March is for basketball — and family

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For more than 20 years, my brother Jim has organized and managed our family’s March Madness pool. In the old days, I think we filled out paper brackets and faxed them to him. Eventually, we went digital.

Neither Jim nor I can remember how we defined eligibility when it all started, but there are now about 80 people in the pool. Some are very young children whose parents complete their brackets for or with them. (In 2006, the median age of the top five finishers was 8; my brother did the math). Some are family friends who are only Neales in spirit. And then there are the most mysterious people of all — our cousins’ cousins (league expansion efforts!).

My brother is an exceptional writer (if there were a Pulitzer for trash talk, he’d win it) who loves the Virginia Cavaliers (which get a disproportionate amount of attention in his tournament-related missives). He somehow manages to take a dig at everyone without offending anyone. And when the tournament ends, he crowns a champion, but also lets us know who performed better in our pool:  husbands or wives, kids or adults, Republicans or Democrats.

I’m not a big college basketball fan. In fact, I will spend far more time writing this newsletter than filing out my bracket. But still, I submit one almost every year. In part, I’m motivated by the fear of being mercilessly ridiculed if I don’t (there’s precedent), but a bigger part of me just doesn’t want to feel left out. If we’re being honest, isn’t that why many of us participate in anything?

Of course, these days a lot of fans have more than FOMO on the line. Since 2018, when the U.S. Supreme Court ruled that a federal statute prohibiting states from allowing sports gambling was unconstitutional, there’s been a bit of a vibe shift. (Actually, it’s not just a shift in vibes: Americans have wagered more than $500 billion on sports since 2018.) I know, I know. Office pools that enable you and your coworkers to compete for a few bucks have been around forever (and are, by the way, often still technically illegal). But sportsbook apps like FanDuel and DraftKings are now legal in 32 states. And prediction markets like Kalshi and Polymarket create a legally questionable workaround where sports betting isn’t allowed because customers are technically putting money on futures-style predictions, not games.

Kalshi’s co-CEO, Tarek Mansour, recently said "the long-term vision is to financialize everything and create a tradable asset out of any difference in opinion.” When will Taylor Swift marry Travis Kelce? When will the war in Iran end? Who will make it to the Final Four?

In a world where everything could be a “tradable asset,” I appreciate the Neale Family Pool precisely because it offers plenty of interaction with zero transactions.

There’s no money at stake — only bragging rights and a big ol’ tacky trophy, which we added in 2003. Each year, my brother takes the trophy to a local jeweler, who engraves the name of the latest winner on a little plaque on the trophy’s base, and then the trophy travels up or down the I-95 corridor to be proudly displayed on the winner’s mantle for 12 months. These are sacred things in our family, this silly rite of spring and the ridiculous trophy with the armchair athlete sitting on top. They remind us of what we share in common, they keep us close to each other — even when we’re very far apart.

This year, one of my cousins filled out an entry for the newest Neale, her 1-week-old son. My 85-year-old mom admits she did quite a bit of research and didn’t want any of the grandkids to know which of their schools her bracket doesn’t favor. I reached out to my own kids, young adults spread across three time zones, to make sure they all still have their sign-in credentials.

And after I finished drafting this, I finally filled out my own bracket. I haven’t won — not once in these two decades — but I also feel like I’ve never lost. Maybe one day that feeling — a sense of belonging to something bigger than me — will even be enough to make me a sports fan on the order of Kimberly Witt, who wrote about her love of basketball this week. But for now, I’m just part of the Neale Nation.

I hope your bracket stays green. And, as my brother would say, “Go ‘Hoos.”