You Want Fries With That

At Burger Syndicate, a customer ordering fries is likely to be met with a follow-up question: “What kind?” Plain, Cajun, lemon pepper, garlic Parmesan, bacon cheese, pork loaded and brisket loaded are the choices offered. The new smashburger shop tucked into Ankeny Alley treats fries like anything but an afterthought.

The twists don’t stop there. The burgers come with gloves. The hours are unusual enough (the place opens at 6 pm and stays open until 1 or 2:30 am depending on the night) that owner Anthony Brown says customers regularly ask what’s with the schedule. On the wall, a timer challenges customers to press a glowing red button and stop the clock at exactly five seconds. Hit it dead-on and the burger’s on the house.

Burger Syndicate, from Anthony and Stephanie Brown, the husband-and-wife team behind Nacheaux, is a burger shop built for a downtown alley trying to become more than a pass-through. It is also the Browns’ latest attempt to distill Nacheaux’s loud visuals and tireless adaptation into something fixed, focused and late-night.

Nacheaux, founded in 2020, became known for “Mexicajun” food with a maximalist streak: fried chicken burritos, Cajun sauces, shrimp and crab rolls, lemon pepper fries, bright branding, and a cartoon unicorn mascot primed for Instagram. The Browns moved through pop-ups, catering, private events and a residency at Swan Dive before building out a food trailer with their children in tow. The cart then appeared at events like Pickathon and Portland Night Market. Today it’s still mobile, alongside a Moda Center kiosk serving loaded nachos, draft beer and the tagline “Southern flair at its boldest.”

“All we know is pivot, pivot, pivot,” Brown says.

That tactic is the result of trial and error. In a recent social media post, Nacheaux acknowledged that online attention didn’t always equate to long lines of customers, describing empty brunch service despite thousands of likes and shares. The Browns eventually shifted more energy toward private events, catering and mobile service.

Burger Syndicate is the latest product of that discipline, trimming Nacheaux’s sprawl into a tighter menu without losing its penchant for flamboyance. The classic smash comes as a double for $9 or a triple for $12, with American cheese, pickles and Syndicate sauce. From there the menu pushes outward: smoked pork and kimchi on the K-Town, house-smoked brisket on the Boss, and bacon crumbles integrated into the Bandit’s cheese skirt.

Brown calls the classic “the Portland smashburger” but says small details distinguish it from others: sweet pickles instead of the traditional crinkle-cut dill, housemade Black Magik Cajun seasoning, and the smoky aioli-style Syndicate sauce. “I do a hybrid,” Brown says. “It’s not smashed super thin, but it’s also not a thick patty. It still adds a little juiciness to the burger.” On the Bandit Burger, Brown sprinkles bacon bits into the crisped cheese, ensuring bacon in every bite rather than a strip that inevitably gets pulled out early.

That same instinct shows up in the fries. Brown insists that he wanted to avoid what he considers the typical loaded-fries formula: potatoes buried under burger toppings. His versions bring in Cajun waffle fries, slaw, pickles, sauces and smoked meat in an aim at more structured excess. The menu also nods to Nacheaux with Cajun fried chicken, a vegan burger, housemade lemonades and a tight sauce lineup.

Brown says his wife, Stephanie, gave him two principles that still guide his work. “The first one is, if you can find it somewhere else, then why would they come here?” Brown says. “And the second thing is, if you flair it well and you cook it well, people will come.” Though he’s self-taught, Brown credits much of his culinary excitement to owner/chef Chris Whaley of the American Local, whose food broadened his palate but whose reluctance to embrace media he considered a fault.

The gloves came from Brown’s own barbecue habit: He often asks for gloves when eating barbecue and gets strange looks. At Burger Syndicate, he wanted the gloves to be practical, playful and “Instagrammable.” They now go with every order. At night their utility is obvious: Dressed-up clubgoers pop in for a meal, then peel off their gloves and continue on with their night.

The Browns originally tested daytime hours but shifted later when lunch traffic lagged (another pivot). Downtown office worker traffic remains unsteady, Brown says, but the alley changes at night. Clubgoers move between doors. Hotel guests drift through. Voodoo Doughnut still pulls tourists nearby. Shanghai Tunnel remains an anchor. The shop’s menus are already inside nearby nightlife venues, allowing customers to order online and pick up food; when the kitchen has downtime, Brown says, the crew will run orders to nearby clubs.

On a given night, Brown estimates 75 to 100 people come through the shop, with several hundred more walking past outside. The alley itself matters. Brown says the same concept would be unlikely to work as well in another part of downtown. Here the surrounding businesses form a loose late-night circuit. He praises Chris Pink of Paris Theater, and says the owner of the District Nightclub has also been enthusiastic in promoting the business.

“To me, he’s actually helping me feed my family,” Brown says. “And I take that very personally.”

Brown admits he worried about safety before opening downtown, having heard the same stories many Portlanders hear about shootings, stabbings, robberies and disorder. But his experience in Ankeny Alley, he says, has been different. Nightclub security, Clean & Safe patrols and Portland police pass through regularly, and the late-night crowd makes space for passersby and checks in on the shop.

He compares the dynamic to food businesses he knew growing up in Los Angeles: places in rougher neighborhoods that people did not vandalize because they belonged to the block. That is what he wants Burger Syndicate to become: a late-night “watering hole” and a small part of the alley’s identity.

Six months ago, Brown says, he and Stephanie Brown were considering moving to Florida. Portland’s post-pandemic malaise had worn on him, and he wanted more sunshine. But construction around Lloyd Center, Live Nation’s planned venue and other projects gave him hope.

“I just bet on Portland,” Brown says. “I feel like it’s gonna be something here—not right now but in the next two years.”

Burger Syndicate is messy, bright, quirky, and designed to be noticed. Elsewhere, the gloves, timer and so on might feel gimmicky. In Ankeny Alley, they give the shop its gravitational pull.

EAT: Burger Syndicate, 221 SW Ankeny St., @burgersyndicatepdx on Instagram, 6 pm–2:30 am Thursday–Saturday, 6 pm–1 am Wednesday and Sunday.