Fears that Michael Saylor’s Bitcoin buying machine is beginning to seize up are spilling across the crypto market, fueling the latest leg of Bitcoin’s selloff and exposing cracks in one of the financial structures that has underpinned demand for the world’s largest cryptocurrency over the past two years.

Bitcoin’s slide back below $60,000 is reviving a fear that has largely been absent from crypto for the past two years: what happens when the market’s biggest buyer comes under pressure just as retail traders lose interest.

Michael Saylor’s Strategy Inc. bought $39.4 million of Bitcoin, leaning again on its common stock to fund purchases of the cryptocurrency for a third consecutive week despite earlier pledges to pivot to perpetual preferred shares.

Bitcoin extended its slide back toward the $60,000 level. The decline is driven by mounting concerns over the unraveling of Strategy Inc.’s funding mechanism, alongside rate-hike fears that are dampening demand for riskier assets.

Michael Saylor’s Strategy Inc. resumed buying Bitcoin a week after a rare token sale by the digital asset treasury company roiled the crypto market.

Bitcoin steadied itself after dropping below the key threshold of $60,000, as Strategy Inc. Chairman Michael Saylor resumed making purchases of the token.

Bitcoin’s selloff extended into Wednesday after Strategy Inc.’s sale of a tiny portion of its massive cryptocurrency stockpile rattled sentiment and widened the token’s divergence from record-setting technology shares. Jim Ferraioli, Director of Digital Currencies Research and Strategy at Charles Schwab, discusses Bitcoin's latest moves and Charles Schwab's report on mining economics and digital asset outlook. (Source: Bloomberg)

Weeks after Michael Saylor opened the door to selling Bitcoin, Strategy Inc. disposed of about $2.5 million of the cryptocurrency, a symbolic break from the maximalist playbook that helped make the company one of the market’s largest buyers and the token’s biggest corporate holder.

For most of its history, Bitcoin’s price was driven by a sprawling cast of buyers: idealists, speculators, early adopters, and, more recently, institutional investors looking for a new portfolio hedge. Demand was fragmented and hard to predict. In 2026, it is neither.

Michael Saylor’s Bitcoin accumulation firm Strategy Inc. has survived yet another crypto market meltdown with some fresh financial engineering.

Strategy Inc. bought $255 million of Bitcoin in the previous seven days, slowing the pace of its buying of the digital currency after spending $3.5 billion over the prior two weeks.

Bitcoin is approaching $80,000 for the first time since January — a stealth recovery built not on euphoria but on short covering and the relentless accumulation by one company: Strategy Inc.

Michael Saylor’s Strategy Inc. bought $2.54 billion in Bitcoin over the previous seven days, marking the digital asset treasury company’s largest acquisition of the original cryptocurrency since November 2024.

For the first time since launching its high-yield securities in July, Michael Saylor’s Strategy Inc. funded its latest $1 billion weekly Bitcoin purchase entirely through the sale of its “Stretch” perpetual preferred shares.

The borrow-to-buy-Bitcoin model pioneered by Michael Saylor’s Strategy Inc. has spawned yet another web of startups tied to its fortunes — all of them exposed if Bitcoin falls.

Bitcoin accumulator Strategy Inc. registered a roughly $14.5 billion unrealized loss in the first quarter as the value of the Michael Saylor-led company’s cryptocurrency holdings fell.

Just days after unveiling plans to raise $42 billion to bolster its purchases of Bitcoin, Michael Saylor’s Strategy Inc. took a pause after 13 consecutive announced weekly acquisitions of the cryptocurrency.

Michael Saylor’s Strategy Inc. is accelerating its Bitcoin accumulation plan, outlining a $42 billion capital raise that would deepen its all-in wager on the cryptocurrency.

Michael Saylor’s Strategy Inc. bought nearly $1.6 billion worth of Bitcoin - the company’s largest purchase since January – leaning more heavily on a security promising investors an 11.5% annual payout backed by the same cryptocurrency.

Michael Saylor’s Strategy Inc. accelerated its Bitcoin buying with a nearly $1.3 billion purchase — the biggest in seven weeks — leaning again on its common stock despite earlier pledges to pivot to perpetual preferred shares.