After the college football bowl season, I typed up a list of lessons that I learned from bowls in hopes that I would actually remember them come next year. The logic behind them was fairly sound, although I am quite certain that I will make the same mistakes again.
I thought about doing the same for March Madness this season, but I learned one lesson and one lesson only: unless you are in a pool with ten people or less, pick a unique team to win the tournament. That seems fairly simple…but it’s actually the opposite of how most people pick their brackets. We’ll get to that a bit later though. First, you get to read a story.
Every year I enter into a March Madness pool that has upwards of 500 people in it. I have never won it (and won’t this year either). The closest I came was in 2006, otherwise known as the year of George Mason. I couldn’t fully enjoy the Patriots’ run though, since they knocked off Connecticut in the regional final.
That year I went with the traditional formula for bracket selection. I picked several upsets in the first few rounds but picked a favorite to win the tournament. Almost all of my upset picks hit. I literally nailed everything. I hit seven of eight Elite Eight picks, only missing the aforementioned George Mason, which virtually no one picked to even win a game. My Final Four consisted of LSU, UCLA, Florida, and Connecticut. The first three all got there.
Then UConn happened. I picked them to win the tournament that year, but didn’t even need them to win. There were about 430 people in the pool, but I was so far ahead that all I needed was UConn to beat George Mason to lock up the title. I had the Huskies beating UCLA in the final. Because of that, no one that picked UCLA to win the title could pass me and no one that picked Florida to win the title could catch me if I got the seven points for UConn’s supposedly inevitable Elite Eight victory (and no one picked LSU to reach the title game at all).
Imagine – the $1200 or so first place prize locked up before the Final Four even began. We all know that the sports gods are cruel though. The Huskies blew it in overtime, I received no more points, and the handful of people that picked Florida to win the next two games (11 points for the semifinal and 16 points for the final) passed me. I finished in sixth place, five points behind the overall winner.
You would think the epiphany would have happened then. I really liked UCLA and Florida, but instead of picking either one of them to win the title, I went with the consensus favorite Connecticut. I would imagine that 30% of the people picked UConn to win it that year. I followed all of them and where did it get me? Sixth place. I think I won something like $50.
And for what? The sixteen points obviously wouldn’t have done me a whole lot of good, since everybody else picked them. Sure, had the Huskies won it all, I would have needed to pick them at least to the finals to hold the rest of the pack that did pick them. But I should have just taken my chances. Although I finished sixth, I ruined an amazing year of picks.
Had I picked Florida over UConn in the Final Four, I would have won something like $1500 between two pools. Had I done so and UConn actually did win, I would have probably won $0. I think I did win about $75 between the pools, but I would gladly (duh!) exchange that for picking Florida, a team I really liked.
Fast forward to this year. Finally, I went with an off-the-wall team to win the tournament. This time, I went with Kentucky almost completely by accident. I liked the Wildcats to do well in the tournament because they really came together at the end of the season, capped off by the dominant SEC tournament run. I didn’t like number one seeds Ohio State and Duke on that side of the bracket, so it was wide open. I also kept hearing about all the parity this year, so I figured why not take my chances with a #4 seed that is playing well.
Eventually I picked Kentucky to make it to the final, where they would lose to Kansas. Then I remembered my track record with Kansas. The last two times I picked them (2006 and 2010), they went out on the first weekend. I quickly erased Kansas and had them go down in the Sweet Sixteen. I ended up with Pitt in the title game for reasons that remain unclear to me. I don’t actually like Pitt, so I picked Kentucky to beat them in the title game.
Other than that, this was my worst year ever. That is not an exaggeration. My ENTIRE Elite Eight on the right side of the bracket was done by Saturday night on the first weekend. When the dust settled, Kentucky was the only team that made the Elite Eight that I got right. To put that in perspective, only four of the 490 people in my pool missed all Elite Eight teams…and you know that includes at least 40 women that picked based on name alone (my wife was one of them, and she performed far better than me). Of 490 people, I finished better than four people on Elite Eight picks.
The early rounds weren’t much better. I picked Florida State to reach the Sweet Sixteen in an upset pick. I picked Richmond to beat Vandy. And that’s it for picks that panned out. Michigan State and Louisville, both Elite Eight picks, went down in the first round. Pitt and Purdue, both Final Four picks, went down in the second. After the first weekend of play, I sat in 423rd place. After the second, I sit in 348th place.
But it turns out almost none of that matters, thanks to Kentucky. If Kentucky ends up winning the title, I will finish in fourth place. I only picked one Elite Eight team correctly, and I still have a legitimate shot to finish fourth in a 490 person pool.
All that time spent looking at first and second round upsets got me nowhere. Sure, I can be proud of my Seminole Sweet Sixteen pick. That got me a whopping three points. I would have had to do that with at least three more Sweet Sixteen picks to finish in first. The three people that would finish ahead of me are the only other three people that picked Kentucky to win.
So that’s my lesson. If you are in a pool with ten people or less, by all means follow the standard route. Pick a favorite to win and try to pick off enough points in the early rounds to win the pool. It is fairly unlikely that anybody will have any team lower than a two seed winning the tournament anyway.
But if you are in a big pool, like I am, you HAVE to go with an underdog to win the title. Don’t go crazy – no team lower than a four seed has won since #6 Kansas in 1988. And of course your #3 or #4 seeded pick actually winning the tournament is still an extreme longshot.
Yet the one strategic question I missed was this: what are the odds that I do well enough in the sixty pre-tournament games that I build up enough of a lead to top the 100 or so other people in the pool that picked the same favorite I did to win the tournament? Turns out quite a bit less than picking a significant underdog to win the title.
I understand that if UConn would have won just one more game in 2006, I would have still won the pool while picking the runaway favorite to win. That took a great deal of luck and magic to get me in that spot, and I seriously doubt I will end up in that position again. The larger point remains: even the biggest favorite to win the tournament will have less than a twenty percent chance to win. Why not roll the dice on a unique team to win the tourney and take my chances?
The lesson is simple yet a bit counterintuitive. I have picked NCAA brackets every year since I was a four-year old in 1989 (that is not an exaggeration). In my best ever year, I picked the runaway favorite to win the title and finished in sixth place. In my worst ever year, I picked an underdog to win the title and have a very realistic shot at finishing fourth place.
I like those odds. And go Kentucky!