NCAA Tournament Moneyline Rollover Strategy: Dr. Giffen’s Guide to Betting 2023 March Madness

Over the years I’ve developed a low-risk, high-reward approach to betting March Madness.

The general idea is to identify teams seeded fifth through 16th that have a good shot of making it far in the tournament. We'll bet these teams on the moneyline each game (with a few exceptions, as well 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:

1. two of our chosen teams face each other
2. the team makes the Elite Eight*

*there will be two exceptions to this rule this year, which I'll talk about in those picks.

Using this approach, we can identify eight teams and invest a small amount on each. For this example, let's use one-quarter of a unit, or $25.

Using this $25 quarter-unit bet on eight teams, the $200 initial investment will pay off as long as at least one of our eight identified teams makes the Elite Eight. If none do, we limit our losses to $200.

However, the upside is pretty big.

First, we get to sweat eight teams and root for them, giving us plenty of interest throughout the first (and hopefully second) weekend. Even better, most of them are underdog teams. Cinderella stories, if you will. And who doesn't love a good Cinderella run?

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Second, this strategy has the chance to produce some big returns.

In 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.

In 2018, that team was another 11-seed in Loyola Chicago. It returned about half of what Xavier did. Per my system, I cashed the Ramblers out in the Elite Eight, but Loyola continued the Cinderella story onto the Final Four.

In 2019, 5-seed Auburn was one of my teams. The Tigers also reached the Final Four. In a bit of an exception, I bet them to cover the spread in the first game, which they did, then rolled them up on the moneyline thereafter. That earned me 10 times my initial investment on them before cashing out in the Elite Eight.

There was no tournament in 2020 due to the COVID-19 pandemic, and I skipped 2021 because I felt the roster turnover made evaluations tough with players missing plenty of time throughout the year because of COVID.

And unfortunately, last year, my eight teams combined for a paltry one win. That only win came in the play-in round.

But that's the fun part about this system. When we do lose, we limit our losses. And when it hits, it has the chance for some very nice returns.

So, how do we go about applying this system? Let's dive in.

For an audio version of this piece, listen to The Giffen Guide to March Madness Podcast, presented by FanDuel.

Identifying Teams to Bet

As mentioned, we want to find eight middle- or lower-seeded teams that have a shot to make the Elite Eight.

Ideally, we’d like one team from each eighth of the bracket, but in practice, it doesn’t work out that way because some eighths have teams we want to avoid or have no identifiable values.

As a result, there will be eighths of the bracket where we need to double up. That's why I've added the first rule above. If two of our teams meet in the Sweet 16, we'll cash out our winnings.

My process of identifying value includes blending together predictive team rankings from multiple ranking sources. I hand-pick the ones that have been the most predictive over a multi-year sample and weigh them accordingly to get a baseline power rating for each team. I then adjust for injuries or other roster changes.

From there, I take it on a more granular level, identifying matchup-level or variance-increasing spots that help the underdog. Slower-paced games, 3-point shooting matchups and free-throw shooting matchups are some of the situations that can help an underdog.

Bolting all this together, it’s time to dive into my eight picks to target to make the Elite Eight in this year’s NCAA Tournament.

NCAA Tournament Elite Eight Picks

South Region

I'm avoiding Alabama's eighth of the bracket because the Crimson Tide are second in my power ratings and because they push tempo, which helps them realize their advantage more often. I also think it's tough to choose between Maryland and West Virginia in that 8/9 game.

While there are good 12- and 13-seeds with solid matchups in that eighth of the bracket, I have a hard time seeing either topple Alabama should they make the Sweet 16.

So, onto our first pick, which comes from the bottom half of the South Region.

1. Creighton Bluejays (6-Seed)

My power ratings say the Bluejays should be a borderline 3- or 4-seed if we rank the 68 teams from 1 to 68. However, they've been placed as a 6-seed and will face NC State in the first round.

The Wolfpack's best win came at home against Duke. However, they have no notable road or neutral-site wins and just don't measure up to Creighton's level. Additionally, NC State plays a bit uptempo, which should help Creighton's efficiency advantage be realized more often.

Should Creighton advance to the second round, it'd likely face 3-seed Baylor. The Bears are a talented but inconsistent team. It's likely Baylor would be favored by oddsmakers, but I have this as a true coin-flip and would love to get plus-money on the moneyline here.

In the Sweet 16, Creighton faces an Arizona team that should be a high 3-seed rather than a 2-seed by my power ratings. The market will once again give us plus-money on the Bluejays, while I have this as a very close game by my power ratings.

How to Play: I'm betting Creighton to cover the spread against NC State, and rolling them up on the moneyline until the Elite Eight after that.

2. Utah State Aggies (10-Seed)

I'm doubling up on this eighth of the bracket because the market appears too low on Utah State, per my own and Sean Koerner's projections.

I make the Aggies a 3-point favorite against Missouri, but we can get them as 1.5-point favorites. That translates to the moneyline as well.

Should they win, they will likely get Arizona, but Utah State has a good shot there. Arizona is not a great free-throw shooting team and is not good at defending the 3, which is the Aggies' strength. There's some added variance here to help the underdog team.

In the Sweet 16, ideally both Crieghton and Utah State face off, so we can cash them both out.

But if not, Baylor has been particularly lucky with its win/loss record this year. The Bears enter as the 96th-luckiest team by KenPom despite having 10 losses. There's enough inconsistency that the Aggies have a shot to make the Elite Eight.

How to Play: I'm betting the Aggies on the moneyline every game to the Elite Eight.

