Traders placed over $1B in perfectly timed bets on the Iran war(theguardian.com) |
Traders placed over $1B in perfectly timed bets on the Iran war(theguardian.com) |
Nice insider trading scam you have going. Be a shame if something happened to you.
Then defenetrate them.
They aggressively pursue other leaks, including searching journalists' property.
The result is always a loss of credibility. With time, only the dumbest keep betting.
It’s still shocking corruption and absolutely should be enraging. But that’s because it’s a 10s of millions dollar trade. Not a billion dollar one.
They might as well quote the Quadrillions changing hands in the OTC derivative package markets.
> Sixteen bets made $100,000 each accurately predicting the timing of the US airstrikes against Iran on 27 February
How many bets and for what ammounts were made for other days, or that it wouldn't happen on the 27th?
These markets are global with global demand and many of the insiders are on the receiving end of American foreign policy. If an Iranian with a starlink sees a b-2 spirit fly over their house that information will find its way to somebody who will profit from that knowledge, it's just part of the new information economy.
You're claiming the U.S. government is impotent against holding Polymarket to account?
> These markets are global
The trades in question are bets on Polymarket and Intercontinental Exchange Brent oil futures. These are well within the remit of American law enforcement.
Yes, if US regulators quash Polymarket their lunch will be eaten by a global competitor HQ'd in a country the US can't touch.
A lot of the insider weekend trading of oil is happening on hyperliquid, a DEX associated with developers in Singapore, what can the SEC or CFTC do to them?
same administration who has a son sitting on the board and a father president who has lifted all sanctions and investigations.
we even have video of representatives placing their bets or buying stock during session, right before voting on the matter.
"Solving" the problem of administration juniors compromising our military for profit doesn't require sabotaging anything. Just the exchanges turning over records.
Though it’s not that different from the stock market, where the folks at WSB happily give their money to Citadel, Jane Street, and friends, because every once a while, one of them hits it big after going all in that the ball lands on green.
Gambling is a hell of a drug and there are good reasons why it is illegal in so many places. Prediction markets have some good externalities (information), but it’s another addictive outlet for those vulnerable to gambling addiction.
More like a tax on being ethical or having any morality.
Even if you suppose my example is bad, you should be able to envision some case where such hedge is helpful.
Because they are grossly mis-priced for anyone mildly informed.
If people who do the obvious trades (sell oil right now - it's going down) lose money, all you have to do is do the opposite (buy oil right now - it's going down) and gain money. Is it not that simple? You will profit along with the insiders when Trump blockades the strait again, although you won't have such perfect timing.
Politics is already full of these pay to play incentives but now anyone with enough cash can influence world events.
Most of the other prediction markets seems rather stupid to me (they are completely detached from any real world activity), other than their prices being a fairly reliable source of information for bystanders.
You just described what is happening, you didn't actually provide any reason for why this is good for anyone but the individuals profiting from it.
I was thinking about what you said w/r/t the proximal issue (gambling in prediction markets) and my 1st though was "why is this a big deal? If you're not an insider, just don't participate in these markets ... and then the insiders don't have a counterparty to fleece."
But I thought a little more about and I think you're right. Insider's fleecing others in prediction markets just erodes trust everywhere. And we need a considerable amount of trust in people we don't know for society to function properly.
I don't know the owner at my local hardware store, but I trust that he won't sell me shoddy tools. The same goes for every societal interaction. We need to trust people we don't know. If that gets eroded, we go back a several centuries.
This is remarkably similar to how workers in the Soviet Union got ahead. Your job provided a lot of ways to make money on the side, none of them were beneficial to productivity/trust. I think this kind of reality might just be normal for societies in collapse (also, "gerontocracy")
Go on, I'll wait for those "merits"
It helps that some states are bringing criminal charges vs these companies. But it looks like a no contest as to how we'll look back to these kinds of things in 5 years.
