Photography: Alisha Sommer

You could say that Derrick Westbrook was destined to be a lover of food and wine. Born into a family of great cooks, the Nashville native grew up eating elaborate — and tasty — meals.

This exposure to a bounty of Southern cooking is what started his love affair with food. As for the wine? Well, Westbrook, certified sommelier, manager and buyer for 57th Street Wines, and owner of wine consulting and pop-up tasting company VINE Culture, has his godaunt to thank for that.

He remembers being a curious 8-year-old eyeballing a glass of bubbly at a family New Year’s Eve party. Westbrook’s godaunt, in an act of reverse psychology, offered him a taste of the wine, “It was this tart, bitter note and she saw me make a face and she was like, ‘Yeah, so you don’t want anymore?’ And I was like, ‘No, I do!’ And that’s when I fell in love wine.”

College took Westbrook to Birmingham, Alabama where a mentor advised him to get a job in a restaurant. “He told me that working in a restaurant, I’d always have food, money, and something to drink.” It was in this small family-owned restaurant where he began to work around wine, helping them to build their wine list and tasting along the way. “The wine bug bit me and it stayed with me,” Westbrook says.

Soon after graduating, the economy crashed taking Westbrook’s opportunities to work in the nonprofit sector with it. Thus, began his journey to Chicago where he first landed at steakhouse III Forks as a server but made his way to the cellar quickly. Always one for a challenge, he left III Forks for Alinea Group’s highly-acclaimed Next. Westbrook recalls, “It was one of the first times where I would leave work tired and a little bit stressed and unsure if I could be good enough to achieve, so that pushed me. I was like, ‘No. There’s no way I’m not going to succeed.’” 

But if Westbrook was born with a sophisticated palate, he was also born with an entrepreneurial spirit. Even after a successful interview at Michelin-starred Elizabeth, he knew he wanted to step out on his own and do something new, building VINE Culture, a wine consulting business that hosted pop-up tastings and developed menus for restaurants and bars. Though a promising concept, VINE Culture did not take off as well as Westbrook had hoped and suddenly, rejecting the job offer from Elizabeth had seemed like a bad idea.

Lucky for him, his bold move paid off just in time. A friend called to let him know that a beverage director position at Elizabeth had become available and he took it. “I ended up in the place I wanted to be. I learned the lessons I needed to learn,” Westbrook says. “It was affirmation that the universe is on my side, it’s acting on behalf and I’m doing what I need to be doing. If you get your stripes in a wonderful place and you show that you can excel in that space, then people give you opportunities. So that’s why I say it was a mixture of luck and diligence.”

Westbrook’s time at Elizabeth was unforgettable, “[Elizabeth] is probably the single best fine dining experience as an employee and one of the best fine dining experiences as a diner — just because of the culture that Chef Regan creates is second-to-none…because she’s authentically herself.” Yet, he couldn’t let go of the call to entrepreneurship and it was an old friend who introduced him to the fellows of Open Produce, part owners of his current venture, 57th Street Wines.

“Chicago’s arguably the best wine market in the US. New Yorker’s will argue me up and down because they have more access, but as far as concentration per capita, and knowledge of the wine populous here, Chicago is second-to-none. We’ll call the other city ‘The Second City’ in that case.” Westbrook is encouraged by the changes he’s seen in Chicago’s wine community such as the influx of new blood in the local distributorships. These younger salesmen and women on the street understand the current trends, are more knowledgeable and understand how to provide him with the best selection of products for the customers in his Hyde Park store.

“The thing that excites me is that [with consumers] there’s a real interest and thirst for knowledge,” Westbrook shares with a flip of his dreads. 57th Street Wines is unassuming. It’s long and narrow, the front window showcasing old empty bottles and vintage wine books. Tables and a whole wall of shelves are stocked with wines from every wine region you can imagine — and even a few that may catch you by surprise. It is located in Hyde Park, just east of The University of Chicago, bringing in an extremely diverse clientele of locals and international visitors. “I get to operate in this bubble away from the noise of downtown. In building a wine shop we got to build what we wanted to.” He finds that his clientele love finding wine from their home countries, are open to experimenting and exploring with wine, and the range of income levels pushes him as a buyer to provide a solid range of wine options.

But does the diversity Westbrook see in the customers of 57th Street Wines reflect his experience in the industry? “I feel a great sense of community around the Black somms in Chicago and nationally,” he shares. However, he’s disappointed when he looks at who is getting recognition for their contributions to the wine industry, “There’s wine giants who will never get their just due — people here in Chicago who have changed the landscape of wine in Chicago and won’t get the love that they deserve.” He considers influential men and women like Brian Duncan, Wanda Cole-Nicholson and Regine Rousseau, to be a few of the influential Black sommeliers and tastemakers in Chicago’s food and beverage scene. “How are we not getting the publicity?”

It is not just a lack of ethnic diversity in the restaurant industry that Westbrook is noticing. “When we talk about the landscape of the wine world, it is still a boys club and it still a male dominated club and it is still very straight too. So I think about other people I come across who are in the [wine] world who don’t subscribe or who are not a part of those social norms and it’s like you are missing their voice,” he says taking a sip of sparkling wine. He continues, “When I think about all of the big breaks that I’ve ever gotten, [they] have been from women and support from people of color who look like me as well.”  

Westbrook believes that many young Black men and women have yet to be exposed to the truth that work in the food and beverage industry is a sustainable profession. It is this lack of exposure that he sees as one of the biggest hurdles to becoming a Black sommelier. But you can look to Westbrook as an example: he’s worked at some of Chicago’s most acclaimed restaurants, become a beverage director before turning 30, and is now running one of the hippest and most eclectic wine shops in Chicago. 

His advice to the up-and-comers, “You have to love it and treat it like a profession — like doctors, teachers. Treat it like those professions that we think of as prestigious. Look for the jobs in spaces where not a lot of you are and then when you get in those spaces, learn the jargon, learn the language and then create your own. Make sure that you’re genuinely yourself when you come into these spaces and then Robin Hood that shit — take everything you learned, everything you experienced, and bring it back and show someone else.”

Westbrook is definitely bringing it to Hyde Park. 57th Street Wines will continue to expand its educational experiences with more tastings and there is a podcast in the works. With an unpretentious and warm personality — not to mention a killer palate — he’s following in the footsteps of the greats before him and continuing to make sure that Chicago is making its mark in the wine world. 

-Alisha Sommer, Winter 2018

Derrick Westbrook // Sommelier & Buyer // 57th Street Wines // @57thStreetWines