Pick'em League

May 29, 2025

Every year my friends rope me into participating in an NFL “Pick‘em league.” Weekly, during the regular season, you pick which team you think will be the winner of each game, and the person with the best overall win/loss record for the season takes the top prize. There are typically about 30 people in the league, who each pay $50 to join, and the winnings are paid out across the top five places, with 1st place getting the most, and 5th place making a little more than the entry fee.

My strategy is simple. Every week, for every game, I always pick the Vegas favored team, period. Not only do I never deviate from this strategy, I also set my selections to “auto pick favorite” so there are no annoying weekly to dos. The rationale for this strategy is equally simple. I am letting the collective bets of millions of people, through tens of millions of dollars of betting, inform me of the most likely winner.

With this strategy, I am unlikely to win in any given year—I haven’t, but I do consistently land in 3rd, 4th, or 5th place. In fact, over years of playing, I’ve only landed outside the money on a couple of occasions. The elusive and hefty annual top prize gets everyone’s focus, but folks ignore what really constitutes 1st place—who has earned the most money in total across all the seasons. The exceedingly boring and hands-off strategy has earned me the highest total aggregate payout to date. No one seems to care or pay much attention to this, and that suits me just fine.

You might recognize this for what it is, a passive index investment strategy. The market, through millions of trades (bets), is efficiently pricing securities (in this case the odds-on favorites) and I am simply free riding off the collective wisdom of market participants. While it is possible to beat the market, the odds of doing so consistently and over the long-term, are very low. Ironically, those that try to “outperform” the market make it statistically likely they won’t. To capitalize on this activity, just be Vegas, not one of the gamblers.

My screen name for the league is “Dumb Agent,” and no one has ever asked me why.

- John Bass