Betting on war is war, you may argue that it's an individual's right to participate in war, (I don't think so, I think that it's a war crime for unmarked civilians to participate in war), but funding bellicose action is war.
No it isn't. When this sets in, it becomes insidious and distorts the entire system.
This is a product of a secular neoliberal culture (certainly including this website) that there is no 'society', really, or at least nothing that's BAD for society - effectively the same thing. If profit is king above all else, there's nothing wrong with vice, with scams, anything to chase the bag. It used to be that neoliberals understood community, but even suggesting that the health of society exists is considered reactionary now.
Anyway, one thing I don’t understand yet is how new markets are created. They aren’t user generated, so how did an “Iran strike” market exist to begin with?
Having the US presidents kids as multimillion dollar investors in the platforms and on the advisory board of one them would be a good place to look
Users absolutely can propose markets
Similarly to how people would pay premium over inusrance
Math wins over your feels every time.
And yet there are folks like me who have been on them for years before kalshi/polymarket making a very good side income from them without having insider knowledge.
Prediction markets as a whole are very very inefficient. That's not to say that insider trading doesn't exist but you can't claim that they require insider trading to function.
I personally don’t know any, and I worked at one of the biggest HFT firms for a few years.
The losing side(s) of these positions are heavily hedged, and are happily making money on volume and volatility. (And making record profits this year)
Because it won't be prosecuted by 2029 but could be afterwards
Personally I think it's a bigger problem when the President sues his own government for billions and then orders them to pay it out
Because -that- is not an official act. It could be prosecuted but no-one will touch it even after 2029
Just one more thing this administration has brought into mainstream.
It certainly wouldn't perfectly solve things but the further out a prediction is made the more risk there is that the outcome could change - even for someone with insider knowledge.
E.g. I've worked in businesses where an M&A has looked a nail on cert - as part of a small discreet team involved we were being readied for the announcement etc. only for it to stumble a few days before completion.
Obviously there are some markets/situations where a few extra days won't make a difference at all, but I could see how something like that would introduce more risk/uncertainty for those with insider knowledge.
Traders place $760M bet on falling oil ahead of Hormuz announcement
It protects 99% of people who want to have fun by losing money and prevents insider trading at no virtually no cost.
This is an open kleptocracy now. Nobody will be punished for any of this. Any regulatory authorities have had milquetoast deregulatory sycophants put in charge of them. The powers of those agencies have been consistently eroded by a Supreme Court of radical ideologues.
That same court completely invented presidential immunity out of thin air for the person who appointed 6 of them. That president will continue actively selling pardons. If he's not involved in these trades, he'll sell pardons to those who are. And the president himself is free from any consequences. You might be tempted to say "impeachment". I chortle.
A lot of poeople misunderstand the source of the power of the American dollar. They then go on to say nonsensical things like "trading oil in [other currency] will destroy the petrodollar". No. Oil is traded in dollars because of the demand for dollars, not the other way around. What underpins the strength of the US dollar is the US military.
That US military has been humiliated in Iran and really hasn't won a conflict since 1945 (not countin Grenada). This latest war has alienated current allies. If this continues, I can honestly see people looking for an alternative where whoever controls the currency will actually maintain the integrity of the market by prosecuting this kind of kleptocracy.
You need centralized regulation to make it work.
(And I do not see how this first-order viewpoint is problematic, precisely. It’s the second-order consequences of people making the currently-considered-unlikely decision in order to cash in on a bet that I have an issue with.)
I guess, how many not perfectly timed bets did traders bet on these things?
because if it did you would print money by following occam.
https://www.theatlantic.com/politics/archive/2025/06/trump-p...
Would be ironic if Iran was getting funding this way.
I predict these will be banned when someone finally uses them as an "assassination market".
So the perception of insiders is pretty bad for prediction markets as a business imo.
The sooner they knock off the rhetoric about the “theory” behind prediction markets and start thinking about it like a business, the sooner they will take insiders seriously.
