Polymarket question "Will Sam Altman go to jail?" can be used to incentivise insiders who can put Altman in prison
Disclaimer
Contains politically sensitive info
Using Polymarket is in a grey area in the US and in India and in many other countries
Insider trading is clearly illegal in most countries, although some polymarket and crypto cases have escaped actual enforcement.
I have not done too much research on the exact legal and political risks involved here. I spent maybe a day or two on this, that's it. Maybe pay me or message me (ideally keeping yourself anonymous), if you want to nudge me towards doing more thorough research of this topic.
Summary
Consider purchasing a Limit Buy No order at $0.97 on the polymarket question "Will Sam Altman go to jail by 2026-06-30?", probably anonymously.
If an insider actually knows how to get Altman in prison, for instance by leaking proof of crimes Altman has done, then they can reduce financial and other risks to themselves by accepting your bet first and using this money to fund themselves. Also, they might be able to accept your bet while staying anonymous, in some edge cases.
The main downside is you might incentivise someone to entrap Altman on purpose, or even lie about insider knowledge, in order to shift the market prices. I consider this unlikely but not impossible.
Contains list of previous examples of Polymarket incentivising insiders
Most importantly, as of 2026-05, the courts involved have not confiscated the money yet in many of these cases, even after they have deanonymised the identities of the traders. This means the insiders successfully profited off of their insider trading.
See also: Robin Hanson's long history of working on this idea, including his recent comments that insider trading is sometimes fine actually.
See also: Polymarket's attempts as of 2026-05 at doing PR damage control instead of actually fixing insider trading on their platform.
How to use this Polymarket question to incentivise insiders?
Just set a Limit Buy No order at a price noticeably below the market price. For example, as of 2026-05-21 the market price is around $0.99 for No, so you can set a Limit Buy No order at $0.97.
If an insider has information that can get Altman in prison, they can market buy Yes against your order, then leak the information or take other steps to get Altman in prison. You will lose your money, and this person will gain it.
If nobody accepts your order, you make neither profit nor loss.
If someone accepts your order but Altman doesn't go to prison, you make a small profit. Although, after adjusting for interest rates and the platform risk you've taken by trusting Polymarket with your money, it is definitely not the most profitable thing you could do with your money.
Even if the insider cannot 100% guarantee Altman ends up in prison, if they can shift the odds of the prediction market significantly in their favour, this again allows the insider to profit by matching against your order and then selling Yes at a higher price.
Why use this Polymarket question to incentivise insiders?
Assume there are insiders who have compromising information on Sam Altman, that they can use to put him in prison. For instance they may have information on his case of sexual abuse of his sister, or of him committing financial fraud, or of corruption of democratic processes such as bribing or intimidating politicians, and so on.
There are two reasons why an insider may want to be paid this way
Reason 1: They want to hedge the financial risk upfront. (I find this reason more persuasive.)
If the insider comes out publicly in the US and sues Altman in the US, they are taking on massive financial, legal and reputational risk. They can ask for donations publicly for their lawsuit, but there is still uncertainty in their head as to how much money they will raise this way. Also, they may have personal expenses such as hiring private security or private investigators or similar. The court can confiscate their gains from the market by claiming it was insider trading. However, there have been cases recently where money earned by insiders hasn't been confiscated.
If the insider leaves the US and then comes out publicly, then too they are taking on massive political and reputational risk. There is no guarantee they will get asylum, it might take a while to get a new job even if they did get asylum, they will need money for a lawsuit and so on.
In both of the cases, if the insider can get paid upfront, before they take on all these risks, it makes sense for them to accept this payment.
Reason 2: They want to stay anonymous. (I find this reason less persuasive, but it might be valid in some edge cases.)
If the insider is actually dealing with classified information or similar, I am actually quite skeptical of their ability to stay anonymous for long, the US intelligence will eventually deanonymise them. See for example the person who bet on US-Venezuela war on Polymarket using classified information, and got arrested and then released.
If the insider is dealing with lower-stakes information, maybe they can stay anonymous, leak the information and claim their winnings from Polymarket. But also, I am not entirely sure what "low-stakes" information is sufficient to get Altman in prison, without also facing either private investigators or a govt investigation yourself. There may be some edge cases here though.
There are some reasons to not pay an insider this way, although I am skeptical of these reasons.
Reason 1: An insider might just lie about what happened, and shift the market.
I agree the public is stupid, but I am not convinced they are that stupid. If the insider lies about what happened without any actual hard evidence (such as emails with DKIM headers, photographs, or similar), I am skeptical they will be either able to shift the polymarket price or actually get anyone in prison. I agree this is not impossible though.
Reason 2: An insider might take this money as an incentive and then deliberately try to trap Altman in a situation where he does something illegal. Legally this is called entrapment.
I think Altman is quite good at politics, and is unlikely to fall for dumb traps like this, atleast given the current small amounts of money on the polymarket question. (My personal speculation here, I could be wrong.)
I might also be okay on moral grounds if someone does manage to trap Altman this way and get him in prison. (I haven't thought this opinion through, so take this as an off-the-cuff comment again.)
More bets similar to this
In theory, you can have such bets on all the AI company and govt people, not just Altman. Tag Polymarket team on twitter and ask them to list the others too. Also, maybe put your money where your mouth is, actually bet on the market, thereby giving Polymarket a signal that many people want to bet on such markets.
In theory, you can organise this bet without using Polymarket at all, you just need a trusted third person to settle the bet. Polymarket relies on UMA Optimistic oracle to settle their bets, and Polymarket has a reputation of settling bets honestly. You can use UMA optimistic oracle too. Or the simple version is just find a trusted arbiter and put the money in a multisig involving the arbiter and the bettors.
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