Microsoft, March Madness & Moneyball — Playing in The Big Leagues

Microsoft is leveraging AI to beat March Madness, but where have we seen a reliance on historical data for sports speculation before? Moneyball!

Catriona Campbell
4 min readApr 8, 2022

As my regular readers must surely know by now, I have a real weakness for links between tech or business, on one hand, and pop culture, on the other. I usually find these connections in science fiction films, series and books, but not always. Sunday’s edition of Indie Writer & Futurist Michael Spencer’s awesome Artificial Intelligence Report reminds me of the latest exception: Brad Pitt’s 2011 baseball movie, Moneyball.

Partially repurposing a great piece by Walter Sun, Microsoft’s Vice President of Applied AI, Michael reports that the tech giant — which I’m proud to say is one of EY’s most valued partners — is turning to artificial intelligence to beat March Madness. For the uninitiated, March Madness is just another name for the United States NCAA Division I Men’s Basketball Tournament, also referring to the unprecedented excitement it elicits in fans.

During the annual tournament, those fans fill out forms called brackets as they try to predict who will win. Now, in a bid to showcase its jaw-dropping tech capabilities, Microsoft is using AI for help making the firm’s own bracket picks. And it seems to be doing — to put it mildly — rather well, beating no less than 17 million other brackets to climb near the very top of this year’s leaderboard. This means Microsoft’s algorithms are more accurate than 99.9997% of all brackets. Wow!

If you want to learn more about how Microsoft’s model works and how it can help businesses remain competitive, read the articles by Walter and Michael.

An example of a baseball bracket

But what does all this have to do with a Brad Pitt film? Based on Michael Lewis’ 2003 must-read non-fiction book Moneyball: The Art of Winning an Unfair Game, Moneyball is a sports drama flick co-written by Stephen Zaillian and Aaron Sorokin — the latter of whom is the genius behind tech films like The Social Network (2010) and Steve Jobs (2015), not to mention one of my all-time favourite series, The West Wing.

This smart, funny and heartwarming movie tells the true story of Billy Beane (Brad Pitt), General Manager of the Oakland Athletics baseball team. Following a crushing loss to the New York Yankees and the subsequent departure of his star players, the 40-something attempts to put together a winning line-up for the 2022 season. Only, a massive problem stands in his way: a meagre budget.

(By the way, to whoever I can hear chanting “show me the money”: wrong sports flick, buddy! You’re thinking of Jerry Maguire, starring Tom Cruise and Renée Zellweger. Come on, keep up.)

Anyway, without revealing the entire plot, Beane recruits Peter Brand (Jonah Hill), an economics graduate armed with left-field ideas about scouting and assessing the value of players. Using Brand’s advanced sabermetric technique, relying on the empirical analysis of baseball stats that measure in-game activity, the pair starts to build a team of previously overlooked players.

A picture of Brad Pitt and Jonah Hill in Moneyball

The controversial move unsurprisingly ruffles a lot of feathers among those who believe Beane and Brand are recklessly setting up the Oakland Athletics for failure. However, I’ll leave you to bet on what happens between this point and the end credits beginning to roll. One word of advice, though: do keep a box of tissues at hand!

Since the events dramatised in Moneyball and the ensuing broad exposure Lewis’ book gave the sabermetric technique, times have moved on rapidly — the Microsoft case study discussed here illustrates this pretty well. Organisations across the globe are now leveraging the full force of AI to knock the ball out of the park with better, more impactful decisions based on historical data, leading to improved outcomes for consumers and shareholders alike.

In my upcoming book, AI by Design: A Plan for Living with Artificial Intelligence, I make no secret of the fact that I’m passionate about looking to the past for solutions to today’s greatest challenges. Although I’m no sports buff, I am a tech/business leader, constantly seeking answers to difficult questions. For that reason, it’s no wonder I’m drawn to compelling stories like Moneyball, not just because I love the rich association between reality and pop culture, but also because they prove that we sometimes need to look backwards to hit a home run moving forwards!



Catriona Campbell

Behavioural psychologist; AI-quisitive; EY UK&I Client Technology & Innovation Officer. Views my own & don't represent EY’s position.