This week in prediction markets, Donald Trump Jr. somehow managed to secure himself a seat on both sides of the table. The man has officially joined the advisory ranks at Polymarket while also moonlighting at Kalshi. One imagines the awkward small talk when both companies end up at the same cocktail party.
Polymarket made the splashy announcement that Trump Jr. was not only on the advisory board but that his investment firm, 1789 Capital, had put money into the company. Over at Kalshi, they reminded us that Trump Jr. has been in an advisory role since January, though Axios dryly noted this is a paid gig rather than an investment. In other words, cash one place, consulting fee the other.
Excited to welcome @DonaldJTrumpJr‘s fund @1789Capital as a strategic investor in Polymarket ahead of our US launch.
Don will also be joining our advisory board.
Assembling the avengers. We’re coming home 🇺🇸 pic.twitter.com/w6MdZuoCXv
— Shayne Coplan 🦅 (@shayne_coplan) August 26, 2025
If you are confused about how the same person can advise the two biggest players in a niche industry that thrives on wagers about who sneezes next in Congress, you are not alone. But then again, we live in an era where conflict of interest is more of a conversation starter than a career-ender.
Polymarket, for its part, is preparing for its grand re-entry into the United States after a time-out courtesy of the Commodity Futures Trading Commission. The CFTC had scolded the company in 2022 for allegedly running unregulated prediction markets, which is basically the financial regulator’s equivalent of sending you to your room without dessert.
Now, with its acquisition of a licensed exchange this summer, Polymarket hopes to come back stateside within weeks, or maybe the fall if the paperwork moves at government speed.
The only thing harder to predict than the next election is how Trump Jr. plans to balance his new double life. Luckily, there are two companies ready to let you bet on it.
What’s on this week’s prediction markets
Kalshi
For reasons known only to the gods of finance, Kalshi’s users are once again glued to the Federal Reserve. Last week it was interest rates, this week it is whether Fed governor Lisa Cook will be booted before the year is out. The market gives it a 31% chance, which is prediction-market speak for “probably not, but wouldn’t it be fun if.”
The drama stems from President Trump’s announcement that he had fired Cook, accusing her of mortgage fraud. In the grand tradition of Trump statements, it was accompanied by a social media letter spelling out her alleged sins.
JUST IN: Fed governor Lisa Cook, who was “fired” by Trump, says she will continue to carry out her duties
Only 39% chance she’s out this year pic.twitter.com/XrQJoaouzH
— Kalshi (@Kalshi) August 26, 2025
The law, however, says Fed governors can only be removed for cause, usually interpreted as serious misconduct, not a mortgage paperwork spat. Legal experts lined up to politely suggest the president may have a tough time making this stick.
Meanwhile, Kalshi got an unexpected marketing boost from El Salvador’s President Nayib Bukele, who gleefully tweeted about the platform’s market on whether the country’s Bitcoin stash will hit one billion dollars by the end of 2025.
I could do the funniest thing right now… https://t.co/82lENa4hgN
— Nayib Bukele (@nayibbukele) August 27, 2025
Odds on Kalshi jumped from 20% to 38% after Bukele hinted he “could do the funniest thing right now,” a phrase that no doubt made both his finance minister and the International Monetary Fund reach for aspirin.
Not to be outdone, Polymarket quickly listed its own version of the bet, where the odds sit a touch higher at 43%. Apparently nothing motivates the global prediction market industry quite like a Bitcoin-loving president with a Twitter habit.
Polymarket
Not to be left out of the Lisa Cook drama, Polymarket has its own market on whether she will be out by the end of 2025. Bettors are giving it only 28%, a slight notch lower than Kalshi’s take. Cook herself has brushed off Trump’s dismissal letter, arguing that “for cause” removals have to do with actual misconduct in office rather than anything in her past mortgage paperwork.
Polymarket traders also see little chance of Jerome Powell being shoved aside in 2025, pricing his early exit at just 10%. The message is clear: investors believe central bank independence has a stronger spine than the headlines suggest.
But Polymarket’s crown jewel this week had nothing to do with the Fed and everything to do with Taylor Swift’s ring finger. One user, who goes by the name “romanticpaul,” saw the writing on the Instagram wall before the rest of us. Less than 24 hours before Swift and Travis Kelce announced their engagement, romanticpaul loaded up on “Yes” shares of the couple tying the knot by year-end.
By the time the couple posted their coordinated selfies, he was sitting on a 153% profit worth more than $3,000. The speed with which Polymarket bettors pivoted to wagering on pregnancy timelines suggests Swifties may be outpacing Wall Street in their use of alternative data.
Of course, Polymarket cannot resist wandering into darker corners of speculation. The platform is now offering bets on whether Houthi rebels will successfully attack another ship by August 31.
The market appeared barely two weeks after real-world strikes killed at least five seafarers, which has led to outrage from human rights groups and the shipping industry alike. Critics call the contracts abhorrent, accusing the platform of normalizing the monetization of violence.
Despite the condemnation, volume has already topped $23,000, with traders buying “Yes” shares for fifteen cents.
It is the kind of bet that reminds you prediction markets are not just mirrors of public curiosity but also of its worst impulses. For every romanticpaul riding a wave of celebrity gossip, there are others willing to wager on whether missiles will fly.
Featured image: Canva / Federal Reserve / Grok
