Executive chef Christian Ragano is helping to expedite in the bustling kitchen of Cindy’s, the rooftop restaurant at the recently opened Chicago Athletic Association Hotel. Between calling out orders for cauliflower and burrata, he alternates sips of Spanish sparkling mineral water with bites of smoked soy shoyu, momotaro vinaigrette and a rapturously pungent Foxglove cheese. These are a few of the products brought in by purveyor Michael Clark, a representative of Fortune Fish who’s been working with Ragano since 2002. Clark sips espresso as he guides Ragano through the tastes, but little explanation is necessary. He focuses on items he thinks Ragano would be into, and after 13 years, he has a good idea of what the chef wants, such as the ginger-flavored drinking vinegar and the whole meagre fish he brought that day. Ragano is surprised by the mineral water: “It’s rich — almost too rich, but I like it,” he says, pushing his glass in front of Clark with a smirk. “You need to hydrate after your 18 fucking espressos.” Clark leaves Ragano with a hug, and the chef beckons him to come back for drinks soon.

Relationships seem very important to Ragano, especially in his new position at the helm of a considerable food and drink operation inside this very high-profile hotel property. When his attention isn’t on the plates coming out in front of him, it’s on the people creating them, all of whom have been assigned nicknames by Ragano. There’s “Oh-Fuhh” for Franklin, “Tres” for José, “Bubble Gum” for Kevin, and anecdotes to accompany them all — and that’s just the 13th floor. The 8th floor houses the main hotel kitchen, and Ragano descends to it frequently to ensure the day’s meetings and events menus are running smoothly. Today, a pastry cook stops him with a knuckle and hip bump to put in a good word for a friend of hers who will be coming in for an interview tomorrow — someone she swears “isn’t a caveman, nor a pirate.” To call Ragano an active listener is an understatement: “Pirates are OK,” he says. “Find out his last name.”

Cindy's Cauliflower Credit Neil Burger (1)
Roasted cauliflower with caper, raisin and pine nut ragout at Cindy’s, the rooftop restaurant at the newly opened Chicago Athletic Association Hotel. (Photo: Neil Burger.)

But Ragano wasn’t always so socially inclined, at least not in the academic setting. “I hated going to high school,” he says. “I was little and went to an all-male boarding school, and I got picked on — a lot.” It wasn’t until the five-foot-five Queens, New York, native (“on a good day, five foot seven in clogs,” he adds) started working at his dad’s Italian restaurant that he began to find the social circles he wanted to be a part of, and where he felt the camaraderie that the industry offered. “It was about pulling together with these people to make it all happen, and being a part of something that we all felt was special,” says Ragano. “Suddenly it was like, ‘I want to go to work. I want to be there more than I want to be at school, more than I want to be anywhere else in my life right now.’ To a certain extent, I found a place where I felt like I really fit in.”

From there, he picked up shifts at restaurants throughout Long Island, including Tuscany, where the chef’s dishes of ribollita and Tuscan white bean soup turned Ragano’s understanding of Italian food on its head. “Italian food to me was red sauce — meatballs, spaghetti, lasagna — and this guy was doing stuff that was completely different and absolutely beautiful,” he recalls. “I decided that I wanted to learn how to make that, that I wanted to learn how to do that.”

He enrolled in the Culinary Institute of America in Hyde Park, New York, and loathed the first six months. “I had never really worked in a real kitchen before, and I got my ass beat every single day,” he says. “It was rough. It wasn’t easy for me.” That struggle only continued during his externship at the Trillium Room at the Sagamore, where the chef laid into him. “He screamed at me, yelled at me and he absolutely broke me,” says Ragano. He carried that humility back to culinary school, determined to flee the industry as soon as he graduated. “I kept my head down the first month I was back and didn’t talk to anyone, but once I picked my head up again, I realized I could cook better than the majority of the people in my class,” he says.

