Fantastic Voyage - 405 Magazine

Fantastic Voyage

  Thomas Upshaw’s job is to pair cocktails with the extraordinary food at Grey Sweater.

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Thomas Upshaw’s job is to pair cocktails with the extraordinary food at Grey Sweater. For a bartender, this is either the greatest or scariest (or both) job ever. Chef Andrew Black’s tasting menu concept in Deep Deuce continues to garner national attention – as well as the 405 Magazine cover in November – and rightly so; the team offers a culinary experience like no other in the state. 


“We wanted guests to experience the same creativity with cocktails, too,” Black says, “and Thomas is perfect for the task. He’s smart, creative, very talented.”


Upshaw worked in a few bars, including the now defunct, but uber-creative, Savings & Loan when it first opened. The Uptown 23rd cocktail lounge was a mecca for bartenders who wanted to push the boundaries of mixology. Ultimately, though, it’s not about the bartender; it’s about the guest experience, something Upshaw understands well.

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“I really want our guests to enjoy the people they’re with,” he says, “so the cocktails need to be something they love, something they can talk about. But I don’t want to overthink things.”


The Cocktail Journey is one of the options at Grey Sweater, and like the dining experience, this cocktail experience is a distinct marvel. For $60, Upshaw interviews the guest, ascertains likes, dislikes, allergies and level of adventurousness, and then creates a three-cocktail “journey” that introduces bar guests to new flavors, new combinations and even new spirits. 


During one interaction, he convinced a guest to try a drink with gin, not vodka. Noticing the skepticism on the guest’s face, he said, “If you don’t like it, I’ll make you something else, but I like to use dry gin in place of vodka when it makes sense.” The drink was stellar, of course, so the gentleman had a great cocktail and gained an expanded palate. Upshaw’s demeanor is more evangelist-scientist than salesman, so guests tend to trust his motivation.


I sat down for my journey, and he said, “I hope you like Chartreuse,” to which I replied, “Yellow, but I hate green.” 


“Your third drink is green Chartreuse,” Upshaw said. It’s the moment when you decide you’re along for the ride (or in this case, journey), and trust the bartender. The third drink was a clarified “punch” with Chartreuse as the main ingredient – and it was stunning. I now know I don’t always hate green Chartreuse.


Upshaw’s nerdy side emerges when he considers what flavor combinations to deploy. “For your first cocktail, I made tepache, with fermented prickly pears.”


Tepache? Yes, the learning curve can be somewhat steep, but tepache is a drink popular in Mexican culture made from fermented pineapples. Upshaw simply used prickly pears instead. The Pramble, a riff on a classic bramble, relied on Rogue Pine Spruce Gin as the base, and a house-made pomegranate Grenadine for sweetness. Still, the drink bordered on dry, and the interplay of flavors, including smoked chili bitters, was up to the task of matching the food in terms of quality, beauty and complexity. 


Like the dining journey at Grey Sweater, the Cocktail Journey is a deep dive into new ingredients, beautiful presentations and complex, delicious and often whimsical flavor combinations.