Cassandra E. Sakai

Corporate Director of Beverage Operations, Gibsons Restaurant Group

Born and raised in the Bay Area, Cassandra (“Cassie”) Sakai grew up experiencing wine culture through the eyes of her food- and wine-loving family. After college, Cassie moved to Chicago and quickly fell in love with the Windy City and its restaurant industry. Inspired by a few notable wine professionals while working in Chicago, she became a certified sommelier at the age of 22. It was not long before she made her way to Girl & the Goat, where she started serving and working in the cellar before eventually taking on her first Wine Director role there. Cassie soon curated an award-winning wine program and, shortly after, began overseeing four restaurant wine lists within Boka Restaurant Group. Most recently, in 2021, she became the Wine Director for Chicago’s iconic Gibsons Restaurant Group.

Within the next year, Cassie earned the opportunity to manage all aspects of beverage within the company as Corporate Beverage Director of Operations, channeling her expertise to over 14 properties across 3 states. Her approach to hospitality and education has always been to make food and wine as fun and approachable as possible while incorporating Gibsons Group Values of Family, Hospitality, Quality, and Value. In her free time, she enjoys traveling, checking out new restaurants, and running with her dog.

Meet the other judges

Christian Shaum

Lead Sommelier at Bazaar Meat & Bar Mar Chicago & CMSA Advanced Sommelier, Chicago

Valerie Cao

Director of Operations and Beverage Director at Le Colonial Chicago