Within minutes of watching her cook, Bailey Sullivan’s kitchen jargon sticks in the brain. A skewer of octopus, plated with sauces, vegetables and garnishes, simply becomes “octo.” Soon, it’s sweet in your head. As in, “can we do octo rollout?” or “we need a second octo.”
At least, that’s what happened to me and likely to the audience of Bravo’s “Top Chef” Season 22.
About a month after her top-three finish on the show, Sullivan, free of cameras and in her comfort zone, was back to working as executive chef at Monteverde Restaurant & Pastificio. For the past few months, diners at the West Loop restaurant have received their bill with a glowing portrait of Sullivan, celebrating her appearance on the show.
Sullivan’s personal style is memorable — ever-colorful hair, large glasses and rotating patterned bandanas. It seems to tell you everything about her on first look: quirky and easily creative. But that belies a scholarly understanding of Italian cooking history, techniques and terminology, and a serious competitor.
“Competition is about building a sense of community,” said Sullivan. In her view, instead of aiming for domination, it’s key to challenge yourself and others in the hopes of reaching higher peaks as a team.
On the first day of July, Sullivan bantered with the staff on her way to the kitchen. A bartender called her promotion to executive chef the “best thing that ever happened” at the restaurant. Line cooks responded to her lessons or demos with a “sheesh” or “hell yeah, brother.” She told stories about dishwashers who worked up to the kitchen, the women who have loyally manned the pasta station for years and the diverse personalities that make up the restaurant.
“Monteverde is Bailey. And Bailey is Monteverde,” said Sarah Grueneberg, head chef and co-owner. “Just as much as I am Monteverde.”
The octo spiedino was new to most that day, but it was served when the restaurant first opened in 2015, inspired by a trip to Spain. On “Top Chef,” Sullivan and Houston chef Tristen Epps won Episode 6’s elimination challenge with a dish that echoed the Monteverde classic: grilled octo with Kalamata caramel glaze and charred green olive honey relish.
“(Initially,) when I left Monteverde to go to ‘Top Chef’ I felt very confident and comfortable,” said Sullivan, who had run some practice quickfires with Grueneberg, a “Top Chef” alumnus.
But Sullivan’s time on the series started rocky, with an elimination in the second episode for a maple tart. It was her debut on national TV and her first time on camera. She hadn’t even done local TV — and here she was vying for attention with 15 other contestants.
“It was hard going from something very community-based versus being just someone in the crowd,” she said.
Executive chef Bailey Sullivan leads a team meeting with servers at Monteverde Restaurant & Pastificio on July 8, 2025. (E. Jason Wambsgans/Chicago Tribune)
Her journey of rediscovering her confidence in front of the cameras became a major part of her arc. Rather than cooking her authentic self, she tried to anticipate others’ expectations. But she dug in and returned to the competition by winning “Last Chance Kitchen.” Many of her competitors weren’t surprised; frequently, fellow “Top Chef” contestants and Chicago chefs Zubair Mohajir and Cèsar Murillo refer to her as a beast in the kitchen. She made it to the finale in Milan, Italy, where she cooked a four-course progressive meal. Though Sullivan didn’t win the show, judge Gail Simmons told me at the James Beard Awards in June that it was one of the best finale meals she’s ever had.
Of course, Sullivan served octo at the finale. This time, it was pulpo e mozz, a combination that guest judge Richard Blais called “dumb and brilliant.”
Sullivan has no hard feelings about being a runner-up and is proud of her fellow contestants; frequently, she would be the first to hug them and tell them she loved them after a win or a loss.
“With the show, as proud as I was of all of her cooking, I was just as proud of the way she carried herself and the way she treated other people,” said her father, Mike Sullivan.
Bailey Sullivan fell in love with the industry growing up in Goldyburgers, the longtime Forest Park neighborhood staple her father has run since he bought it in 1981. She remembers fondly listening to stories of the Irish immigrants who worked at the restaurant and the patio with ivy.
Bailey Sullivan, executive chef at Monteverde, eating a burger as a child at Goldyburger’s, the restaurant her father, Mike Sullivan, has run since 1981. (Diane Sullivan)
“I would run around and have such a great time,” she said. “So I had this positive image of what restaurants were in my brain.”
Sullivan’s father recalls his daughter and wife watching “Top Chef” during the early years, engrossed in the competition and craft. He didn’t encourage her to join the industry; but from a young age, she had the bug — she joined him on supply runs to Fulton Market, made wing sauce for Super Bowl parties and signed up for cooking classes. His daughter speaks with admiration of his work ethic. She said he still opens and closes down the restaurant every day.
While Goldyburgers may have inculcated that love for restaurants in Sullivan, her father laughs when comparing Goldyburgers to Monteverde.
“This place is completely different than Monteverde,” said Mike Sullivan, beaming. “She’s in a whole different realm.”
He means it literally; Italian food was not a cuisine of personal culinary significance for the Sullivan family. Her entry was actually through noodles — some of her early line cook jobs included working at restaurants like Yusho and Parachute. That led her to a fateful meeting with Grueneberg when they worked together in a ramen battle.
