This Is Kevin Brennan

Kevin Brennan. Photo by Attilio D'Agostino.

Long after we come to a stop, the red, once-fuzzy dice sway on the rearview mirror of Kevin Brennan’s ‘79 Dodge Ramcharger. The halt coincides with an email alert on Brennan’s phone. He digs in his pocket to find a message about a Cuban immigrant living in Miami who Brennan is considering as a host for a series of cigar-rolling pop-up events.He holds up the phone to Carlos Zamora, who created the branding for Brennan’s new cigar line, in the passenger seat. Zamora, a native Cuban, sips on a chalice of Stella Artois and glances at the phone after Brennan attempts to read her name.“Niurka,” says Zamora, emphasizing the pronunciation in his native accent and interrupting Brennan—who had it wrong on the first syllable and then again on softly rolling the “r.”I’m in the seat-belt-free bench behind the two captain’s chairs, and as we lurch forward, the bench rocks backward, attempting (unsuccessfully) to lock into place.We are commuting from the Central West End to Randall’s Wine & Spirits to view the culmination of four years’ work by Brennan, Zamora and a host of others. The effort has included international business connections, countless design revisions and the applied wisdom of years of hard-earned retail experience. If risking our lives in this maniacal vehicle to view an end cap display of cigars seems anticlimactic, it helps to know the backstory.Approximately 13 years prior to this car ride, Brennan’s opened as a bar and retail space near the corner of Euclid and Maryland. To characterize it as such, though, is akin to saying there was once a little coffee shop that opened in Seattle. Brennan’s featured an upscale-ish, laid-back environment with hidden surprises that gave patrons the opportunity to make unexpected discoveries, such as the basement speakeasy behind an unmarked door. It was the kind of place you would show off to your friends from out of town—an enigma that had to be experienced in order to fully appreciate its artistry and clever twists.“People found us a bit confusing at first,” says Brennan. “They didn’t know if we were a store or a bar. There were no TVs or other St. Louis bar paraphernalia. You could just hang out here and have some wine or beer and talk. More and more people started coming, so we kept adding other levels and different things.”Most retail store owners with a growing business would take it as a sign to stick with what is working. That is Business 101: Find the one thing you are doing well and keep doing it. But Brennan doesn’t subscribe to this sort of conventional wisdom.“We realized we could do some interesting things that were needed in the Central West End,” says Brennan. “We started to change the way we looked at spaces we had and what meaning they could have for the neighborhood.”Brennan’s ability to view his space from unconventional perspectives and his openness to experimentation allowed him to have a different take on the trends he saw developing in the industry—a flexibility that required a creative mind and a high tolerance for entrepreneurial risk. The end result was a host of new opportunities both within and outside the business’ walls. Prior to opening a location,Brennan created Durango Cigars, a pipe tobacco company whose products he sold in his retail space.A solid following had developed for the distinctly sweet cigar he created, which features a small amount of pipe tobacco rolled with long filler cigar leaf. Unlike the savory spice of traditional cigars, Durango’s recipe contained hints of vanilla and fruit so distinct Brennan created the tagline “This Is Not A Cigar,” inspired by Belgian surrealist René Magritte’s influential painting, “The Treachery of Images,” which bears the phrase “Ceci n’est pas une pipe” (this is not a pipe) under an image of a pipe.A little more than five years ago, Brennan opened the Durango Cigar Lounge on the second floor above the main retail space. The club lounge feels like the set of a mob film—if the mob were full of hip Gen Xers. The contemporary space is lined in dark oak with upcycled music artwork and the Durango buffalo logo on the low tables. Cigar clubbers can select tobacco from their personal humidor, then kick back with their favorite vinyl records in the sneaker-collection-lined cave.