OPENING ALERT
Buzzy new pickleball club opens on San Antonio's North Side
A local fabricator built custom fencing for the pickleball courts.
When Ross Krachey first introduced Outlaw Pickle to San Antonio, it already had ambition. Now, the entertainment complex, opening Friday, May 15 at 618 NW Loop 410 #202 in the Park North shopping center, is a whole new (pickle) ball game.
When CultureMap last caught up with Krachey, Outlaw Pickle was in the developmental stage. The founder and CEO and his partners — commercial real estate pro Romie Chaudhari and Jonathan Bricklin, the cofounder of table tennis chain SPiN — were preparing for a fall 2025 opening. The timetable was delayed as the project got more ambitious.
“We’re six months overdue on a three month project,” laughs Krachey.
The first big change was the hospitality program. Originally, the partners planned to serve food out of automated vending machines supported by an in-house kitchen. Krachey says he switched gears when he hired general manager Mario Garcia, who some locals may remember as the chef of bygone Broadway restaurant Tacos and Tequila.

Garcia crafted an original menu of bar snacks and other handhelds that includes pizza, burgers, sandwiches, Brussels sprouts, and fries (the latter two come in five varieties each). Larger groups can dine on packages like the Desperado (pan-Latin fare) and Rebel Yell (Tex-Mex and Southern barbecue) during private events, each sneaking in some Tacos and Tequila classics.
The bar program shifted, too. While Krachey first envisioned a bar focusing on agave spirits and Bourbon, the new menu went “over-the-top.” The cofounder says his team voted a white chocolate matcha martini as the likely bestseller, but his personal favorite is a little more playful. Outlaw Pickle ships in fresh miracle berries, the red berries from a West African evergreen shrub, to perform a little magic on a paloma.
Krachey said the base drink is intentionally made super sour and served with a half lemon. Then the berry does its trick, turning puckery flavors into a sweet, balanced sipper.
Although the food and drink are not what the entrepreneur first pictured, his love of pickleball has stayed the same. He first fell in love with the sport on his 32nd birthday, hosting a 100-person pickleball party the following year. But his take on the game isn’t as serious as some of the other facilities in town.

Firstly, he based Outlaw Pickle on open play, where players of all skill levels can sign up without pre-arranging a foursome. While staff will ensure that pros don’t get paired with newbies, Krachey wanted the experience to reflect the more social aspects of the game.
“You just put your paddles in the rack and wait your turn,” he explains.
Still, that doesn’t mean that he short-shrifted the five climate-controlled courts. Even though it cost “twice as much money,” the team cushioned each court to be kind to joints. All are equipped with state-of-the-art technology like high-res TVs, AI ball tracking, and a replay system that sends celebration clips that can be posted on social media.
Each court, named after Krachey’s niblings and Bricklin’s children, is also themed. The team even hired a local fabricator to build custom fences to keep the motif going.

“It’s one of the most beautiful courts I’ve ever seen,” says Krachey.
The courts may be named after kids, but Outlaw Pickle will set aside some time for adults. After 4 pm, the complex has a 21-plus policy. Krachey said the facility is bar-centric with amenities like table tennis and a video jukebox stocked with ‘80s hits. There’s also plenty of grown-up programming planned, such as trivia nights and poker.
“There’s so many places for kids and none for adults,” he says, referring to Park North’s surplus of entertainment options like Pinstack and the upcoming Taroko Sports. “Chicken N Pickle is for kids.”
Outlaw Pickle is currently offering memberships, ranging from $9.99 to $49.99 per month, but locals are also invited to just drop by. Following this weekend’s hours of noon-10 pm, it will be open from 7 am-1 am daily.
