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MoneyBrackets: How to win your March Madness pool without knowing a damn thing

March 18, 2019
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Last year, I won $500 as the winner of a 200-person March Madness pool, and finished second in Will Leitch's 389-person newsletter pool, missing out by a mere 10 points. This was not a fluke—I'm not going to pretend I win every single year, since March Madness is too chaotic, but I win far more than my fair share, and if you put me in a small pool (20 people or fewer) I'm a terror; I win at least once every two or three years. My bracket is deadly.

Is this because I watch a ton of college basketball and identify myself as an "expert"? Nope! I used to write about the sport, and in those days I watched games almost every night, but my brackets were an unmitigated disaster. I never won, and never really came close. It wasn't until I invented the patented MoneyBrackets system, which identifies underlying patterns that persist from year to year, that I gave myself a real chance to win. Today, I watch almost no college basketball—a handful of Duke games, and that's it—but I come into every tournament knowing I'll have a chance to win my pool.

The system has developed and evolved over the years, and today, I can boil it down to ten key tips. Follow these, and you don't need to know a thing about college basketball—you'll be playing the odds, wielding historical patterns as a weapon, and using a few ironclad rules to give you an edge over the field. I'll post my bracket at the end, so go there if you want the short version—copy it if you want, or just use the tips you like best.
We'll start with the most important advice of all...

1. Pick a smart champion

The Washington Post has a wonderful searchable database where you can look at specific match-ups between seeds or for specific rounds. When you click the link above and look at championship match-ups, what do you notice? Ten of the last 12 champions were either one- or two-seeds. The two exceptions were both UConn, a blue-blood program with a star player. The lesson here is obvious—the "madness" happens in the early rounds, but the champion is almost always one of the top dogs.

In a bracket pool of any size with normal scoring, you have to pick the correct champion.

There's no winning if you screw up, because it tends to be worth a disproportionate number of points; even if you slay in the early rounds, you'll get leap-frogged by all the lurkers if you can't nail the last game.

So be smart—if there's an overwhelming favorite, pick that team. Last year, that was Villanova. This year? Unfortunately, there's not an obvious choice. In my opinion, the two teams with the best chance to win are Duke and North Carolina, but others will make an argument for Virginia and Gonzaga, and maybe Tennessee or Michigan State or Kentucky. For reasons we'll get into, I'd stay away from those five, but the point is that you can't be a hero with this pick—go with the closest thing you can find to a sure bet. I'll be picking North Carolina, because as much as it pains me to say, I think they have a more complete team than Duke (who just cannot shoot) and have all the ingredients of a classic Roy Williams title team—experience, a great point guard, shooters, and the ability to run opponents to death.

2. The One, Two, and Three-Seeds are your Final Four friends

Similar idea here—looking at Final Fours since 2007, 33 of 48 teams have been one, two, or three-seeds from their respective regions. That's a little better than two of every three, which means that yes, there will likely be a team from outside those seeds in this year's Final Four—BUT, and this is important, you have no idea which region that team will come from, and if you guess wrong, you're in big trouble. To give yourself the best chance to hit as many big-point Final Four teams as possible, don't deviate outside the top three seeds in each region, and if you're going to pick a three-seed, make sure you have a good reason (I picked three-seed Michigan to go to the final game last year, but there was a lot of supporting evidence to back them up).

3. Be extremely careful about killing a one-seed early

Here's a stat for you: In second-round matches between a one-seed and an eight- or nine-seed, the one-seed is 116-19 since 1985. That's a lot of wins and not many losses! Last year, I really, really felt that Florida State would beat Xavier in the second round, and they did. But did I pick it? No, because the odds were against me! The problem is, every one-seed has a chance to make the Final Four, and you can bet that a lot of people in every pool are going to pick them to do exactly that. So if you make a huge gamble in the second round and it doesn't pan out, that means you're losing points to a ton of your enemies for at least one round, and possibly more—and those points get higher with each round. In short, the absolute soonest you want to pick a one-seed to lose is the Sweet 16, and even then you better have an extremely good reason.

4. Kill the imbalanced teams, and kill them dead

In my days of extensive research, I found that teams with good offense and bad defense never fare well in the tournament, and teams with good defense and bad offense do even worse. I measure it using Ken Pomeroy's ratings—if a team is top ten in one category and below 70th in another, they almost never make the Elite Eight, period. And in general, when deciding lower-ranked teams, watch out for anyone with a rating that's too low on either side of the ball.
This year, watch out for: VCU (great way to pick that 8/9 game), Belmont (if they win the play-in, everyone will tell you to pick them over Maryland...don't), Oregon, Washington, Baylor, Iowa, Ohio State, Oklahoma, Seton Hall, and Kansas St.

5. Trust regular season conference champions, be suspicious of trendy conference tourney champs

Some very simple rules:

If a team wins both the regular season and conference tournament, trust them.

If a team wins the regular season and loses the conference tournament, don't worry.

If a team doesn't win the regular but wins the conference tournament, RUN.

There are exceptions, of course—Michigan last year was a big one. But in general, the trendy conference tournament winners don't keep the momentum going into the NCAA. Your guess is as good as mine, but since 2000, only eight of the conference tourney-only teams have made a Final Four, only four have made a title game, and only Kemba Walker's UConn team won a title. Don't fall for the recency bias: This year, watch out for Iowa State, Auburn, Oregon, and Cincinnati. Iowa State especially terrifies me, since they ended the season on a three-game losing streak before the out-of-nowhere Big 12 tourney run.

