Thomas Kakalios approaches wine in a philosophical way—by asking better questions. Before he became the beverage director overseeing three of Eat Well Hospitality’s restaurants, he was in fact a philosophy student learning how to examine ideas, trace meaning, and build narratives from a set of facts.

That instinct now shapes everything he does, from constructing wine lists to training his team. In his hands, a bottle isn’t just for pairing; it’s a story about place and the people behind it. And this clarity of thought has made him one of Chicago’s most compelling voices in the beverage world, as well as a recent James Beard semifinalist for Outstanding Professional in Beverage Service.

Kakalios started as a barback in a downtown Chicago basement bar before taking his first major step at Daisies, where he helped open the restaurant and build its wine list from the ground up. The role gave him an early window into how a beverage program functions from both the guest and staff perspectives, experience he carried into increasingly demanding positions.

He moved to the Alinea Group’s NEXT, joining during its French Nouvelle menu period, a meaningful moment for someone who had studied abroad in France and carried a deep affection for the cuisine. At NEXT, he absorbed a level of discipline and attention to detail that still guides his work. “Everything is done for a reason,” he says.

His next chapter, at the now‑closed Yūgen, expanded his lens even further. Immersing himself in sake added another dimension to his beverage vocabulary, one that would later inform the breadth he brings to Eat Well Hospitality’s concepts.

He carried that broadened perspective into Smyth and The Loyalist, where his palate sharpened and his sense of narrative deepened. Working closely with chef John Shields and wine director Kevin Goldsmith, he gained a deeper understanding of how wine can carry a narrative through a meal. “People connect with stories,” he says. “My job is often to translate a list into terms they can understand.”

In 2023, he joined Asador Bastian shortly after its opening, helping to shape its systems and build out its wine program under chef Doug Psaltis. Within a year, his role expanded to overseeing beverage operations across all three Eat Well Hospitality restaurants—Asador Bastian, Andros Taverna, and Mano a Mano. Across all three restaurants, the lists stay anchored in the cuisine’s landscape, leaning into regional depth rather than global breadth. 

“These cuisines and wines evolved hand in hand,” he says. “Owning that identity lets us explore their potential to the fullest.”

Thomas Kakalios’s Wine List

Kakalios’s selections reflect the landscapes and traditions behind each concept, but they also reveal how he guides guests: meet them where they are, then offer something that expands their sense of what a wine can do. These five bottles—spanning Spain, Italy, Greece, and Champagne—illustrate the range of his thinking.

Champagne Coessens “Largillier” Extra Brut (Multi‑Vintage) - $300 (Asador Bastian)

Champagne is one of Kakalios’s favorite tools at a steakhouse because he believes it’s unexpected. Coessens, a Pinot Noir–dominant bottling from a single clay‑rich vineyard, is a standout. “People are surprised by how well Champagne works in this setting,” he says. “It can move from seafood to richer courses without losing its footing.” It’s a bottle with enough structure and acidity to cut through marbling while still carrying the elegance guests expect from Champagne.

Bodegas Muga “Torre Muga” 2005 - $285 (Asador Bastian)

This Tempranillo from Rioja Alta hits what Kakalios calls a “Goldilocks” balance—dark fruit at the core, grounded by earthy, savory notes and fine tannins. The 2005 vintage, acquired by one of his team members, brings two decades of evolution without losing its fruit. He also appreciates the personal connection—the winemaker’s family roots in the Basque region echo Asador Bastian’s culinary identity. “The complexity that’s developed over time is remarkable,” he says.

Cà Nova Colline Novarese Nebbiolo “Bocciolo” 2020 - $95 (Mano a Mano)

At Mano a Mano, the goal is to make wine feel democratic, encompassing thoughtful bottles at prices that encourage exploration. This Nebbiolo from Alto Piemonte embodies that philosophy. Higher elevation and volcanic soils give it clarity and precision, while several years of age and a proper decant bring out its more savory tones. “Nebbiolo is a great transmitter of terroir,” he says, and this bottling shows exactly why. It’s a natural fit for the restaurant’s richer dishes and a compelling alternative for guests who love Piedmont but want something outside the Barolo/Barbaresco lane.

Oenos Mittas Naoussa Xinomavro 2022 - $115 (Andros Taverna)

Greek wines are a personal passion for Kakalios, and this Xinomavro from Macedonia is one of the bottles he’s most excited about. The grape is notoriously difficult to work with, but this winemaker handles it with finesse. “It’s one of the most compelling examples I’ve seen of the grape,” he says. The wine’s prominent acidity and elevated tannins make it ideal for hearty, mountain‑inspired dishes — lamb, mutton, stews — and its flavor profile stands entirely on its own. “It’s not trying to be Nebbiolo or Burgundy,” he says. “It has its own identity.”

Estate Argyros Santorini Assyrtiko “Cuvee Palatia” 2022 - $35 by the glass (Andros Taverna)

Offering a bottle‑worthy wine by the glass is a signature across all three restaurants, and this Assyrtiko from Santorini is the standout. The vines, many between 200 and 400 years old, grow in volcanic ash on an island that’s essentially a desert. The result is a white wine with tension, precision, and a distinctly Greek character. “It would go toe to toe with some of the great wines of the world,” Kakalios says.