What you will see if you scroll down👇
👮 Disclaimer & Editors Note: staying out of jail.
💬 State of Sports Gambling, 2026: a random collection of thoughts and predictions.
🗣️ Story Time: sharing some perspective.
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Editor’s Note: I’m back. I’m using the first day of 2026 to return to the scroll and share my perspective on the current state of the industry.
Tomorrow, in a separate email, I’ll include a personal (Dillon) and a betonu update for the half of a quarter of a dozen people who have asked where I’ve been.
**Disclaimer: For the purposes of the written word, I’m sometimes bucketing ‘prediction markets’ under the umbrella of ‘sports gambling’ to make it easier for both of us. I have zero opinion about the “is it technically gambling or not” battle because I’m not a lawyer or a politician or Merriam or Webster.
💬 State of Sports Gambling, 2026
a random collection of thoughts and predictions…
The New Operating System - Historically sports gambling has been an industry for Sports and Casino brands. Very quickly fintech, social media platforms, skill-games, have all entered the mix. I find it exciting, assuming everyone acts responsibly (more on that in Story Time).
The Prediction Market Experience For Sports Gamblers, Today? - Today the experience is incredible for sharps, and limited players. There’s a ton of value in this. But sustain long term, the experience will need to be amazing for everybody else. Someone unfortunately has to lose money. How to get there? Parlayability, promotions, ad hoc bonusing (see VIP), streaming, breadth, depth.
The Best Experience For Sports Gamblers, Today? - Nothing has changed my opinion here. The best pure experience is clearly still a fully functioning OSB platform. This includes grey market offshore sites, black market bookie/PPH sites, and of course the legal OSBs. I’m excited to see if predictions or any other new mechanism will ultimately be similar, better, or different.
The Fix Is In - Match fixing and insider trading scandals are hot right now. It’s the most common thing that gets brought up to me among non-industry people. I’m extremely confident these instances will continue to decrease in Sports due to oversight and tooling stemming from legalization. The bigger issue is markets that have known outcomes. These are ridiculous IMO but I suspect we’ll see even more of them in 2026.
The TAMspansion - A decade ago I felt like we were making products for a niche group of people who were already doing a similar action. Today there’s a push toward make gambling ubiquitous. That’s a meaningful shift.
Don’t Be a Coward, Make Some Predictions
Prediction markets add a piece to the overall sports gambling ecosystem. They don’t take from OSBs in legal states. I don’t think the scale gets to OSB levels (I’m including grey and black markets when I say OSB, and the fact is those experiences are much stronger today.)
I expect sports volume to be spread out across operators in 2026, I don’t think we’ll see a duopoly in the revenue numbers like we did so quickly in legal OSB.
I do think Sports brands like DK, FD, and Underdog (my employer) have the upper hand, with Robinhood as the next best shot.
Whales become the constraint and the toughest players to win for prediction platforms due to some of the reasons mentioned in the second bullet of this email.
Integrity scandals shift away from sports and into everything else.
With public discourse on PMs, nothing materially changes in traditional OSB, FD/DK continue to dominate. Fanatics and Hard Rock will be known as the next tier if they’re not already, eclipsing MGM/Caesars.
🗣️ Story Time
In 2014, I worked at a then Daily Fantasy Sports company called FanDuel. We weren’t allowed to say the G-word in the office.
In 2026, the next phase of legal US sports gambling may hinge on how that same G-word is interpreted.
Time is a roulette wheel. Or something.
There are a few high profile G-words. One of them is the oldest idea humans ever named, responsible for wars, laws, comfort, and the best dribble move in history.
There’s also a far less volatile word that I’ve always understood as “risk something, for the opportunity to win something”. That word is Gambling.
In 2026, the word gambling is no longer taboo, yet all I see on X are Gen Z prediction market enthusiasts arguing with the legend @DustinGouker about the definition and its implications.
“Are prediction markets gambling?” is already fighting for a chapter in a history book Dustin will surely write in 2046.
Over a decade ago, when I was at FD and Dustin was covering Daily Fantasy Sports, there was a very similar discourse.
And that is why we didn’t say “gambling” in the office.
This discussion lacked common sense then, and still does, though I understand why it’s happening.
(I also acknowledge semantic debates can be fun, though I prefer ones like “is Jalen Brunson a Superstar?”)
What actually matters is whether companies that provide us with an opportunity to “risk something, to win something” do so responsibly. This was true then and it’s true now.
I’ve always been pro gambling legalization. Largely because of the dangers of grey/black markets that have no responsible gambling safeguards, ability to go into debt playing on credit, and players/bookies getting stiffed, to name a few.
The legal space has work to do, but it’s FAR stronger in these areas than the alternative. Any new entrants will hopefully build on that progress, not reverse it.
We’re entering an era where the gamblification of everything feels inevitable in the US, whether through prediction markets or whatever mechanism comes next.
I have mixed feelings. On the one hand I’m supportive of choice. On the other hand I’m skeptical that this is good for society.
2026 will bring even more of this to the forefront with the bull case on prediction markets being one that goes way beyond sports and into, well, anything you can think of.
As a fan of innovation, startups, and business, I’m enjoying this change of pace and learning a ton. As someone who understands the psychology of a gambler, I’m curious to see what this experiment leads to.
We’re all stuck with the G-word now, whether we like it or not.
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