Issue 65: Tips for Winning Your March Madness Bracket

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Last issue, I gave a primer on how March Madness works. While knowing the ins and outs is handy, there’s one real reason you’re here: you want to know how to win your March Madness bracket.

I must preface this part by saying college basketball is extremely random and sometimes you really stupid stuff just happens. Let’s also remember these are kids that are 18 to 22 years old, and sometimes kids don’t make the right decisions.

If I had every one of my moves as a teenager held under a microscope, I’d probably have a lot of middle-aged men cussing me out, too.

Okay, now that that’s out of the way, here are the tips. I’m going to go by each round, so you can have a leg up every part of the tournament. Thanks, data!

The First Four

First off: The First Four. Back in 2011, the NCAA was like, “You know what? We don’t have enough teams represented every year. Let’s add three more.” And just like that, the tournament field went from 65 to 68. HOW EXCITING. These “First Four” teams play on the Tuesday and Wednesday before the main part of the tournament kicks off on Thursday and Friday, and office productivity slows by at least 87 percent.

This year, with COVID-19 still impacting things, all of these games will be played on Thursday, March 18. Then the tournament’s first round will happen on Friday and Saturday (March 19-20).

Technically, four of these teams are the final at-large schools chosen, while four are among the worst conference champions, usually from a smaller school. For the purposes of your bracket, we’re going to look at the at-large teams in the First Four.

Namely, you should always pick at least one First Four team to win an additional game after that opening “First Four” round. This literally happened every year from the round’s introduction in 2011 all the way to 2018.

Virginia Commonwealth University made it all the way to the Final Four (not to be confused with the First Four) in 2011, while Syracuse earned a Sweet 16 spot after barely making it into the tournament at all in 2018.

Then 2019 rolled around and the Belmont Bruins had to go and botch things. After winning their First Four matchup, they very nearly knocked off Maryland in the Round of 64, which would have continued this streak at a perfect 100 percent.

I’m not deterred, though. Pick a First Four squad to win an additional game—this year, your options are Michigan State, UCLA, Wichita State, or Drake—and you’ll be sitting pretty.

The Round of 64

People LOVE to see upsets. And I get it – it’s super fun to watch a school you’ve never heard of knock off some blueblood powerhouse that seems full of arrogant basketballers, like a Kentucky or a Duke. Actually, Kentucky and Duke aren’t even in the tournament at all this year, so we’re halfway there!

Don’t go too hog wild and only pick the underdogs though, or you’ll rip up your bracket faster than Jimi Hendrix ripped on guitar strings. You see, he was very good at guitar and being able to rip on the guitar is something you say when someone is very good at guitar. That’s a positive thing, not a negative like ripping up your bracket, so maybe this was a stupid analogy.

Anyway, only pick eight total first-round upsets when you’re filling out your bracket. The average has hovered around eight since the “modern-day” format of the 64-team main field. If you’re a mathlete, you’ll see that’s around 25 percent of all games that should be upsets by seeding. Of course, there are always exceptions, but if you stick around eight, you’ll be doing okay with your life.

The Round of 32

For the longest time, the only thing I knew about the NCAA Tournament was that you should always take a No. 12 seed over a No. 5 seed. “This happens EVERY YEAR,” some talking head or a classmate would tell me. “You’d be a fool not to do it.”

Of course, that meant I usually picked all four No. 12 seeds to win, which is just a stupid strategy no matter how you slice it. And while it does happen a lot, you’ll get years like 2018 where not a single No. 12 seed won. Way to slack off, fellas.

However, if you DO pick a No. 12 seed to win, you may as well slot ‘em to win their next game, too. 12-seeds have won 42 percent of the games they play in this round, which is the most of any team seeded 9th or worse.

The Sweet 16 and The Elite 8

At least one No. 2 seed should get the boot before the Sweet 16. All No. 2 seeds have advanced that far just twice in the past 25 years. And here I was believing that nursery rhyme, and thinking second was the best…

Since seeding began in 1979, a team seeded 6th or lower has made it to the Elite 8 in 35 of 42 tournaments. That’s good for 83.3 percent. Loyola Chicago and their 98-year-old mascot, Sister Jean, were an 11-seed during the 2018 NCAA Tournament, and they made it all the way to the Final Four. Spectacular.

And good news: Sister Jean (now 101 years old!) and the Ramblers are back in the tournament this year.

The Final Four

Since the modern-day format began, there’s only been one occasion where zero No. 1 seeds made the Final Four. That was in 2006.

Perhaps you vaguely remember George Mason, a No. 11 seed that shocked everyone en route to the Final Four. Their coach at the time was Jim Larrañaga, who did not have a tilde over the n in his name while coaching at George Mason. However, he took a job at the University of Miami and then the tilde appeared. It’s fascinating stuff.

That George Mason team also had a guy that punched another man in the groin during their conference tournament run, so they had all kinds of nonsense surrounding them. I should clarify the other man was on an opposing team. It wasn’t like the George Mason player was just wandering around the arena throwing out rogue punches.

Conversely, only once has every No. 1 seed made the Final Four. That was in 2008. So, you’ll definitely want some upsets along the way. If you’re feeling really feisty, a No. 11 seed has made it four times, which is more than No. 9 and No. 10 seeds combined and equal to how many times No. 7 seeds have reached the Final Four.

A weird side note: 2006 was the year where no top seeds made it; 2008 was the year all the top seeds made it. What about 2007? It was a boring year, with only 12 lower seeds winning throughout the entire tournament. And only four of those games were actual “upsets,” since a team beating a seed one position higher than it (like a No. 9 beating a No. 8) is kinda not really an upset. And that makes me upset just thinking about it.

The moral of the story, once again, is that college basketball is ridiculous, and you should take all of this advice with a grain of salt. Or maybe with a cookie cake, because that’s way more tasty than a little salt morsel.

The Championship Game

Okay, you’ve just got one more game to fill out. And this is the largest one of all. The big kahuna. The grand piano. The championship game.

I’ll be honest with you: I’ve been filling out brackets since about 2003, and 2018 was the first time I ever got both championship game participants correct. Filling out these brackets is not an easy task.

You could spend hours watching college basketball throughout the season, hoping to catch a glimpse of a team that could put it all together and win six games in a row on their way to a championship. Or you can save yourself all that trouble and go with this equally effective strategy.

Pick a team with blue as part of their school colors. Since 1979, every single team that has reached the championship has had blue as part of their color scheme, except for two years: 1983 and 2002.

Granted, the team wearing blue hasn’t actually won all of those games, but at least you have a good shot at getting one of the championship participants correct. And since that last “non-blue” championship game, 16 of the past 17 NCAA basketball champions have, in fact, had blue as part of their color scheme.

The only exception was Louisville in 2013, and that title got rescinded because Louisville did some WILD things with their college recruits. I won’t link to it because I don’t want this email to be NSFW, but MY GOODNESS.

The moral of the story is that you can feel comfortable slotting in a team wearing blue as your champion, and maybe even wear a little blue yourself on the day of the big game in a show of support. You know blue looks great on you, right?

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That’s all ’til next time. Thanks for reading!


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