Although Polymarket is currently spending a lot of money trying to market itself to working-class regular people to get hooked and scam their paychecks out of[0]
[0] https://nypost.com/2026/02/12/us-news/nyc-gets-its-first-fre...
What are the chances of large bets being made by anyone who isn’t an insider?
Sweet summer child…
It is widely accepted that this is happening. Dumb money continues to be poured into these markets.
Being indicted for treason and treason like charges sounds worse than the SEC coming after you.
Gambling should be judged as any other vice - people get something out of it (rush, hope, whatever) not by rational money allocation standards.
This is not a "crypto prediction market" problem.
Prediction markets are supposed to be providing the most accurate predictions.
The most accurate predictions come from insider information.
Poeple complaining about insider trading on prediction markets seem to be missing the point. They're supposed to have insider trading. That's the whole idea.
https://x.com/peterjliu/status/2024901585806225723
But there is still the problem of knowing which new trades the insiders made before the bet is settled (maybe solved by being an insider of the prediction market), and also since prediction markets need money on both sides (you are betting against other people, not the 'house') when the insiders make their buy they probably eat up most of or all of the action on the other side.
If you had a reliable edge, your income would be exponential. Why isn’t it?
Prediction markets are all the buzz, but banning them isn’t fixing the problem. This has happened forever. Let’s not forget there was an unusual amount of put option buying right before 9/11: https://ideas.repec.org/a/ucp/jnlbus/v79y2006i4p1703-1726.ht...
https://thehill.com/opinion/white-house/5829203-presidential...
Unless they're absolute morons, the people doing insider trading for large sums of money will have already built a strong alibi.
My theory is they are banking on preemptive presidential pardons in Dec 2028.
If you have perfect opsec, sure, you'll just waste a few years and hundreds of thousands of dollars in court. If you texted a friend, or told a friend who then texted a friend, or traded too soon after receiving privileged information, you're probably fucked.
> Unless they're absolute morons
At least in securities, the dirty secret is most insider traders are in Congress and/or morons.
In other nations you can illegally sell arms to Iran in order to illegally evade congress's attempts to stop you supplying money to terrorists, illegally shred evidence and lie to congress under oath about it all and get a job as a pundit on Fox News.
An employee with access to Truth Social's backend can in theory do this by reading the tweets he's writing before he sends them.
Democrats have historically not really been willing to do anything if there's any plausible sounding reason for doing nothing, so I'm guessing they'll jump at the opportunity to wave away the insider trading stuff. Let bygones be bygones, you know, in the spirit of bipartisanship and comity. They slow-rolled prosecuting the crimes of the first Trump administration. So slow that he was re-elected before anything began to happen.
I think it's just that we create useful tools: futures, the pre-emptive pardon, and so on. Then people figure out how to use those tools to enrich themselves in ways we did not anticipate. It's just a question of how we fix our machinery in this cat and mouse game or if it is fixable at all.
But if they _are_ rational, eg, a zimbawean inflation nightmare, then if you're not trying to "escape the permanent underclass" then _you_ are the irrational person.
So ignoring all politics, we're really dealing with a zeitgeist of people who think wealth inequality is endless, and the only way to survive is to lobster bucket and YOLO every chance to gamble.
Don't create artificial scarcity. Don't play zero sum games.
Maybe this is just my lack of understanding in how most SaaS companies operate... But to me making software that people find valuable and charging them for that is not inherently immoral. Surely that is the majority of cases?
The original idea behind SaaS is to align the incentives of the customers and the software company.
Historically software companies made money on selling upgrades. This meant bug fixes were not a priority, and security fixes were something companies got shamed into doing.
SaaS fixes that incentive problem. With reliable ongoing revenue a company can keep software patched and updated and doesn't have to cram a bunch of new shiny marketable features in just to make a huge sale every 3 or 4 years, while engineers try and add whatever bug fixes they can after the shiny new features have been polished off.
