100 John Does

Susquehanna Investment Group, the large options market making firm founded by Jeff Yass, sued 100 anonymous defendants after suffering approximately 70 million dollars in losses on Chinese brokerage options. The alleged scheme centered on a Chinese government crackdown on cross-border trading announced around May 22nd, which caused share prices of Chinese brokerages including Futu Holdings and Tiger Brokers to plummet. The defendants bought short-dated out-of-the-money put options on those brokerages, many sold by Susquehanna as market maker, and Susquehanna described the coordinated activity as one of the largest insider trading schemes in recent memory.

Susquehanna filed naming defendants as John Doe 1 through 100, with 100 being a placeholder rather than a precise count, because identities were unknown at filing. The immediate legal objective was to freeze defendants' brokerage accounts and compel brokerages to disclose account holder identities. Because most defendants are likely in China and may not appear in court, Susquehanna may be able to keep the frozen funds by default. Grouping all defendants together also allowed Susquehanna to cite the larger aggregate 70 million dollar figure, making the case appear comparable in scale to prominent insider trading precedents.

Not all 100 defendants were necessarily insiders. A retail trader who observed unusual put option activity and simply followed the crowd could be swept into the conspiracy complaint despite having no insider information, and Susquehanna has withheld payment to winning traders without yet proving insider trading in court. Yass argued as far back as a 1992 interview in Jack Schwager's New Market Wizards that tighter SEC enforcement on insider trading allows market makers to quote tighter spreads because they lose less money to informed traders. If insider trading were legal, as Interactive Brokers founder Thomas Petterffy has argued on the grounds that it gets information to market faster, market makers like Susquehanna would charge wider bid-ask spreads, shifting costs onto retail investors to subsidize insider trader profits.

MicroStrategy, where Michael Saylor serves as chairman and driving force, borrowed heavily through a preferred stock instrument called Stretch to buy Bitcoin and is now under pressure as Bitcoin has fallen in value. Stretch was issued in July 2025 at a par value of 100 dollars per share with an original dividend rate of 11.5 percent, but the market-clearing rate has risen to 15 percent and MicroStrategy raised the dividend only to 12 percent, leaving Stretch trading in the 80s. Bloomberg reported in May that MicroStrategy represented the majority of corporate and ETF Bitcoin buying for the year, and the company is now trading at or below net asset value, meaning the creative dilution strategy of issuing stock at a premium to buy more Bitcoin no longer works.

MicroStrategy has announced it will sell some Bitcoin to raise cash and is buying back Stretch preferred stock, effectively abandoning its stated intention to keep Stretch at par less than a year after issuance. Reversing the leveraged trades on the way down involves large frictional costs because assets were bought high and are being sold low. MicroStrategy's perpetual preferred structure means there is no contractual obligation to ever pay dividends, giving it the option to skip payments and hibernate rather than face a hard default. Matt Levine, drawing on his background as a corporate equity derivative structurer, says he cannot identify a new capital markets instrument that actually makes sense for MicroStrategy given current conditions, and predicts the company's overall strategy could look substantially different within six months.

The SEC has received multiple applications for prediction market ETFs and has slowed the approval process, issuing a request for public comments on unusual ETFs generally. The current ETF filing process does not allow the SEC to formally reject an application, so the SEC instead backchannel discourages issuers who then voluntarily withdraw. Sports bets can now be made on a regulated U.S. commodities futures exchange, and one speaker predicted in March 2025 that within two years there will be sports gambling ETFs in the United States. One proposed strategy involves betting on heavy favorites to achieve a bond-like return uncorrelated to broader markets, a concept traced to a Wharton paper whose author subsequently ran a sports gambling fund in the early 2010s. Both speakers noted the SEC has already approved double and triple leveraged single-stock ETFs, making any regulatory line on sports gambling ETFs appear arbitrary.