Midwest Region

3. Drake Bulldogs (12-Seed)

The Bulldogs come into the tourney as the strongest 12-seed, per my power ratings, and immediately face off against the weakest 5-seed in Miami. We all know the classic 5-12 upset happens with great frequency. This is the best chance for it to happen this year.

Should Drake advance to the second round, Indiana is a weak 4-seed. My power ratings make the Hoosiers more of a borderline 6- or 7-seed. It's also possible Drake faces Kent State, which would enhance its chances of making it to the Sweet 16.

From there, things get complicated, and this is one of the two asterisk marks I gave in my intro above.

If the following exact scenario happens, we can cash out the Bulldogs in the Sweet 16:

1. They beat Miami in the first round
2. They beat Indiana (not Kent State) in the second round
3. They face Houston (not any other team) in the Sweet 16

We can then cash out knowing we made a nice profit off of Drake before it faces a dangerous Houston team it doesn't match up well against.

Any other scenario means I'll bet Drake on the moneyline to the Elite Eight.

4. Mississippi State Bulldogs (11-Seed)

Apparently the Midwest Region is where I pick all of the Bulldogs. But I really like Mississippi State in this eighth of the bracket.

This is also the second asterisk mark scenario.

Since the Bulldogs are in the play-in game, we just need them to advance to the Sweet 16 to achieve our goal rather than the Elite Eight.

They start off facing Pitt, which I have as the worst 11-seed. On the flip side, Mississippi State is the second-best 11-seed, per my power ratings.

What I really like is the next two matchups. The Bulldogs would face an Iowa State team in the second round, and that game may have one of the lowest totals of any NCAA Tournament game under the current shot-clock format.

Iowa State is also overseeded, per my power ratings, and should be more like an 8-seed.

If Mississippi State advances to the second round, it would most likely square off against Xavier. Again, we have an overseeded 3-seed in the Musketeers. I have Xavier more like a borderline 4- or 5-seed. Beating Xavier would achieve our goal.

I'll bet Mississippi State on the moneyline to the Sweet 16. I may even re-evaluate if I want to take it further depending on its opponent there.

West Region

This is an absolutely brutal region. I'm going to avoid the bottom half of the bracket because UCLA and Gonzaga are incredibly strong 2- and 3-seeds, respectively. I also have many of the higher-seeded teams in this section of the bracket underseeded.

The top half of the bracket is also brutal, but I do have one pick that I think can go far.

5. Arkansas Razorbacks (8-Seed)

I'll start off by saying, I think 4-seed Connecticut and 9-seed Illinois were also contenders as picks from this region. But I like the plus-money odds we'll get on the Razorbacks should they face Kansas and UConn in winnable games.

We'd get the same plus odds on the Illini, but I fancy the Razorbacks' chances of making a deep run more, as I see them having more upside.

Instead of an 8-seed, my power ratings make Arkansas a borderline 4- or 5-seed.

Meanwhile, Kansas should be a 2-seed based off its power rating.

And while I think a matchup against the Huskies would be quite difficult for the Razorbacks as both teams are quite underseeded, the Huskies do play a bit slower than the national average.

I'll bet Arkansas on the moneyline to the Elite Eight.

East Region

6. Florida Atlantic Owls (9-Seed)

I'll start by saying I have zero issue if you want to take Memphis here because the Tigers are a strong 8-seed who should be more like a 7-seed and are coming off a win over Houston in the AAC Championship.

They could just as easily make a run as Florida Atlantic.

I'm simply backing the Owls because I have their game against Memphis closer than oddsmakers have it. My power ratings make this a 1-point game instead of the 2.5 points that the books have.

From there, the winner would get Purdue, which is the weakest 1-seed and plays at a slow pace. Certainly a winnable game.

Then, they'd face either Tennesse or Duke if things go according to plan.

The Volunteers have lost two of their last three and are without Zakai Zeigler, who had played the most minutes on the team prior to his injury. Duke would be a small favorite over FAU by my power ratings but would likely be a bit bigger favorite thanks to the national love they receive.

I'll bet FAU on the moneyline to the Elite Eight.

7. Providence Friars (11-Seed)

Like FAU vs. Memphis, I can totally understand if you want to roll with Kentucky here. I almost did just that.

However, I do have this game a bit closer than oddsmakers have it, so I'll have to back the Friars here as a result. I make this a 2.5- or 3-point game for Providence instead of the 4.5-point line that's currently out there.

Should Providence advance, it'll likely play a severely overseeded Kansas State team. In fact, I have Kentucky rated higher than the Wildcats.

That leads us to the Sweet 16, where Providence would square off against the weakest 2-seed in Marquette should things go according to the seed plan. More on that in my next pick.

I'll bet Providence on the moneyline to the Elite Eight but cash out in the Sweet 16 if the Friars face USC.

8. USC Trojans (10-Seed)

USC and Michigan State are just a couple of spots apart in my power rankings, making them nearly a coin-flip at a neutral site.

However, Columbus isn't perfectly neutral, as the Spartans will have a regional advantage. But it's still not a home game for them. That means the two points they're laying against USC is maybe half-point too much. FanDuel even has this at 2.5 points.

From there, the winner meets the most overseeded 2-seed in the region. Marquette grades out more like a borderline 3- or 4- seed in my power ratings.

Hopefully, USC and Providence meet in the Sweet 16, and I can cash out both bets. If not, Kansas State is a vulnerable 3-seed, and Kentucky has both big upside and also big downside. There's a path here for the Trojans to make the Elite Eight.

I'll bet USC on the moneyline to the Elite Eight but cash out in the Sweet 16 if it faces Providence.

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