Sommelier Derrick Westbrook Savors Success in Chicago

It would be understandable if appearing on the cover of Wine Enthusiast Magazine went to the head of a still younger than 40 sommelier. After all, the magazine’s photos of the “40 Under 40 Tastemakers” selected in 2016 and 2017 do not appear to include any black faces. Chicago’s Derrick Westbrook is one of five blacks honored in the October 2018 issue, but he is taking nothing for granted.

“It fuels my fire to do more. There’s this excitement and then there’s this feeling of I love this, but I don’t want it to be the apex at 31,” says Westbrook. The native of Nashville is happy that his family and friends can share in the success he knows he achieved with their help, influence and encouragement. He also knows certain expectations come with Wine Enthusiast’s recognition of him as among the 40 “trailblazers” who are shaping the future of wine, spirits, beer and cider.

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“There’s a little bit of pressure to continue to grow, to continue to try to produce at the highest level possible in my field,” says Westbrook, a consultant, certified sommelier and service manager for Bibliophile in Hyde Park. He worked alongside the owners of the newly opened gastropub that is also a bookstore and cocktail bar. The neighborhood spot where people can “read, eat, drink and be merry” represents the next step in Westbrook’s evolution as a wine expert, educator and entrepreneur. “Being a sommelier and being an educator, I like when a light bulb goes off for people. I like showing them something they haven’t seen or giving them a better understanding of complex concepts. My joy comes in that.”

From First Taste to First Job

Surprisingly, Westbrook did not know what a sommelier was when he moved to Chicago after graduating from the University of Alabama at Birmingham. His love affair with wine buying and wine education began many years after a family friend let a curious and rambunctious eight-year-old take a sip of her sparkling wine. “The first time you have alcohol at that age, it’s never pleasant. I don’t want to call it bravado, but I didn’t want to admit that I didn’t enjoy it,” says Westbrook.

The family-owned Italian restaurant he worked at during his college years gave Westbrook an introduction to the world of wine. “They were rebuilding the wine list and I got the opportunity to taste things that I otherwise would never have been able to get my hands on. That’s when I realized this is interesting.”

Working for owner Zack Lovoy also taught Westbrook what kind of boss he wanted to be someday, even though he thought his English and sociology majors would lead him to a career in the nonprofit field. “Zack cared about the entire person. That really shaped my understanding of how to own a business and manage a business with a sense of family, community and connection.”

By the time Westbrook got his diploma and moved to Chicago in 2012, the economic crisis and challenging job market had eliminated opportunities to go into grant writing or other nonprofit work. His experiences at Alinea and NEXT restaurants eventually led him to a job as beverage director for the Michelin-starred Elizabeth. That is where his exposure to owner and chef Iliana Regan’s independent and unique style gave him the confidence to believe he could pursue a career as a sommelier. “Being at Elizabeth allowed me to rethink the way I need to approach that environment. There’s space for everyone in it, and there’s not one right way to be great,” says Westbrook.

His next stop reinforced Westbrook’s determination to do what makes him happy and to trust his instincts when it comes to being a wine buyer and educator. He was on board from the beginning at 57th Street Wines, helping build the eclectic shop into a place to find Old World Mediterranean and Central European wines. “If I teach, train and talk about it, then it will sell. It’s taken a long time for me to get to that point, and every day I become a little bolder in that feeling.”

A Passion for Helping Others

Being a wine educator allows Westbrook to enjoy his passion for interacting with people and helping others. So does coaching the Near West Little League team. He loves passing on the lessons he learned playing Little League baseball. His team, The Greys, won the championship this year, but Westbrook gets more out of investing in the boys than winning games. “I’m glad we won, but it was the little things; the things that showed growth that gave me as much, if not more joy than the winning,” says the Bibliophile sommelier. “It keeps me grounded. It reminds me that if I approach life the same way that I approach teaching these kids, then I’ll be okay.”

He’ll be more than okay if his pop-up wine-tasting business also gains followers as it expands to other cities. Westbrook’s Samples & Samples pairs wine with music, bringing together the harmony of how each makes you feel. The pop-ups, which resulted in two sold-out tastings at City Winery Chicago, will go on the road to other major cities across the U.S. “It allows me to be in other markets and connect with everyone because music is the universal language.”

At the moment, Westbrook is still appreciating the honor of being named one of the people under 40 whom Wine Enthusiast believes will “leave a lasting influence on the world of food and drink for generations to come.” He sees his photo on the magazine’s cover as a door of opportunity opening for others. “This is not just about little black boys and me, although that is what I represent,” says Westbrook. “It’s about the whole of society being open to allowing multiple palates. Hide tide raises all the ships and that creates a better society for us all.”

Follow the Chicago sommelier on Instagram and Facebook.


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The joy of cooking became a part of her life when Phyllis was a child learning her way around the kitchen with her mother and grandmother. Her retirement from a demanding career in broadcast news has given her time to write about African-American chefs and restaurant owners as well as other black professionals succeeding in the travel and wine industries. Phyllis still loves to cook and try out new recipes.