Confessions of a Casual Bettor on March Madness Opening Day

Today, ESPN.com revealed that more than 28 million brackets were created before March Madness tipped off at 12:15 p.m. ET.

Depending on how things unfold, there’s always something inherently wonderful and/or crushing in pulling for your bracket over these next three weeks. After competing in 40(ish) of these bracket contests over the years, I’ve come out on top only twice, but man, those wins were sweet.

If memory serves, both paid out in the $800-$900 range, but the trophy pictured above is all that remains.

Record $4.5 Billion Handle Expected for March Madness

I accepted an invite from my friend and former co-worker, Brant James, one of the industry’s best enterprise writers, to compete in his ESPN bracket contest this year. Strange thing: No entry fee was mentioned. It’s downright un-American to play for nothing, so we agreed on a double-or-nothing bet on a 6-pack of DC-based beer he owes me from the NHL’s Panthers beating his Capitals in last year’s playoffs.

In an interview last week with former DraftKings exec Matt Bakowicz, now head of the Sports Management Program at American University’s Kogod School of Business, he estimated that $4.5 billion would be wagered on March Madness. I realized just how pithy my contribution to that will be, with only a $10 entry fee required for my primary bracket contest at CBS Sports.

There will probably be a couple of hundred more wagered by the time a new NCAA champion is crowned on April 6. I’ve been betting with the same $300 since the start of the year, primarily at DraftKings Sportsbook and DraftKings Predictions.

The balance has been a couple of hundred to the good and bad at times, with no significant effect on the bottom line. Realizing long ago that I’m not in the ranks of +EV (positive Expected Value) bettors out there, that’s probably for the best.

Thanks to Kalshi, too, for the chance to win $1 million in its free bracket contest.

Another Chalky Bracket

Conventional wisdom held that five or six teams had separated from the pack entering March Madness. After four No. 1 seeds advanced to the Final Four last year for just the second time ever, maybe that’s what we can come to expect in the NIL era. Hopefully, there will be more epic upsets to come, though.

Last year, national champion Florida helped me finish runner-up in the office pool. I’ve got Duke over Michigan in the title game this time around, and Cameron Boozer as the winner of the March Madness Most Outstanding Player award (along with four other longer shots).

Too chalky? Perhaps. No. 16 Siena leads top-seeded Duke, 22-16, in the opening round as I type this.

Enjoy the madness.