The Process Top Financial Leaders Use to Make Their March Madness Selections

When selecting teams for March Madness brackets, leaders in the finance industry are not so different from the average fan. Some prefer to analyze games, conduct research, and create their own strategies; others cling to sentimental choices; some trust their instincts and luck; and some simply consult an AI bot to make their decisions for them.

Mark Attanasio, owner of the Milwaukee Brewers and co-founder of Crescent Capital Group, opted for the latter method this year in Bloomberg’s Brackets for a Cause challenge.

“We had meetings in Arizona with our Brewers and Norwich City FC sporting and business executives, so I had to rely on a last-minute AI tool for our selections,” Attanasio mentioned in an email.

It seems that the anticipated AI takeover is still far off. As of Tuesday, Attanasio’s men’s bracket placed second to last, while his women’s bracket stands 54th out of 61. “There’s always next year,” he remarked.

This marks the 10th anniversary of Bloomberg’s Brackets for a Cause, where participants contribute $20,000 and choose a charity to receive funds if they rank in the top three for either the men’s or women’s bracket. This year, over $1.2 million is up for grabs, prompting us to ask various CEOs, hedge fund managers, and investment banking advisors about their selection processes. Quite a few even have ownership in sports teams.

After two rounds in both tournaments, with the field trimmed down to the Sweet Sixteen, Jeff Meskin, partner at Brown Brothers Harriman & Co., leads the men’s competition with 92 points, while Jim Zelter, president of Apollo Global Management, tops the women’s bracket with 103 points.

Zelter, a Duke alumnus, stayed loyal to his school by picking the Blue Devils to emerge victorious on the men’s side.

“With 25% of the public backing Duke to win the tournament this year, this may be the least contrarian perspective I’ve taken in my nearly two decades at Apollo,” Zelter stated. “As a value investor, it bothers me a bit to select four number one seeds for the final four and to predict Duke to win it all, but their size and both defensive and offensive efficiency give substantial downside protection.”

Not surprisingly, the University of Connecticut is the favorite in the women’s bracket, while Duke is the preferred choice for the men’s title, with approximately 40% opting for the storied program led by freshman sensation Cooper Flagg. Sometimes, hard data gives way to traditional biases.

Gregg Lemkau, co-CEO of merchant bank BDT & MSD—who recently counseled on the sale of the Boston Celtics—selected Duke because a colleague is related to team head coach Jon Scheyer.

“She’d be furious with me if I picked anyone else,” Lemkau remarked. Don Cornwell, CEO and co-founder of Dynasty Equity and a stakeholder in Liverpool Football Club, also chose Duke, partly because he favors the color blue.

Debra A Cafaro, Chairman and CEO of real estate investment firm Ventas Inc., prefers to conduct her own research. As March approaches, Cafaro starts watching games and gathering information on teams. She also has shares in the Pittsburgh Penguins, Baltimore Orioles, and Chicago Stars.

“There’s a quantitative element involved and the aspect of watching games,” she noted. Cafaro confessed to picking Notre Dame to win it all on the women’s side due to her alma mater status, but she didn’t consider it overly risky as a three-seed.

Jamie Dinan, chairman and CEO of York Capital Management, selected the Florida Gators as his men’s champion and the UConn Huskies for the women.

“They have the championship pedigree and arguably the best player (Paige Bueckers), who has been dominant. They’re peaking, having won ten straight, plus they bring coaching experience and strategic prowess to the table,” he shared about his UConn choice, echoing the enthusiasm of a typical sports radio caller. This aligns with his role as co-owner of the Milwaukee Bucks basketball franchise.

As for the Gators? “They are the deepest and most talented team from the best conference I’ve observed in recent memory. They possess outstanding guard play, versatile wings, and authentic size,” Dinan added.

Both Heather Brilliant, CEO of Diamond Hill Investment Group, and Michelle Seitz, founder and CEO of MeydenVest Partners, advocate for a mixed methodology in bracket picking.

“I utilize a combination of data-driven strategies and insights from family and colleagues who have more expertise in this area,” said Brilliant, who has made a strong start in the women’s bracket. “This year, I specifically looked for potential upsets where performance was particularly strong in the last ten games of the season.”

Seitz finished third in 2023. “Start with matchup-based analytics, but don’t rely solely on them,” she advised. “Select a top-five team to clinch it all—you’re competing for $1.2 million in charitable donations, so avoid getting overly clever.”

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