In most gambling, as in the casinos or in betting on the outcome of sporting events where there is no doubt as to what the result is, there is usually a clear way of deciding whether you won or lost the bet. But the new betting markets like Kalshi and Polymarket allow you to bet on events where the outcome may not be that clear-cut. Hence there has to be some standard associated with the bet that tells you how the outcome is to be judged.

So, for example, take the bet that the US and Iran will agree to a permanent peace deal by a specific date, where the options for dates are April 22, April 30, May 31, and June 30. How would one judge that? The rules state it as follows.

This market will resolve to “Yes” if Iran and the United states agree to a permanent peace deal by the specified date, 11:59 PM ET. Otherwise, this market will resolve to “No”.

A permanent peace deal refers to any agreement which explicitly indicates that military hostilities between the United States and Iran have ended or will permanently cease, or uses equivalent language clearly signaling a lasting end to military hostilities between the United States and Iran. Agreements that are explicitly temporary or which do not include a definitive agreement to end military hostilities between the US and Iran on a lasting basis (e.g. a temporary extension of the two-week ceasefire agreement announced on April 7, 2026), will not qualify.

A qualifying agreement will be considered to have been established if either of the following conditions are met:

– The United States and Iran each sign or formally adopt a written agreement (e.g. a treaty or multi-point agreement) which meets the above criteria.

– Both the governments of the United States and Iran provide clear public confirmation that a qualifying agreement has been definitively established. Negotiations, statements of progress, or other statements which do not constitute a definitive announcement that a qualifying agreement has been reached will not count.

The primary resolution source for this market will be official information from the governments of the United States and Iran; however, a consensus of credible reporting may also be used.

I can see many points of contention that can arise. The words ‘explicit’, ‘clear’, and ‘definitive’ are all open to interpretation. The sources for resolution as stated in the last sentence is also problematic. In the case of the US, Trump is notoriously fickle and a liar, who can say one thing and then switch to the opposite without compunction.. Hence any statement from him is not worth anything. But what about ‘credible’ reporting? Furthermore, this kind of thing is ripe for people with insider information to bet on that knowledge, And we know that the venality that runs through the Trump circle will not hesitate to use it.

As a result of this kind of ambiguity, it can lead to aggrieved bettors who lose a lot becoming disgruntled.

“Horekunden” was rapidly losing patience.

His frustration was with the Institute for the Study of War, a US thinktank which produces a daily map of the frontline in Ukraine.

For Horekunden, and other anonymous gamblers, the map was a “disjointed, incoherent mess … like the painting of a five-year-old”. Therefore it was no use to them in their aim: to settle a bet on the online prediction market Polymarket.

The map they were unhappy with depicted the city of Kostyantynivka, which Ukrainian troops have been holding for five months amid shelling and swarms of drones. Thousands of civilians still live there.

There is now more than $500,000 (£371,000) staked on whether Russia will capture Kostyantynivka this year . These bets will be settled if the ISW releases a map showing Russia holds the city’s train station.
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But longtime users say it increasingly resembles a casino – where everything, from Trump’s fury to the second coming of Jesus Christ can be monetised. So where they can, players in this powerful “casino” have started trying to shape the world to secure a payday.

Some may resort to threats of violence to change the outcome.

Polymarket gamblers recently threatened an Israeli journalist, demanding he change his copy so that they could win a bet over whether Iran had struck Israel on a given day. Experts say that users on Polymarket might be able to manipulate broader markets, with effects that could ripple out to institutions and pension funds.

Now that gambling has become legal in the US, the existence of apps on one’s phone where one can place bets at any time means that it has become so easy to bet that we have seen an explosion in the number of ways that people can gamble and the things that they can gamble on. It has resulted in a raising of the stakes as people bet more than they can afford and where losing can be devastating.

In the early days of the 20th century, organized crime was heavily involved in gambling because it could generate huge amounts of revenue for the people running the gambling operations with very little overhead costs. There were no tangible goods like drugs and stolen merchandise to be moved around, lowering the risk of apprehension. I suspect that it is only a matter of time before crime syndicates enter these new betting markets and then try to ‘work the refs’ in much more effective ways than hapless individuals. I would be surprised it it has not happened already.

As always, gambling is a mug’s game where the odds are almost always stacked against you.