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Tips to win your NCAA tournament pool

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Covering the Las Vegas sports betting beat for more than two decades, I’ve been a huge proponent of handicapping contests in all forms, covering the Hilton/Westgate SuperContest and World Series of Poker since 1999 and horse racing’s National Handicapping Championship every year since 2000. I not only cover them but also participate as I really believe it’s the best way to maximize your profits when you’re “in the zone” and having the best day/week/season of your life.

This also extends to March Madness. When it comes to turning short money into long money, the three-week NCAA tournament is a great way for a quick score if you’re able to outpick your competition.

If I know my readers at all, you’re receiving invitations to all sorts of contests (brackets and otherwise) for March Madness. The same thing happened to me last year before the COVID-19 pandemic led to the cancellation of the tournament, but this year I swear I've received twice as many invitations to join brackets and contests even before Selection Sunday, and I’m sure more are to come as it seems more people than ever are champing at the bit to get involved.

You’re probably also entering a bracket contest or two (or several dozen in my case!). Here are the strategies I’ve developed over the years.

Pick the champion

This seems so obvious that you probably think it doesn’t merit discussion. But even though everyone loves the first two rounds to see who was smart enough to pick the right upsets and whose brackets got busted before even getting to the weekend, very few bracket contests are won or lost in the opening round.

Even if you totally kill it on Thursday and Friday (or Friday and Saturday this year), if you don’t have the overall champion winning your bracket, it’s almost a certainty that you’ll be overtaken by the title game, if not before. That’s because almost all bracket contests have weighted point systems that increase during the tournament, so no lead is safe. What most bracket contests come down to is who among those picking the champion did better in the early rounds. To a lesser degree, this also extends to the Final Four; even if you have the champion, if that’s your only team in the Final Four, you’re probably going to be beaten by someone who has more.

In my main bracket submitted for this issue, I went with Gonzaga as my champion, and I’ll be

using this bracket in a lot of contests, though the undefeated Bulldogs are going to be the most popular champion in brackets all over the country.

But again — as a huge fan of contests — I’m going to fill out upward of 50 brackets in everything from huge online contests to smaller online contests to even smaller ones with friends or former co-workers and will have a wide variety of champions and Final Four qualifiers. The fewer contests you enter, the more precise you must be in finding that champion. Just know that if you choose Gonzaga, you’ll have to hit an even higher percentage of your earlier picks too.

Know your competitors

This isn’t much help in the huge pools, as the players will cut across all spectrums of society, but I’m talking about smaller office pools. If you live in Big Ten country, you’re certain to have a higher percentage of your competitors using Illinois, Michigan, Ohio State and Iowa to win the championship or fill multiple spots in the Final Four than we’ll see in other parts of the country. You can get an edge by correctly predicting which of those teams get knocked out earlier and especially if you have a team from another conference winning the title (though, again, Gonzaga is going to be popular all over).

Understand the trends but be prepared to fade them

I’m assuming you’re well aware that a No. 1 seed had never lost to a No. 16 seed — until two years ago, when Virginia was upset by Maryland-Baltimore County. So it wasn’t surprising that very few took a shot with UMBC, but don’t get fooled into picking No. 16s over No. 1s all the time as it’s still very unlikely to happen.

Of course, everyone also knows that No. 12 seeds have a long-earned reputation of upsetting No. 5 seeds. While it certainly is important to know that type of information, don’t be so robotic that you’re doing what everyone else does; you need to handicap each game individually and

let that steer your decisions. You might end up coming to the same conclusions anyway, but don’t just pick a No. 12 seed just because it’s a No. 12 seed. Who knows? Maybe all the No. 5 seeds will win this year and all those people loading up on No. 12s will be behind early. Of course, if a 12 does beat a 5, you better have it or you’ll also be spotting a key game to a lot of competitors.

Don’t take your upset picks too far

We all love finding those first-round upsets and being able to say we knew Cinderella before she was the belle of the ball, but the truth is that midnight usually comes all too quickly. First-round upsetters usually come back to earth in the second round (even all No. 12 seeds, who usually have to face a No. 4 in the second round). Sure, we occasionally have a double-digit seed that sneaks into the Sweet 16, but it’s a rarity, so only pick that first-round upsetter to make the Sweet 16 if you’re willing to risk your bracket life on them.

If you pick most of your first-round upsetters to lose in the second round, it also prevents you from losing a lot of ground in the standings if the favorites beat your teams in the first round. In addition, you can make up those points in the next round as long as you have the team reaching the Sweet 16 from that sub-regional.

Use brackets to hedge underdog bets

There are many ways to diversify your portfolio during the NCAA tournament. If you’re playing multiple brackets, you can certainly flip-flop on toss-up games.

But there’s another strategy that I like to employ. Let’s say you like an underdog to cover the spread in a first-round game, but you’re not sure they can pull the outright upset. You can bet the dog plus the points but take the favorite in your bracket. It’s also a chance to “hit a middle” if the favorite wins to advance in your bracket but the dog covers the spread to win you some cash.

This approach also helps because if you’re cashing a bunch of these dogs plus the points, you won’t be as upset if your chalky bracket is busted. On the other hand, if you’re losing more of your side bets, maybe you have a very live bracket in a big pool for a lot more money (or, again, if the games fall right, maybe you win both ways).

Last rule: Have fun

This is supposed to be fun, and bracket contests are something so many of us share, whether it’s in an office environment or interacting online with other players. I know I’m sounding like the rah-rah dad-type here, but this should be a fun weekend following all the games and grading our brackets (especially after missing out on all the fun last March). But as I tell my kids, it’s more fun when you win!

Happy handicapping and bracket filling.

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