If your goal is to win:
- Rely on advanced models like KenPom , Sagarin , and Nate Silver’s rankings  to compare teams. Everyone has their pet heuristic (always pick an experience, defense wins championships, mid-majors are underrated, Duke will always win/choke–the list goes on), but the best data-driven methods consistently outperform everything else. Sometimes actual basketball knowledge like matchups or tendencies is useful, but I only use this information for games that the models tell me are toss-ups.
- Understand the ramifications of your scoring system. If you use a standard 1-2-4-8-16-32 scoring system, correctly picking the national champion gets you 63 out of a possible 192 points, and an entirely correct national championship is worth 94. Get these picks right and you’ve assured a finish near the top. Get them right with non-top seeds and you have a really good chance of winning most small to moderately sized pools. For example, I’m considering picking Florida (a 3 seed) over Louisville as my national championship. I’ll probably be the only person to pick Florida in my pool of around 15 people (except my dad, since he uses the same strategies I do), so if Florida wins, everything else I do is irrelevant.
- Know where you can separate yourself. Congratulations on getting your point for picking that 1-16 game correctly, but everyone else got it too so you haven’t actually made any progress. You’ll gain or lose ground based on your picks that go against conventional wisdom and toss up picks, so choose carefully. It’s tempting to pick the sexy mid-major double-digit seed to make a Sweet 16 run, but ask yourself if you can really defend that pick or if you’re just trying to show how smart you are (guilty right here). On the flip side, if you find a game where the selection committee has blatantly mis-seeded the teams (UCLA-Minnesota and Memphis-St. Mary’s this year), relish in the glory of the points you just gained with a probability greater than 0.5.
- Tailor your picks to the size of your pool. If you’re in a large competition, you need more picks that might separate you from everyone else and can justify picking upsets more aggressively. On the other hand, if you’re in a small pool, you can probably stick with your “maximum likelihood” bracket and still have plenty of places to build a lead. Determine your goal (winner, top 3, in the money, etc.) and the size of your pool, and adjust your picks accordingly.
If your goal is to have fun:
- UPSET CITY BAY-BEEE! Every year I pick a few wild upsets and obnoxiously talk them up to anyone who will listen. When they actually work out, I look like a genius and get to brag about it for years, and when they don’t, I just stay quiet. Last year I picked St. Louis to knock off Michigan St (lost by 4) and Belmont to take down Georgetown (not close). This year Davidson is upsetting Marquette and Pittsburgh is headed to the Final Four. Remember, you heard it here first from the Bracket Whisperer.
- Pick the teams you want to root for. Are you a proud graduate of Florida Gulf Coast University? Send them to the Sweet Sixteen! Your obnoxious ex went to Duke? First-round upset special! It’s fun to have some picks where you ignore all the analysis and go with the team you like better. My mom always picks North Carolina to make a run. Is it because of their run-and-gun offense or consistently high talent level? No, it’s because my sister is named Caroline and she likes picking a team that reminds her of her daughter. She also picks teams with bird mascots because of her birdwatching hobby. Of course, the risk in this strategy is if your team loses, you’ve lost both as a fan and in your bracket. But hey, that’s all part of the Madness!