In this week's P.O. Box:
Playoff week bonanza
Content roundup: Plus some Wildcard DFS
Book Club: A selection for January…
What do they say? You can sleep when you’re dead.
That’s how I felt about taking a break from drafting. I certainly feel some burnout after a long season and am looking forward to some downtime in the coming weeks/months, but this pre-playoff week always gives me one final jolt of enthusiasm for drafting.
Here’s what I’ve been up to this week…
🏆 Underdog Playoff Best Ball
I think playoff best ball is the most fun fantasy format going. It’s the ultimate puzzle that requires balancing both raw points in the early rounds and reverse engineering how to construct a team that can score points in the final Super Bowl round.
For noobies, I put together a strategy guide for Fantasy Life and also hopped on a show with Underdog’s Hayden Winks to discuss basic strategy.
For sickos, I fired up a playoff edition of Best Ball Breakfast on Monday with Mike Leone and Pat Kerrane and an Off & On The Clock where we focused on how to 1) build stacks from the bye week teams (Denver and Seattle) and 2) navigate the sim-heavy meta.
Tally: I dug deep into my reserves to get 150 entries into The Gauntlet—Underdog’s flagship contest with a $500,000 top prize. I’m going to settle at around 170 drafts, including a couple Big Mittens ($500 entry) that I drafted with Neil Farley on the Bash.
👴 FFPC Playoff Contest
Since the dawn of Ship Chasing, we’ve obsessed over the FFPC Playoff Contest ($500,000 top prize) and dedicated an entire week of shows to it. On the surface, it’s a much more simple contest than an Underdog playoff draft (just pick one player from 12 of the playoff teams and fade two others), but there’s a deep, deep rabbit hole of strategy that we dive down each year…

For noobies, this piece on Legendary Upside gives a quick primer. We also explained the basic premise on the “Boomer Opto” show earlier this week where we try to figure out what will be the “chalk” aka the most popular lineup.
For sickos, there’s a 3-hour show dissecting Kerrane’s ownership projections (you can get access to these in the Ship Chasing Discord, btw) for the contest, a show discussing leverage angles with the Stat Chasing guys, and a final wrap-up show with Leone and Dink tonight.
Tally: We’ll have somewhere around 75 lineups in the $200 contest after a mad dash to finish lineups before lock.
👙 Guilloteenies
I love the playoff version of the Guillotine leagues. They are super simple (draft with either 4 or 7 friends depending on if you want to single or double chop) and feature a FAAB run after each week where the recently eliminated roster(s) are available to be bid on by the remaining teams.
For noobies, I put together a primer in Tuesday’s newsletter and there is a full strategy guide + rankings up on the site, as well.
For sickos, I shared my four favorite sleepers, three macro strategy tips, and a recent draft board.
Tally: Drafts with Newsletter subs, Fantasy Life co-workers, and college buddies.
You can create your own private league to do with friends or hop in a free or paid league in our contest lobby.
💦 Splash Survivor Contests
I didn’t even get a chance to enter the Swolecast playoff Survivor contest before it filled, but I did toss a handful entries in the Splash $1M contest ($150 entry).
It’s also a simple format where you pick two teams for the Wildcard Round, two for the Divsional, one for the Conference Championships,, and one for the Super Bowl. The rub, of course, is that the teams do not reset so you need to plan accordingly.
Top teams to select for Round 1: Packers, Rams, Eagles, and Patriots.
Speaking of Splash, my buddy Rick (aka RickRunGood) is hosting a massive One & Done contest ($1.25M guaranteed; $250/entry & $100k to first) for this golf season. You pick one golfer each week and (like Survivor) you can only use them once. The deadline is the first tee shot of the Sony Open on Thursday, January 15th so register now. I just dropped an entry in myself…

Rick also has a great newsletter if you want to get his tips for the contest:

💎GEMS: My favorite Wildcard sleepers on Underdog. This will be my final gems of the year. YouTube members can grab them here and Masterclass subs go here.
⏰ OFF & ON THE CLOCK: Top Plays & Best Scrolls for Wildcard Round. I don’t mind the Divisional Round slate, but I do consider this the last good/real/full slate of the year.
Here’s how we used our “Gimme” pick (add gimme last as Caleb), btw.
🤯 BULLY THE SIMS: Wildcard DFS Strategy: Top Plays & GPP Angles. Youdacao and ShipMyMoney share some contrarian angles for tournaments this weekend.
💪 THE SWOLECAST: Wildcard NFL DFS Picks. Dave just loves football more than us, I guess.
☣ LOLZ: Luckily I Can’t Log Into This “Portal to Hell.” Classic ep where we discuss discuss best ball collusion, touting, Dave Ramsey's viral clip about sports betting, and whether Karoline Leavitt is guilty of market manipulation.
🎉 BEST BALL BASH: A Guest From Brazil Drafts Their First Team. In addition to those Big Mitten drafts, we also met two very fun guests—a man from Brazil who takes us on a rollercoaster ride and a father/son duo from New York who love fantasy football.

No other shows this weekend other than tonight’s Ship Chasing finale. I’ll be back on Monday (or maybe Tuesday) for a Pourtfolio Review/recap, though.
Also, I’ll have a resolutions/2026 goals post either next week or the following week. I’m spending more time this year really thinking through what I want to tackle, so I’m not rushing it. I should have a show with Davis on it soon, as well.

Well, I guess it’s time to fire up another year of the PO Box Book Club.
To ease me back in, I’m circling back to the only Haruki Murakami book I haven’t read—his latest novel from 2024, The City and Its Uncertain Walls. If you aren’t a Murakami fan, feel free to sit it out, but as a completionist and someone who loves the majority of his work (start with The Wind-Up Bird Chronicle if you are new to him), I wanted to finally get around to this one.
"A man's lifelong search for a mysterious girl who vanished, leading him to a surreal, walled city where reality blurs, he works in a dream-reading library, and must confront the porous boundary between worlds and his own past.”
🧱 Book #1 for January (15%): The City and Its Uncertain Walls by Haruki Murakami.
Got a question for me? Reply to this e-mail and I’ll get back to you…