“We found that the more you offer the cigar club guys, the more they come back, and then they want to do other things in the space,” says Brennan. The enthusiastic response from his members stoked Brennan’s passion for innovation. Fast-forward to today and the cigar club has grown in membership. It now resides upstairs next to the The Maryland House—a speakeasy-inspired lounge open to the public and available for private events.The Maryland House was where Brennan and I ran across the long, lean figure of Frank McGinty with his ever-present grin sipping on both a pint of pale ale and what seemed like a small bucket of ice water. McGinty, director of customer service and culinary at Kaldi’s, was not a scheduled meeting. But his presence was not really a surprise to Brennan—very few things are. The two agreed to sit down in a room located in The BHIVE, a 3,000-square-foot office space on the other side of the stairwell from The Maryland House.The idea for The BHIVE, launched in 2015, came to Brennan as he was focusing more energy on growing his online cigar business. He found himself attracted to the possibilities around creating one-off experiences—unique concepts that would be built around collaboration and innovation. He saw opportunity in reimagining an underutilized space on the second floor by capitalizing on St. Louis’ startup buzz and network of creative business people—the kind who are attracted to working in a space like Brennan’s. He envisioned a daytime co-working space that would double in its evening hours as asalon for events.Brennan brought in Martin Goebel of Goebel & Co. Furniture to design signature pieces and elevate the space with a contemporary “Mad Men” feel. Currently, a wide range of businesses use “the hive” as their center for operations—from consulting servicesto a nonprofit baseball league. It has become a hub for a tight-knit group of well-known Central West End-based entrepreneurs—all no doubt attracted by the modern aesthetic, ample natural light and idiosyncratic spaces, like the Dead Wax Records vinyl lounge—a space designed for the temporary, liminal moments creative entrepreneurs experience during the day.Seated in one of the office spaces in the hive, McGinty and Brennan hatched the vision behind what will be the next iteration of This is Not a Restaurant. The use of another Magritte-inspired name is intentional; many of the featured chefs do not currently serve in restaurants, and the ones who do craft food experiences unique to the evening—further playing with the surrealists’ ideas about our perceptions of reality. Not to mention the product synergies—Brennan notes Durangos are a perfect after-dinner cigar. McGinty, who is taking on many of the organizational duties for the series, tossed ideas across the room about what makes for the best possible experiences.But quickly, both men got off-track and discussed more experiments—a sous chef challenge and an interactive evening with cigar rollers. “I want to get the most interesting people in the space, and I want them to come back and be surprised,” says Brennan. “I remember reading the Starbuck’s CEO’s book, ‘Onward,’ and he talked about creating a third place. People have home, and they have work. He talked about the importance of a third place—Starbucks. I see what we are doing with Brennan’s as creating a fourth place—it is all those places.”After McGinty takes off, we meet up with Zamora in the hallway. He pours his Stella Artois into a chalice. Brennan gets a text, and we are off in his Dodge to Randall’s. On the way there, Brennan reveals his vision for a pop-up franchise within retail locations. He sees the beer and spirits craft movement making its way to tobacco, and each retailer of cigars has the opportunity to become his own microtobacconist. He believes so much in this idea that he has launched a line of traditional cigars called Micro Tobacconist. Retailers can choose their own blends, sizes and other variables, and Brennan will put their brand on the wrapper creating a distinctly unique product.When we arrive at Randall’s, Brennan approaches the end cap, puts on a pair of cheater glasses and reads the labels on the black oak case—it has a screen with rotating messaging about each custom cigar blend created in collaboration with Micro Tobacconist and descriptions of the flavor profiles. The case also features Durango cigars and other major brands. He rearranges the top row of cigar boxes with the Randall’s custom wrapper and then moves them back to the original place all the while analyzing and critiquing in minute detail the placement, lighting and overall presentation.After a few minutes, Brennan and Zamora stand back from the display. For a rare moment, they stand still. They see what most do not. They have already visualized where cigar rollers will be placed. They already know the looks of surprise and intrigue future shoppers will have. They know those looks because they see them every day at Brennan’s.This story comes from ALIVE's Let's Come Together issue. Read more from that issue online, or find where you can pick up a copy around St. Louis.