NCAA Tournament 2016: Strategies For Winning Your Pool

Reading Time: 6 minutes

The NCAA Men’s Basketball Tournament is here again. Time for my annual foray in to sports prognostication.

(Note: All of the following presumes you’re operating in the standard bracket scoring setup that rewards increasing points as the tournament progresses.

If you’re in a pool that gives bonuses for upsets or some other unorthodox scoring system, adjust accordingly.)

Every year I publish my bracket and suggestions for winning your own pools.

Last year saw my bracket flame out in the wee hours of the tournament.

I’m no expert on college basketball; I watch about as much NCAA ball as I do Lifetime Television.

Ironically, my lack of interest in the college game doesn’t disqualify me from giving advice on picking a bracket. I know what it takes to win these sort of “roll-the-dice-and-pray” competitions, especially when no one you’re playing against has a marked competitive advantage over the rest of the field.

First thing you have to do is adopt the right perspective.

Understand this: If you’re in a pool of any reasonable size, you’re unlikely to win.

A grim outlook, but a fact.

Once you’ve got the right mindset, it’s easier to produce a bracket that maximizes your chances of winning. Given the slim odds that any single entry has of winning a  large pool, the importance of differentiation cannot be overstated.

Facing tough odds, you’ll need some special moves to clear a path.

That’s where “risk” comes in.

If you’re playing in a small office pool, you can ignore this advice. Stay conservative. You don’t have to take nearly as many risks because there isn’t that much opposition.

Play in a big pool, however, and you’ve got to venture out on a limb.

In a competition where most of your competitors are likely to have the same few picks in the Elite 8 and Final Four, the spoils ain’t going to the risk-averse.

Some notes, from my previous entries, on how you should approach winning a large pool:

The best long-term success goes to those who adopt one of two strategies:

1) Pick a tourney favorite to win it all, along with a number of significant upsets throughout your bracket.

2) Pick an unconventional winner and stay conservative throughout the rest of your bracket.

Both of these strategies infuse risk into your bracket, instead of going “chalk”, like most of the nation.

Going all chalk again, eh? Plenty of room!

The best path to winning a big pool is to gamble on plausible upsets, stepping out on a limb to gain an edge on competitors. The talent gap between most tourney teams is minimal, outside of the big dogs, so you might not even call it an upset when some of the lower seeds win.

The most frequent cognitive bias in bracket selection is getting caught up in seed numbers. As difficult as it is, you have to try to ignore gaps in seeding (e.g. #3 vs. #14) when filling out your bracket. If some of the available data says your #11 seed has a legitimate chance to topple that #6, buck up and roll the dice, especially if most of the nation is going the other way.

Again, winning is not about how many correct picks you make. It’s about how many points you score relative to the rest of your pool.

If you make a correct pick, along with 95% of the nation, you don’t gain much. Correctly call an upset, however, while everyone else gets it wrong, and that’s a big step forward.

So, who am I rolling with this year?

Final Four: Kansas (#1), Duke (#4), Kentucky (#4), MSU (#2)

Championship Game: Kansas, MSU

Champion: MSU

(Note: I actually filled out three brackets, for entry in to my annual 600+ entry pool. I’ll update this post with pictures of those entries after the tournament starts.)

Update: See my picks here:

Notes on my selections:

– I went against the public favorite in several key spots, staying true to the “scarcity” strategy I espoused in this article.

I put my money where my mouth is.

– Each entry has the same exact picks through the Final Four. I just changed the participants/winners of the championship game in the second and third entry.

As predicted, the overwhelming majority of entries in the pool selected Kansas, MSU/Virginia, Oklahoma/Oregon, North Carolina for the Final Four..

– Correctly selected 15 of 16 winners on Day 1, putting me near the top of the leader board early in the game. A nice bonus, but nothing to beat my chest over. My picks are geared towards the latter rounds, which determine who takes home the gold.

– A run to the Elite 8 for either Duke or Kentucky will almost certainly result in a stellar finish for all three brackets.

And my “bracket busters”, which I’ll define as teams without a top seed that advance to the Sweet Sixteen (or deeper):

Gonzaga, Wichita State, Kentucky, Duke.

The first thing you’ll notice about my picks are the placement of Duke (#4) and Kentucky (#4) in the Final Four.

Sure, it’s a big risk to knock out a #1 seed in the round of 16; Few people will do it.

Remember the point of the game: Finishing in one of the top spots, not generating a “respectable” score.

Taking Duke and Kentucky to win their regions is exactly the type of variance you should introduce in to your bracket if you’re in a massive pool; bet on a traditional power with a lower seed.

A #4 seed coming out of a region!? Crazy like a fox.

That goes double if you’re picking MSU and Kansas to win their regions.

Historical power (Duke) matched up with a weak #1 seed (Oregon)? Worth a gamble. Kentucky is always a tough out; lots of talent. When most of the country is picking Carolina to emerge from the East, it made sense to lean in another direction.

If Duke and Kentucky are knocked out early, i’m finished.

But If I get those picks right…how much of the rest of the country–and my pool–would’ve made those same choices? Can’t be too many.

Heck, getting either one of those teams in the Elite 8 will almost certainly result in a very-high finish for my bracket. If Kansas or MSU go down early, I take a major hit, but so does the rest of the country.

Remember, the chances of your bracket winning a big pool are remote to begin with. You want to maximize your chance of taking down a huge pot in the event your picks are correct.

You go all chalk and get those right….you’re still likely to finish empty-handed. Most of your competition has done the same and there are probably a dozen other entries who got that Dayton/Syracuse or Cincy/St. Joes matchup right that you got wrong to edge you out by a couple points.

You only gain ground when you score points missed by the rest of the field.

With most pool setups, it does you no good to finish anywhere but the very top of the standings. 20th place is as good as 200th place.

Give yourself a chance to win by looking for arbitrage opportunities. Shoulder some risk when others are afraid to.

On Yale Basketball:

I also took Yale over Baylor in my entries because…..why not? Roll with the Ivy League and the game is in Rhode Island. Not hard for the Connecticut crowd to make it to the game.

Off the court, Yale is embroiled in a serious case of judicial overreach:

When it’s all said and done, this should be a landmark case. Colleges have to be held accountable for both student enrichment and due process. Students need fewer calls for “safe spaces” and more exposure to real-world dynamics.

You shouldn’t sacrifice individual liberties to satisfy the whims of a mob.

Bonus Link:

Since we’ve spent so much time discussing team sports, a great read on teamwork in the workplace:

New York Times and Google go deep on the science of building good teams.

Synopsis: Encourage free speech and Emotional Intelligence.

Create an atmosphere where people feel encouraged to speak freely. Have firm leadership in place that allows the group to move in the desired direction while allowing everyone a chance to share their opinions without feeling judged

Self-disclosure and the ability to read signals does wonders for building bonds.

People need to feel like they can be themselves; Cultivate environments free of the backbiting and one-upmanship that characterize many work spaces.

The fewer corrosive elements present in a group, the better chance said group churns out quality work.

Need help with a problem or goal?  Click here to learn more.

Leave a Comment

Your email address will not be published. Required fields are marked *