The Mystery Polymarket Trader Who Reportedly Made $12 Million Betting on Sports
Lara Johns • Oct 28, 2026 A headline like that makes AI betting sound like a shortcut to easy money. That’s not what happened. Below, we break down what Kirby actually built, what’s still unknown, and what it means for US bettors.
Key Insights: Scott Kirby’s AI Sports Betting Tool
Scott Kirby’s AI sports betting tool is a personal web page he built for himself, not a public product. Here’s what’s on the record so far:
- Kirby took three one-hour sessions with a tutor, then built the page alone in about 2.5 hours.
- The page uses four or five drop-down menus for sport, date, and bet type.
- It pulls odds from four platforms, and Kirby named only one: the prediction market Kalshi.
- He says it places the bet wherever the odds are best, so it goes beyond odds comparison.
- Kirby hasn’t shared a public version, and he hasn’t named the AI model he used.
Who Is United Airlines CEO Scott Kirby?
Scott Kirby has run United Airlines since May 2020, when he took over as CEO during the pandemic. Before that, he served as United’s president from 2016 to 2020. He also held president roles at American Airlines and US Airways.
His background leans heavily on numbers. Kirby graduated from the US Air Force Academy and holds a master’s in operations research from George Washington University. On the podcast, he added that he has a computer science degree.
Gambling is a big part of his story too. In April, Kirby told The Wall Street Journal he was kicked out of casinos for card counting in blackjack. On Cheeky Pint, he said a Bellagio manager reminded him in 2024 that blackjack was still off-limits.
That history makes the betting tool less surprising. Still, a CEO running a 120,000-person airline just showed how fast AI can turn an idea into software.
How Scott Kirby Used AI to Build a Sports Betting Tool
Kirby’s project started with a gripe about how most people use AI. He told hosts John Collison and Ben Thompson that AI summaries feel pointless to him. “I can read my calendar,” he said.
Instead, he hired a tutor and took three one-hour sessions. Business Insider’s headline calls it an AI tutor, but on the podcast Kirby simply said “a tutor.” He didn’t say who the tutor was or what each session covered.
After those sessions, Kirby built the page on his own one Saturday morning. He worked out in his home gym, typing prompts on his laptop between sets. The build took about two and a half hours.
Business Insider describes his method as vibe coding. Vibe coding means describing what you want in plain English and letting an AI model write the code. You test the result, ask for fixes, and repeat until it works.
For Kirby, the speed was the point. He called it an epiphany that he could write a program like this after three hours of tutoring. That Saturday, he phoned his United team and said the airline was going all in on AI.
How Does the AI Sports Betting Tool Work?
Kirby described the tool in a few sentences, so the details are thin. Here’s the process he outlined:
- Pick a sport, a date, and a bet type from four or five drop-down menus.
- The page pulls up odds from four betting platforms.
- Choose your bet and type in a dollar amount.
- The tool places the bet at whichever platform has the best odds.
Step 4 is the big one. Kirby’s page doesn’t just compare odds; by his account, it bets for him. That makes it an automated betting tool, not only an odds comparison tool.
Kirby named only one platform, Kalshi, and noted himself that it isn’t really a sportsbook. It’s a prediction market, where people trade yes-or-no contracts on real events. The Commodity Futures Trading Commission (CFTC), a federal regulator, oversees it.
CasinoUS has covered how Kalshi’s sports contracts tie into the NBA in more depth. For this story, the open questions matter more. Kirby didn’t name the other three platforms or explain how the page connects to his betting accounts.
He also didn’t say how fresh the odds are when the tool bets. Thompson joked on air that the sportsbooks would block him soon. That joke points to a real issue, which we cover below.
Can AI Help Sports Bettors Find Better Odds?
Yes, AI can help you find better odds, because sportsbooks rarely agree on the exact price. Each book sets its own lines and moves them based on its own betting action. So the same bet often pays a little more at one book than another.
US sportsbooks use American odds. A minus number, like -110, shows what you risk to win $100. A plus number, like +150, shows what a $100 bet wins.
Our guide to reading American betting odds goes deeper. For now, here’s a simple example of the same NFL spread at two books:
- Book A at -110: a $100 bet wins $90.91.
- Book B at -105: a $100 bet wins $95.24.
That’s $4.33 more for the exact same bet. If you win 50 of 100 bets like this, the better price adds about $216. Better prices also lower your break-even point: 52.4% of bets at -110, but 51.2% at -105.
