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Teddy Covers' Las Vegas Wiseguy Report: How to beat your NCAA Tournament office pool

03.14.2016     10:27 AM     Teddy Covers     Printer Friendly

Submitted by Teddy Covers blog entry.
I could go off on the NCAA Tournament committee for screwing the mid-majors again, something that’s becoming an annual tradition.  But complaining about the committee is akin to complaining about the weather – everybody does it, but it doesn’t help one iota.  Instead, in this week’s Wiseguy Report, I’m going to focus on the casual fan and strategies for winning office pool bracket contests.

It’s bracket time, the annual intrusion every March of the general public into our college basketball sportsbetting world.  And when it comes to filling out brackets, there aren’t many bigger experts than Ed Feng from, who I had the chance to interview last week.

Feng is an interesting guy, earning his PhD from Stanford – he’s no dummy.  He’s written for Grantland , Deadspin and Bleacher Report, just to name a few of the sites he’s been affiliated with.  Last year, advanced analytics website conducted a study that found Feng’s predictions for the 2015 NCAA Tournament to be the most accurate among their forecasts, culminating in Duke’s championship run.  So who better to talk brackets with than a guy like Ed?  Nobody, that’s who!

Ed had three main points when it comes to winning your bracket pool.  All three made sense to me from an empirical perspective as well as from his more quant based approach; hence my decision to write about them in this week’s Wiseguy Report.

The single best strategy for beating the brackets in an office pool type of format is perfectly simple and makes perfect sense – join smaller pools.  A pool with 5000 entries is akin to a lottery – even a good, or very good bracket is no sure thing to finish in the money.  A pool with 100,000 entries is essentially unwinnable.  But if you can get into smaller pools, with fewer than 100 entries, you’re far more likely to cut down the nets with a nice cash prize for your bracket prowess. 

Again, you are FAR more likely to cash if you enter 20 smaller pools compared to one or two massive pools.  Combine the other two primary tournament pool strategies listed below with a smaller pool of entrants and you’ve probably maximized your chances of winning.  This one makes perfect sense – although the prize pools are smaller in smaller pools, cashing a decent percentage of the total potential winnings in a small pool is one heck of a lot better than winning zero percent of the prize in a bigger pool.

Ed Feng’s second key point was to pick a contrarian champion, based on the cumulative results of the bigger brackets.  If you log on to or CBS and you’ll find enormous pools with hundreds of thousands of entrants.  Everyone focuses on picking a few early upsets correctly, but in most standard format brackets the ‘big points’ get earned once the Final Four rolls around.

Feng’s suggestion is to look at the bigger pools consensus numbers.  Take the top two or three champions picked by the public and throw them out – too much competition if they win.  Instead find a #1 or #2 seed that is under-represented as the champ in those consensus numbers; a contrarian pick.  Last year, Kentucky was the most popular choice to cut down the nets, while #1 seed Duke didn’t attract much love.  This year, we can project that Kansas and Michigan State will be very popular choices, two teams that won’t help your brackets very much if they win.  Pick somebody else!

Again, this is a strategy that passes the ‘does it make sense’ test.  Pools offer excitement in the early rounds, for sure, but to actually win or at least cash in any pool, you’re going to have to pick the eventual champ, and most of the Final Four correctly in order to show a profit.  Finding and settling on a contrarian champ – still a capable team, since #1 or #2 seeds have won 21 of the last 26 titles – is a positive expectation way to examine the brackets for a potential champ.

Feng’s third and final office pool suggestion is to avoid the teams that take a high percentage of three point shots.  History shows that teams who shoot a bevy of three’s are prone to suffering that one cold shooting game that sends them home.  Teams that pound the ball into the paint tend to be better bets to win it all.  On the other hand, the teams that rely heavily on three pointers have historically underperformed in the Big Dance at the Final Four level.  The Iona’s of the world (the Gaels shot more three pointers this year than any other NCAA Tournament team) are capable of pulling off an upset or two, but they don’t tend to put together extended tourney runs.

And when it comes to the chalk that shoots three pointers for a significant portion of their offense, these teams have consistently been bad bets to reach the Final Four or to win the tourney if they get there.  Two teams that stand out in that regard this year are #2 seeds Oklahoma and Villanova, both of whom jack up nearly 25 three pointers per game.  If you’re looking for a #2 seed to cut down the nets this year, I’d avoid picking either the Sooners or the Wildcats.

Again, this passes the smell test, unlike so many of the advanced analytics analysis papers that were presented at the Sloan Advanced Analytics Conference last week.  Teams that win championships tend to have a balanced offense with a solid low post game.  Three-point shooting teams are prone to bad shooting nights without the ability to consistently pound the ball into the paint, and one bad shooting night from a three point heavy squad is likely to send them home.

Winning your bracket pool requires plenty of luck – there’s a reason the office receptionist who picks based on uniform colors or team names is ‘live’ in many of these brackets, year after year.   But these three strategies help savvy office pool players get the best of it in terms of mathematical positioning to produce the best chance of cashing in with a March Madness bracket pool payday.

Follow me on Twitter @teddy_covers.

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