The Z Files: Strategy and Rankings for the Underdog Fantasy Playoff Contest

The fine folks at Underdog Fantasy are running an MLB postseason contest called The Pennant. It's a best ball format with six teams per league and very small rosters. The entry fee is a manageable $10, with a maximum of 150 teams. The carrot is a $10,000 first prize. The official rules are HERE.

The drafts are over in less than an hour. Waiting times are currently just minutes during normal waking hours. The contest closes on Tuesday October 2, in advance of the beginning of the Wild Card Round.

The Pennant consists of three rounds:

• Round 1: Wild Card Round and League Divisional Series
• Round 2: League Championship Series
• Round 3: World Series

Round 1 is composed of six-team leagues. The top team in each league advances to Round 2. There will be 312 teams lumped into the Round 3.

Each team drafts 12 players. The active lineup is as follows:

• 3 Pitchers
• 1 Infielder and 1 Outfielder
• 2 Flex (Infielders or Outfielders)
• 5 Bench

That's it, just seven players comprise an active lineup. Scoring is as follows:

Hitters

• Single: 3 points
• Double: 6 points
• Triple: 8 points
• Home Run: 10 points
• Walk: 3 points
• HBP: 3 points
• RBI: 2 points
• Run: 2 points
• Stolen base: 4 points

Pitchers

• Win: 5 points
• Quality Start 5 points
• Strikeout: 3 points
• Inning Pitched: 3 points
• Earned Run: -3 Points

It should be apparent the contest is designed with multiple entries in mind, each focusing on one or two teams, or perhaps three. With a maximum of 150 entries, there is ample opportunity to cover every permutation. This isn't meant to dissuade you from entering. if you land on the World Series entrants, your chances are the same as everyone else with the teams as the focus.

That said, keep in mind that Round 1 encompasses both the Wild Card Round and the Divisional Series. Loading up on players from teams with a bye limit what you can score in Round 1. Even if a wild-card team is eliminated in the Divisional Series, their players accumulated points for the entirety of Round 1.

Last season, a pair of wild-card teams made it all the way to the Fall Classic, so rosters focusing on the Rangers and/or Diamondbacks collected points in every playoff series. If you are committed to a World Series featuring the Yankees or Guardians facing the Phillies or Dodgers, you need to have ample players from a wild-card team contributing sufficient points to allow you to advance to Round 2.

This entails loading up on the club you favor to win the whole thing. You don't necessarily need your seven-man active lineup from this team. You can dedicate one or two spots to the team you expect to face the projected champion. This leaves five spots for players participating in a wild-card series. You don't need to stack from the same team. Instead, select the best players, since at most you'll have five players contributing to the seven-man active roster during the Wild Card Round. This isn't as daunting as it may seem, since the lower-seeded wild-card teams will be stacked the least, availing better options in the draft.

Ideally, choose wild-card players from the opposite league relative to your predicted World Series winner. This serves as a hedge in case the team you expect to lose the World Series doesn't make it.

Roster construction is more straightforward if you expect at least one wild-card club to play in the World Series, and even easier if they're your projected champion. Stack your favorite while filling in with quality players from other teams. The rules require selections from at least two MLB teams, so even if draft flow allowed, you can't draft the entire dozen from the same team.

While it doesn't always manifest in this nature, the entries with the superior trio of pitchers usually fare the best. This often entails drafting a solid starting pitcher from the team you expect to lose the championship since you'll likely be sniped from choosing one of the top three starters on your targeted team. On the other hand, you can usually load up on the lesser batter from your primary team and there are usually surprise performances from this type of player.

Unless you are committed to entering just one or two rosters, it's best to keep your strategy/roster construction fluid and let your draft position and draft flow dictate your approach. If your goal is stacking the Dodgers and you pick fourth, fifth or sixth, Shohei Ohtani will probably be off the board. If another team not drafting Ohtani also wants to focus on the Dodgers, they'll probably select Mookie Betts, so you're starting your stack with Freddie Freeman, which is fine, but not optimal.

By the way, the draft order is determined once six participants confirm an entry. Leagues are formed on a running basis. That is, after six teams enter, the draft begins. The next entries are placed in a queue and once there are six, that draft begins. There is a one-minute lag after the order is determined, and a 30-second timer per pick.

My approach is stacking at least two, and hopefully three of the best players from the targeted team. Ideally, I'll have ample players in the final round to achieve points from all seven active spots. Having bench spots from the involved teams is icing on the cake.

While I don't play anywhere near the maximum 150 entries, I have hit double-digits in past seasons. As such, I go the fluid route with strategy and targeted team(s). Since I am making the decision on the fly, I prepare a table with the top two hitters and one or two pitchers on every playoff team. My current version is the following.

I feel the best about the Astros and Phillies. Not so coincidentally, they each have two pitchers among the top four, facilitating drafting three top players. My Astros-focused team will probably include some Padres or perhaps Diamondbacks, though Arizona needs to make the playoffs first. My Phillies-laden roster will also be composed of Astros and possibly Tigers and Royals.

Deeming rankings useless is an overstatement, but compared to most drafts, they're significantly less useful. The reason is that picks are less a function of ranking and more related to strategy and optimizing roster construction. Even so, a set of rankings based on the Underdog Fantasy scoring will be posted.

As am example of how rankings aren't as applicable as usual, I have completed two drafts, mainly so I am not writing this piece completely blind. Shohei Ohtani, by far, is the highest ranked player on the board. However, mostly due to the piecemeal nature of their pitching, the Dodgers are not favored to win the World Series. The No. 1 pick in my two entries have been Bryce Harper and Zack Wheeler, each with the clear intent on stacking Phillies. I mention this not to recommend stacking Phillies, but to illustrate roster construction overshadows rankings. In my first draft, Harper, Aaron Judge and Mookie Betts were the first three picks. Being naive to the player pool and not having thought through 2024 strategies, I made the mistake of drafting Ohtani fourth. Well, I guess we'll see if it was a mistake, but I didn't stack Dodgers. 

Before sharing my rankings, be aware the Underdog Fantasy site enables you to download the default rankings so you can customize and reload to your preference. This makes finding players a bit easier, which is important with a short 30-second timer.

Without further ado, here are my rankings, ordered by projected points per week. Good luck, and if you are in a draft room with ToddZ, be a doll and let him stack who he wants. Thanks.