Letters from Leo — the American Pope & US Politics

Letters from Leo — the American Pope & US Politics

DEADLINE TODAY: Letters from Leo Bracket Pool

$26 entry fee. $500 to the winner. $750 if you pick a Catholic school to win it all. $1,000 if you pick Pope Leo XIV’s Alma Mater Villanova.

Christopher Hale's avatar
Christopher Hale
Mar 17, 2026
∙ Paid

Dear friends —

Welcome to the Letters from Leo Bracket Pool.

March Madness is here, and our community deserves a little fun alongside the fight for justice. So we’re doing something new this year: the first-ever Letters from Leo NCAA Tournament Bracket Pool.

We need at least 20 entries in both the men’s and women’s brackets to fund the full prize structure below. If we fall short of that number, prizes will be adjusted in proportion to the number of entries.

The Rules

The entry fee is $26 per bracket.

The winner takes home $500.

But here’s the twist — if you pick a Catholic school to win the national championship and that school actually cuts down the nets, the top prize jumps to $750.

Pick Pope Leo XIV’s alma mater, Villanova, and they win it all? $1,000.

Catholic schools in the men’s field: Gonzaga, St. John’s, Saint Mary’s, Villanova, Saint Louis, Santa Clara, and Siena. Catholic schools in the women’s field: Notre Dame, Villanova, Gonzaga, Holy Cross, and Fairfield.

One entry per person per men’s and women’s pool. Men’s brackets lock today, Thursday, March 19, at 12:15 PM ET — submit by 12:10 PM ET. Women’s brackets lock Friday, March 20, at 11:30 AM ET — submit by 11:15 AM ET.

This is only open to paid subscribers of The Letters from Leo. You can subscribe at the link below. Prefer a one-time gift instead? If you make a one-time donation of $80 or more, you’ll be given access to the competition.

Thank you for playing. I’ll see you on the road.

Make A One-Time Gift to Support My Work

How to Enter

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