Suicidal Shorts and Nine-Digit Leverage: The Top 10 Boldest Trades in Crypto History

Poker face. In 2008, Lady Gaga made it the title of a global hit built, by her own admission, on the imagery of poker and bluffing. In crypto, the formula fits a handful of traders. These individuals never reveal their hand until the market forces them to show their cards.

There are those who read charts, and those who bet their reputation on a single number. This list belongs to the latter category: ten moves played in public, documented by the press or by the blockchain itself, on Hyperliquid or elsewhere. Some have exploded fortunes, while others have swallowed hundreds of millions of dollars in just a few hours. Here is the top 10 of the boldest trades in our little crypto history.

The choice of these ten bets is obviously arbitrary: crypto is not lacking in other equally bold candidates.

Before diving in, a methodological point is necessary. Several identities cited in this list rely on on-chain tracking. This is the case for the trader known by the pseudonym GCR, or the two addresses behind the panic on UST. Finally, this is also the case for the account linked to Garrett Jin. This work is carried out by companies like Arkham Intelligence or Chainalysis. It connects wallets to transaction patterns but does not establish a judicial identity in the strict sense. Unless convicted or explicitly confessed, these attributions remain solid presumptions, not facts adjudicated by a court.

The Ranking of the Ten Bets at a Glance

1. Tim Draper buys 30,000 bitcoins blindly at US Marshals auction

The name Tim Draper is not new in Silicon Valley. This third-generation venture capitalist has already bet early on Skype, Hotmail, or Tesla. But this pedigree does not reassure anyone in 2014. Crypto is coming out of a sensational scandal, and many believe it is finished. In June of that year, the US Marshals auctioned off 29,656 bitcoins seized during the dismantling of Silk Road.

The market has just barely recovered from the collapse of Mt. Gox, bitcoin is worth about 630 dollars, and no one wants to touch it. Draper, however, scoops up all three lots in a single bid. The exact amount has never been publicly confirmed. But the US press at the time estimates it at about 19 million dollars, or nearly 640 dollars per bitcoin. He announces that he will never sell.

The bet has paid off, largely: Tim Draper remains one of the most active and vocal investors in the crypto ecosystem. In April 2026, he announced again a bitcoin price of $250,000 within eighteen months, citing inflationary pressures on the dollar. He had already made this type of prediction in the past, with uneven success. He continues to deem it "irresponsible" for a company not to hold bitcoin.

2. Sam Bankman-Fried Launches Alameda with Korean Arbitrage

Before FTX, there was the kimchi premium. At that time, Sam Bankman-Fried was still an unknown quantitative trader to the general public. Alameda Research, the company he just founded, was looking to make a name for itself on this kind of market inefficiency. Between 2017 and 2020, bitcoin sometimes traded 50% higher in South Korea than elsewhere. In other words, this premium is explained by local capital controls.

Sam Bankman-Fried then set up a machine to buy bitcoin abroad to sell it in won. The profit reached up to a million dollars per day, according to his own statements reported by CNBC at the time. Thus, it was necessary to act quickly. The operation was legal, repetitive, and terribly bold logistically. It required moving capital across jurisdictions hostile to such flows, day after day.

After FTX: The Fall, Then Prison

The rest is known. Sam Bankman-Fried built FTX on this reputation as a skilled trader, before the empire collapsed in November 2022. Sentenced to 25 years in prison for fraud, he lost the appeal of his conviction on June 12, 2026. As a result, the Second Circuit Court of Appeals fully upheld the verdict.

He is serving his sentence in a low-security federal facility near Santa Barbara, California. His release is theoretically scheduled for 2044, unless he appeals to the full court, the Supreme Court, or seeks a presidential pardon, which he is already trying to obtain. He is even considering launching his own cryptocurrency once free.

3. GCR, the Phantom Trader Who Shorted LUNA Before Anyone Else

GCR's style stands out in a universe where traders willingly flaunt their gains in stories on X. He communicates almost never, except to deliver a market tip every eighteen months.

The pseudonym GCR (Gigantic Rebirth) refers to an anonymous trader who started with about $1,000. According to estimates from Arkham Intelligence, he has built a traceable on-chain wealth that could reach several hundred million dollars. In April 2022, he opened a short position of $20 million on LUNA. A month before the collapse of Terra, the bet nearly doubled in value when the ecosystem collapsed in May.

GCR has remained true to his legend: no one has uncovered his identity. His last notable public appearance dates back to April 2024, when he briefly broke his silence to comment on a market drop. Since then, only a few on-chain movements betray residual activity, such as claiming an airdrop of the CULT token at the end of 2024, which was sold a few weeks later for a fraction of its initial value, according to Arkham Intelligence. Finally, the phantom trader has never reappeared.

4. The Two Anonymous Traders Who Triggered Panic on UST

UST was not just any stablecoin. Its yield of nearly 20%, offered through the Anchor protocol, attracted hundreds of thousands of savers. In reality, many were unfamiliar with the risks associated with a purely algorithmic peg.

