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I've Got Five On It: Five first-round upset picks

The NCAA Tournament bracket has been released and the speculation will run rampant until things get under way later this week. Today in I've Got Five On It, Rivals.com national analyst Rob Cassidy looks at five potential upset picks ranked in order by the amount of courage -- misplaced or otherwise -- it would take to pick them in your bracket.

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More: Potential candidates for Indiana opening

2021 Rankings: Rivals150 | Team | Position

2022 Rankings: Rivals150 | Team | Position

2023 Rankings: Top 30

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No. 12 Winthrop over No. 5 Villanova  

Charles Falden
Charles Falden (USA Today Sports Images)

How brave do you have to be to pick it? Not at all.

It will likely be the most commonly picked upset in the bracket for good reason. Villanova doesn't look like nearly the same team without injured star Collin Gillespie. The Wildcats seemed lost at times in recent losses to Georgetown and Providence and now encounter a team with an under-heralded star in box score-stuffer Chase Vaudrin, who does it all for the Eagles.

A combination of an injured team being over-seeded and a low-major having the talent and coaching to stand toe to toe with an opponent low on confidence makes this a rightfully trendy upset pick. The spread on this is hovering around Winthrop +5.5 and, boy, is that number tempting. Whether or not the Eagles pull it off, picking this upset requires the same courage level of swatting a fly.

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No. 14 Eastern Washington over No. 3 Kansas 

Kim Aiken, Jr.
Kim Aiken, Jr. (USA Today Sports Images)

How brave do you have to be to pick it? A touch.

Eastern Washington has won 13 of its last 14 and is certainly hot at the right time. Kansas, on the other hand, is coming off a week that saw it have to pull out of the Big 12 tournament because of COVID-19 protocols. If there’s anything to a program being “in rhythm” at this time of year, it can be said about the Eagles and not the Jayhawks. Forward Tanner Groves leads Eastern Washington’s offensive attack and shoots 55 percent from the floor, which could be a problem for a team that hasn’t always been great on the interior.

Bill Self’s bunch played their opening game in the Big 12 Tournament with David McCormack and Tristan Enaruna, both of whom tested positive for the virus prior to the event and could be missing more players this week because of contact tracing. McCormack and Enaruna are expected to join Kansas in Indianapolis later this week depending on testing, but KU is certainly operating through some level of uncertainty. The Jayhawks are 11-point favorites for a reason, however, so picking the upset would take some courage despite the chaos that surrounds Self’s team.

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No. 14 Colgate over No. 3 Arkansas 

Jordan Burns
Jordan Burns (USA Today Sports Images)

How brave do you have to be to pick it? Moderately crazy.

The potential pace of this contest makes it intriguing, so, if nothing else, the game will likely provide the public with a fun game to watch. Colgate averages 16 seconds per possession, while Arkansas plays even faster than that at 15.9. This is certainly going to be a track meet. An upset scare seems like a longshot, but not impossible by any stretch.

Arkansas is a -480 moneyline favorite for a reason, but much stranger things have happened in March. The Raiders average 84.6 points per game (second highest total in the country) and shoot better than 40 percent from 3-point range. If Colgate comes out hot from deep on Friday, there could be some white knuckles in Fayetteville.

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No. 15 Oral Roberts over No. 2 Ohio State

Max Abmas
Max Abmas (USA Today Sports Images)

How brave do you have to be to pick it? Six beers and three shots deep.

On one hand, Ohio State is a 16.5-point favorite and has enough depth to run the Eagles out of the gym in the first half. On the other hand, Oral Roberts boasts two players capable of scoring at massive clips in sophomore guard Max Abmas and junior forward Kevin Obanor.

Abrams averages an eye-popping 24.3 points per game, while Obanor averages 18.2 points and 9.2 rebounds. Things could get really dicey for the Buckeyes if the Eagles, which average an incredible 29 3-point attempts per game, get hot when chucking from the outside. Picking this upset would take some serious guts, but talking yourself into it isn’t nearly as difficult as the spread suggests it should be.

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No. 15 Iona over No. 2 Alabama 

Rick Pitino
Rick Pitino (USA Today Sports Images)

How brave do you have to be to pick it? Totally bonkers.

Alabama is a massive favorite (-16.5), and a No. 15 seed has only knocked off a No. 2 eight times in the history of the NCAA Tournament. The SEC champs are certainly a more complete, talented and battle-tested team and should cruise to victory over the Gaels.

Unless ...

Iona, which has not lost a game since Feb. 17, is led by one of the greatest living basketball coaches and the sample size on the Gaels is pretty small. The fact that Rick Pitinio’s team has played just 17 games this season and none against NCAA Tournament teams, making the Gaels a tough team to feel comfortable scouting.

The Gaels have serious problems with turning the ball over and will need to change that to have any chance to shock the world. An upset here would be a truly insane occurrence, but this season has been built on a foundation of chaos, so what’s another notch on the bedpost?

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