When it comes to making picks for March Madness brackets, finance industry leaders are like the rest of us. Some like to watch games, do research and devise their own systems; some go with sentimental favorites; some rely on intuition and luck; and some just ask an AI bot to do it for them.
Milwaukee Brewers owner and Crescent Capital Group co-founder Mark Attanasio went with the latter strategy this year for Bloomberg’s Brackets for a Cause competition.
“We had meetings in Arizona this week with our Brewers and Norwich City FC sporting and business executives, so had to resort to a last minute AI program for our picks,” said Attanasio in an email.
It’s clear the impending AI apocalypse is still some way off. Attanasio’s men’s bracket sits second from bottom and his women’s 54th out of 61 as Tuesday. “There’s always next year,” said Attanasio.
This is the 10th year of Bloomberg’s Brackets for a Cause, where entrants donate $20,000 and select a charity that receives funds if they are a top-three finisher in the men’s or women’s bracket.
This time around, there’s more than $1.2 million at play, so we asked some of the CEOs, hedge fund managers and investment banking advisors how they make their picks. Quite a few even own sports teams.
With both tournaments through two rounds and the field narrowed to the Sweet Sixteen, Jeff Meskin, partner at Brown Brothers Harriman & Co. leads the men’s competition with 92 points, while Jim Zelter, president at Apollo Global Management, leads the women’s side with 103.
Zelter, a Duke graduate, stayed true to his school, picking the Blue Devils to win on the men’s side.
“With 25% of the public picking Duke to win the tournament this year, this may be the least contrarian view that I have taken in my nearly 20 years at Apollo,” said Zelter.
“It pains me slightly as a value investor to pick four number one seeds to make the final four and Duke to win the final, but their length and defensive and offensive efficiency provide a lot of downside protection,” he added.
Unsurprisingly, University of Connecticut is the top pick for the women’s bracket, while Duke was the most popular pick for the men’s title ahead of the University of Florida, with about 40% choosing choosing the blue blood program led by freshman sensation Cooper Flagg to win this year.
Sometimes, quantitative analysis is ditched for old fashioned bias.
Gregg Lemkau, co-CEO of merchant bank BDT & MSD — which just advised on the sale of the Boston Celtics — picked Duke because one of his colleagues is a sister of team head coach Jon Scheyer. “She’d kill me if I chose anyone else,” said Lemkau.
Dynasty Equity co-founder and CEO, Don Cornwell, owner of a stake in Liverpool Football Club, meanwhile, said he picked Duke, in part, because he likes the color blue.
Debra A Cafaro, Chairman and CEO of real estate investor Ventas Inc., favors doing her own homework. Cafaro starts watching games and reading up on teams as March approaches. She also owns stakes in the Pittsburgh Penguins, Baltimore Orioles, and Chicago Stars.
“There’s the quantitative part and probabilities and there’s the watching part,” she said. Cafaro did admit to picking Notre Dame to go all the way on the women’s side because it’s her alma mater but as a three-seed she didn’t think it was too risky.
Jamie Dinan, chairman and CEO of York Capital Management, picked the Florida Gators for his men’s champ and the UConn Huskies for the women.
“Championship pedigree and arguably best player (Paige Bueckers) who’s dominated. They are peaking, have won ten in a row and have the coaching and experience to win it all,” he said of his UConn pick, sounding like a regular caller on sports talk radio. Which makes sense given he’s a co-owner of the Milwaukee Bucks basketball team.
And the Gators? “They are the deepest and most talented team coming out of the best conference I’ve seen in a long time. Have great guard play, intangible wings and true size,” Dinan added.
Both Diamond Hill Investment Group CEO Heather Brilliant and MeydenVest Partners founder and CEO Michelle Seitz endorse a hybrid approach to bracketology.
“I use a combination of a data-driven approach and help from family and colleagues with more insight than I have on this topic,” said Brilliant, who’s had a strong start in the women’s bracket. “This year I looked for potential upsets where the performance was particularly strong in the last 10 games of the season.”
Seitz finished third in 2023. “Start with matchup-based analytics, but don’t live by them” she said. “Pick a top-five team to win it all — you’re playing for $1.2 million in charity money, so don’t get too cute.”
(Credit: Jeff Turner via Wikimedia Commons)
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