The Guy Winning America's Money

EPISODE 357: Edges.

You may have seen us scrutinize the incentives and unintended consequences of legalized sports betting and the rise of multibillion-dollar prediction markets.

We’ve investigated the gambling scandals that threaten the NBA; we’ve covered scams that touch the White House; you’ve heard me interrogate experts and call for actual regulation.

But part of the reason I wanted to speak to a 40-year-old partner at a quantitative hedge fund named Galen Hall is simple.

During March Madness — America’s longest-running prediction contest and also Galen’s “favorite thing in the world” — I keep thinking about these increasingly competitive and allegedly enriching pools of money.

I first met Galen years ago, through friends, here in New York City, where he lives with his wife, Sierra. And when I recently asked him how much he’s won — across all sorts of NCAA brackets and legal wagers and high-stakes competitions — his estimate was more than $15 million.

From various World Series of Poker… to the 2023 Backgammon World Championship, in Monte Carlo… to the record-setting 2025-26 Circa Las Vegas NFL Survivor Pool. Where only five entries — out of an unprecedented 18,718 submissions — made it to the very end.

And Galen Hall didn’t have one of those five winning entries, which shared a $18.7 million pot.

Galen had two of them.

Which is all to say that this episode is a case study in the type of brain that’s wired to dominate a game that so many of us don’t even realize we’re playing.

YOUTUBE SPOILER ALERT:

Thanks,

Pablo