Are Prediction Markets an Unserious Venture?

Aug 31, 2026

newsletter

Two Takes on Canadian and American Prediction Markets

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word-wrap:break-word'>

<span style='font-size:17.0pt;

line-height:125%'>Two Takes on Canada's Prediction Markets<o:p></o:p>

We're doing something

different this month. Keeyan and I are taking opposite sides on the

introduction of prediction markets in Canada, and we want to hear your thoughts

and takes in the comments.<o:p></o:p>

Last month, <a

href="https://abcnews.com/US/white-house-teleprompter-operator-made-100k-betting-trumps/story?id=134764573">ABC

News reported</a> that the man who had been running Donald Trump's teleprompter

since 2016 spent the winter betting on what the president was about to say.

Gabriel Perez won around $100,000 over more than a dozen speeches, using

Kalshi's Mentions markets, which pay out when a particular word gets said on

stage. Kalshi's surveillance team caught him, <a

href="https://www.cnbc.com/2026/07/16/trump-kalshi-teleprompter-cftc-investigation.html">froze

most of the money</a> and handed the file over to the CFTC. <o:p></o:p>

In April, prosecutors brought

the first U.S criminal insider trading case these markets have produced,

against an Army sergeant accused of using classified details of the Maduro

operation to turn $33,000 of Polymarket positions into <a

href="https://www.forbes.com/sites/walterpavlo/2026/04/27/prediction-markets-first-insider-trading-case/">more

than $409,000</a>. A Google engineer was <a

href="https://abcnews.com/US/inside-race-quell-prediction-markets-insider-trading-woes/story?id=133201587">charged

in May</a> with making over $1 million betting on which search terms would

trend, using data from inside the company. And Maria Corina Machado's Nobel

odds went from under 4 percent to over 70 in the hours before last October's

announcement.<o:p></o:p>

Canada made its own move in

March, when the CIRO <a

href="https://stikeman.com/en-CA/kh/competitor/prediction-markets-a-narrow-and-ambiguous-path-forward-in-canada">set

out a narrow path</a> for event contracts sold through registered dealers, and

in June <a

href="https://www.cbc.ca/news/business/prediction-markets-wealthsimple-9.7239575">Wealthsimple

Predict</a> became the first of these products most Canadians could actually

buy. Interestingly, Wealthsimple holds both a banking license and this

exemption for prediction markets, simultaneously (most financial institutions

restrict these kinds of businesses as clients). However, regulations have

remained tight, allowing predictions only on economic data, financial markets

and climate, with sports and elections left out. And despite their presence at

a recent Blue Jays game (MLB), Polymarket is <a

href="https://www.theglobeandmail.com/investing/article-predictive-markets-canada-regulators-polymarket-kalshi/">still

banned in Ontario</a> after the OSC pushed it out last year.<o:p></o:p>

So, Canada has opened up

something the rest of the world is still fighting about, in the same year it

produced its first real insider trading cases. Keeyan thinks that was a

mistake. I think we've got a shot at writing rules nobody else has managed yet.<o:p></o:p>

<h2 style='margin-top:.25in;margin-right:0in;margin-bottom:8.0pt;margin-left:

0in'>Prediction Markets: What George Carlin Would Call “Gambling”<o:p></o:p></h2>

Much of my worldview is

informed by libertarian principles, so I recognize the irony in taking a

restrictive stance on people’s rights to freely transact. However, I see two

fundamental issues with prediction markets, which transcend borders. Canada’s

approach is just the perfect example of how regulation sometimes creates more

issues, instead of solving them.<o:p></o:p>

The main problems are the

trustworthiness and centralization of oracles (who “resolves” a market?), and

malicious engineering of outcomes. Recently, a market on Polymarket which

allowed users to predict whether Strategy, Inc (formerly MicroStrategy, the

company run by Michael Saylor) would sell Bitcoin between May 27-31 resolved to

“No”, <a

href="https://www.galaxy.com/insights/research/strategy-bitcoin-sale-polymarket-resolution-dispute-may-2026"></a>despite

Strategy’s reported sale of 32 BTC on an SEC filing. Since Polymarket uses UMA,

a decentralized truth-verification protocol, one would assume that markets

always resolve correctly – especially given that Polymarket itself has no stake

in the outcome (they make their money on fees). UMA tokenholders vote to

resolve markets in dispute, with each vote carrying a weight proportionate to

the amount of their holdings. Nothing is stopping prediction position holders

from simultaneously holding UMA tokens. The result of this kind of unjust

market resolution <a

href="https://wp.decrypt.co/wp-content/uploads/2026/07/158389_2026_William_Wood_et_al_v_William_Wood_et_al_SUMMONS___COMPLAINT_1.pdf"></a>was

a lawsuit, in this case, and could lead to many other similar ones in the

future.<o:p></o:p>

The obvious but misguided way

to fix the issue with unreliable or corrupt oracles would be to adopt a

centralized resolutions model, as Kalshi (the U.S.’s largest prediction market

operator) <a href="https://help.kalshi.com/en/articles/13823826-market-outcomes">has

done</a>, but that comes with obvious drawbacks too. Notably, the involvement

of a market operator in the decision-making process around who makes, and who

loses money, could lead to clear conflicts of interest. This is the same issue

that insurance companies have been accused of perpetuating, when they

adjudicate claims in-house, instead of using independent adjusters, and exactly

the kinds of thing that decentralized

finance has the potential to fix.<o:p></o:p>

While insider trading is

nothing new, the damage it could cause was mostly limited to financial crimes

and undue losses caused to others. Using insider information to buy a stock

before earnings would not, for example, crash a plane, or derail a train. But

prediction markets are now expanding to cover flight delays, <a

href="https://www.wsj.com/pro/bankruptcy/fortresss-brightline-private-railroad-teeters-under-heavy-debt-burden-ea7f2680">bankruptcies

or seizures of train companies</a>, and even the ousting of foreign leaders.

