Get an Edge in Your March Madness Bracket Contests

Covering the Las Vegas sports betting beat for more than two decades, I’ve been a huge proponent of handicapping contests in all forms. I’ve covered 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 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 can outpick your competition.

If I know my readers, you’re receiving invitations to all sorts of March Madness contests (brackets and otherwise). You’re probably entering a bracket contest or two (or several dozen, in my case!). 

 

Here are a few 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 crush it in the first round on Thursday and Friday, if you don’t have the overall champion winning your bracket, it’s almost certain that you’ll be overtaken by someone in 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 as they’ll get those additional points.

I will 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. I 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. If you choose one of the No. 1 seeds –  currently projected to be HOUSTON, UCONN, PURDUE and TENNESSEE as of deadline for this VSiN Betting Guide – 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 and not be affected as much by regional bias, but I’m talking about smaller office pools. If you live in Big 12 country – regarded as the toughest overall conference – you’re certain to have a higher percentage of your competitors picking Houston, Iowa State, Baylor, etc. 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, especially if you have a team from another conference winning the title.

A No. 1 seed had never lost to a No. 16 seed until 2018, when Virginia was upset by Maryland-Baltimore County, so it wasn’t surprising that very few bracket players took a shot with UMBC.

Of course, most people treated that like a fluke and went back to picking all No. 1 seeds to advance, only to be shocked last year when Fairleigh Dickinson upset Purdue 63-58.

I believe we will see more people taking stabs at No. 16 teams upsetting No. 1s, but even though I’m the biggest longshot bettor I know, I’m here to tell you not to go overboard in that. The fact is that even if everyone felt their “bracket was busted” last year with Purdue ousted, the fact of the matter is that because nearly everyone had Purdue advancing, it hurt nearly everyone just the same. It still came down to who had the best overall brackets with the remaining teams, right?


So, my advice is to still treat those 1-16 matchups as “free bingo squares.” Even if the upsets happen, you won’t lose much ground to the vast majority of your competition (as long as the losing top seed isn’t your pick to go all the way like those who had Purdue last year).

Of course, everyone also knows that No. 12 seeds have a long-earned reputation for 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. In fact, the No. 5 seeds went 4-0 last year, so all those searching for the upsets were burned. 

Having said that, if a 12 does beat a 5, you’d better have it, or you’ll also be spotting a key game to a lot of competitors. I believe the key is to be selective in which upsets you choose.

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 return to earth in the second round (even 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.

Here’s another key point I love as a “dog-or-pass” bettor: 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 March Madness Rule: Have Fun

March Madness is supposed to be fun, and bracket contests are something so many of us share, whether 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. But as I tell my kids, it’s more fun when you win!

Happy handicapping and bracket filling.