Today we want to apply our usual what is the market actually pricing lens to the 2028 presidential markets — specifically, why Donald Trump Jr. will run. That possibility is currently at 23¢ on Kalshi (he's the blue line at the bottom).
Assuming Thomas Massie's loss in KY-4 was legitimate — and after a couple days of "internet on fire" conspiracy theories, Massie himself told everyone he's good and moving on — Donald Trump is on a burner of a winning streak with his primary endorsements. After Massie's loss he endorsed Ken Paxton in the Texas Senate primary, which shot Paxton's odds to win from 47.6¢ to 95¢. With Kentucky and Indiana wins under his belt, Trump is in king-maker mode as far as the Republican party is concerned. Whether any of that carries over to the general elections remains to be seen; we had been seeing a mini "blue wave" in smaller local and special general elections, so this could still be confined to the party. Still, that's what we're looking at today, so we will assume Trump's endorsement is gold and stays that way for another year, at least.
There has been speculation for a while that Trump would try to run for a third term. He's said it's "pretty clear" he can't. But the man is obsessed with his name and his legacy. And his only loyalty seems to be to his family; he will cast aside anyone at any time. When The Apprentice saw a ratings lull in 2006, he replaced the beloved George and Carolyn in the boardroom with Ivanka and Don Jr. And so if Donald Trump Sr. can't run for a third term, why wouldn't he just trot out his son as a proxy/heir apparent? Or, not to discredit Don Jr.'s own accomplishments — maybe an "extension of his legacy."
The official Trump store is selling a $55 "Trump 2028" hat. Most people read it as an antagonistic joke that he'll run again, but why aren't we taking Don Jr. more seriously as a candidate? Like him or not, he's very good on TV and as a public speaker. He has the Trump name (I learned a lot of political lessons from Eddie Murphy's The Distinguished Gentleman). Don Jr. will almost certainly have his father's blessing and full-fledged support. And he has a lot more relatability than people give him credit for. From the Tulsa World in 2012, we learn Trump used to have a ranch in Caddo, Oklahoma:
He also has a ranch in Montana, and spent some time after college as a "Colorado ski bum." While he's had a number of controversies, most of them are related to business and, of course, big-game hunting (and possibly misunderstood big-game hunting, at that, if you ask the hunters who write about him).
They even want him to host a new Apprentice.
I am not a political spinmaster, but Don Jr. has the name recognition, the following, the name, and the tireless endorser. He has a decent storyline — continue my father's legacy, I worked my way up and wasn't some spoiled NYC club-going rich kid, I have ranches and can relate to the middle of the country, I've been successful — while also downplaying a lot of his father's more sordid aspects: my dad came from a different era, I do things differently, I'm not part of the Washington machine. And, of course, he now has the clincher: my dad didn't even come to my wedding, folks (and then, on the stump, Trump Sr. grabs the microphone and says something funny about saving the country from the war in Iran and preventing them from making a nuclear weapon, and the crowd goes wild).
And that 23¢ market is just for whether he'll run. If you can get past that idea, I have two much more tantalizing markets for you.
A nickel for him to win the nomination:
And a 1.5¢ contract on him winning the presidency:
A Crazy Twist
One minor wrench in the plans here is Ivanka Trump, who can say a lot of these same things but with fewer questionable tweets and civil fraud cases. Her biggest controversies? Violating the Hatch Act (which nobody cares or knows about) and using personal emails for White House business (which her voters don't care about and didn't really care about with Hillary Clinton either). Her husband, Jared Kushner, has been far more controversial — but she has bonus storyline points: a continuation of all the Trump stuff while also being the first woman president.
This scenario is so far-fetched there isn't even a market for it. But in the spirit of what have we learned? — don't put any scenario past Donald Trump Sr. Nothing is unachievable.
History and The Competition
As far as relatives of presidents go, George W. Bush's presidency ended just 17 years ago. You have to go a little farther back for John Quincy Adams, but Adams' brother, Charles Francis Adams, ran as a VP in 1848. Robert A. Taft tried several times to get the nomination. Hillary Clinton ran. Benjamin Harrison was the grandson of William Henry Harrison. Jeb Bush ran. There are the Cuomos and the Romneys. There's a long list of family ties to politics. So this isn't out of the ordinary; it just seems weird because the Trumps are such lightning rods, and because Donald Sr. has bent the government to his will, so we're all kind of blinded by the idea of "Trump 2028" being his third term and not his son (or daughter) running as the nominee.
And if you can establish that Don Jr. running is plausible, it's not a giant stretch for him to beat the favorites, especially with his father's endorsement. I'm not even sure Trump endorses either of the front-runners; it doesn't fit his style. They're kind of dorky and have messed up a few times.
Marco Rubio has been a meme machine over the last 15 years. A poorly timed drink of water during his 2013 response to the State of the Union. His 2016 campaign debate debacle where Chris Christie schooled him after he repeated a rehearsed line several times. And just last year, he became infamous for his slouched "couch" moment.
J.D. Vance, meanwhile, has his own couch issues. He once compared Trump to Hitler before falling in line to run for VP. Elle asked makeup professionals if he wore eyeliner. And there was the whole donut shop thing.
After those two, the field is wide open, with Tucker Carlson currently the third favorite. And while we still hold positions on Rand Paul, that's just one of the many, MANY strands of the multiverse that could play out. But right now, after all we've seen dating back to the 80s tabloid headlines? Trump's name is supreme. And he has a very real chance to essentially anoint a Trump as the next Republican nominee for President. Because they will do what he says.
The Play
We're completely skipping the 23¢ contract on him running for the nomination (it's still 5-to-1 if you like that route — we will not judge) because we believe if he runs, he'll win, based on the current sway his father holds over the party.
YES at a nickel for Donald Trump Jr. to be the 2028 Republican nominee.
(That market has drifted since the screenshot above — Don Jr. is sitting near 4¢ at publish time, the presidency contract is closer to 5¢. The thesis doesn't change; the size of the position you take might.)
A Quick Note Before We Go
Benny Ricciardi, co-founder of this beautiful burgeoning company, locked himself in a room and built a World Cup model that ran 10,000 simulations of the tournament after rosters were finalized. It's pretty fantastic. And it's free — you can check it all out here.
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Trade responsibly. Prices captured May 26, 2026 — markets move fast and a televised debate, an endorsement, or a single Truth Social post can move them faster.
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