Embrace the madness: 5 potential 1st-round upsets

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We attacked the tournament responsibly in our looks at each region, with a mix of short- and long-shot bets in the East, West, Midwest, and South.

It's now time to embrace the madness by targeting five potential first-round upsets to create our patented round-robin underdog moneyline parlay.

How it works

We parlay five underdogs on the moneyline in 10 different three-team parlays. Using every combination of a three-team parlay is called a round-robin. We'll use a total of 1.1 units to make 11 different bets: 10 three-team parlays and one five-team parlay, each .1 unit. You'll likely double your money if three teams pull off the upset. If four or all five teams win, you'll be diving into a silo of gold doubloons like a young Scrooge McDuck.

Who to play

Every few years, a monster upset in the first round will complicate your bracket. While you can pick any school to make a Cinderella run, we're looking for first-round victims that aren't the best version of themselves, have a glaring weakness, and likely won't ruin your bracket's Final Four.

(14) Morehead State (+550) over (3) Illinois

Morehead State opened at +13.5, but the line has dropped to our fair projection of 11.5. The top 25 teams in KenPom's adjusted efficiency ratings made the tournament. However, Illinois was one of three teams in that group to have a defense rated below 65. If Morehead can get a lead, its slow pace of play and good rebounding can give the Illini that familiar feeling of dread.

(15) South Dakota State (+900) over (2) Iowa State

Iowa State's defense is excellent, but any team can have a bad day. The Cyclones' offense goes into lulls, with ShotQuality having their "Rim and 3" rate in the 300s. If the scoring bar is lowered, a team that is this season's high-seed surprise relative to preseason expectations is worth testing at almost 10-1.

(13) Samford (+230) over (4) Kansas

We noted how the Kansas vibes are low coming into this tournament in the Midwest preview. While it's possible the Jayhawks are saving their best for the Big Dance, if they show the same lackluster play that they did in their 20-point defeat to Cincinnati in the Big 12 Tournament, Samford will happily take advantage.

(13) Charleston (+360) over (4) Alabama

Like Illinois, Alabama is one of three bad defensive teams among KenPom's top 25. And like Morehead State, Charleston has taken money since Sunday night, shortening the line a couple of points from when it opened. This isn't an ideal matchup for the Cougars, but Charleston hasn't lost since the start of February and dominated the regular season and CAA tournament.

(12) Grand Canyon vs. (5) Saint Mary's

We hope to close at least three legs of this bet with another team that won its conference's regular season and tournament. Grand Canyon is the best 12-seed and, according to KenPom, better than three of the 11-seeds. Ideally, it'd be up against a team that's easier to handle than Saint Mary's, but the Lopes' trio of Tyon Grant-Foster, Gabe McGlothan, and Ray Harrison is just as formidable as the Gaels' difference-makers.

How the odds look for Round 1

Matt Russell is the lead betting analyst for theScore. If there's a bad beat to be had, Matt will find it. Find him on social media @mrussauthentic.