On May 7, 2022, Terraform Labs withdrew part of its liquidity from the Curve 3pool. Thirteen minutes later, a first trader exchanged 85 million UST for USDC. Within the following hour, a second trader sold an additional 100 million UST, in increments of 25 million, according to on-chain data documented by Chainalysis.

These two massive sales broke the peg of the algorithmic stablecoin. As a result, the ensuing spiral wiped out more than $40 billion in value within a few days. Their identities remain unknown to this day.

Nothing has changed on this specific point. The two traders have never been identified, despite the efforts of several on-chain analysis firms in the months following the crash. They remain, to this day, the most discreet ghosts on this list.

5. Three Arrows Capital and the One-Sided Bet on the Discount of GBTC

Three Arrows Capital was not a marginal player at that time. The fund, co-founded by Su Zhu and Kyle Davies, manages several billion dollars and enjoys an undisputed reputation as "smart money" in the ecosystem. By the end of 2020, Three Arrows Capital became the largest institutional holder of shares in the Grayscale Bitcoin Trust. Specifically, its position exceeded $1.2 billion, leveraged.

The bet was based on a simple conviction: the premium of GBTC over spot bitcoin could only persist. However, it reversed into a discount and never recovered. Combined with exposure to Terra, this trade would leave heavy debts during the fund's liquidation in the summer of 2022. According to court proceedings, these debts are estimated at $3.5 billion.

Su Zhu and Kyle Davies, After the Fall

Their trajectory then took a different turn, marked by a forward flight. Su Zhu was arrested at the Singapore airport at the end of September 2023 while attempting to leave the country. He was subsequently sentenced to four months in prison for refusing to cooperate with the liquidators. He emerged in early 2024, describing his prison stay as "pleasant".

With Davies, he then launched OPNX, a platform for trading crypto bankruptcy claims. This, in turn, closed in February 2024, while the liquidators of 3AC demanded $1.3 billion from the two men. Kyle Davies, for his part, continues to claim he has "nothing to be ashamed of" and refuses to recognize the jurisdiction of U.S. courts.

6. Avraham Eisenberg, a Conviction That Did Not Last Two Years

Mango Markets was then just a modest-sized decentralized trading protocol built on Solana, far from the security standards that would be imposed afterward. In October 2022, Avraham Eisenberg manipulated the price of the MNGO token by multiplying cross-swaps between two of his own accounts. The value of the token soared by over 1,000% in twenty minutes. He used this artificial valuation as collateral to borrow $110 million from Mango Markets users, with no intention of repaying, according to the accusation.

On X, he claims a << highly profitable trading strategy >>, asserting the exploit as a legitimate trade under the protocol's code. On April 18, 2024, a federal jury finds him guilty of fraud and market manipulation.

A Conviction Overturned, Then Challenged on Appeal

On May 23, 2025, Federal Judge Arun Subramanian overturns all of these convictions for two distinct reasons. First, a jurisdictional issue: Eisenberg neither traded, called, nor sent any emails from New York. This, according to him, deprives the prosecutors of the Southern District of New York of any legal basis for the charges of fraud and manipulation.

On the charge of electronic fraud, the judge rules differently. For him, borrowing on a protocol << without rules or explicit prohibitions >> does not constitute a punishable false statement. However, the prosecutors appealed this decision in January 2026. They argue that the judge ignored the terms of use of Mango Markets, which did impose collateral ratios. Therefore, a new conviction on the fraud aspect remains possible. Eisenberg remains incarcerated for a separate case unrelated to Mango Markets. He was sentenced in May 2025 to over four years in prison for possession of child pornography materials.

7. CZ, the $2.1 Billion Tweet That Sank FTX

Changpeng Zhao is the founder of Binance and its former CEO. As such, his opinion weighs on prices well beyond his own order book. On November 6, 2022, CoinDesk reveals that Alameda Research holds 40% of its $14.6 billion in assets in the FTT token. Four days later, Changpeng Zhao announces on X that Binance will liquidate its remaining holdings in FTT. He cites the << recent revelations >>.

He also reminds of a figure: Binance had received approximately $2.1 billion in BUSD and FTT. This was during its exit from FTX's capital in 2021. More than a classic short, it is a public admission of distrust towards a direct competitor, posted by the most influential man in the industry. The FTT loses more than 80% of its value by November 8. FTX immediately wobbles and files for bankruptcy on the 11th, dragging down an empire valued at $32 billion just a few months earlier.

From Prison to Presidential Pardon

CZ has also had dealings with the U.S. justice system in the meantime. He pleaded guilty in November 2023 for failing to meet anti-money laundering obligations at Binance and served a prison sentence in the United States. On October 23, 2025, Donald Trump grants him a presidential pardon, a decision immediately criticized by several Democratic lawmakers.

