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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)

I normally like to have one 13-4 upset in my brackets, but I’m heavy on 12-5’s, so I can’t take any 13s. According to my calculations, the numbers point towards an off-year for 13 seeds. FSU to advance.

6. BYU vs 11._____

I am letting you know right now that I love BYU. They have two senior guards, Alex Barcello and Brandon Averette, who can both shoot and get their teammates involved, averaging a combined 8 assists. Team them up with Matt Haarms, a 7’3" senior big man from Purdue, and Trevin Knell, a 6'5" swingman who can get going from three, and you have a team with serious potential in March. They had a chance to hand Gonzaga their first loss of the season in the WCC conference championship, and I think they are coming into March confident. I am looking for them to make a deep run, and potentially be the only team who can knock off Gonzaga (they would meet in the Final Four). The play-in game hasn’t happened yet, but I like BYU to advance so much that I am taking BYU - whatever Vegas chooses as well.

3. Texas to advance vs 14. Abilene Christian

(3 seeds win 85% of the time)

7. UConn to advance vs. 10. Maryland

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

2. Alabama to advance vs. 15. Iona

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

I feel like I always see one corner go almost completely chalk in the first round. I have the 9 over the 8 but other than that I don’t see any upsets.


South Region

1.Baylor vs 16. Hartford

Baylor is very good. Boring pick but I have them in the final four out of this region. Baylor to advance.

8. UNC vs 9. Wisconsin

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

This pick has nothing to do with basketball. I tend to like picking two 9s and two 8s in the 8/9 matchups. The odds would support this strategy. I have already taken two 9s, and plan on possibly taking Georgia Tech, so I can’t have all 9s. It’s also UNC in March and they are starting to play well. Whoever wins this game has to play Baylor in the next round anyways. UNC to advance.

5. Villanova vs 12. Winthrop

(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)

This game has upset written all over it. I told you I love teams with a senior PG, and Winthrop happens to have Chandler Vaudrin, a 6’7” PG (what) averaging 12, 7 and 7. He can cause serious matchup problems for any defense in the nation, and if he gets some help, Winthrop could be dangerous. The D2 transfer controls the game well and finished the season sixth in the nation in total assists. I don’t love when teams rotate lineups as often as Winthrop does, but the 6’7” senior PG is too electric to pass up on. I also hate Villanova so I would love to see them lose. Winthrop to advance and Winthrop +6.5.

4. Purdue vs 13. North Texas

I explained in the East region that I was not feeling any 13-4 upsets this year. I thought about it with Ohio v. UVA but decided against it. Trevion Williams is coming off an incredible end to their game against OSU, which they eventually lost in OT after he carried them back in the second half. Averaging 15.6 and 9, he is a serious March breakout candidate that can carry a team. Purdue to advance

6. Texas Tech vs 11. Utah State

I haven’t watched Texas Tech play live as much as I wanted to this year, but I still like them. Mac McClung and Terrence Shannon Jr. have led them in some very competitive games against some of the top teams in the nation. I knew absolutely nothing about Utah State, so I clicked on ESPN’s take when I was filling out my bracket. They said not to overlook Utah State because they lack name recognition, and I almost fell into the trap. If I had researched them, I would have found a reason to like the upset no matter what, so I stayed away. Don’t overthink it. Don’t reach for upsets. Vegas putting the line at -210 was enough for me. Texas Tech to advance.

3. Arkansas vs 14. Colgate

This game was very tough for me. Colgate is led by Jordan Burns, a very good senior PG, and he is surrounded by shooters everywhere. This team has everything I normally ask for in a first round upset pick, but they are playing Arkansas, and I really like Arkansas. Any other draw and I probably take Colgate to advance. It goes against everything I stand for in March to take a team led by a freshman PG over a team led by a senior PG, but Moses Moody is that good for Arkansas. Arkansas to advance.

7. Florida vs 10. Virginia Tech

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

I had this one written for VT already and just got a bad feeling. Florida to advance.

2. Ohio State vs 15. Oral Roberts

I have seen some talk about Oral Roberts having serious 15-2 upset potential. I don’t like to see too many people predicting the same 15-2 upset. The hype around Max Abmas and his nation-leading 24.2 PPG may be well deserved, but a stat like that can make people forget that Ohio State is also very good at basketball. Ohio State blows them out. Ohio State to advance and Ohio State -16.5.


Midwest Region

1. Illinois vs 16. Drexel

Illinois to advance.

