It's hard to ignore the Ambassador Hotel's giant orange neon lettering on the Milwaukee skyline as one drives in from the west at night. A social fixture since 1928, when affluent people with names like "Pabst" were often seen milling about the lobby, the hotel's history makes it a prime spot for an almost eerily traditional cocktail or two this Halloween.
Over the last ten years, owner Rick Wiegand and his staff have worked to restore the Ambassador to its glory days, all but erased as the surrounding neighborhood fell into decline during the 1980s. In the decades following the hotel's construction, names like Walter Busterkeys—later known as Liberace—and The Beatles would stop by and entertain guests in the lobby, before crashing in one of its guest rooms after performances downtown. But the celebrity most famously associated with the Ambassador has likely been serial killer Jeffrey Dahmer, who murdered his first victim in Milwaukee in his room there before smuggling the body out in a suitcase in the fall of 1987.
Strangely enough, even as the Ambassador has sought to distance its name from that of the notorious cannibal, small connections between the two still seem to emerge. Barry Leach, my server at the hotel's lobby bar—Envoy Lounge—tells me about the two taverns he owned previous to his stint here, starting in 1980: Barry's Water Street Pump and Just Arts Saloon. Both were located in Walker's Point, a now-bustling area of town that Dahmer frequented.
"We were the first popular straight bar in the neighborhood," he tells me about Just Arts, alluding to Walker's Point's history as the gay district in town. "But I started making Old Fashioneds long, long, long ago, bartending for my parents when I was too young to drink, when they'd have card parties and things. The trend now with a lot of these places doing older nostalgic cocktails, is that they're doing it with recipes they make up themselves. The recipes here were here long before I was."
Leach's bar sits in the Ambassador's lobby, across from its restaurant, Envoy, all of which looks and feels like the original incarnation of the Tower of Terror at Disney World. That isn't to say the place feels like climbing onto a Twilight Zone theme park ride, but it definitely seems otherworldly and pulled from the sands of time. Envoy's cozy dining room reeks of elderly sophistication, with all the trappings of your parents' favorite place to grab a celebratory dinner or anniversary, despite the diners who have all come in off the street for lunch (soup, sandwiches, and salads for all). You can smell how old the place is: After passing the scent of grease from the kitchen near the hotel's main entrance, you'll be more inclined to notice buried wood, old paint, and dust in the air.
That kind of dedication to history and preservation commands a certain kind of respect, and Leach isn't one to mess with his city's favorite heritage cocktail. The classic Wisconsin Old Fashioned Leach makes me features a sugar cube soaked in bitters, muddled with a cherry and a slice of orange. The customer picks whiskey or brandy, and their choice of mixer—sour, sweet, seltzer, or a combination.
"If you look it up in some books, they don't include a mixer with it—it's just the liquor, sugar, bitters, and you dissolve the sugar in the liquor," he continues. "Milwaukee has always added some kind of mix with it. We don't like to have to wait for sugar to dissolve. Mixer means more, faster."
Beyond cocktails, supper club fare like a prime rib special, fish fry, pork chops, and other old-timey Midwestern selections feature prominently in the Ambassador's restaurant. Together with the hotel's restoration, they make a step through its (now-automatic, sliding) doors like walking into a portrait of Milwaukee's golden era, when the Miller, Pabst, and Schlitz breweries defined Milwaukee's image.
The hotel's two eras stand in stark contrast to one another, especially since sitting in the lobby bar with Leach, it's hard to see the place as anything short of a shining landmark. The Ambassador's marble floor is original, restored from its pre-Prohibition construction, along with the crown molding, sconces, and elevator doors. Much of its original drink menu remains intact, and even features its original prices during happy hour: $.25 for a Gin Fizz or a Tom Collins, $.35 for a Stinger.
But that history, coupled with the ghost of one of the country's most famous murderers in its walls, lends the Ambassador a kind of Kubrickian eeriness, and makes one wonder whether each new patron pulling a chair up at the bar is a ghost or a living person. The building also sits across from The Rave, one of Milwaukee's most popular live music venues: a stone complex of ballrooms and abandoned chambers, including a giant empty swimming pool in its basement, long rumored to be haunted.
And the mystery surrounding the Ambassador's existence early on only adds to its pallored history.
"Most of what we know about the hotel's early days has come from word-of-mouth," says Amy Schneider, the Ambassador's assistant general manager. "We wouldn't know as much as we do if people hadn't stopped by with stories and photos."
Those memories of the Ambassador's glory days, however, have only fueled its owners' commitment to the neighborhood that surrounds it.
"Our owner is a Marquette grad," Schneider adds, referring to Milwaukee's Jesuit university just a few blocks east of the hotel. "And he fell in love with the neighborhood as a student. His entire livelihood is wrapped up in its success—in several apartment buildings and other properties in the area."
That makes the Ambassador more of a growing pillar in Milwaukee's rebound than a creepy venue for costumed drinking this Halloween. Come for the cocktails, stay for dinner, watch for the glamorous undead on October 31, and come back knowing your choice is fueling the rebirth of the city's heyday.