This can create perverse incentives for financially motivated individuals to

practically influence the outcomes of certain predictions (for example, by

booking a ticket, flying on and disrupting a flight). Of course, the

ill-motivated actions would likely be illegal, and so would the fraudulent gain

if the contract resolved in such a person’s favor because of their meddling.

And certain kinds of prediction markets are already <a

href="https://levin.house.gov/media/press-releases/rep-mike-levin-introduces-death-bets-act-to-ban-death-and-war-prediction-contracts">disallowed

by federal law</a>, with more restrictions proposed (Congress has been debating

this <a href="https://www.nbcnews.com/id/wbna3072985">topic since 2003</a>).

But as long as prediction markets operate and offer betting opportunities on

public infrastructure and foreign policy outcomes, people will find ways to

turn the odds in their favor, moral or not.<o:p></o:p>

Dan made great points in his take,

and I agree that Canada (and the United States, for that matter) should take

initiative and write a regulatory playbook for prediction markets imminently. As

Dan points out, Canada could benefit from taking a leadership role in this,

because it is often losing “regulatory capture” when its citizens resort to

using offshore or US platforms to transact in ways which their own country

doesn’t sanction. I do think, however, that Dan is missing one important point:

the regulation of prediction markets should have as much or even more to do

with demanding market operators to be transparent and honest (never trust the

casino!) as it does with regulating consumers’ access to them.<o:p></o:p>

<h2 style='margin-top:.25in;margin-right:0in;margin-bottom:8.0pt;margin-left:

0in'>Daniel Says: “Write the Rulebook Here”<o:p></o:p></h2>

Let’s start with what all four

of those insider-trading stories have in common, which is that we know about

them at all. The exchange's own surveillance desk flagged Perez and froze most

of the money. The sergeant's positions were reconstructed from the blockchain,

and the Nobel leak showed up on a price chart while it was still happening.

Each situation was identified and controlled within weeks, meanwhile the

insider trading of equities usually surfaces years later, if at all.<o:p></o:p>

Keeyan sees a product that

attracts insiders, and he's right that it does. What I want to know is how fast

the venue catches them, and doing so within three months is quick in the

standard of business. <o:p></o:p>

There's also the question of

what a ban gets us. Single game sports betting was a criminal offence here for

decades, which did nothing to stop Canadians wagering billions offshore with

books that answered to nobody, until Parliament gave up and legalized it in

2021. Crypto went the same way and cost people more, because when there was

nowhere legitimate to trade, the volume went to whoever would take it, and some

of that was on FTX. Polymarket is banned in Ontario right now and somebody was <a

href="https://www.casino.org/news/canadian-regulators-prediction-markets-must-follow-the-rules/">handing

out flyers for it</a> at a Blue Jays game in the spring. A ban mostly decides

whose rules people trade under, and it usually isn't ours.<o:p></o:p>

Keeyan’s claims are legitimate:

Thin markets can be moved by one patient wallet, and a lot of contracts have no

business even existing. The offshore platforms have listed their fair share of

those, including bets on whether particular people would live out the year. It’s

no question that this is gambling, all of which a regulator should get to

decide. <o:p></o:p>

By treating these as

derivatives sold through registered dealers rather than licensing them as a

casino product, Canada has made the right move in upping the scrutiny and

obligations these markets receive. The

obvious missing piece is that people who already know the answer shouldn’t be

allowed to bet on it. Perez knew the words before the president said them.

Clear insider-trading, but the Americans are still arguing about whether he

broke any law at all, which will take years. Canada should be writing our laws

down right now. <o:p></o:p>

There's a second reason this

should matter to our dear readers. The best evidence in the Maduro case came

off a blockchain, because that's what these venues settle on, and a public

ledger tied to a verified account is about the strongest audit trail in finance.

A regulated market here would also give institutions something they can't get

cleanly today. A fund wanting to hedge a rate decision or a tariff ruling has

no simple venue for it, and this would be one. <o:p></o:p>

Canada has traditionally

favored a “follow the herd” mentality, but it’s also no stranger to being the

first mover. The world's first spot Bitcoin ETF was approved here in February

2021 while the Americans spent three more years litigating, and when they came around,

they borrowed the structure. Prediction markets will exist at scale whether we

take part or not, and there will be more Perez’s either way. I'd rather the

rules everyone copies were ours.<o:p></o:p>

So, who has it right? Tell

us in the comments which of us you're with or make the case we both missed.<o:p></o:p>

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