It also means software companies don't have boom or bust cycles with hiring. Funding stays consistent, and so does staffing. It makes the financials much easier to manage. Companies used to hire a bunch of temp employees in the run up to a release.
Ongoing release cycles also led to better software engineering practices. More automated tests, reproducible builds, better version control systems, and a lot more things that we take for granted now days.
There are obvious downsides to SaaS as well, but the original idea was good.
Nah. You know what the answer is? Get to a mental and physical state where you need very little. Right now the only way to win is not to play.
Granted, maybe I should be less surprised given the fact that this is all being posted on the promotional website of a technology-focused private equity fund, but it's disappointing nonetheless.
[1] https://www.cultivatelabs.com/crowdsourced-forecasting-guide
The benefit to those outside the insider class are that we now have a better idea of the potential outcome.
[1] https://www.psychologytoday.com/us/blog/inside-out-outside-i...
Akey, Gregoire, Harvie, Martineau (2026) on Polymarket find that the top 1% of wallets capture about 84% of all profits, and that the largest whale wallets are NOT the most sophisticated. Large capital systematically bleeds expected value to small order traders. Reichenbach and Walther (2025) document within-Polymarket skill persistence at the 124M-trade scale, so skill differentials are measurable across users distinct from the insider trading question.
https://polymarket.com/event/trump-out-as-president-by-april...
which is effectively an assassination market on him. And there other such crowd-sourced hits on other heads of state.
That’s why these platforms saying things like “we will roll out insider trading” is laughable.
Is anyone using AI to track these audacious and large bets? Seems like you could actually do this to tell which ones are insider info and which are just stupid random bets?
It's worth noting that these prediction markets just run on blockchains, so pretty much anyone with the mathematical and technical knowhow can analyze those data streams and do much better than your average degenerate gambler who has no idea what they're getting into
Key is reconstructing the historical data from the smart contracts that run these things, that's a bit of a challenge but last I checked there's some companies which have figured this out [1]
They believe that everything that is created should be public domain when the cost of replicating it is zero (books, media, software, music, most art). Those people also generally believe that borders and countries shouldn't exist.
Whilst I respect their worldview, I have found that it's not worth arguing with this group because they typically refuse to explain how such world would work, handwaving away any problems you'll bring up.
Do you believe it is moral to restrict access to something that is effectively infinite?
The first seems arguably treasonous. And the latter seems directly supported and funded by these "prediction markets".
If the argument is that prediction markets are truth machines, their social function seems to be support crime on a massive scale and get away with it.
If we take a completely utilitarian and amoral viewpoint, the insiders are selling their material, non-public information. The rest of the market participants are buying. From the latter's utilitarian perspective the former are providing a valuable service and getting paid for it. I'm pretty sure there was a legal term for such sales activity...
The only people playing fair are those who don't know how to cheat well enough.
Kalshi and poly market are going after mass market appeal which is why they buy Super Bowl ads.
Military operations go awry. Countries react in unexpected ways. Leaders change their minds.
And as a potential event gets closer, insider information changes. Different insiders have different sets of partial knowledge.
You don't even need scheming and tricking. Just regular reality is already complicated enough.
Let's say that you know that event Y is going to be announced that will make event X more likely. Before Y is announced you buy shares in X on a prediction market or buy some asset that has price correlated with X. After the announcement you liquidate your position and pocket the difference.
Whether X actually happens or not is irrelevant to you. All that's relevant is the timing of the announcement of Y and the directional effect of Y on X.
There are good reasons why insider trading illegal for publicly traded stocks.
But those reasons don't translate to prediction markets.
As I see it, insider trading leads to insiders making decisions purely to game the (prediction) markets which means that markets become more erratic and will surely lead to less money being available for companies to grow as investors realise that they are being robbed.
A great example was this market from the most recent primary election.
https://kalshi.com/markets/kxtxsenatedemturnout/voter-turnou...
