March Madness Guide to Win Your Bracket & Beat Your Bookie (1st Round)

Updated: Mar 19, 2021

Overall, I wouldn't say fading these picks is a terrible idea. However, it is the four-year anniversary of the greatest betting run I have ever hit (2017 March Madness). So, if you are fading, don’t let me get hot.

Disclaimer, I didn’t watch as much college basketball this year as I normally do. I take that as a good sign for my picks. Some of the logic on these picks will make no sense basketball wise, and that’s what makes them good picks. You can’t logically reason your way to a perfect bracket.


West Region

1. Gonzaga vs 16. Does It Even Matter

Gonzaga. (1 seeds are 139-1)

8. Oklahoma vs 9. Missouri

This was the second game I saw when making my bracket. Everything about it was screaming Oklahoma. I looked up the line and Oklahoma was -130. I smell a trap (The history of the 8/9 matchup is about 50/50 ). Can’t fool me this early Vegas. Missouri to advance and Missouri +2.

5. Creighton vs 12. UCSB

(5 seeds win 64.3% of the time, but 2019 was the third time in the past seven years that the 12 seeds won 3/4)

I’ll start this off by saying you always need to consider having a good 12-5 upset. As you will see, it is my favorite upset to pick. Creighton is a tempting choice coming off of getting blown out in the Big East championship, but I wouldn’t look too much into that game. The big thing here is after doing about 5 minutes of research on UCSB, I stumbled across my favorite thing in March: a senior PG. JaQuori McLaughlin is 6’4” and averaging 16 ppg, 3 r, and 5 assists, while shooting almost 50% from the field and 40% from three. He is a future NBA talent. I dug a little deeper and found out that the current Big West player of the year was named Washington Mr. Basketball in high school and started his career at Oregon State. He broke Oregon State’s freshman three-point record with 58. Unfortunately, he had some personal issues, took some time off, and ended up transferring to UCSB. Now, he’s back. Please watch his highlights. I love the story and I am all in on UCSB. We have seen what a dominant, NBA ready guard can do for a cinderella team in the past.

I would mostly recommend UCSB +7 in this game, but I am also taking UCSB to advance.

4. Virginia vs 13. Ohio

(At least one 13 seed has beaten a 4 seed in 25 of the last 35 years)

I really don’t like the way UVA plays basketball, but I have seen them at their worst and at their best. I’m going to be mature here and say I have severely underestimated how good they can be when Tony's system is working (I also would say I almost predicted the first-ever 16-1 upset but that’s not what we are talking about). Sam Hauser gives them a much-needed boost on offense, and I don’t love the news with COVID, but as long as they are able to go, I’m taking UVA to advance.

6. USC vs 11

(6 seeds have won at least once since 2013)

I’m not going to worry about who USC is playing because I have to take USC here. It has nothing to do with the actual game, but I just took a 12-5 upset and then briefly considered a 13-4 upset right after that. Following it up with an 11-6 upset would be irresponsible. Do not get upset crazy.

I will say that the stat shown above has me nervous as I review my picks. In the history of the NCAA tournament, 11 seeds have won 37.1% of the time. Trusting this 37.1% success rate of 11 seeds, there is a 15.65% chance of a 6 seed sweep. 11 seeds have played so well the past few years that I think they are due for an off-year. I'm going with the 6 seed sweep.

USC to advance.

3. Kansas vs 14. E Washington

(3 seeds historically win 85% of the time)

I filled out my bracket and noticed that I had every 3 and 4 seed advancing. After going back, I felt like one of them had to get upset, and I decided on Kansas. There is no logic or reasoning here, but as a reach, their Big 12 tournament got cut short due to COVID and I'm not sure if this Kansas team is as strong as it's been in the past. Just have a feeling. So much for not getting upset crazy. EWU to advance and EWU +10.5.

7. Oregon vs 10. VCU

(7 seeds are 99-65 in this game, or 60.4%)

VCU is always tempting in March, but I’m big on Oregon. They are a very experienced team and they shoot the ball well. Led by Chris Duarte and Eugene Omoruyi, they have a bunch of guys who can step up in any given game. Duarte is the perfect example of what an experienced lead guard can do for a team. If Gonzaga wasn't the 1 seed in their region, I would have strongly considered putting them in the final four. Also, they get my green jersey play. I always take the Seahawks when they wear their neon green jerseys, and I don’t think the bet has ever missed. Oregon to advance and Oregon -5.5. See the greens.

(Image via 247 Sports)

2. Iowa vs 15. Grand Canyon

(2 seeds are 132-8 with one loss in the past six years, but four losses since 2012)

A 15-2 upset is always tempting. Grand Canyon is coached by Bryce Drew, so they do have some tournament magic on their side, but I’m not buying it. Iowa to advance.


East Region

1. Michigan vs 16.______

I don’t absolutely hate going with a 16-1 upset because it just seems like it would fit this year. And, if I had to choose, I would pick this game as the most likely for it to happen. Star guard, Isaiah Livers, is out with a foot injury and Michigan saw those effects in their loss to Ohio State in the Big Ten tourney. However, it is too early to take a crazy shot and ruin the slight hope everyone has for a perfect bracket. Michigan to advance.

8. LSU vs 9. St. Bonaventure

(The history of the 8/9 matchup is about 50/50 )

This game is scary. I don’t know much about St. Bonaventure, but I did watch LSU almost win the SEC after a nice win over Arkansas (and I’m big on Arkansas). After the SEC tournament, I liked LSU's chances until I saw the line set at LSU -130. I do believe in the reverse psychology trap game, where the trap is making you think it’s a trap when it’s not actually a trap. But I’m not giving Vegas that much credit here. They want the money on LSU ML, and I won't do it. St. Bonaventure to advance and St. Bonaventure +2.

5. Colorado vs 12. Georgetown

Georgetown is a tempting pick for a nice 12-5 upset. They have some serious momentum coming off of the Big East tournament, and I have had a soft spot for the Big East champion ever since Kemba’s run (I have attached my favorite YouTube video of all time if you want to revisit that run). I don’t see it here, though. Colorado has played well this season and is led by a nice senior PG/F combo. Colorado to advance.

4. Florida State vs 13. UNC Greensboro

(At least one 13 seed has beaten a 4 seed in 25 of the last 35 years)