In this week's P.O. Box:
March Madness
Bracket Battle link roundup
Content recap
Book Club: It’s picking up
Before fantasy football consumed all of my attention, March Madness was my jam.
I got college basketball pilled in the early 90s because of that Christian Laettner and Grant Hill Duke team (yes, I was one of those bandwagon fans). We named our dog Duke (RIP). I threw a remote across the living room in 2002 when the Blue Devils lost to Indiana in the Sweet 16 after Jay Williams failed to convert a 4-point play for the win. I indoctrinated all of the dudes in my freshman dorm and forced them to experience the magic of the opening weekend of the tournament.
But like so many things in life, somewhere along the way I got busy and stopped caring as much.
I will say, though, this year is pulling me back in. I think it’s a few different things…
For one, Underdog is hosting bracket contests for the first time and there are a ton of free rolls available (more on that below). We went game-by-game on Off & On The Clock this week as we attempted to build the perfect bracket. There’s also just more action than ever available—including the Survivor contests on Splash and our now annual Swolecast Calcutta, which we drafted yesterday.
But I also think it’s because it’s never been easier to spin up cool March Madness tools with A.I. assistance. RickRunGood built a very fun bracket tool that helps you find the best leverage angles by comparing ownership data to win probability. And with a few simple prompts, Claude helped me spin up a tool to dynamically value teams in our Calcutta draft.
So ya, March Madness never left, but it certainly feels “back” for me.
March Madness Free Rolls
Underdog hooked us up with our own Bracket Battle with $2500 prizes. It is completely free to enter. Join here:
In addition to the $2500 in prizes below:
First place will also win a spot on an upcoming Best Ball Bash episode to draft a $100 team with me
Second place will get a $100 gift card to the merch store
1-10th will get a free NFL monthly sub to Run The Sims
Also, if we get more people in our pool than Pat Mayo’s, we’ll get an extra 1k added to the prizes below.
There are a ton of other Underdog free rolls out there as well, so there’s no excuse not to enter all of them. Here are all of the ones I’ve found/entered so far (click the links to join):
Gil’s Arena (signed merch)
Snapback (30k in prizes)
The Flock ($1000 to first)
The PME($1250 to first)
Important notes:
NY and FL users can enter and play, but are not eligible to win prizes due to state regulations
Not available in: NV, IA, LA, CT
Other content notes:
I had A.I. write my jokes for my Swolecast Overview on Tuesday and it should definitely stick to coding as opposed to comedy.
I got extremely tilted during Monday’s Best Ball Breakfast after repeatedly getting sniped on QBs. I can’t believe this man is now my highest owned QB.
It was a busy week in the NFL. I wrote about Justin Fields to KC and Jaylen Waddle to Denver. The ADP Chasing guys dove deep into the fantasy fallout on Tuesday night.
Saturday on After Dark (8pm ET), the brothers Gumby join me to discuss their experience shipping the Dawg Bowl for $200k in LA. Want access to DFS After Dark shows on Saturday & a private DFS Discord channel? Become a Best Ball Value Hounds member on Youtube.

🧱 Book #2 for February (100%): Lincoln In The Bardo by George Saunders
Mentioned this last week, but I’m glad I stuck with it. I like the idea that Saunders ultimately explores here as Lincoln processes his son’s death with a war looming. We have to choose whether grief is going to trap us or transform us.
I’m not sure if I would go out of my way to recommend this since it takes a while to find its footing, but it was a solid read and really picks up in the second half.
I don’t have anything picked out yet for our next read. I’m going to be away on vacation next week and want to ditch my Kindle for a paperback. Any reccs?
🧱 Book #1 for January (COMPLETED): 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…