That observation gave him the confidence he needed to carry on in the restaurant scene, and a school-sparked romance gave him reason enough to pick up and move with her to Chicago. He landed his first job at fine-dining French fixture Tru, where he harnessed his interest in the French classics and the people who helped propel them over the years, including Alain Ducasse and Joël Robuchon. His passion for Old World cuisine took him to NoMI in the Park Hyatt, where his education in French cooking evolved under the tutelage of the chef who would eventually become his biggest mentor: Christophe David. “He taught me what quality products really, really are,” says Ragano. “That there doesn’t need to be overmanipulation of ingredients, to let the product speak for itself.” David’s advice extended beyond the treatment of just food. “He showed me what it was to be respectful to your employees, and to lead by example — that you have to work just as hard or harder than them.”

“A lot of the chefs I called were just like, ‘Sorry, you’re on your own — you have to figure this shit out for yourself.’ That’s not every chef in New York, but I did encounter a lot of people like that. In Chicago, they’re more than happy to tell you, if not give you, those people’s contacts. It’s all about bettering the population of chefs in the city.”

Ragano pocketed that advice when he moved back to New York in 2010. He quickly realized, though, that the city that had raised him wasn’t welcoming him back with entirely open arms when it came to trade secrets and purveyor tips. “A lot of the chefs I called were just like, ‘Sorry, you’re on your own — you have to figure this shit out for yourself,’” he says. “That’s not every chef in New York, but I did encounter a lot of people like that.” It was a hard knock compared to his time in Chicago, where he had mingled with a chef cohort that was, for him, much more forthcoming with such facts. “In Chicago, they’re more than happy to tell you, if not give you, those people’s contacts,” he says. “It’s all about bettering the population of chefs in the city.”

That rejection from his hometown caused Ragano to reverse course, returning to the community in which he’d put his trust for the previous 10 years. The team behind the Chicago Athletic Association brought him on in April to oversee the new hotel’s food and beverage execution, along with the menu at Cindy’s: the feminine, rooftop counterpart to the four drinking and dining venues that coexist below, including Chicago’s second Shake Shack. With communal, picnic-style seating, fire pits and towering skylight ceilings, the vibe at Cindy’s plays off of a high-end Michigan beach house, with high-end art to boot: An original Andy Warhol portrait of philanthropist Cindy Pritzker (for whom the restaurant is named and whose son, John Pritzker, is one of the hotel’s owners) overlooks the private dining room. The dishes align with this feeling. Think Frogmore stew, michelada-style clams and fried local walleye, sourced from nearby Lake Superior. Everything is meant for sharing, but make no mistake about it: The dishes are far from measly.

“We don’t do anything small here,” says Ragano. “It’s meant to be a family dinner.” Making sizable plates was the easy part for the chef, who grew up in an Italian-German family with blowout dinners of bresaola, ravioli, sausage and meatballs for 30 strong every Sunday. This upbringing instilled in him a lifelong love of food, he says. “My dad can’t go a day in life without eating pasta and red sauce, and my grandfather on my mother’s side was a butcher and blacksmith by trade — my mom grew up riding pigs in the backyard.” It was those days, too, that Ragano received his own moniker: “Keeshy,” the closest his younger brother came to pronouncing his name.

The restaurant’s 3 p.m. opening time isn’t so conducive to long-form, seated family meals, so the staff takes it when they can, in the kitchen and in turns. Today, it’s pasta with chicken, corn and poblano cream sauce from Kevin, aka “Bubble Gum,” and Ragano dives into a bowl of the stuff once a handful of cooks have taken a fair stab at it.

And while this particular comida is not so Italian, nor so planned, it packs in everything else you might expect from a family gathering: sounds of clanging pots and jestful verbal jabs, high fives and handshakes, spinning plates, a stereo blasting OAR (chef de cuisine Jeff Arasi is on music today). Along with all this, there is an air of familiarity and acceptance in this kitchen. For Ragano, and perhaps for the others who inhabit it, it’s a place to call home, if needed — and a place to fit in.