the worst month on record for US spot Bitcoin ETFs, with about $4.06 billion in net outflows – topping the previous record of $3.56 billion in February 2025, according to Bitfinex analysts.
Jake Kennis, senior research analyst at Nansen, noted that Strategy’s sale last week has yet to trigger a broader sell-off – signaling the market might be more resilient than initially expected.
However, “that does not mean the overhang is gone. We still expect excess leverage and the broader DAT [Digital Asset Treasury] unwind to continue playing out, which could include further corporate selling,” Kennis told The Post.
Strategy’s sale could prompt individual investors to reassess their holdings of Bitcoin, which has already suffered some brutal trading this year.
Analysts have already warned that more downside could be in store for crypto as investors look to free up extra liquidity as they pivot to massive AI IPOs.
SpaceX’s IPO last month marked the largest-ever stock market debut, and analysts are expecting OpenAI and Anthropic to make similar waves with IPOs later this year or in early 2027.