Only One Scenario Saves Bitcoin

Bitcoin and crypto prices have been hit by a massive sell-off this week, with the bitcoin price plunging to levels not seen since before President Donald Trump retook the White House (alongside fresh fears of U.S. dollar collapse).

The bitcoin price, down more than 50% from its October 2025 peak of 126,000 per bitcoin, has led to billionaire Mark Cuban suddenly flipping on crypto as2 trillion is wiped from the combined market.

Now, as JPMorgan chief executive Jamie Dimon issues a stark crypto warning, bitcoin traders are braced for Strategy founder Michael Saylor to reveal whether he sold more of the company's $52 billion worth of bitcoin—or bought back.

"This selloff appears to be driven less by a breakdown in bitcoin's long-term fundamentals and more by a short-term confidence shock around Saylor and Strategy selling," Matt Mena, senior crypto research strategist at crypto asset manager 21shares, said in emailed comments.

"If 60,000 fails to hold, bitcoin will likely revisit the55,000 support level."

This week, Strategy, the bitcoin acquisition company led by Saylor, followed through with a promise to sell some bitcoin, offloading 32 bitcoin worth $2.5 million in what Saylor claimed is part of a plan to make the company's controversial, high-paying, monthly dividend stretch shares "the best credit instrument in the world."

This is the first time Strategy has sold bitcoin since December 2022, when it sold around 700 bitcoin to harvest tax losses that could offset future gains, buying 800 bitcoin just a few days later.

"Because Strategy recently sold 32 bitcoin, contrary to the 'never sell' mantra of the company, it's creating uncertainty even if the scale of the sale was modest," Richard Green, Head of Institutional at RootstockLabs, said in emailed comments.

Strategy raised the possibility of selling some bitcoin last month to meet dividend payment commitments and reassure the market that there were buyers if the company ever needed to sell bitcoin in the future.

"We will probably sell some bitcoin to pay a dividend just to inoculate the market and send the message that we did it," Saylor said in May during the company's first quarter earnings call, adding the company planned to "buy bitcoin with credit … let it appreciate, and then … sell bitcoin to pay the dividend."

The timing of these sales has proven particularly painful for market sentiment. Bitcoin had already been struggling to maintain momentum after its record-breaking rally last year, with macroeconomic headwinds including persistent inflation data and shifting Federal Reserve policy expectations weighing on risk assets across the board. The additional pressure from one of bitcoin's most visible institutional champions has amplified anxieties that were already simmering beneath the surface.

Analysts note that Strategy's bitcoin holdings have become something of a bellwether for institutional confidence in the cryptocurrency. When Saylor began accumulating bitcoin in 2020, he effectively turned his enterprise software company into a leveraged bet on the digital asset's long-term appreciation. That strategy proved wildly successful during the bull markets of 2021 and 2024, but it has left the company exposed during prolonged downturns. With over $52 billion in bitcoin on its balance sheet, even relatively small sales can trigger outsized market reactions simply because of the symbolic weight they carry.

The dividend structure that Saylor has championed adds another layer of complexity. By committing to regular monthly payments to shareholders, Strategy has created a recurring obligation that must be met regardless of market conditions. In a rising bitcoin environment, this can be managed through strategic sales or debt financing. When prices are falling, however, each sale locks in losses and risks accelerating downward pressure on the very asset that underpins the company's entire valuation thesis.

All eyes are now on Strategy founder Michael Saylor's X account for his usual Sunday teaser that could reveal if, and to what extent, the company has bought back the bitcoin it sold in May, recreating its 2022 bitcoin sale game plan.

However, some are expecting Saylor to announce Strategy sold more bitcoin, framing it as the only option to save bitcoin and the company.

"Only one scenario saves bitcoin and Strategy in the short-term," Jeff Dorman, the chief investment officer of bitcoin and crypto investment company Arca, posted to X.

"Saylor has to come out and say, 'I sold $4 billion of Strategy [stock] and bitcoin,'" giving the company over two years of runway before needing to raise money for dividends again.

"If he does that, the market rips, and might even rip 20% to 30%," Dorman wrote. "It once again makes Strategy uninteresting for years, but that's a good thing. And while capital markets might be closed to Strategy for awhile, it at least buys a ton of time, and in that time who knows what other catalysts might pop up."

The scenario Dorman outlines would represent a dramatic reversal of Saylor's public posture, which has long been characterized by unwavering conviction and an almost theological commitment to holding bitcoin indefinitely. Yet in the face of sustained selling pressure, even the most committed believers may be forced to recalibrate. A significant liquidation, while painful in the near term, could paradoxically restore confidence by demonstrating that Strategy has the liquidity to weather extended downturns without being forced into distressed sales.

Dorman fears that, "if he doesn't, and he continues to just wait it out … this selling won't stop."

The broader implications extend beyond any single company. Bitcoin's narrative as "digital gold" and a hedge against currency debasement has been tested repeatedly during this selloff, with the asset proving more correlated to traditional risk assets than many advocates had predicted. Whether Saylor's next move can help decouple bitcoin from this pattern—or merely confirm that even its most prominent institutional backers are subject to the same liquidity constraints as everyone else—may determine the trajectory of the market for months to come.