Why Are There Different Picks For Winning Season vs. Weekly Prizes?

We offer two sets of picks: "Win the Season" and "Win the Week." We also explain why those options may be vastly different.

If you created a custom pool that has prizes for both season-long performance (the top cumulative scores at the end of the year win a prize) and weekly performance (the top scores in an individual week win a prize), then you’ll see two types of pick recommendations in our custom picks tool — “Win The Season” picks and “Win The Week” picks.

We’ll also suggest on that screen that you use one type of picks over the other.

Why Are There Different Types Of Picks?

The two types of picks are created specifically to aim for two different goals — winning a season-long prize, or winning a weekly prize. The reason we have two different pick suggestions is that the strategy for each goal can differ greatly.

Repeat: The pick strategy that maximizes your odds to get the best score of the week can be much different than the picks you’d make if your goal is to get the highest overall score at the end of the season.

We hear this a lot: “But if my goal is to win the season, shouldn’t I obviously be trying my best to win every week?”

And the answer, in most cases, is no.

Season prize goal. If you want to win a season prize, then your goal, relative to your opponents, is to get a good score for the week while also limiting your risk of getting a terrible score, since a bad score stays with you for the whole season. If you finish in the top 5% of scores every single week, but never actually come in first place, you will almost certainly win a season prize in most pools, if you don’t win it outright.
Weekly prize goal. If you want to win a weekly prize, on the other hand, then your goal is to maximize your odds to get the absolute highest score of the week. Nothing else matters, since in many weekly prize pools, second place for the week and last place for the week both get zero. If you finish in the top 5% of scores every single week, but never actually come in first place, you win nothing. And if you get a horrible score, it’s no big deal, since the slate is wiped clean each week.

We dug into the topic of weekly versus season-long picks in more detail in our Strategy section, which you can read here.

Implications For Picks

So when it comes to our recommended picks, the most basic difference is that Win The Week pick suggestions usually take a higher-risk/higher-reward approach, compared to Win The Season suggestions.

Win The Week picks focus more on picking teams that the public undervalues, so that in cases where the public is wrong, you can leapfrog most of your opponents, and finish at the top of the weekly standings.

Win The Season picks focus more on making steady, conservative picks that maximize your expected average number of correct picks, at least early in the season.

Why Are You Suggesting I Use One Type Rather Than The Other?

If your pool has both season and weekly prizes, we try to estimate the expected monetary value of aiming for one prize or the other, given your standings info, pool rules, and prize payouts. Then we recommend you use the pick suggestions that hav the highest expected value.

To estimate the value of aiming for a season-long prize:

Based your pool rules, current standings, number of weeks left in the season, and your average number of picks per week (and assuming that everyone in the pool is equally skilled) we estimate your expected probability of finishing the season ranked 1st, 2nd, 3rd, etc.
Then we multiply those probabilities by the season payouts you entered when setting up your pool, in order to determine your expected average season prize winnings.

To estimate the value of aiming for a weekly prize:

We assume everyone in the pool has an equal chance of finishing 1st, 2nd, 3rd, etc in a given week.
Then we multiply those probabilities by the weekly payouts you entered when setting up your pool to determine your expected average weekly prize winnings.
Finally, we multiply your expected weekly winnings by the number of weeks left, to determine your total expected weekly winnings.

Of course, it’s not quite that simple. Since you can switch your strategy from week to week, what we really care about isn’t the season-long expected value for each prize type, but how the expected value for both prize types is projected to change this week, depending on which type of picks you use.

We assume you have some chance of lucking into a weekly prize if you use season picks. And we assume that if you win a weekly prize, your place in the standings will improve, making your season prize expected value a bit higher.

We take all of the above into account, and suggest you use the picks for whichever goal we think will most improve your combined season+weekly prize expected value (including, of course, any weekly prizes you might win this week).

Note that this means that during the course of the season, we might switch from recommending you use Win The Season picks to recommending you use Win The Week picks, or vice versa.

That’s because every week, the expected value of aiming for season prizes can go up or down, depending on what your standings look like. Plus, the amount of damage from a bad weekly prize outcome (or the benefit of a good weekly prize outcome) changes based on your standings, as well.

If you fall far behind, we might switch from recommending Win The Season picks to recommending Win The Week picks. If you shoot to the top of the standings — or even if you’re just doing a little better than average — we might switch from recommending Win The Week picks to recommending Win The Season picks.

Conclusion

At the end of the day, the key takeaways here are:

Win The Season and Win The Week strategies can be very different. Win The Week picks are typically more risky, and will score poorly more often. But they will also get the #1 score of the week more often.
If you play Win The Week picks in a pool with both season and weekly prizes, you will be lowering your chances to win a season prize in order to increase your chances to win a weekly prize.
We are running basic calculations every week to let you know if and when that tradeoff is worth it for you or not, according to what you’ve told us about your pool’s prize structure. Based on how things are going, that recommendation may change once or even several times over the course of the season.

By the way, a nice strategy for pools with both types of prizes can be to play two entries in the pool. Each week, use Win The Season picks for whichever entry happens to have the higher score so far on the season, and use Win The Week for the other entry.