CBT’s guide to running a perfect 2019 NCAA Tournament bracket pool

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Whether it’s your office, your family, favorite bar or that random email list you got on a decade ago, you’ve got all kinds of options to jump into an NCAA tournament pool or 12 this week. Not all tourney pools are created equal, though. Some go off without a hitch, others are annoying and some are downright train wrecks. 

Since the CBT staff has been in dozens of different NCAA Tournament pools over the years, we decided to help guide you in the right direction on the ways to make your pool the best that it can be.

REGIONS: East | South | Midwest | West

WHAT SHOULD YOU PLAY FOR? 

Sure, “money” is the obvious and correct answer here, but not every question has only one right response. Also, I’d argue money isn’t the best answer here. It is simply “stakes.”

But money is the easiest so let’s start with that.

Whether it’s $5, $10, $20 or $500 an entry, putting some dough in the pot keeps everyone interesting. Depending on your audience – are they college basketball junkies or have never heard of Coach K – you’ll want to adjust the buy-in accordingly. If it’s an office pool, keeping the entry low might entice the less-enthusiastic to get involved without too much pain. If it’s your ball-crazy group of friends, maybe up the ante a little. Your friendships can handle taking each other’s money, promise.

Here’s the deal, though. Stakes don’t have to be money. Yeah, you can have some sort of prize – maybe a parking space at work or you get to be first in line to the Easter brunch with your family – but the more interesting direction here is a punishment. At least if you’re into seeing your friends and family humiliated.

Finish last in your pool? You get to stand at busy intersection holding a sign that says “MY TITLE PICK WAS THE ONLY ONE SEED TO EVER LOSE TO A 16.” Or you’ve got to name your fantasy football team in the fall after the winner. That’s why CBT editor Rob Dauster’s squad was named “Hines Is The Best” last year (don’t fact check me on this). Something that makes the worst bracketeer feel bad is really the only rule here. Winning money is great, but being able to laugh at your loved ones and dearest friends is better, right?

This can be a component of any pool. The NCAA tournament has winners and losers. Your bracket pool should, too.

WHAT SHOULD THE SCORING SYSTEM BE? 

There’s a couple of ways to go here.

If you want to add weight to picking the games that mean the most in the broader college basketball landscape – ie the Final Four and title game – then go this way:

First Round: 1 point

Second Round: 2 points

Sweet 16: 4 points

Elite Eight: 8 points

Final Four: 16 points

Title Game: 32 points

If you want to de-emphasize the later rounds a little bit – but still obviously give them their due – go here to make the difference between picking a first-round game and a national champion a little less dramatic.

Round of 64: 1 point

Round of 32: 2 points

Sweet 16: 3 points

Elite Eight: 4 points

Final Four: 5 points

Title Game: 6 points

SHOULD YOU ALLOW PEOPLE TO BUY-IN WITH MULTIPLE BRACKETS?

If you’re playing for money, yes. Now, it’s incredibly annoying to here people brag about how they picked that 15-seed over a 2 in one of their 37 brackets as if that’s some major accomplishment, but if they’re going to pony up the entry fee for each one of those, it’s worth listening to. Nod, curse them internally and take their money.

But if you’re playing for a prize and/or a punishment – and I’m really stressing the latter here – stick to one bracket.

HOW SHOULD YOU SEND THE INITIAL EMAIL/WELCOME LETTER? 

Again, know your audience here.

If you’re running your office pool, maybe stick to the basics. Deadlines, rules, stakes and pleasantries. Maybe save the inside jokes and savage personal attacks for a pool your friends or annoying in-laws are in. I mean, have the rules and stuff in that one too, but feel free to let some digs in. You’re only joking anyway, right?

One thing to stress in every opening letter is how to pay up. There are so many options now between digital payments directly to the administrator or a company that will hold the money for you, that you should never, ever have to touch a personal check. Yes, they still make those, and Bob in accounts receivable will absolutely make you deal with that outdated piece of paper unless you tell him otherwise.

Also, be crystal clear about the scoring system and payouts. That way when someone comes back to complain about something – and someone will absolutely complain about something – you can point to the initial letter and not have to argue about whether or not finishing 11th in the pool should get any cash.