Michael Saylor and Crypto Titans See Billions Vanish in October Market Meltdown

The October crash didn't just rattle retail investors—it carved a massive chunk out of the fortunes held by crypto's biggest names.

Portfolios in Freefall

For figures like Michael Saylor, the market's sudden plunge translated into paper losses measured in the billions. These aren't just numbers on a screen; they represent a dramatic recalibration of wealth concentrated at the very top of the digital asset ecosystem. The volatility that defines crypto giveth, and with brutal efficiency, it taketh away.

The Institutional Wobble

When titans stumble, the whole market feels the tremor. Such concentrated losses trigger a cascade of questions about leverage, strategy, and the sheer scale of institutional exposure. It's a stark reminder that in crypto, even the most bullish convictions can meet a very hard floor.

A brutal but classic finance lesson: what the blockchain minteth, market sentiment can vanish in a heartbeat—proving that decentralized money still bows to centralized panic.

Bitcoin Pullback Wipes Out Gains From Strategy’s Aggressive Treasury Bet

Bloomberg noted that Strategy’s aggressive bitcoin treasury strategy delivered outsized gains through early October, when Bitcoin reached fresh record highs.

That momentum quickly reversed as Bitcoin prices slid, dragging Strategy’s share price down by more than 50% and cutting nearly $6 billion from Saylor’s net worth from its peak.

Other major crypto figures were also hit. Changpeng Zhao, known as CZ, saw his fortune decline by about 5% since Jan. 1, leaving his estimated net worth at $50.9 billion, according to Bloomberg.

Meanwhile, Cameron Winklevoss and Tyler Winklevoss were among the hardest hit, with the twins losing roughly 59% of their combined wealth over the same period as crypto prices slid and trading volumes cooled.

The losses stood in contrast to broader billionaire wealth trends. Bloomberg reported that just eight individuals accounted for roughly 25% of the $2.2 trillion in total gains among billionaires in 2025, underscoring how uneven the year was across industries.

Did you destroy all your shareholders and lose $7b this year or not? pic.twitter.com/FfZLWcVNFD

Not all crypto-linked executives fared poorly.

Jeremy Allaire, chief executive of stablecoin issuer Circle, reportedly increased his net worth by 149% since June, buoyed by growing interest in dollar-backed stablecoins and the passage of the US GENIUS Act, which established a federal framework for payment stablecoins.

Despite the volatility, corporate interest in digital asset treasuries continued to grow.

Data from Bitcointreasuries.net shows that 192 public companies now hold Bitcoin on their balance sheets, up sharply from a year earlier.

Bitcoin itself remains under pressure. The cryptocurrency is down about 7% since the start of 2025, after peaking above $126,000 in October before falling to around $80,000 by late November.

Bitwise CIO Sticks to Bullish 2026 Bitcoin Outlook

Bitwise chief investment officer Matt Hougan has downplayed expectations that US politics will drive the next leg higher.

While Bitcoin rallied to fresh highs earlier in 2025 following Donald Trump’s inauguration, Hougan said the administration is unlikely to unlock significant new upside.

Looking ahead to 2026, the industry remains divided. Fidelity’s director of global macro research, Jurrien Timmer, has suggested 2026 could be a pause year, with prices potentially sliding toward $65,000.

Others remain more optimistic. Strategy CEO Phong Le has argued that Bitcoin’s underlying fundamentals held up throughout 2025 despite weaker prices, while Bitwise chief investment officer Matt Hougan said earlier this year that he expects 2026 to be an “up year” for the asset.

According to Linh Tran, market analyst at XS.com, Bitcoin’s recent price action underscores the market’s sensitivity to monetary policy expectations rather than headline economic data.