Based on just simple math there was basically no chance of turnout being over 2.5m and yet the market for multiple days had the higher buckets at exorbitant prices.
https://www.msn.com/en-us/news/politics/trump-plans-to-pardo...
https://www.independent.co.uk/news/world/americas/us-politic...
[1] https://www.criminallawlibraryblog.com/preemptive-pardons-co...
I don't understand why insider trading would only happen as something becomes news. The inside knowledge haver is risking the information leaking some other way before they make their bet. Some very risk averse insider traders (lol?) may do so, but others are going to make their bets when they learn their information.
Assuming that they don't though, and every insider trader only ever makes their bets right before an event, I don't see how that changes anything? People working with non-insider knowledge are still going to be betting against each other before that point. They are still going to establish a likelihood of a thing happening that's more accurate than I would by myself.
The potential for scamming is high at low dollar figures sure. At some point of volume though, it's going to become too expensive to do.
> People working with non-insider knowledge are still going to be betting against each other before that point. They are still going to establish a likelihood of a thing happening that's more accurate than I would by myself.
How is this useful information at all? Other than to sate your curiosity and undiagnosed gambling problem.
Price discovery in capital markets is useful because, well, there is no other way to discover price. By definition, the price of an asset is what someone is willing to pay for it.
Event discovery in prediction markets is throwing your money away hoping you guessed right, despite the fact that the biggest markets have insiders who are always going to outperform you. It's a sucker's game.
In other terms, it allows people to transfer risk to money , or information for money.
As usual, it's a tax on naive and those who get addicted; the twist is that they are willing to pay it, demand and beg to pay it, so providers spring up, legal or not.
> WONG: However, Gerry says most of the major airlines in the U.S. eventually soured on fuel hedging. One reason - the Wall Street transaction fees to make these hedges got expensive.
> WOODS: Plus, Gerry says the airlines found that they could make money the old-fashioned way by raising prices. Today, none of the major airlines in the U.S. are hedging.
Hedging is one of those things that sounds cool but then when your service is x% more expensive than a competitor and you lose customers you just stop doing it. It's kinda like being on AWS; when everybody has an outage together nobody asks "oh what can be done differently".
[1]: https://www.npr.org/2026/03/27/nx-s1-5759203/fuel-hedging-on...
https://www.irishtimes.com/business/2026/03/25/ryanair-to-ho...
> European carriers have hedged about 80 per cent of the fuel they need for this year and typically take out new hedges on a rolling basis to lock in future prices.
If your go-to reasoning for why we need prediction markets is so airlines can have more predictability in their fuel costs, you're inadvertently making a solid argument that we don't actually need prediction markets. And this isn't even getting into the other ways these airlines could satisfy the same need.
The reason it works better is because in a prediction market, the person betting against you has no resources or ability to go after you for fraudulent behavior. Whereas an insurance company has both.
So you are renaming something that doesn't and won't ever exist.
Exploiting people with gambling addiction is not a reasonable replacement for insurance.
Conceptually, I think that is the right analogy to think about. Prediction markets "want" to be a more accurate source of information, just like stock markets, so from that lens "getting" information to be more accurate is good. When government officials are placing bets on prediction markets, though, it's a massive violation of operational security, and leaking confidential information. They probably think that they are acting anonymously, but it creates so many opportunities for unfriendly state actors to get information, especially if people do it consistently.
The goal should be to balance the information asymmetry, not burry it.
Government officials using their power to affect war decisions ought to be a crime on it's own, not surfacing the information to the public through a prediction market.
Like if I look up home depot they talk about price volatility and that's the exact opposite of what a hedge produces. I'm honestly starting to doubt if they hedge at all; like why bother using Wall Street as an intermediary and just talk to your suppliers.
> [1] This was another historic quarter for lumber price volatility. During the first few weeks of the second quarter, prices for both framing and panel lumber reached all-time highs before quickly falling from their peaks. As an example, during the second quarter, framing lumber peaked at approximately $1,500 per thousand board feet before falling over $1,000 to approximately $500. While pricing for both framing and panel has come down from the peaks, the average price during the second quarter was still significantly higher than the same period last year. Inflation from core commodity categories positively impacted our average ticket growth by approximately 420 basis points during the second quarter.
