How many James Beard Award nods does it take to get a city recognized as a food city? In the last five years, Baltimore’s restaurant scene has earned praise and curiosity from the in-crowd of culinary awards. At the same time, the revolving door of high commercial rent and bad actors blaming their restaurant’s failure on crime makes restaurant discourse a tense topic in town.
With the restaurant business being a sizable slice of our local commerce pie, one that only seems to keep growing, I wanted to spend some time with folks inside the labyrinth. On a chilly Friday night in early fall, we took a peek behind the curtain at The Empanada Lady on South Street to understand why Elisa Milan and her team keep clocking into an industry that many outsiders consider to be a field of mounting obstacles at best. What keeps restaurant owners and workers coming back to their culinary path?
The Empanada Lady is tucked inside the first floor of the Maryland Life Building. I haven’t been down here since La Calle vacated years ago, but the building’s neoclassical style feels like the quintessential uniform of downtown Baltimore’s architecture. The beige stone facade opens to a lobby with a charcoal gray stone floor, shiny and reminiscent of a 20th century bank vault.
Soon I find Elisa Milan, owner-founder of The Empanada Lady, and get introduced to Sheldon Dudley, the head chef. Right away, I see the obvious: Dudley is a man at work with little enthusiasm for the fanfare of a visiting writer and photographer with a long lens following him around during Friday dinner service. Immediately, I respect Dudley more. Truthfully, I’d be skeptical of any head chef who was excited to see me poking around. He’s receptive enough, open to questions while keeping his objective clear: he has paying customers to feed. With a deep green apron tied over his black chef’s coat, Dudley works, and I sit at the high-top chef’s counter to observe. It’s clear this counter and station are his domain. Prep and line cooks pop in for brief spurts, simmering sauces and chopping garnishes, but Dudley is the steady beat of this kitchen.
The 4 p.m. opening crowd is a mix of happy-hour event guests and early dinner service walk-ins. As minutes tick by, more people arrive, filling the room, eating and drinking around the space. Vintage black-and-white photos taken by I. Henry Phillips Sr. for the AFRO Newspaper (whose archives I work for as my day job) are reminders of mid-20th century Baltimore, a contrast with the purple, orange, and green contemporary art and murals in the room. Primary colors are few and far between in the mosaic-esque dining room framed by fuchsia walls. The restaurant feels like it sits on the petal of a flor de maga, the national flower of Puerto Rico.
Professionally, Dudley got his start 20 years ago as a dishwasher before shifting to being a line cook. But his first memories of cooking come decades earlier. “Inspiration is always family, right? When Grandma wasn’t home to cook, then I figured something out.”
Dudley is pulling oxtail from the broiler when I ask him about his culinary career. Professionally, Dudley got his start 20 years ago as a dishwasher before shifting to being a line cook. But his first memories of cooking come decades earlier. “Inspiration is always family, right? When Grandma wasn’t home to cook, then I figured something out,” he tells me while plating the seared cuts over rice. The deep black-brown of the meat and gravy lay against the red-orange hill of rice underneath. He tops the dish with a purple pickled garnish before closing the lid on the to-go order.
“Now, I’m teaching my kids. I’d rather teach ’em how to fish than watch ’em keep buying fish, you know? I tell ’em I’ll teach ’em how to make Snickers at home,” he says with a smile. When I ask him how he came up with the newer menu items — oxtails and lamb chops — he says, “People eat with their eyes first, so I treat food like [visual] art: contrast and colors.”
Milan and Dudley also know that the new menu items bridge a consumer gap for customers less familiar with traditional Puerto Rican flavors. Dudley’s use of Puerto Rican staples like sofrito and proteins like oxtail and lamb, which are also found in African American and West Indian cuisine, offers customers a more approachable entry point into the menu. Dudley suggests folks new to Puerto Rican cuisine start with the Salmon Bites or their classic Beef Empanada.
Before opening as a brick-and-mortar location in 2023, the restaurant started as a pop-up and grew steadily into a catering concept as well over the course of six years, during which Milan was a fixture at Motor House on North Avenue. Milan functioned as head of operations, lead cook, chief marketer, and everything else for The Empanada Lady during those early days. Her early success serving empanadas and coquito, a traditional Puerto Rican holiday drink, to Baltimoreans earned her high praise and notoriety.
The early days at South Street were rough, not just for Milan and her team, but for customers too.
“We were figuring it out,” Milan says. “I wish people knew everything that was going on when we started. It took six months to start to figure it out here.”
Criticism was loud in the early days of the brick-and-mortar era.
Milan’s earliest and biggest supporter has always been her mother, who since 2017 has lent her own talent to assisting in the kitchen.
“I’m scared for her, and I have her back, always. I don’t want to cry, but she’s doing well, especially as she’s sharing flavors with folks who don’t know the culture,” Melissa Milan shares about her daughter’s role as owner-founder.