8. Loyola Chicago vs 9. Georgia Tech

This one was tough. I didn't really know anything about Loyola, and after looking at their schedule very quickly, I was ready to write them off. Then, I noticed that the team they beat in the MVC conference championship, Drake, also got into the tournament in a play in game. That’s a plus. After watching the highlights, I became a Loyola fan. I don’t normally like teams with a big man as their main weapon, but senior Cameron Krutwig looks like he can play and is surrounded by some solid guards. Finishing the season in the top ten in player efficiency rating, he certainly has the potential to carry a team. They are senior heavy, and like I said before, I like to take two 8s and two 9s. Winning the ACC is impressive, but I can’t help but think it was a little bit of a fluke for GT. They got to play Miami, a bye v UVA because of COVID, then pulled off the upset v FSU. Trust the first instinct. Two 8s and two 9s. Loyola to advance and Loyola -3.

5. Tennessee vs 12. Oregon State

This pick also has nothing to do with basketball. I like to make a parlay of a bunch of heavy favorites in the first round. After making one for this year, I had about 9 teams and had a + line for the parlay. Because of that I knew at least one of them had to miss.

I don’t know why but Tennessee is the pick that jumped out at me as the one to miss. Oregon State has some momentum coming off an unexpected Pac-12 title and I think they might pull off the upset. This does give me three 12-5 upsets, which seems like it probably won’t happen based on it already happening three times in the last seven years, but lets make it 4/8. Oregon State to advance, Oregon State +7.5 for my no way the parlay I made hits bet.

4. Oklahoma State vs 13. Liberty

I don’t know much about Liberty, other than the fact that they have some very good shooters, but I do love the Big 12 this year. Baylor is the clear favorite out of the conference, but any of the top 5 teams are capable of making a deep run. Unless Liberty can have a record setting day from three, I think Cade Cunningham has serious potential to lead this team to the Elite 8. Oklahoma State to advance and Oklahoma State -7.5.

6. San Diego State vs 11. Syracuse

I had Syracuse until I decided on the 6 seed sweep. I'm flipping to SDSU to advance and SDSU -3.

3. West Virginia vs 14. Morehead State

West Virginia is my pick to win the tournament at +4000. Look for Taz Sherman and Miles McBride to carry this team deep into the tournament. I believe they will have the easiest road to the final four and hopefully they can parlay that into a national championship. West Virginia to advance and West Virginia -12.5.

7. Clemson vs 10. Rutgers

No idea. Rutgers because I wrote Clemson at first and don't have any other 10s winning. Fade myself pick.

2. Houston vs 15. Cleveland State

I watched the Horizon league championship and the Vikings looked very good. With that being said, there is not much analysis needed here. If you pick a 15-2 upset correctly, it is mostly luck.

Cleveland State +20.5 and Cleveland State to advance


First Round Bets

If you are looking to turn a recent +$1400 from Joe into some serious money, you are in the right place.


Missouri +2

1 unit


1 unit

EWU +10.5

1 unit

Oregon -5.5

1 unit

St. Bonaventure +2

1 unit


1st Round Best Bet

BYU Spread

2 units


Winthrop +6.5

1 unit

Loyola -3

1 unit

Oklahoma State -7.5

1 unit


1 unit

Ohio State -16.5

1 unit

Oregon State +7.5

1 unit

Cleveland State +20.5

1 unit


USCB +260

0.75 units

Winthrop +220

0.5 units

Oregon State +280

0.4 units

EWU +450

0.3 units

Cleveland State +1175

0.3 units

Favorites Parlay

Oregon -240

UVA -370

Oklahoma State -350

Arkansas -420

West Virginia -900

Purdue -340

Texas -450

+403 odds

0.75 units

Don’t do it but now I have to in case it hits parlay

Winthrop +225

Cleveland State +20.5

USCB +270

St. Bonaventure +105

1.5 units

Light the money on fire instead 💸🔥 parlay

Drake (EVEN)

EWU (+450)

USCB (+255)

Winthrop (+215)


0.15 units



Top Seed

1 seeds have been to the championship game 34 times with an overall record of 22-14. Seven championship games have included two 1 seeds. Gonzaga is at +210 which seems ridiculous for NCAA tournament odds, can’t do it

Baylor (+600)

I have no interest in putting money on this line, but if I was taking a line for a 1 seed, this would be it.


West Virginia (+4000)

(3 seeds have reached the championship game 11 times, with a 4-7 record in the title game)

1.25 units

Arkansas (+3500)

0.7 units


BYU (+8000)

(Three 6 seeds have reached the Final Four)

0.75 units

Oregon (+8000)

(Three 7 seeds have reached the Final Four)

0.6 units


GOAT 🐐bet if it hits


BYU to win the East (+1400)

WVU to win the Midwest (+825)

Gonzaga to win the West (-200)

Baylor to win the South (+155)


0.2 units


WVU to win the Midwest (+825)

Gonzaga to win the West (-200)

Baylor to win the South (+155)


0.25 units


Ignore this bet🙅‍♂️

(No team seeded higher than 8 has ever reached the championship game. No team higher than an 11 seed has ever reached the Final Four)

USCB (+25000)

0.1 units

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