[1]: 2021 Q2 - https://ir.homedepot.com/financial-reports/quarterly-earning...
If there are no consequences for the cheaters, it becomes essentially mandatory, and that's without there being money on the line.
The good point of prediction markets is that they provide information. This information is available to everyone, for free, which benefits everyone.
Insiders help achieve this. Insiders have information and by participating in the market they then expose and share that information. So this is good. If we ban insiders, we're just banning accurate information from getting into the market. If we do that, we might as well just ban prediction markets altogether. I don't have a strong opinion either way on that, but a prediction market without insiders is pointless.
It is not a free market if there is insider trading. If insiders are trading other market participants are by definition getting screwed by what was advertised as a fair, impartial system.
You certainly wouldn't participate in a market where you did not think you had fair odds. Tho maybe you're inclined towards the rigging side of things.
Finally, since you're trying to work the information angle, would you care to share any legitimately meaninful information you've gained from prediction markets?
It is illegal to insider trade in financial markets, which makes sense to me. But financial markets and prediction markets are different; one exists to surface capital, the other information.
Insider trading is forbidden in financial markets because allowing it would be a disincentive to participation by non-insiders, which would be bad because it would reduce the amount of capital the market was able to provide.
In prediction markets, allowing insider trading would be disincentive to participation by non-insiders, which would be a good thing, because the market should surface the most accurate information as possible and insiders have more accurate information than non-insiders.
> and has long been recognized as such.
Prediction markets are in their infancy. They've only really existed for about a decade and even now are tiny compared with markets like commodities or equities. So I don't see how this could have been "long recognized."
> It is outrageous for you to suggest that it is a good thing.
This is not an argument.
> You certainly wouldn't participate in a market where you did not think you had fair odds.
Of course I wouldn't and I wouldn't advise anyone else to do so. But why would we want uninformed people participating in prediction markets? I don't think they should.
What does "fair" even mean here? If Alice is more informed than Bob about X, she'll probably be better at making predictions about X. I guess it is "unfair," but what would the point of a prediction market be if we only allowed uninformed people to participate? Then it's more like a survey of what the average person thinks will happen, which is probably common knowledge, so we don't need a market to find that out.
> Finally, since you're trying to work the information angle, would you care to share any legitimately meaninful information you've gained from prediction markets?
Prediction market odds for elections and important world events are regularly quoted in the press and AFAICT seem to more accurate than pundits and and oped writers at predicting the future. A low bar, but still, if we are going to speculate about the future, we might as well see what actually informed people think.
The wild thing is that prediction market dabbler rationalists who think they're betting on the outcome of a pre-written fiction story are actually just upping the reward for someone to come along and bomb people to death. Your participation is not neutral. You are culpable in the outcome of the situation you're "gambling" on which has not been determined yet and you are literally throwing fuel on the fire. No matter which way you bet it's fuel.
I'm sorry, I don't believe you personally deserve it but for the betterment of the everyone we have no choice but to shame people like you (prediction market rationalizers) via downvotes and hot replies until you can see through the limits of your overly simple model of reality.
I don't think you're a bad or stupid person, but when it comes to your views on prediction markets, they are very bad and very stupid. Thankfully you are not your beliefs and you are free to change them at any time. I beg you to reconsider this one.
Let's start of with something simple. Should a single wager between two people be illegal, should sports betting at all be legal? Is it only illegal if one or more entities facilitate the bet?
All anyone knows is that some bloke put money down an hour before the bet resolves.
They don’t know squat about what info those betters have.
Stop telling us the moon is cheese
Insurance works on repeatable, predictable risks based on models.
You can't get insurance against a military attack. But you can hedge using a prediction market. It's essentially the version of insurance for one-off events, that relies on wagers since you can't use models.