6. Pick your Cinderellas, then calm down

I loved Loyola-Chicago last year—LOVED them. They had great metrics, a bunch of upperclassmen, and won the regular season and conference tourney, and I thought they were in a weak region. They had a great chance to make the Elite Eight, I thought, and so I made them my upset special of the year. As it turned out, they did the job, winning very close games against Miami, Tennessee, and Nevada. Of course, then they went a step further and actually went to the Final Four. I didn't pick that, but it didn't matter—by correctly having them in the Elite Eight, I gained a boat-load of points on everyone else. They more or less won me the tournament, and I didn't have to pick them to the Final Four, because nobody else did.

Here's the thing, though: I was lucky. They could have lost each of their first three games. Once you find your Loyola-Chicago, you need to restrain yourself. I arguably took them a round too far, even. Once you over-shoot with your upset team, you are in dangerous territory. This year, I don't see a Loyola. I like UC Irvine and New Mexico State, but I'm not taking any of them even to the Sweet 16. The place for "Cinderellas" is in the later rounds—I think FSU can make the Final Four in any bracket, so I'm pulling that trigger. I think Texas Tech is a really strong 3-seed, so I'm taking them to the Elite Eight.

7. Use your mid-majors wisely

In the first round, mid-majors with a HIGHER seed than a major conference team are an excellent 46-32 since 1985. It makes sense—these teams are powerhouses in their small pond, and they're playing mediocre major conference teams. But what happens when mid-majors play major conference teams in the Sweet 16? 33-58. Elite Eight? 17-24. And as you see, only 17 have ever made it to the Final Four. The only three to ever win are Louisville, UNLV, and UConn, which were "mid-major" only by the loosest definition of the term. You get the point—they get less and less valuable as time goes on, and that's if they're any good in the first place.
Oh, and the Mountain West is always overrated. Pick them all to lose.

Trying to fill out college basketball tournament bracket on paper


8. Conservative mindset rules the day in round one

The eight-seed vs. nine-seed games are literal toss-ups: Teams are 68-68 against each other since the current format began in 1985. But go up to the seven vs. ten games? It starts to get lopsided at 84-52. Six seeds are 86-50 against the elevens, fives are 89-47 against twelves, and once you get to fours vs. thirteens, you're in never gonna happen territory.

In short: Don't pick any 13-seed or higher to win, because there's no money in it. And if you're going to choose a 12, 11, or 10, have a damn good reason (and you should be pretty sure that if you're wrong, the team that wins can't win another round—my one "crazy" pick is 13-seed UCI over a highly imbalanced Kansas St. team, but I'm confident that if I'm wrong, Wisconsin will clean up my mess in the second round). Bracket pools are won by accumulating points, and even though crazy upsets are fun to pick, every one you miss can cost you points for more than just one round. Be safe in the opening rounds, and reap the benefits.

9. Slow teams are a dangerous mystery

Here's a simple mathematical truth: if you play fewer possessions in a game, there's more variance from game to game. In other words, play slow and you increase your chances of losing on a bad day. It gets worse under pressure, and Virginia proved the point yet again last season in the most dramatic way possible: They lost to a 16-seed in the first round. It had never happened before, but the truth is it could only happen to a team like Virginia—a team that plays slow, doesn't function well playing from behind, and has no second gear when things go bad. Of course, we're not going to see something that crazy every year, and we may go our entire lives without seeing it again, but the Virginia-type teams become vulnerable as the tournament goes on. There's a reason the Cavs themselves have been total disappointments in the Tony Bennett era, despite routinely dominating an incredibly tough ACC conference in the regular season. HOWEVER...can they sometimes win, as with ultra-slow Michigan last year? Yes! Does slow pace sometimes screw other teams up? Yes! Can they win titles? Not very often. This year, along with Virginia, be cautious with Cincinnati, Florida, Kansas St., Wisconsin, Virginia Tech, Oregon, Villanova, and Michigan.

10. Beware the bad coaches

Bad coaches lose tournament games, period. I realize this forces you to know something about college basketball, so here's your shorthand, with an assist from Bleacher Report college basketball obsessive Kerry Miller: Beware Fran McCaffery at Iowa (notice how he never wins many tourney games, and also notice how imbalanced Iowa is), Travis Ford at St. Louis, Rick Barnes at Tennessee, Matt Painter at Purdue (especially having to face Jay Wright in round two), and Roy Williams (just kidding, UNC fans). A lot of people are down on Mark Turgeon at Maryland, but with LSU's mess and a weak 11-seed in either Belmont or Temple, I can't see the Terps going down before the Sweet 16.


Now, with that all said, time to put my money(brackets) where my mouth is. Here's my bracket—as you'll see, there's still some guess work. I originally had Wisconsin over Virginia, but realized that since I basically believe it's a coin flip, I'd be losing points to Virginia pickers if I didn't take them. Florida-Nevada is almost impossible to pick. I hate that I have a Rick Barnes team in the Final Four. Nevertheless, I think this is a smart bracket. As I said, use what you want, reject what you must. Good luck out there: Glory awaits the prudent bracketeer.