Some see a potential conflict of interest related to the business ties between Binance and the Trump family, which CZ's entourage firmly denies. Binance, the platform he co-founded, alone held about 87% of the USD1 stablecoin from World Liberty Financial. This crypto project, launched by the president's sons, started in early February 2026, according to Forbes. The platform also distributed $40 million worth of WLFI tokens at the end of January 2026 as part of a joint promotion. Nevertheless, CZ continues to express optimism about a Bitcoin supercycle. CZ's tweet announcing the liquidation of FTT by Binance, followed by Caroline Ellison's response offering to buy back the position at $22, on November 6, 2022 -- Source: X

8. James Wynn, from Memecoin to Seven Thousand Dollars to a Billion on Bitcoin

James Wynn made a name for himself in 2023 by turning about $7,000 into $20 to $25 million on the PEPE token. This feat transformed him into a cult figure in trading rooms on Telegram. Two years later, he replays his notoriety on Hyperliquid, the platform that then becomes his new stage of choice. On May 21, 2025, he opens a long position of $830 million on Bitcoin. He raises it to $1.25 billion on May 24, at 40x leverage, according to CoinDesk.

The market turns. By the end of May, his positions cascade, resulting in over $100 million in losses in just a few days, confirms The Block. Few traders have embodied both extremes of leverage so quickly. The meteoric rise, followed by public liquidation, under the gaze of thousands of accounts that were following his wallet live.

Despite everything, James Wynn never really left the table. By July 2025, barely recovered from his liquidation, he reopens leveraged positions on Ether and PEPE. The scenario repeats several times over the following months: new positions, new ephemeral gains, new liquidations. By April 2026, his account had shrunk to $900 after a sixth liquidation in two weeks. In total, he had experienced more than two hundred liquidations since his beginnings on the platform.

9. The Mystery Trader Who Shorted Thirteen Minutes Before Trump

The political context matters as much as the trade itself. Since his return to the White House, Donald Trump has made the trade war with China a near-daily political tool. The crypto market now reacts within seconds to each of his messages on social media. On a Friday in October 2025, an anonymous whale opens short positions on Hyperliquid. They bet $80 million on Bitcoin and $30 million on Ether, at 10x leverage.

The timing is almost perfect. A few minutes later, Donald Trump announces a 100% tariff on China, causing the entire crypto market to plummet. The profit is estimated between $150 and nearly $200 million according to Arkham Intelligence. On-chain investigators point to Garrett Jin, former executive of the BitForex platform, who denies any anticipation and denounces the disclosure of his identity by CZ himself.

The presumed identity of the trader has never been officially confirmed, but Garrett Jin remains the name most frequently mentioned in on-chain investigations. His previous track record does not help his defense. BitForex, the exchange he founded, collapsed in 2024 amid accusations of misappropriating client funds.

The wallet linked to this trade, however, continued to operate on Hyperliquid after October 2025, accumulating nearly $100 million in cumulative gains. The turnaround came at the end of January 2026, after switching back to highly leveraged long positions. This account suffered a liquidation of about $250 million on ether, according to Arkham Intelligence. Its cumulative net result thus returned to negative territory.

10. Machi Big Brother, the account that refuses to leave the table

Jeffrey Huang is no stranger to the Taiwanese crypto scene: an entrepreneur and former music producer, he had built a local reputation. On Hyperliquid, he became one of the most followed accounts in the market, for all the wrong reasons. With long positions on ether at 25x leverage, he earned the nickname "king of liquidations."

Between October 2025 and May 2026, he lost over $75 million, according to Arkham Intelligence. He had, however, experienced a peak of $44.5 million in unrealized gains at one point during the sequence. His transaction thread is followed live by thousands of accounts. He has become an involuntary case study on what leverage does to an account that refuses to exit.

Machi Big Brother's account has never really stopped turning. It was fully liquidated again at the beginning of 2026, before reopening highly leveraged positions with the little capital he had left. Each time, he reloads and starts over, in a cycle that on-chain analysts describe as "resilience" rather than strategy.

The Case of Do Kwon, for Comparison

Do Kwon, on the other hand, no longer has the opportunity to reload an account. The founder of Terra was sentenced to fifteen years in prison in December 2025, a sentence confirmed by the ruling of the federal court in New York. He had orchestrated a much larger leveraged system than Huang's, with $40 billion in losses at stake.

The comparison stops where it becomes dangerous. Following a wallet on the blockchain says nothing about its owner's criminal record. It also says nothing about where he sleeps at night. On Hyperliquid, the order book is public. Prison, however, is not.

These ten stories share neither the same amount nor the same era, but one common reflex: to bet big when everyone is looking elsewhere. The bluff works for a time. Then the blockchain stops playing along. Each position remains recorded, public, and accessible to anyone who knows where to look, long after the table has emptied. On Hyperliquid and elsewhere, dozens of anonymous accounts are today replaying the same patterns, under the watchful eyes of the same on-chain sleuths.