Last year, my dad asked me to join his work football pick ’em confidence league. Despite being in 4 fantasy leagues, I accepted. I did some Google searching for pick ’em strategies, but didn’t find much. For those of you not familiar with the Pick ‘Em format, you basically choose which team will win each game, and assign a “confidence” value to it from 1 to 16. If you guess right on the game where you assigned 16, you get 16 points. And so on down the line.
Here’s a screenshot, the league uses Yahoo’s Pick ‘Em site to track the picks:

I did some trial and error the first few weeks. But I just wasn’t sure how much risk to take. How many upsets do I pick? And should I go big on confidence points or go easy on it? I ended up coming up with a system that I used the rest of the year. I ended up winning 4 weeks last year, which basically made my money back, my dad’s money back, and a 2 week profit. Not sure if it’s the optimal method, but it did me pretty good.
There are two things you need to pick well – or well enough – to win. One is obviously picking the games right. But it doesn’t help to pick games right if everyone else is picking the same games right. So the second thing is you need to pick against the crowd enough to separate you from the pack. I call these my “contrarian” picks.
We’ll start with picking the games right. First point: there’s no way to pick games right. So you have to settle with picking them as best as you can. And sorry to burst your bubble, but no amount of research, intelligence, or gut feel will help you pick the winners better than anyone else. If you have some way to do that, you’d be betting in Vegas and not doing Pick ‘Em leagues. So I use the Vegas odds… the more a team is favored, the better chance they have of winning.
So the basically, I give 16 points to the team that’s favored the most, 15 to the next, and down the line. I’ll then deviate a little off this base condition based off of what everyone else is picking.
What games to deviate from? Well, the best ones to deviate from are ones where the team is favored, but for some reason everyone else is picking against them. In the Yahoo league I’m in, it shows what percentage of the general public is picking that team to win:

So I look for one where the favored team (top team) has a very low percentage. This week, the Philadelphia is favored over Baltimore, but only 16% of the people picked them. This is a no brainer “contrarian” pick. Once I’ve identified a contrarian pick, I go all in on it… i.e. I choose 16 confidence points on it. This is my best shot to pick up a lot of points on people; everyone’s picking against, I’m going to go 16 the opposite way. Plus I’m favored to win. Last year, most of the Denver Broncos games were like this… call it the “Tebow” effect. Denver was not favored, but people picked them to win anyway.
This week I went with Philly with 16, and then on down the line picking the favorite and assigning the confidence points according to the point spread.