Michael Saylor & Winklevoss Twins: The Billion-Dollar Crypto Losses That Shook 2025
Billion-dollar paper cuts. The crypto elite just got a brutal reality check.
The Paper Gains That Vanished
Forget the moon—2025 saw some of crypto's biggest names crash back to Earth. The paper fortunes built on digital dreams evaporated faster than a meme coin's liquidity. Michael Saylor's MicroStrategy and the Winklevoss twins' Gemini found themselves at the center of a financial storm that wiped out billions. It was a masterclass in volatility, served straight up, no chaser.
When HODL Turns Sour
The strategy was simple: accumulate and hold. But when the market tide recedes, you see who's been swimming naked. Aggressive acquisition met with aggressive depreciation. The bets that made them legends became the anchors dragging down their portfolios. A stark reminder that in crypto, even the most diamond-handed conviction can't defy gravity forever.
The New Math of Crypto Wealth
It's the oldest story in finance, just with a blockchain twist: what goes up must come down. The paper losses highlight the razor-thin line between visionary and bag-holder in this market. One quarter you're a genius on CNBC; the next, you're a case study in risk management gone wrong—proving that sometimes, the most sophisticated investment thesis can't compete with good, old-fashioned market panic.
The sector recalibrates. The true believers double down, calling it a buying opportunity. The skeptics nod, muttering about tulips and greater fools. And the rest of Wall Street? They're just glad it's someone else's turn to explain a nine-figure loss to the board. After all, diversification is for people who don't have a crystal ball.
Early winners locked in gains as IPOs, fees, and dividends piled up
But Circle CEO Jeremy Allaire came out ahead, as USDC ended the year still the world’s second‑largest stablecoin with more than $77 billion in circulation.
Tether is of course still bigger at $186 billion, but Circle still pushed through an upsized IPO at a $6.9 billion valuation. Its stock CRCL remains 168% higher despite cooling from June after an astounding rally that left Wall Street as baffled as it was impressed.
Cryptopolitan previously reported that Circle saw $214 million in third‑quarter net income, up over 200% from a year earlier.
Tether founder Giancarlo Devasini also won, as Tether expanded USDT supply by more than 15% and paid out over $10 billion in dividends to owners. Giancarlo’s net worth reached $13.2 billion, and there are currently talks around raising $20 billion at a valuation that could hit $500 billion, a level that would place him on top of crypto wealth rankings at roughly $225 billion.
Figure Technology founder Mike Cagney balled out too after the company went public in September at a $6.6 billion valuation. Mike’s stake put his wealth at $2.1 billion, from $1 billion less than a year ago.
Meanwhile, Galaxy’s Mike Novogratz used volume, not price to boost his net worth. Galaxy Digital oversaw holdings for at least 20 corporate treasury companies, which translated into fees.
Galaxy’s third‑quarter gross revenue reached $28.4 billion, more than 200% higher year over year, pushing Mike’s net worth to $6.7 billion.
Crypto executives held ground amid lawsuits, ETFs, and rapid industry expansion
Grayscale CEO Barry Silbert returned to leadership after stepping aside in late 2023 during scrutiny tied to the collapse of Genesis, though lawsuits related to that are still active as of press time.
Still, Grayscale pushed toward an IPO, and in October, Barry launched Yuma Asset Management, targeting AI infrastructure through the Bittensor network and pushing his net worth to $3.1 billion.
Bullish CEO Brendan Blumer also took his company public in October at a $5.4 billion valuation, with a focus mainly on institutional clients. Then Bullish gained a New York license in September and launched US services the next month.
But Brendan also co‑founded Block.one, which raised $4.2 billion through EOS, a token that later lost most of its value.
Brendan dropped his US citizenship in 2020, and bought a $200 million villa in Sardinia this year, shortly after his net worth reached $1.8 billion from $990 billion.
Coinbase founder and CEO Brian Armstrong made his company enter stock trading, prediction markets, tokenized assets, and joined the S&P 500, all this year. But the COIN stock ended the year NEAR where it started and Brian’s wealth stayed around $11 billion.
Meanwhile, Changpeng “CZ” Zhao stayed steady at $50.9 billion. In October, Cryptopolitan reported that TRUMP pardoned him for earlier money‑laundering violations after he served four months.
Binance secured a $2 billion investment from an Abu Dhabi‑linked firm using a stablecoin issued by Trump’s World Liberty Financial and provided technology support. Asked about the pardon, Trump said he did not know CZ and “heard it was a Biden witch hunt.”
Binance has officially begun planning a US reboot.
Ripple’s Chris Larsen closed a long case and paid a civil penalty to end its SEC dispute without admitting wrongdoing. Chris holds more than $5 billion in XRP, and Ripple raised $500 million at a $40 billion valuation in November, adding him to the uber rich list at $14.6 billion.
Justin SUN stayed visible. The SEC paused a fraud lawsuit, and Justin attended conferences around the world, dined with Trump privately, and flew briefly on a Blue Origin rocket.
His TRON blockchain processed over $20 billion a day tied to stablecoins and became a public treasury company.
Though in September, Trump memecoins Justin bought for a presidential dinner were frozen amid speculation of sales. So his net worth fell to $10.3 billion, driven by token declines blamed on him by the crypto community.
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