Melissa championed her daughter’s culinary career from the beginning. The Empanada Lady began years ago when Milan was laid off from a nursing gig and had two weeks to make rent. “I called my mom, and I didn’t know what I was going to do. She said she’d help me prep the empanadas to sell at a friend’s party.” Being laid off spurred Milan’s entrepreneurship and brought her grandmother’s recipes to Baltimore diners.
Sitting now inside the latest iteration of the business, Milan comes across as a stressed owner-founder who still smiles amidst the setbacks, a down-to-earth woman on a path she never imagined for herself.
Sitting now inside the latest iteration of the business, Milan comes across as a stressed owner-founder who still smiles amidst the setbacks, a down-to-earth woman on a path she never imagined for herself. During any given week, Milan and the team are juggling full-service lunch and dinner on South Street, catering orders for food and bar off-site for private events, and managing their on-site location at Camden Yards. On particularly stressful days where South Street is open, they’re vending off-site, and catering, Milan is in the kitchen from open til close.
“If you could ring a bell right now and solve an immediate need as a small business owner, what would you ask for?” I ask Milan as Dudley continues his sauce work beside us. After a deep breath, she answers, “The first thought is funding, capital. One of the hardest things is not being able to afford mistakes. Every little mistake is a big mistake. There’s just no wiggle room because the food margin is so little. There’s no mistake capital. Every mistake is costly.”
“Everyone sees us working with the Orioles and think it’s all glamorous. They don’t know that the work they see online today won’t be paid out for a month or even two months and I have to buy ingredients, pay my staff, other materials right now. I can’t tell people they’re getting paid in two months.”
But still, Milan’s demeanor as she sits beside me is a familiar beat, a marrying of the unpredictable and low, slow acceptance of one’s preferred chaos. Not frantic, panicked, or downtrodden. She’s spinning no less than five delicate plates of customer service, staff management, inventory, back-of-house logistics, and chatting me up about the business. She’s taking stock of the day’s unique mix of chaos and she’s not the fire-breathing restaurateur that exists in the contemporary culinary imagination.
“My dishwasher’s late,” she says coolly with a smile and a shrug, eyeing the kitchen doorframe. Out of view, but likely looming large in the mind of an owner-operator, is a sink with dishes waiting for their steward. It’s like a track coach noticing their anchor sprinter didn’t get the best sleep on the bus to the relay: she’s not airing him out, she’s accounting for how his late start impacts the rest of the race. Javier Torres, the dishwasher, has been with her since she started on South Street. “I trust him so much. He’s been with me since the first day. He left briefly, to another state, because his brother passed away.”
Milan trusts that Torres will show up soon. And so do I. In the meantime, I busy myself watching Avelis Contreras, resident prep woman of the kitchen and Torres’ wife, hard at work prepping pork pernil in the back.
Contreras is diligent. Her hands move from saucepan to basting brush as she gets trays of protein ready and marinated. When the roasted pork is ready, she sets a small deli container aside for me with a spoon, inviting me to try the Puerto Rican staple. It’s incredible. Hot roast pork with peppers and spices is a welcome gift after my hectic day. “I always tell people if they eat pork to get the pork. It’s a must,” Milan emphasizes.
Widespread economic strife and inflated ingredient costs are the usual big obstacles for any restaurant owner. Keeping good staff on payroll, however, seems to be what Milan loves most about running her business. The Empanada Lady began because of Milan’s own precarious future as a single mother striving to earn income, and paying her staff full of Baltimore locals is a point of pride. “A lot of my team are here as their first or second shot in the business,” Milan says.
For Black and Latinx Baltimoreans, the restaurant business is a hard place to be. Friends in the industry tell me about the demanding hours, scarce opportunities, and racism they face when trying to sustain careers in town. Speaking with Milan, I learn how her high school years in alternative school set the foundation for her hiring practices. “I went to alternative school and I know how hesitant people are to hire alternative school grads,” she says.
Cinya Savage, a recent Baltimore City Schools grad, is a server at The Empanada Lady who started two years ago after Milan visited her high school for career day. “I never wanted to be a server, really. Then she came to speak and I liked what she was saying,” Savage tells me when we chat at a high-top table. Her long-term goal is to become an immigration rights attorney, defending folks facing deportation and other legal battles. Savage’s interest in immigration law is a direct result of her time working at the restaurant with her immigrant coworkers.
The restaurant business is turbulent, and for Black-owned restaurants like The Empanada Lady, scarce funding and harsh criticism are major obstacles.
When I look around the dining room, though, there’s not a frown in the house.
Patrons share laughs and urge each other to try different dishes as bartenders mix bright happy-hour cocktails, and the empanadas seem never-ending. There’s a reason chefs, servers, and bartenders keep showing up: it’s because we, the hungry public, await them.