AI Brackets Face Off Against a Pro Gambler in $1 Million March Madness Challenge
Perhaps the ultimate sign that artificial intelligence is truly taking over will be the day it dominates your March Madness bracket pool. That day may be fast approaching.
In an experiment destined to happen, one that might actually make us all seem smarter, and possibly frighten everyone, a successful CEO-turned-disruptor is organizing a $1 million March Madness bracket challenge.
This high-stakes competition will pit the picks generated by his AI programmers against those of a well-known sports gambler.
“We’re not a crystal ball,” says Alan Levy, whose platform, 4C Predictions, is running the challenge. “But it’s going to start to get very, very creepy. In 2025, we’re making a million-dollar bet with a professional sports bettor, and the reason we feel confident to do that is because data, we feel, will beat humans.”
Levy isn’t alone in exploring how AI can give people an edge in the popular “pick ’em” pool. The Supreme Court ruling that legalized sports betting in 38 states has made these pools even more lucrative in recent years.
Even ChatGPT, OpenAI’s chatbot, is offering services to help bracket fillers find the stats and track trends. The chatbot makes no guarantees of success, of course.
“With upsets, momentum shifts, and basketball’s inherent unpredictability, consistently creating a perfect bracket may still come down to luck,” said Leah Anise, a spokesperson for OpenAI.
Also trying to build a better bracket through science is Sheldon Jacobson, a computer science professor at the University of Illinois. He may have been using AI principles long before AI became a buzzword.
“Nobody predicts the weather,” he explained in a 2018 interview. “They forecast it using chances and odds.”
$1 Million on the Line in AI vs. Sean Perry Showdown
Levy is betting $1 million that the AI bracket produced by his company will outperform that of professional gambler Sean Perry.
Perry refused to accept a four-way split in a pot worth $9.3 million in an NFL survivor pool a couple of years ago. The next week, his pick, the Broncos, lost and he ended up with nothing.
However, Perry has won millions over his career, using extensive data, analytics, and insider information. For decades, casinos and legal sportsbooks have relied on this type of edge, which has allowed them to build massive hotels.
Levy seeks to bring that same advantage to the average person, the weekly football bettor who doesn’t have access to extensive data, or the March Madness bracket filler who relies on a team’s mascot.
“The massive thesis is that the average person are playing games that they can never win, they’re trading stocks where they can never win, they’re trading crypto where they can never win,” Levy said. “4C gives people the chance to empower themselves. It’s a great equalizer. It’s going to level the playing field for everyone.”
Can AI Predict the Unexpected?
Finding an edge is one thing, but eliminating chance is another. Some of the unexpected factors that will factor into the games include the potential for a half-court game-winning shot, the unexpected breakout of a player, the questionable calls made by referees, or a team rising up and winning for reasons nobody quite understands.
For those who fear AI is heading in a bad direction, Levy reassures that the human element will still be the deciding factor, at least in sports.
That’s one of the reasons why, according to the NCAA, the likelihood of a fan correctly picking all 63 games is 1 in 120.2 billion. It’s also one of the reasons why almost everyone knows someone whose 8-year-old niece won their bracket pool because she picked George Mason or North Carolina State to make the Final Four.
“You can’t take the element of fun and luck out of it,” Levy said. “Having said that, as AI develops, it’s going to get creepier and creepier and the predictions are going to get more and more accurate, and it’s all around data sets.”
Levy suggests that AI is an advanced version of “Moneyball,” the book-turned-movie that followed Oakland A’s GM Billy Beane’s quest to leverage data.
Now, it’s all about maximizing data to build a winning bracket.
“We’ve got to understand that this technology is meant to augment us,” Levy said. “It’s meant to make our lives better. So, let’s encourage people to use it, and even if it’s creepy, at least it’s creepy on our side.”
The AI’s prediction: Houston to win it all. Perry is going with Duke.
—Eddie Pells, AP national writer
