By Molly Snyder Senior Writer Published May 20, 2025 at 6:01 AM

This article was written in partnership with Old Guard Games.

It’s been one year since Ben Checota opened his dream shop – a massive tabletop gaming store called Old Guard Games – and he and the staff are ready to celebrate. 

On Saturday, May 24, the revelry kicks off with a store-wide, 20-percent-off sale. “That’s a thank you to everyone who's made Old Guard Games a part of their life,” says Checota.

The official one-year anniversary bash takes place Sunday, May 25, from 10 a.m. until 11 p.m. The shop will host free demos and events all day, including a Bolt Action tournament, Magic: The Gathering duels, paint-and-take miniature figure painting experiences and more.

The recently opened Valentine Coffee next door will get in on the fun with coffee drinks and treats for sale that can be brought over to Old Guard Games' new streetside patio. Folks can borrow cribbage, backgammon, chess, checkers and dominoes for free to enjoy in the outdoor cafe.

old guardX
old guardX

Checota’s vision of Old Guard games took decades to bring to fruition. As a kid, he spent much time at the now-defunct Napoleon’s in Shorewood, where he developed his penchant for tabletop games and, even more so, the inclusive community that the hobby creates.

old guardX
old guardX

“For me, gaming has always been about the connection of people and the building of community,” says Checota. “It’s about putting politics aside. Work aside. Troubles aside. It’s about sitting down with a bunch of people and having a great time.”

Old Guard Game’s inaugural years surpassed Checota’s projections. “It blew my expectations out of the water,” he says.

When the business first opened, Checota prepared himself for a flurry of attention and then a year of building a customer base and finding its groove. Instead, the buzz never waned.

“The continued support from the gaming community and the East Side community never dissipated. It was a bit of a surprise in the best of ways,” says Checota.

After this weekend, the shop will enter its second year of business, and Checota has colossal plans that include additional tournaments and expansions of games.

“We’re going to build on everything we’ve done and provide more options and opportunities,” says Checota. “We’ve established some incredible groups, now we want to expand that.”

old guardX

Checota also hopes to see more gamers try new and different games. Traditionally, people are into one type of game – historical, fantasy, etc. –  but there isn’t a lot of overlap. 

“Our staff is excellent at this. They are into multiple games, all different games,” he says. "They pull people in from all different directions and it makes everything more interesting."

During the second year, Old Guard Games plans to further its relationship with Valentine Coffee. The aforementioned patio scene naturally intersects the two businesses, and in the future, Valentine might host game nights.

“The Valentine space and our space have a lot of room for symbiosis,” says Checota.

old guard patioX

Checota was born and raised within walking distance of his Downer Avenue shop. His first job was at Wendy’s when it was on the same block. Today, he continues to live in the neighborhood with his wife and two children. His investment in the neighborhood is personal and it runs deep.

“During this past year, nothing was more satisfying than coming into the shop on a Saturday afternoon and see 20 or more people gaming together,” says Checota. “It’s the community I’ve wanted to build for a long time that’s made up of all different people with different thoughts and different lives, but sharing the same interest.” 

old guardX

Follow Old Guard Games on Facebook and Instagram for more information about the first anniversary weekend extravaganza!


Molly Snyder started writing and publishing her work at the age 10, when her community newspaper printed her poem, "The Unicorn.” Since then, she's expanded beyond the subject of mythical creatures and written in many different mediums but, nearest and dearest to her heart, thousands of articles for OnMilwaukee.

Molly is a regular contributor to FOX6 News and numerous radio stations as well as the co-host of "Dandelions: A Podcast For Women.” She's received five Milwaukee Press Club Awards, served as the Pfister Narrator and is the Wisconsin State Fair’s Celebrity Cream Puff Eating Champion of 2019.