Poker faces. In 2008, Lady Gaga made it the title of a worldwide hit built, by her own admission, on the imagery of poker and bluffing. In crypto, the formula sticks to a handful of traders. These people never show 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 second category: ten moves played in public, documented by the press or by the blockchain itself, on Hyperliquid or elsewhere. Some have exploded fortunes, others have devoured hundreds of millions of dollars in a few hours. Here are the top 10 cheekiest trades in our little crypto history.
The choice of these ten bets obviously remains arbitrary: crypto has no shortage of other equally cheeky candidates.
Before attacking, a methodological point is necessary. Several identities cited in this list are based on on-chain tracking. This is the case of the trader known under the pseudonym GCR, or of the two addresses behind the panic on the 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 links wallets to transaction patterns, but does not establish a literal forensic identity. Unless convicted or explicitly admitted, these attributions therefore remain solid presumptions, not facts decided by a court.
The ranking of the ten bets, at a glance
1. Tim Draper buys 30,000 bitcoins blind at US Marshals auction
The name Tim Draper is not new in Silicon Valley. This third-generation venture capitalist already bet early on on Skype, Hotmail and Tesla. But this pedigree reassures no one in 2014. Crypto is emerging from a resounding scandal, and many believe it is finished. In June of that year, US Marshals auctioned off 29,656 bitcoins seized during the Silk Road takedown.
The market is just coming out of the Mt. Gox collapse, bitcoin is worth around $630 and no one wants to touch it. Draper, however, won all three lots in a single offer. The exact amount has never been publicly confirmed. But the American press at the time estimated it at around $19 million, or nearly $640 per bitcoin. He announces that he will never sell.
The bet paid off, largely: Tim Draper remains one of the most active and vocal investors in the crypto ecosystem. In April 2026, he again announced bitcoin at $250,000 within eighteen months, citing inflationary pressures on the dollar. He had already formulated this type of prognosis in the past, with uneven success. He continues to consider it “irresponsible” for a company not to hold bitcoin.
2. Sam Bankman-Fried launches Alameda with Korean arbitration
Before FTX, there was premium kimchi. At the time, Sam Bankman-Fried was still just a quantitative trader unknown to the general public. Alameda Research, the company he just founded, is seeking to make a name for itself on this kind of market inefficiency. Between 2017 and 2020, bitcoin sometimes traded 50% more expensive in South Korea than elsewhere. In other words, this premium is explained by local capital controls.
Sam Bankman-Fried then sets up a machine to buy bitcoin abroad to resell it in won. The profit reaches up to a million dollars per day, according to his own statements reported by CNBC at the time. So, we had to act quickly. The operation was legal, repetitive and terribly logistically cheeky. Capital had to be moved through jurisdictions hostile to this kind of flow, day after day.
After FTX: the fall, then prison
The rest is known. Sam Bankman-Fried built FTX on this reputation as a skillful 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. Result: the Second Circuit Court of Appeal upheld the verdict in full.
He is serving his sentence in a low-security federal facility near Santa Barbara, California. His release is theoretically scheduled for 2044, barring appeal before the entire court, the Supreme Court, or presidential pardon which he is already seeking to obtain. He would even consider, once free, launching his own cryptocurrency.
3. GCR, the ghost trader who shorted LUNA before anyone else
GCR's style stands out in a world where traders willingly show off their earnings in stories on X. He almost never communicates, other than to deliver market advice every eighteen months.
The pseudonym GCR (Gigantic Rebirth) designates an anonymous trader who left around $1,000. According to Arkham Intelligence estimates, he has built a traceable on-chain asset that could reach several hundred million dollars. In April 2022, he opened a $20 million short position in LUNA. A month before the collapse of Terra, the bet almost doubled in value when the ecosystem collapsed in May.
GCR remained true to its legend: no one discovered its identity. His last notable public outing was in 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 the claim for an airdrop of the CULT token at the end of 2024, resold a few weeks later for a fraction of its initial value, according to Arkham Intelligence. Finally, the ghost trader never appeared again.
4. The two anonymous traders who triggered the panic on UST
UST was not a stablecoin like any other. Its return of almost 20%, offered via the Anchor protocol, had attracted hundreds of thousands of savers. In fact, many were unfamiliar with the risk specific to purely algorithmic anchoring.
On May 7, 2022, Terraform Labs withdraws part of its liquidity from the Curve 3pool. Thirteen minutes later, a first trader exchanges 85 million UST for USDC. In the next hour, a second sells an additional 100 million UST, in increments of 25 million, according to on-chain data documented by Chainalysis.
These two massive sales break the peg of the algorithmic stablecoin. Result: the spiral that follows will erase more than $40 billion in value in 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-way bet on the GBTC discount
Three Arrows Capital is therefore not a marginal player. 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. At the end of 2020, Three Arrows Capital became the largest institutional holder of shares in the Grayscale Bitcoin Trust. Concretely, its position exceeds 1.2 billion dollars, borrowed with leverage.
The bet is based on a simple conviction: the GBTC premium over spot bitcoin can only persist. However, it reverses downward and never rises again. Combined with the exposure to Terra, this trade will leave heavy debts when the fund is liquidated in the summer of 2022. According to legal proceedings, these debts are valued at $3.5 billion.
Su Zhu and Kyle Davies, after the fall
Their trajectory then takes a different turn, marked by headlong flight. Su Zhu was arrested in late September 2023 at Singapore airport while trying to leave the country. He was then sentenced to four months in prison for refusing to cooperate with the liquidators. He came out at the beginning of 2024, describing his prison stay as “pleasant”.