Still, a better price isn’t a better pick. Shopping for odds raises your payout when you win, but it can’t tell you who will win. Before you bet, check that both prices are for the same market, such as full game versus first half.
Price shopping only works across books you can legally use. Our reviews of legal US sportsbooks are a useful place to start.
How AI Is Changing the US Sports Betting Industry
Kirby built a one-person version of ideas the betting industry already uses. Odds comparison sites have helped bettors shop prices for years. What’s new is that one person can now build a custom version in an afternoon.
Sportsbooks use AI on their side too, and regulators are watching. In Massachusetts, regulators have asked sportsbooks how AI shapes their promotions. CasinoUS covered this in our report on the DraftKings AI controversy.
AI also shows up in responsible gambling. In 2025, Underdog became the first US operator to adopt Sportradar’s Bettor Sense. Sportradar describes it as an AI-powered responsible gaming tool.
So AI now sits on both sides of the bet. Bettors use it to research and compare prices, while operators use it for marketing and player protection.
Could AI-Powered Betting Tools Become More Common?
Probably, because building one keeps getting easier. Kirby is a busy CEO, and he says he built his in one morning.
The upside is real:
- Faster price checks: a tool can scan several books in seconds instead of minutes of app-switching.
- Easier access: custom filters put your sports and bet types in one place.
- Quicker research: AI can sort stats and trends faster than a manual spreadsheet.
The limits are just as real:
- Wrong answers: AI models make mistakes, and one coding error can misread a price.
- Stale odds: lines move fast, so a price can change before your bet goes through.
- Account rules: Michigan requires sportsbooks to ban bots in their account terms.
- Legal gray areas: prediction market sports contracts face court fights in several states.
- Overspending risk: one-click betting across several books can make it easy to bet more than planned.
That legal fight is very much alive. Kalshi sued Louisiana and Missouri in October 2026 to block state enforcement. On October 29, Law360 reported that Utah filed criminal charges against Kalshi and its co-founders.
Here’s the line between established and emerging. Odds comparison is a standard practice. Personal AI bots that place bets across books are not, and sportsbooks may push back.
What Should Bettors Know About AI Sports Betting Tools?
If Kirby’s story has you curious, start with these basics:
- Confirm every price on the sportsbook itself before you bet, since odds can change in seconds.
- Know whether a tool only compares odds or actually places bets for you.
- Read your sportsbook’s terms on bots and automated access before connecting any tool.
- Check your state’s rules first; see our list of legal US sports betting sites.
- Never give your sportsbook login or banking details to an unknown app or website.
- Skip any tool that promises guaranteed wins, because no tool can deliver that.
- Set a dollar limit and a time limit before you start, using deposit and time limit tools.
Sports betting is legal in 39 states plus Washington, DC, while 11 states still have no legal market. Laws change often, so check your state before you bet.
If betting stops feeling like fun, call or text 1-800-GAMBLER for free support. Kirby’s AI sports betting tool shows how quickly AI can build software. It doesn’t change the basic math: every sportsbook builds a margin into its prices.
Frequently Asked Questions
What AI sports betting tool did United Airlines CEO Scott Kirby build?
Kirby built a personal web page that pulls odds from four platforms and bets at the best price. He described it on the Cheeky Pint podcast in October 2026 and named only one platform, Kalshi. He presented it as a personal project and hasn’t shared a public version.
How did Scott Kirby use AI to build his betting website?
He took three one-hour sessions with a tutor, then had AI write the code from his plain-English prompts. Business Insider calls this method vibe coding. Kirby says he built the page alone in about 2.5 hours, typing prompts between sets in his home gym.
Can AI compare sports betting odds?
Yes, AI tools and simple scripts can pull odds from several sportsbooks and flag the best price in seconds. That matters because books often price the same bet differently, such as -110 at one and -105 at another. Always confirm the price on the sportsbook before you bet, because odds can move quickly.
Can AI predict winning sports bets?
No, AI can sort stats, spot trends, and compare prices, but it can’t know who will win a game. Injuries, weather, and plain luck all change results. Treat any AI pick as one opinion, and avoid any service that promises guaranteed wins or “sure things.”
Are AI sports betting tools legal in the United States?
It depends on what the tool does and where you live. Comparing odds with software is common, but placing bets means following state law and each sportsbook’s terms. Michigan, for example, requires books to ban bots, so check your state’s rules and your book’s terms first.
