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Over the years, I’ve developed a low-risk, high-reward approach to betting on March Madness.
The general idea is to identify underseeded teams that have a good shot at going far in the tournament. We'll bet these teams on the moneyline each game (with a few exceptions, as we'll discuss).
As long as these teams keep winning, we will keep betting them on the moneyline, rolling up both our bet and our winnings into each subsequent moneyline bet on that team until either:
- Two of our chosen teams face off, so we can cash out both.
- The team makes the Elite Eight.*
*There are occasionally exceptions to this rule. If there are, they will be noted in the picks.
Using this approach, we can identify eight teams and invest a small amount in each.
For this example, let's use one-quarter of a unit, or $25.
We can take this $25 quarter-unit and bet on eight teams. This $200 investment will likely pay off as long as at least one of our eight teams reaches the Elite Eight. If none do, we limit our losses to $200.
But the upside is pretty big.
First, we get to sweat and root for eight teams, generating a fun first (and hopefully second) weekend. Even better, a lot of them are underdogs — Cinderella stories, if you will. Who doesn't love a good Cinderella run?
Second, this strategy has the potential to deliver significant returns.
Here's how it's fared over the years:
- 2017: My analysis identified 11-seed Xavier. The Musketeers made the Elite Eight while knocking off the No. 6, No. 3, and No. 2 seeds, returning 33 times my initial $25 investment on them.
- 2018: Another 11-seed in Loyola Chicago was one of my picks. Per my system, I cashed out the Ramblers in the Elite Eight, returning 16 times my initial investment, but Loyola continued its Cinderella story into the Final Four.
- 2019: Five-seed Auburn was one of my teams. The Tigers also reached the Final Four. I bet them to cover the spread in the first game, which they did, then rolled them up on the moneyline thereafter, earning me 10 times my initial investment on them before cashing out in the Elite Eight.
- 2020: COVID
- 2021: I skipped 2021 because I felt the roster turnover made evaluations tough with players missing plenty of time throughout the year because of COVID.
- 2022: My eight teams combined for a paltry one win. That was the only win in the play-in round. Certainly a disastrous year, but that's why we play the lose-small, win-big strategy. We limit our losses to just two units, with the upside of winning much more.
- 2023: While I did have No. 8-seed Arkansas upset No. 1-seed Kansas to reach the Sweet 16, their run ended against eventual national champions Connecticut. Two other teams, No. 6 seed Creighton and No. 9 seed Florida Atlantic, reached the Elite Eight. However, because I chose to bet on Creighton to cover the spread against NC State in the opener and it didn't, that didn't count. Similarly, Florida Atlantic was primed to face Purdue in the second round, but Fairleigh Dickinson pulled off the second-ever No. 16 over No. 1 upset. That meant, in an audible, I ended up betting FAU to cover against Fairleigh Dickinson, and they unfortunately did not.
- 2024: Another big success! NC State made it to the Elite Eight as an 11 seed and returned 15 times the initial investment on them for a total profit of 1.75x the initial two-unit investment.
- 2025: With seven of eight possible one or two seeds making the Elite Eight, and the other being a three seed, it was a tough year. I rightly noted in my piece last year that 2025 was the toughest year for this strategy because teams were top-heavy that year.
That makes four out of seven successful years, and while this year's tournament is also pretty top-heavy, I feel a bit better about this strategy's chances this year than last.
So let's dive into our NCAA Tournament moneyline rollover picks in the 2026 Giffen Guide to March Madness.
NCAA Tournament: Moneyline Rollover Picks
I have a familiar team from the First Four in Dayton, so we'll start with them since the game is on Tuesday!
West Region
This is a standard two-pick region, with one pick from each half.
However, the bottom half picks a team from the First Four, so let's start there.
No. 11 NC State
The team that made 2024 a rousing success is again in my Giffen Guide.
Longtime readers may recall I went to NC State for grad school. But this is no homer pick, I just like how things are set up for the Wolfpack.
N.C. State power rates better than Texas by about 0.75 points, yet the odds for this game show you can get the Wolfpack at +1.5 in some spots and at -108 on the moneyline.
Should they get past Texas, NC State gets BYU, which has been on a bit of a slide, losing 10 of its last 17 games.
NC State also plays a relatively high-variance style, shooting 3s at a top-90 rate nationally while forcing opponents to shoot 3s at a top-30 rate. That naturally leads to both upside and downside, but we're playing for upside with this strategy.
The Wolfpack also don't need to make the Elite Eight for this strategy since they come from the First Four. We avoid Purdue, and the key third game would be a date with the No. 3-seeded Gonzaga Bulldogs. I actually have the Zags power-rated as a No. 4 seed, taking a hit from losing Braden Huff, which costs them about a point.
Let's root for my Wolfpack to bring us to glory once again.
How to Play: N.C. State moneyline to the Sweet 16.
