It’s time to take on your family and friends in March Madness bracket pools. Cue trash-talking, bracket-busting upsets and the glory of victory. Today, we’re commemorating bracket history and reliving the moments and stories that you are never living down.
From buzzer-beaters that busted your bracket to bad advice you gave a family member and all the crazy ways someone who doesn’t follow college basketball came upon a winning bracket. We gathered a selection of stories from readers and our staff because March Madness evokes a wide range of emotions, and misery loves company. From the good to the bad and, most importantly, the unforgettable, these stories should give you a good laugh, or maybe even a good cry, as you head into another year of filling out brackets.
Reader submissions are lightly edited for grammar and style.
They told you so
Daniel W.: The first time my wife filled out a bracket she picked a 16-seed to win in the first round. I dissuaded her from that pick because “the 1-seeds never lose in the first round, ever.”
Thanks, University of Virginia. She’s never let me live that down.
Dan Shanoff, sports business editor: The year Villanova beat UNC on Kris Jenkins’ epic buzzer-beater, my then-7-year-old kid wanted to pick Villanova to win it all on his carefully considered bracket. Hoping to protect him from what I knew was a huge mistake, I told him it was a bad idea and to go with the safer pick of Michigan State. He trusted me, and his would-be “99.99th percentile” bracket glory was left behind on Selection Sunday thanks to my atrocious helicopter parenting. In trying to shield him from an L, I took an even bigger one by having his ultimate lesson be: “Listening to Dad steered me so wrong.” My lesson: Enjoy watching your kids fill out their bracket all by themselves.
The ones that got away
Steve A.: Had a pool won. Only need the Fab 5 Wolverines to win the Final Four game and the championship game didn’t matter. Had enough points to win. Then Chris Webber happened…
Dan Santaromita, sports betting editor: In 2005, I was in a big pool at my high school. Members of the basketball team organized the pool, and current Duke coach Jon Scheyer was on the team, so everyone wanted in on this pool. Growing up in Chicagoland, everyone was jumping on the Illinois bandwagon when they were nearly undefeated. Ever being the contrarian, I picked the Illini to lose to Arizona in the Elite Eight. When that matchup materialized, and the Wildcats got up 15 with four minutes to go, I started dreaming of victory. Arizona blew that lead. I correctly had North Carolina winning it all, but I lost too much ground to the throngs of people who had Illinois in the final. I think about what could’ve been every March.
Matt Baker, senior colleges writer: As a freshman in high school, I agonized over a first-round game: fifth-seeded Virginia against the No. 12 seed Gonzaga. My gut said the Zags, but I went with the ACC-tested Cavaliers. Virginia missed a buzzer-beater, and that stupid one-point loss kept me from winning my dad’s office pool.
Anything you can do, I can do better
Mwitten3: Won the Arizona Medical Center NCAA Tournament pool before they even played the championship game because everyone picked Arizona to repeat, and I had watched Kentucky come back from double digits to beat Duke on the road and picked them to win it all. Since I was the only one who had one of the two teams in the championship, someone knocked on my lab door and handed me 4 $100 bills. The next year, my non-basketball-interested wife won the same damn pool just by chance, and she has never let me forget, but what the hell, she won more money than I did!!!
Never forget
Steve A.: I like to tell my kids about the year I picked the Final Four correctly, then the finals and the champion. It sounds impressive, right?
But then I clarify that the year was 1978 (Kentucky, Notre Dame, Duke and Arkansas). Since that was nearly 50 years ago, they became less impressed. And I retell this story every year.
Kevin P.: For the 1995 tournament, I was a senior in high school. The school’s librarian asked me to fill out her bracket for the district-wide teacher and staff pool. I picked the cleanest bracket of my life, having two entire regions right and having three of the Final Four teams and the champion. (I guess this is my “I peaked in high school” story.) She won a substantial amount of money, which she couldn’t share with me, so she brought my prom tickets and paid for a limo.
Love at first bracket
Charlie D.: On a third date a few years ago, my date brought along a hand-drawn blank bracket for us to fill out because she knew I liked college football, but being from and living in the UK, I didn’t really know much about college basketball or March Madness. We filled it out at the pub together as we talked through all the teams and their histories, and I was told that her college (Northwestern) was terrible and never qualified (except for once in 2017!). A few years and two March Madness wins later for Boo Buie and the boys, we got married and we’ve done a bracket every year to celebrate the moment I knew she was the one!
Not to hold a grudge, but…
John T.: I HATE AND ALWAYS WILL HATE CHRISTIAN LAETTNER!
Seeing history
Brad Feldman, creative director: In March 1992, I had just been accepted to UMass. I was suddenly a diehard fan of Minuteman basketball and attended the team’s first Sweet 16 appearance at the famed Philadelphia Spectrum.
The Thursday night matchup featured UMass vs. Kentucky. Kentucky went on to win to advance to its date with Christian Laettner and the greatest college basketball game ever played. My whole family attended the Thursday game, but for Duke vs. Kentucky my parents couldn’t make it, so my father sold two of the tickets and gave the other two to myself and my brother. Just before we left for the game, he said, “You can either go, or you can sell them and keep whatever you get over face value.” My brother and I did one full lap outside the Spectrum, contemplating a scalper profit, then ultimately looked at each other and said, “It’s Duke vs. Kentucky. We have to go in.” That’s how I ended up attending the Laettner-shot game with our seats right behind the basket where he hit the iconic buzzer-beater.
Honorary upset picks
C. Trent Rosecrans, senior MLB writer: In 1996, I predicted that Princeton would beat defending champion UCLA in the first round of the NCAA Tournament, and I was right. Ever since then, I pick the Ivy League champ in the first round, no matter what. I’ve never won a pool. But I have my principles.
Well, that didn’t take long
Michael J.: I’ve done a Survivor pool the past several years. Everyone gets randomly assigned two teams (one from each side of the bracket). Every game is against the spread — win and cover and you move on, lose but cover and you steal the winning team.
In 2023 I drew West Virginia and Howard. Their games tipped at 12:15 and 2 p.m. Thursday — Day 1 of the tourney. By the time I got home from work, I had already been eliminated. WVU lost to Maryland, Howard got blown out by Kansas.
There’s no vacating bracket wins
Brennan M.: The only pool I’ve ever won was in 2013, and I won specifically because Louisville won the National Championship.
Well, they vacated the title, but I’m NOT vacating the $200 I won that year…
Tasted glory, but then…
Pat C.: In 2016, I picked the first two days of games correctly. That was a rush I’ll never come close to experiencing again. I really thought Warren Buffett was going to have to write me a check for a perfect bracket lol. Damn Hawaii upsetting Jaylen Brown and his 4-seeded Cal team. Unfortunately, the rest of the rounds were not as pretty for me, and I don’t even think I placed in the top 10 of the pool. 🤦♂️ But I’ll always have those two days!
Child prodigy
Tim L.: I won my father’s office pool when I was nine years old. It was 1989. I picked Seton Hall to win it all because I thought their name was interesting. No one picked the champion, Michigan. There was one other guy who picked Seton Hall. I won on the points tiebreaker because the game went into OT. I was not even allowed to stay up to watch the game. Entry fee was $1, and there were 60 entries, so I won $60.
(Photo of Christian Laettner: AP Photo / Amy Sancetta)
