Why I’ll Be Creating More Best Ball Content This Offseason

And How You Can Help

I’ve always said the MLB offseason is a strangely satisfying time. No baseball sucks, but the extended break allows for deeper reflection. I find I become a better baseball mind and a better fantasy player during the quiet winter months.

For many, fantasy baseball season begins in March. For me, the real season is about to start, and I’m energized for it. 

Something I’m going to be doing more of this offseason is Best Ball content.

I’m biased because I work for Underdog, but I think it should be a far more popular fantasy baseball format.

And then, a week or so ago, I read this (via @bestballalec):

How My Dad Won $20,000 on Underdog Fantasy

I want to highlight a few things Alec mentions in his piece, which is about how he and his dad won $20,000 by playing Underdog’s in-season fantasy baseball contest.

“I decided to look up if there was anyone on YouTube that created content around Best Ball baseball to see if it was worth getting my feet wet and I came across the only channel to specifically discuss this format called Stacking Dingers. I got to hear from three Underdog Fantasy players in Matthew, Brendan and Chris (these guys have bizarre and hilarious usernames in D4RKSH33P,  Toomuchtuma and B3isbol). Their excitement was contagious and I was ready for my baseball viewing experience to be heightened through Best Ball, just as Matthew promised.”

This passage warmed my heart. Not only did he include the hilarious joke about our X handles, but the last line is crucial to the growth of Best Ball:

This is important because many will frame Best Ball as the “new” way to play fantasy baseball, but I never refer to it as that because it misses the more significant point.

First of all, Best Ball will never replace managed, season-long leagues. I consider myself in the 99th percentile of Best Ball fans, and if forced to choose one over the other, I’d side with my precious managed leagues. There’s nothing like a summer-long grind for glory against your closest family and friends. There’s an art to in-season management that Best Ball lacks.

And yet, what is one reason you wouldn’t draft 25 season-long teams this offseason? How about 50? 100 or more?

It would be impossible to manage, and this is where Best Ball shines. There’s no in-season work required. Draft your teams, sit back, and enjoy the sweat.

Drafting Best Ball teams throughout the offseason helps prepare you for your most prominent leagues in March. It gives you a reason to begin studying the player pool early and to have real stakes in your analysis. However, the stakes aren’t too high as each Best Ball entry is reasonably priced (usually between $5-$25, though more expensive drafts exist closer to the season).

Yet, even with a low entry fee, the potential payoff is enormous! This is due to the tournament structure of Best Ball. In “The Dinger” (Underdog’s flagship MLB Best Ball contest), a $10 entry yielded a $100,000 first-place prize in 2024.

This creates a game that appeals to players who haven’t fully participated before because, unlike a season-long fantasy baseball league, no mastery is required to turn a low-cost entry into the grand prize. Additionally, the multi-entry structure allows diehards to zero in on best practices, whatever we decide they are. To be blunt, we currently have no idea what those are. That’s what this offseason is for.

Unlike DFS, a simulator won’t provide the answers. MLB Best Ball is far from being “solved.” The nature of drafting for a contest that isn’t decided until months later means it likely never will be.

In the long run, some players will learn enough about Best Ball to have a macro-level edge. It’ll still take only one well-constructed entry to claim the top prize.

Here’s how Alec summarized it:

“I’m over the days of questioning which player I should have played instead of another - Best Ball is my preferred game. 

It allows the commoner to come in and take their crack at the top prize. No simulation is going to tell you the perfect players to draft because none of them can predict who the top picks will be weeks (or months) down the line when the final round of the playoffs hits. Best Ball is about finding a way to set yourself up for success off of chaos, about creating an opportunity that no one else does. That’s what drafting Eugenio Suarez looks like.”

Tremendous stuff.

There’s still so much more to explore—rules, strategy, historical trends, player analysis, etc. I’ll get to it all this offseason.

In the meantime, if you’ve never played before and want to try it out or wish to support this Substack, you can do so by signing up for Underdog Fantasy and using code TOOMUCHTUMA.

Doing so helps support me, but there’s a twist. Underdog is tracking the number of “first-time users” we get with my sign-up code, which I’m pitching as an opportunity to see how popular this game can be.

If things go well, more investment in MLB Best Ball's product, marketing, and content can be justified.

If you’re already a Best Ball addict but want to see the game grow, please recommend my code to your friends and family. Our best way forward is to rally the community to show the Dog App that people want more of this.

If it’s easier, here’s my referral link that accomplishes the same thing as inserting code TOOMUCHTUMA during the sign-up process.

Once you sign up with the code or link, you only need to make a deposit and submit a minimum $1 entry on a Pick ‘Em or draft.

You’ll also receive up to $1,000 in bonus cash and a free pick.

2025 Best Ball drafts aren’t live yet, but you can participate in the postseason fantasy contest (The Pennant), play Pick ‘Em, other sports offerings, etc.

Today is Day 1 of my attempt to grow this game alongside the community. If you have questions, reach out. If you’re also a Best Ball content creator, reach out. And if you’re wondering who the heck to draft in 2025 and beyond, then stay tuned.

The most exciting time of year is just beginning.