James Holzhauer: How to win your Survivor, Confidence and Pick ’em contests

Circa Sports will pay out more than $12 million in prizes this season between its Survivor and Pick’em contests. James Holzhauer explains how pros try to gain an edge over the field.

Know the rules and follow them. Most contests score a postponed game as a loss. It's tempting to pick against a team that's playing shorthanded due to illness, but there's a risk that the game could be moved to a later date.

Adam Levin won a Jeopardy! contest with a score of 53,999, but he only received a $2,000 consolation prize. An NFL contest is effectively a tournament that only awards a significant prize to the winner. If you're afraid of playing an all-or-nothing strategy, you shouldn't have entered a jackpot contest in the first place.

When a baseball team is trailing in the division race in late September, they prefer head-to-head contests against their rival. When you're leading a picks contest, you want to play down the middle. In a behind-the-fold situation, play for unlikely outcomes to make up ground.

Confidence pools are popular with casual players. They are usually played by groups of friends or co-workers. The optimal strategy for a confidence pool depends on the prize structure and the size of the pool. If the weekly prizes are substantial, the best strategy is to pick strategic upsets at the top of your card and play the rest straight. If a medium-sized pool has a lot of entrants, you might need to add an extra underdog to the mix. I probably finish last in the standings more often than any other entrant in my pool, but I win the most weeks. i.e. if I finish in last place, I usually finish with more points than the other participants.

Pick’em contests are often derided as coin-flipping competitions. Winning a large contest requires you to hit on more than two-thirds of your picks. Even the best handicappers struggle to beat the point spread more that 54% of the time. If you average a 53% long-term win rate, you”ll hit at least two thirds of 90 selections in a season about one in 170. The odds of winning a pick‘em contest are close to one of 7600 to 1 in 7,600. The chances of a 47% winner are 45 times less likely. Since the contests use the same point spreads for every entrant, they lock the lines early in the week.

The size of the field is the most important factor in a survivor contest. Most players understand the concept of future value and choose the team with fewer easy matchups remaining on its schedule. Some people try to pick the underdog and avoid playing against the favorite. If you're one of last ten entrants and there's only one game on the board, the market suggests the favourite will win 70% of time. It's usually not worthwhile in large pools with diverse selections. However, on a slate with few good options, picking directly against a popular favorite can make mathematical sense. If it's Thanksgiving or Christmas in contests that count those as independent weeks, it might be worth trying it.