We’re taking a quick detour from the Hidden Gems this week to discuss Underdog Fantasy’s Pick ‘Em game.

There’s a ton of chaos and uncertainty in the drafting streets thanks to Week 18 shenanigans, so I thought it would be fun to talk through strategy for building out a Pick ‘Em entry for a single game on Underdog. 

Pick'Em 101

If you’re not familiar with the format, Underdog’s Pick ‘Em contests allow you to string together anywhere from 2 to 5 fantasy picks where you take higher or lower on a player’s performance in a given category and the payout increases with the more picks you include:

  • Two-play entry (pick two) = 3-1 payout
  • Three-play entry (pick three) = 6-1 payout
  • Four-play entry (pick four) = 10-1 payout
  • Five-play entry (pick five) = 20-1 payout
Pick'Em payout structure

On Fantasy Life, we have an entire page dedicated to free Pick’Em plays on Underdog that is spearheaded by the very sharp Geoff Ulrich and regularly updated with new plays for each slate.

You can mix-and-match entries from different games (and different sports, even), but for the purposes of this piece I want to focus on building out picks in a single game.

I find this enjoyable for multiple reasons:

  1. It’s fun to have a sweat that is confined to a single game (no waiting all day to see if the fifth part of your entry hits)
  2. There are some fun correlation angles you can consider (more on that in a sec)

As a reminder, you can play Pick'em on Underdog Fantasy, where you can get a 100% deposit match of up to $100 when you sign up below with promo code LIFE!

Finding a core entry to build around

At the very least, your Pick ‘Em entry must have two entries from two different teams (i.e. you can’t submit an entry with just a Josh Allen and Stefon Diggs play).

I want my two “core” picks to be the plays I have the strongest conviction on because I’m normally going to be building off these core picks for a few different entries.

For this entry, let’s focus on the marquee SNF matchup between the Bills and the Dolphins. Not only does this game have a juicy 50-point total, but the winner will clinch the AFC East title and the two seed.

Ulrich has already flagged the Diggs receiving yards (60.5) over as one of his favorite picks, so let’s use that as a jumping-off point:

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For the second part of this core, we will need to use a Dolphin. I can’t imagine starting anywhere else than with Tyreek Hill, who has been the focal point of the team's offense all year. 

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He’s cleared this number in 9 games this year and is averaging 114.5 yards per game. He also is still chasing his stated goal of 2,000 receiving yards (would need 283), as well Calvin Johnson’s single-season record of 1,964 receiving yards. 

While Diggs has struggled of late and this is a big number for Hill, we are playing for a shootout game in this scenario where both offenses are expected to throw a bunch. 

Telling a story for a 5-pick entry

Now, we could stop there, submit your entry with two picks for a cool 3x, and move on. But that doesn’t sound as fun to me as building a 5-pick entry around these two selections.

The logical extension of those picks is to include their QBs. When Hill and Diggs are going higher on receiving yards, correlation tells us that their QBs will also likely be throwing for a lot of yards in those scenarios.

However, we get a multiplier dock when we do this (7x instead of 10x), which encourages me to seek out other selections with the QBs that will maintain a 10x for picks.

 For these specific QBs, I like leaning into their strengths as far as fantasy categories:

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Passing TDs are obviously not directly correlated to receiving yards, but it makes logical sense that if the Hill is racking up yards, that there will be opportunities for Tua passing TDs. He had 2 last week in a blowout loss to the Ravens, and will likely need to chuck it in this spot as well.

With Allen, I’d much prefer to play him via a rushing TD. He has an eye-popping 15 rushing TDs on the year, including eight over the past five weeks. He hasn’t scored a rushing TD in only four games this year, which makes this a strong selection. 

Spicing it up

We now have 4 picks in our entry for 10x, but adding a 5th pick will double our payout from 10x to 20x. The math indicates that 5-pick entries are a far more profitable entry size than 4-pick versions, so we should definitely find one more entry.

There are a few different correlated ways we could go with this…

We could find another Dolphins pass catcher’s yardage number to pair with Tua.

We could use a kicker (Tyler Bass’ kick points number is set at 7) and play for a scenario where a high scoring game leads to a large amount of FGs and XPs. 

But a really fun way to punctuate a 5-leg entry is to utilize one of the “scorcher” multipliers which can increase your payout with an additional multiplier. 

For example, if we put a Gabe Davis TD into our entry, it multiples our entire entry by 2x.

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So instead of a 20x payout, we’d get 40x on our entry.

Of course, the reason the scorcher offers an additional multiplier is because it is much harder to hit. But they present fun ways to maximize your return when your macro thesis for the entry is correct (i.e. a ton of points are scored in a shootout).

Deconstructing it all 

My preferred way to build out my Pick ‘Em portfolio for a specific game is to lock in a few different entries that all share the same core.

Here’s an example of how I would allocate $50 in entries:

  • 2-pick (Diggs/Hill) $30 to $90
  • 3-pick (Diggs/Hill/Tua) $10 to win $60
  • 5-pick (Diggs/Hill/Tua/Allen/Bass) $5 to win $100
  • 5-pick w/ spice (Diggs/Hill/Tua/Allen/Davis) $5 to win $200

By “laddering” these selections, you give yourself a chance to be profitable even if your core 2-picks are the only entry that hit. 

Disclaimer: while I think the picks assembled here are fun in tandem, the takeaway from this piece should be less about the specific picks and moreso how to logically construct a portfolio of Pick ‘Em entries for a single game in a correlated fashion.

I also highly recommend always checking out Geoff’s picks to see which plays he has the most confidence in.