Okay, so I wanted to share how I run my little home run derby pool. It’s become a bit of a tradition, and honestly, it makes watching the derby way more intense when you’ve got some skin in the game, even if it’s just a few bucks.

Setting Things Up
First off, I had to figure out the basics. Didn’t want anything too complicated, you know? Keep it simple so everyone can join in without needing a rulebook. I decided on a straightforward entry fee, usually ten or twenty bucks, enough to make a decent pot but not break the bank for anyone.
Then, the picking part. How do people choose their hitter? A full draft seemed like overkill for this kind of casual pool. So, I just went with the easiest method: everyone picks one player participating in the actual MLB Home Run Derby. That’s it. Pick your guy.
I usually send out the list of official derby participants as soon as it’s announced. Then, I set a clear deadline – gotta get your pick and your entry fee to me before the first pitch of the derby. No exceptions, otherwise it gets messy trying to track who’s in and who’s out once things start.
Getting the Crew Together
Getting folks involved is usually pretty easy. I’ve got my usual group – some friends, family members, a couple of guys from work who follow baseball. I just shoot out a group message or email explaining the rules, the buy-in, and the deadline. Nothing fancy. Usually get a good response pretty quickly. Sometimes you gotta nudge a few stragglers to get their picks in on time, but that’s part of the fun, right?
Derby Night!
Alright, this is where the real action happens. Come derby night, I usually have a little spreadsheet or even just a notepad ready. As the derby goes on, I’m tracking who picked which player and how many homers they’re hitting. It gets pretty lively!

- I keep track of each player’s total home runs round by round.
- My phone’s usually buzzing with texts from the pool members, especially when their guy is up or hits a monster shot.
- We’re all watching, yelling at the screen, hoping our pick advances.
It definitely adds another layer of excitement to the event. Even if your player gets knocked out early, you can still root against the players picked by the people currently in the lead!
Wrapping Up and Paying Out
Once the final round is over and the official Home Run Derby champion is crowned, figuring out the winner of the pool is simple. Whoever picked the actual derby winner takes the entire pot. Simple as that.
I collect all the entry fees beforehand, so the cash is ready to go. I count it up, announce the total pot and the winner to the group, and then get the prize money to them pretty much right away. Usually use Venmo, PayPal, or just hand over cash if they’re local. Quick and easy, no drama.
Honestly, running this thing is pretty straightforward once you do it once or twice. It’s low effort for a lot of fun, and it gives everyone a reason to tune into the derby and have something to cheer for. Definitely worth doing if you and your friends are baseball fans.