I bring this up because we assume the trading is coming from insiders but I wonder if the parties behind this have baked in a layer similar to my story above.
To close this back to your comment, and I don’t have an answer here: is knowing who the insiders are and acting on that a crime? If you did know and didn’t report them, are you breaking a law? Or worse, you reported it to the deaf ears of a regulator that are focused elsewhere or are under resourced to respond now?
it's legal to follow FBI cars and see who they raid so as to make trades. you could even have a hedge fund specialized on this. it's called alternative data
you can even be a regular employer of a public company and trade based on information sent on internal emails.
the only thing illegal is to be a designated insider - typically a restricted group of people with access to sensitive information
You absolutely cannot.
Sure. But these aren't trades in "the oil market." They're bets on Polymarket and a specific oil-futures exchange.
Don't poop in the public swimming pool and don't feed perverse war games that result in children and their parents being maimed and killed.
Need a strong source for this. The size (and regulatory) disconnect between the two would seem to make making markets in both a bit silly.
The problem is that prediction markets are excellent vehicles for corruption as demonstrated by the article discussed here.
You're arguing that corruption is a good thing.
The fact remains that prediction markets and financial markets are not the same thing. Bets between people happened all the time, and you would wager based on information asymmetry, that is the whole point of it.
By making these markets public facing, you get access to this information asymmetry, whereas before it was behind doors, and these bets were already taking place, you just didn't know it, now you do.
Note also that prediction markets can't be too different from financial markets because prediction markets are in some sense a generalization of financial markets e.g. you can make a prediction market that predicts the price of some stock on some day.
Imagine if a CEO of a company does something that would damage the price of the stock of it's own company, having shorted the stock before? That's not insider trading, that's (probably, I don't know the exact term) fraud and will lead to prison sentence.
Prediction markets enable the policymakers to make these bets. Arguably, there should probably be sorts of limit on who is allowed to be there. But there are still counter examples like Nancy Pelosi who somehow manages to go around these limitations in stock market.
That's whats currently happening.
Even then it would be inaccurate: the regulators are not too stupid to put two and two together that you work for a company and got incredibly lucky with your trade
> the regulators are not too stupid to put two and two together that you work for a company and got incredibly lucky with your trade
You’re implying some specific combination of factors, but it’s not clear what you mean. What qualifies as "timing"? Around earnings, when trading volume is highest or just around some event? And what exactly counts as "lucky"?
Why would regulators scrutinize a sub-$25k purchase of my own company’s stock? That concern feels overstated. Granted, I’m not a lawyer. In practice I can place a trade at any time. If someone is routinely making $20k–$30k transactions, that alone is unlikely to trigger scrutiny.
The claim that you "absolutely cannot do this" is simply incorrect. I stand by that.
Here's a few examples: https://www.sec.gov/spotlight/insidertrading/cases.shtml
Some further advice on the matter: https://www.bloomberg.com/view/articles/2018-08-12/the-10-la...
10 Laws of Insider Trading
1. Don’t do it.
2. Don’t do it by buying short-dated out-of-the-money call options on merger targets.
3. Don’t text or email about it.
4. Don’t do it in your mother’s account.
5. Don’t do it by planting bombs at a company and shorting its stock.
6. Don’t do it while employed at the Securities and Exchange Commission.
7. Don’t Google “how to insider trade without getting caught” before doing it.
8. If you didn’t insider trade, don’t forget and accidentally confess to insider trading.
9. If you are going to insider trade, do it in a company that is far away from a Securities and Exchange Commission office. Like, physically.
10. If you are already under a federal ethics investigation about your ownership or promotion of a stock, don’t insider trade that stock.
If they never make money, you’re fine. If they make a lot of money, it will get flagged ex post facto. Regulators then check if you or your family have any affiliations with the issuer; if they do, it’s flagged further. All of this typically happens automatically after companies’ stock prices move significantly.