With Davies, he then launched OPNX, a crypto bankruptcy debt exchange platform. This in turn closes in February 2024, while the liquidators of 3AC are demanding $1.3 billion from the two men. Kyle Davies, for his part, continues to claim that he has “nothing to reproach himself for” and refuses to recognize the jurisdiction of the American courts.
6. Avraham Eisenberg, a conviction that did not last two years
Mango Markets is then only a modest-sized decentralized trading protocol, built on Solana, far from the security standards that will be imposed after it. In October 2022, Avraham Eisenberg manipulates the price of the MNGO token by multiplying cross swaps between two of his own accounts. The value of the token increases by more than 1,000% in twenty minutes. He uses 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”, assuming the exploit as a legitimate trade under the protocol code. On April 18, 2024, a federal jury found him guilty of fraud and market manipulation.
A conviction overturned, then contested on appeal
On May 23, 2025, federal judge Arun Subramanian annulled all of these convictions, for two distinct reasons. Firstly, a reason for territorial jurisdiction: Eisenberg neither traded, nor called, nor sent the slightest e-mail from New York. This deprives, according to him, the prosecutors of the Southern District of New York of any legal basis on the counts of fraud and manipulation.
On the charge of electronic fraud, the judge ruled differently. For him, borrowing on a protocol “without rules or explicit prohibitions” does not constitute a punishable false declaration. However, the prosecutors appealed this decision in January 2026. They believe that the judge ignored the conditions of use of Mango Markets, which imposed guarantee ratios. A new conviction on the fraud aspect therefore remains possible. Eisenberg remains incarcerated on a separate, unrelated case involving Mango Markets. He was sentenced in May 2025 to more than four years in prison for possession of child pornography.
7. CZ, the $2.1 billion tweet that sank FTX
Changpeng Zhao is the founder of Binance, and its former CEO. In fact, his opinion weighs on prices well beyond his own order book. On November 6, 2022, CoinDesk reveals that Alameda Research houses 40% of its $14.6 billion in assets in the FTT token. Four days later, Changpeng Zhao announced on X that Binance would liquidate its remaining FTT holdings. He invokes “recent revelations”.
He recalls a figure in passing: Binance had received approximately $2.1 billion in BUSD and FTT. It was during his exit from the capital of FTX, in 2021. More than a classic short, it is an admission of public distrust towards a direct competitor, posted by the most influential man in the industry. The FTT loses more than 80% of its value from November 8. FTX immediately falters and files for bankruptcy on the 11th, dragging with its fall an empire valued at $32 billion only a few months earlier.
From prison to presidential pardon
CZ has also had dealings with the American justice system in the meantime. He pleaded guilty in November 2023 to breaching anti-money laundering obligations at Binance, and served a prison sentence in the United States. On October 23, 2025, Donald Trump granted him a presidential pardon, a decision immediately criticized by several elected Democrats.
They see this as a possible conflict of interest linked to business ties between Binance and the Trump family, which CZ's entourage strongly denies. Binance, the platform he co-founded, alone held around 87% of World Liberty Financial's USD1 stablecoin. This crypto project, launched by the president's sons, started in early February 2026, according to Forbes. The platform also distributed, at the end of January 2026, $40 million worth of WLFI tokens as part of a joint promotion. CZ, however, continues to say he is optimistic about a bitcoin supercycle.
8. James Wynn, from the seven thousand dollar memecoin to the billion on Bitcoin
James Wynn makes himself known in 2023 by transforming around 7,000 dollars into 20 to 25 million on the PEPE token. This feat transformed him into a cult figure in Telegram trading rooms. Two years later, he replayed his notoriety on Hyperliquid, the platform which then became his new favorite scene. On May 21, 2025, he opened a long position of $830 million in bitcoin. He brings it to 1.25 billion on May 24, at 40x leverage, according to CoinDesk.
The market is turning. At the end of May, his positions cascaded, resulting in more than $100 million in losses in a few days, confirms The Block. Few traders will have embodied the two extremes of leverage so quickly. The dazzling glory, then the public liquidation, under the gaze of thousands of accounts who followed his wallet live.
Despite everything, James Wynn never really left the table. From July 2025, barely recovered from its liquidation, it reopened leveraged positions on ether and on PEPE. The scenario then repeats itself several times over the following months: new positions, new fleeting gains, new liquidations. In April 2026, his account melted to $900 after a sixth liquidation in two weeks. Clearly, there were more than two hundred in total since its debut 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 an almost daily policy instrument. The crypto market now reacts within seconds to each of its messages on the networks. One Friday in October 2025, an anonymous whale opens short positions on Hyperliquid. She bets 80 million dollars on bitcoin and 30 million on ether, at 10x leverage.
The timing is almost perfect. A few minutes later, Donald Trump announced a 100% tariff on China and caused the entire crypto market to plunge. The profit is estimated between 150 and nearly 200 million dollars according to Arkham Intelligence. On-chain investigators point to Garrett Jin, former manager of the BitForex platform, who denies any anticipation and denounces the disclosure of his identity by CZ himself.
Who is Garrett Jin?
The alleged identity of the trader has never been officially confirmed, but Garrett Jin remains to this day the name that comes up most often in on-chain investigations. His previous career does not help his defense. BitForex, the exchange it
