Beating the Bracket: A Guide to Winning March Madness

Throwback article I wrote 4 years ago when I was a little blogger in college with no girlfriend and not a lot of money. Fast forward to today, I still have no girlfriend, my face has gotten fatter, and I spend money like I drink water. So this is a trip down memory lane, but the advice I give is not terrible, actually. I’ll update it a bit, but I’m still laughing at the fact that I always seem to pick a #2 seed to win it all and they lose in the first round. Maybe I’ll actually listen this time…


March Madness is upon us and I could not be more excited — an exciting, epic, drama-filled 3 weeks that will determine the NCAA Men’s Basketball champion. I feel like it is Christmas but Santa is Jay Bilas.

No matter who you are, whether you know anything about college basketball, whether you watch every game religiously, you have heard of “The Bracket.” The bracket is singly handily the hardest task to predict. The possibilities are endless. Will this be the year a #16 seed beats a #1? Who will be the sleeper team to reach the Sweet 16? Who are the Middle Tennessee State’s or Dunk City’s of the bunch? Who can put a team on his back like Cardiac Kemba a few years back? Will I need the doctor to check my blood pressure when this tournament is over? All of these questions will run through your mind when filling out your bracket.

Have no fear, DG is here.

I have some experience with brackets. I did win a pool for a couple hundred dollars (like 7 years ago lol), so I have had my share of success. Then again, I was the idiot to pick Missouri Michigan State to win the National Championship last year. Needless to say, #15 Norfolk State Middle Tennessee State had to ruin my day and my chances of winning $2500 (I am still bitter to this day).

Now there is no right or wrong way to fill out the brackets, but I am going to give you some tips and preferences that might aid you in choosing your selections.

Pick a Team that won their Conference: Contrary to popular belief, Conference Tournaments do matter. They serve as a preview to how teams will play in a bracket-style tournament. I can make the argument that it is actually harder to win your conference than it is to win the NCAA Tournament. In 2011, before winning the title, UConn was the first team ever to win the Big East Tournament after playing for all 5 days. That means Kemba Walker had to endure 40 minutes of hell, win the game, go to sleep, and do it again for 5 straight days. It was truly magical. Since 2000, 9 of the 13 10 of last 17 National Champions won their Conference Tournament. Trust the hot teams, they will not let you down.

Avoid an all #1 Seed Final Four: Yes, #1 Seeds are the safest bet. Yes, they will most likely get to the Sweet 16, unless they happen to run into Butler. But for all #1 Seeds to make the Final 4 is almost impossible. It has only happened once (2008), where Kansas beat Memphis in an overtime classic to win the title. Mix it up, add a #2 or #3 seed in there, but beware of #1. They are not always the answer.

Perfection will NEVER Happen: I don’t want to sound like Captain Obvious, but frankly, people forget this lesson. Let me say this loud and clear, YOU WILL NEVER HAVE A PERFECT BRACKET. Let me say that again, YOU WILL NEVER HAVE A PERFECT BRACKET. The odds of a perfect bracket are 9,223,372,036,854,775,808 to 1. You will lose games. Stay positive. If upsets happen, they will happen. Just remember that people in your pool probably had the same picks, so just ride the storm and you will be fine.

Blue is Beautiful: When it comes to choosing a champion, pick a team that has blue in it. The last 12 of the last 13 champions have had some shade of blue in their uniforms. Now some of you might argue that Florida is mostly orange, but their letters and away uniforms are blue. Sorry fans of Louisville (although they are the 1 lone champion without blue), Michigan State, Florida St, etc. It is better to be Kansas, UNC, Gonzaga, Nova, Duke, etc. If you choose blue, you will not feel “blue” when the Final Four rolls around.

Pick the #12 over #5 Upset: Since 1989, a #12 seed has beaten a #5 Seed every single year. It has become a rule, not just a weird coincidence. Something about the 5-12 matchup just screams upset. I have no idea what it is, but #12 seeds just come to play that day. Also, 11s and 13s have come into the mix as of late. I’m ALL IN on Rhode Island. Danny Hurley and the boys are going to beat Creighton. Bank on it.

Fill Out Multiple Brackets: Everyone wants to be the guy to have the winning bracket. If you find yourself in a nationwide pool, I would bet my life savings that the winner filled out multiple brackets. I get it — people want to be admirable and invest all of their wits into one bracket. My advice to you: put the most money (BET RESPONSIBLY) into your “best bracket” or the one you invested the most time in. Then, fill out some other brackets and enter different leagues to increase your chances. I am not saying you will win, but your chances dramatically rise in your favor.

Never Bet Against Tom Izzo: There is something about Tom Izzo and March that just makes sense. Izzo has won 46 (!!!!) tournament games, including the 2000 National Championship. His Michigan State teams have been to 7 Final Fours, and has only lost in the first round 4 times. The guy flat out knows how to coach in March. Bet against him and he will make you pay. They’re going to beat Miami and they are going to be a tough, tough out for Kansas.

Do Not Get Upset Happy: Everyone wants to be that guy to say, “Hey, I called that upset!” Yes, that is a great feeling. Picking a first round or even second round upset is more luck than skill, but a feat that can be accomplished. The problem occurs when you want to pick the Florida Gulf Coast’s or VCU’s of the tournament. What Butler did a few years ago is undeniably one of the greatest accomplishments in college basketball history. A mid major that reached the National Championship not once, but TWICE, in back to back years????? Unheard of and honestly, I don’t think it will ever happen again. Be the smart gambler. The #1, #2, and #3 seeds have won 90% of all tournament champions. Don’t be a hero, pick the favorite.

Good Coaching Matters: You always hear the phrase, “Pick them, they’ve been there before.” To a point, this is true. Coaches with previous Final Four experience usually end up in the Final Four. I’m going to rattle off the coaches of the last 10 teams to win it all.

Jay Wright, Mike Krzyzewski, Kevin Ollie (odd man out), Rick Pitino, John Calipari, Jim Calhoun, Mike Krzyzewski, Roy Williams, Bill Self

Besides Kevin Ollie, who’s still TBD since UCONN can’t even make the tourney right now, those are all Hall of Fame coaches. It’s rare for a new kid on the block to come and mark their territory. Brad Stevens is truly the only exception. Will Sean Miller or Mark Few join the club this year?

When push comes to shove, this tournament is all luck. You can develop math formulas and study countless hours of tape, but there is no statistical answer that can predict the outcome of the game. I will leave you with this story. In 2006, my dad decided to let my 5-year-old sister pick one of his brackets. I instantly laughed at this tactic, but my dad stayed true to his promise. That included picking #14 Northwestern State over #3 Iowa. To refresh your memory, watch this. Yes, 5 year olds can predict NCAA Tournament games.

Remember, have fun with your brackets. I hope you do not lose any sleep over these picks or pull out your hair if a #16 beats a #1 (which it won’t). Happy Bracketology everyone.

Good Luck. You’ll need it.