Let me ask you a question: What is your goal when filling out your NCAA Tournament bracket? Is it to actually try and win so you can make some money, or are you just out to brag about the handful of upsets you picked correctly?
That’s a key question, because the two DO NOT go hand in hand.
See, Upset Guy picks every 12 seed to beat a 5, along with two or three 11 seeds beating a 6, and maybe even a 13 beating a 4. Because Upset Guy wants to be able to brag to all of his friends after the first or second day, “Hey, I picked that 12 and two 10s!”
There are two potential problems with Upset Guy’s bracket.
First, while some 11s, 12s and 13s do win every year, you have to be careful picking a bunch of them because a lot of them lose.
Second, Upset Guy not only falls in love with his 11s and 12s in the first round, he’ll often take an even bigger risk by picking that team to win another game and get to the Sweet 16.
If you actually want to win money in your bracket pool, those are some of the worst strategies to have. It all needs to be about risk management.
I’ll give a humble brag here and say that, in my lifetime, I estimate I’ve won or placed in the money in about 14-15 tournaments, over about 35 years. Some people have done better, I’m sure, but I’m batting about .400, so that’s pretty decent.
This is more than decent: I estimate that I’ve won more than $5,000 in NCAA Tournament brackets. That’s not filling out 20 brackets and playing $25 pools, either. I make it a point to do one bracket — maybe two if there’s a particular situation that comes up — and I usually never pay more than $10 for any pool.
My best tournament was in 2003. I’m a lifelong Syracuse fan, and I knew the Orange had a really good shot with Carmelo Anthony and Gerry McNamara. I picked the Cuse not only to get to the Final Four when almost no one else did, but also to win it all.
Syracuse won the title, beating Kansas. And won me about $2,000 in the process because I was in several pools that all paid pretty well.
In the last NCAA Tournament two years ago, I won $750 — thanks to two teams. I loved Texas Tech going into the tournament and picked the Red Raiders to get to the Final Four. When they punched their ticket, it guaranteed me around $250.
I got extremely lucky and won a big pool, thanks to Virginia. I had the Cavaliers winning it all — it was the year after their historic loss as a 1 seed to 16 seed UMBC, so they had revenge on their side — and UVa won some nailbiters along the way to the national title. They edged Purdue in OT to get to the Final Four, then beat Auburn for a miracle victory as Kyle Guy was fouled on a 3 with 1 second left and hit all three free throws for a 63-62 win.
Cha ching! With Virginia and Texas Tech in the title game, I had already locked up one pool worth $500.
What I’m talking about here — and this is my best tip if you really want to win some money — is you’ve got to pick one or two teams that are somewhat under the radar for most bracket contestants. Syracuse was a 3 seed in 2003, and Texas Tech was a 3 seed two years ago. I loved those teams, and they rewarded my love with deep runs.
It can work the other way, too. I’ve lost out on a good bit of money when a team I loved wound up getting beat. And wouldn’t you know it, my favorite team cost me a bunch of money one year for not believing in it.
I had Virginia going to the Final Four in 2016, and the Cavaliers led Syracuse by 15 with 9 minutes left. If Virginia would have won, it would have locked up about $300 for me in some pools because I also had two other Final Four teams (Villanova, UNC). But somehow, Cuse staged an incredible rally and stole one of the most improbable victories in the storied program’s history to get to the Final Four as a 10 seed.
OK, so here are my three big tips when filling out your bracket:
1: Get as many teams as you can into the Sweet 16, which helps you keep racking up more points in the later rounds. This is where Upset Guy falls flat. As I mentioned earlier, he likes to pick a bunch of 12s and 13s to win, and while he might nail one or two, it will cost him in the Sweet 16. Why? Because you’re picking against 4 and 5 seeds in the first round, and a whole bunch of those usually end up getting into the Sweet 16.
2: Find 2 or 3 teams you love and ride them a long way. These usually can’t be 1 or 2 seeds because many other people will pick them, as well, and it’s hard to win a bracket pool that way. A 3 can often be a great pick in this regard. If you land on the right team that’s a 4 seed or below, then you will win A LOT of money. I have two teams I really like this year. I would share them with you, but hey, we’re all competing for money here!
3: There’s a fine line between falling in love with a sleeper team that will make you money, and destroying your bracket because you believed in the wrong sleeper team. You have to do the research to come up with the RIGHT sleeper teams — the ones playing well, that have all the key pieces to make a run, that have a good coach, that are healthy, etc.
You don’t have to follow college basketball religiously throughout the season to win a bracket pool. Anyone can get lucky by picking one team that stuns everyone. But look, if you usually don’t pay much attention to the sport at all until March, it’s usually gonna be tough to do consistently well in bracket pools year after year.
Good luck to all. Hope you win big. (But I hope I win bigger!)
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