“She was a bright shining light of excitement,” Grueneberg said. “All of the things that I love about cooking, about being a young chef … That passion that you have naturally. That you can’t force. It’s a natural passion for the craft. “
Naturally, the first stop of her journey at Monteverde was the pasta station. Over time, she became a student of Italian regional and atypical cooking, learning deeply from staff, cookbooks and, of course, Grueneberg.
Executive chef Bailey Sullivan finishes dishes at Monteverde Restaurant & Pastificio on July 8, 2025, in Chicago. (E. Jason Wambsgans/Chicago Tribune)
Executive chef Bailey Sullivan fills the pasta with sheep’s milk ricotta at Monteverde Restaurant & Pastificio on July 8, 2025. (E. Jason Wambsgans/Chicago Tribune)
Executive chef Bailey Sullivan makes salumi sauce agnolotti filled with sheep’s milk ricotta at Monteverde Restaurant & Pastificio on July 8, 2025. (E. Jason Wambsgans/Chicago Tribune)
Executive chef Bailey Sullivan makes salumi sauce agnolotti filled with sheep’s milk ricotta at Monteverde Restaurant & Pastificio onJuly 8, 2025. (E. Jason Wambsgans/Chicago Tribune)
Salumi sauce agnolotti filled with sheep’s milk ricotta at Monteverde Restaurant & Pastificio on July 8, 2025. (E. Jason Wambsgans/Chicago Tribune)
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Executive chef Bailey Sullivan finishes dishes at Monteverde Restaurant & Pastificio on July 8, 2025, in Chicago. (E. Jason Wambsgans/Chicago Tribune)
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At Monteverde’s pasta station, her original home, she went through the complexities: extruding, the challenges of sourcing dried pasta and all the variety of shapes. From below the station, she pulled out portioned containers of fresh shapes like gramigna, gnocchetti and fusilloni. From above, she brought out a seriously rustic, well-loved wooden pasta-cutting tool, a “chitarra.” It looks like a harp that could kill.
“As a mentor, when you watch someone who you’ve put a lot of time and nurturing into, to see them blossom and see them utilize the skills they have to make it their own, it’s a really amazing part of the process,” said Grueneberg, talking about watching Sullivan win a “Top Chef” elimination challenge with an octo skewer. “It’s just one of those things that she made it her own.”
In many ways, Sullivan has been directly following the path of her mentor. Grueneberg rose up the ranks at a notable and influential Italian Chicago restaurant, the now-closed, Michelin-starred, Spiaggia. Her next step a few years after competing on “Top Chef” was opening her own restaurant, Monteverde.
Given the obvious parallels, I wondered if a restaurant was next in the works for Sullivan. While it’s not set in stone, both speak of “Bailey’s restaurant” like it’s an inevitability, something on their agenda.
“I think what I’ve realized over the last couple of years is that whatever my restaurant will be, I want it to truly evoke a feeling of who I am,” Sullivan said. “I just want it to have that same aesthetic, that it feels lightweight and a little eccentric, but ethereal and fun.”
Executive chef Bailey Sullivan at Monteverde Restaurant & Pastificio on July 8, 2025. “With the show, as proud as I was of all of her cooking, I was just as proud of the way she carried herself and the way she treated other people,” said her father, Mike Sullivan. (E. Jason Wambsgans/Chicago Tribune)
How will Sullivan present that feeling of “Bailey-ness”? She’s confident the food will come. But the rest? Well, just like in “Top Chef,” she’ll figure it out.
For now, the octo awaits.
In the narrow, clean kitchen, the plancha radiated a dry heat. A row of sieves awaited pasta in aggressively boiling water. Woks sat over flaming burners.
That is to say, it was really hot.
But as nearly a dozen staff watched her demo the octo, the vibe was warm emotionally too. Sullivan, clad in patterned tights, clogs and a trademark vibrant bandana, gave history and technique lessons as she went through the steps.
First, Sullivan explains how the octo came to be on the menu after chef Grueneberg saw a simple preparation in a Spanish coastal town; the octo must be boiled in salt water “from whence it came.”
“It makes the most delicious, tender octopus,” Sullivan said. She shared some more superstitious traditional techniques that they don’t use, like using actual ocean water or adding wine tops. Then, she demonstrated how to brush the octo with an herby marinade right before it’s charred on a surprisingly small grill.
“It’s important you’re giving it the love it needs,” she said while letting the flame kiss the skewer on all four sides.
The octopus spiadino, or “octo,” at Italian restaurant Monteverde on July 8, 2025. (E. Jason Wambsgans/Chicago Tribune)
Afterward, it’s garnished with fresh summer pepper peperonata, dusted with smoky pimenton, sprinkled with toasty garlic chips, lemon juice and adorned with a few dollops of aioli. She narrated her thought process, “maybe three or four,” as she squeezes the sauce onto the plate. Sheesh. Octo!
Next, it’s what she calls “Vanna White time.” She snaked her way through the restaurant, holding up the plated demo octo, servers taking orders glancing over to give her a brief nod. It’s a sign that it’s time to sample. A few moments later Sullivan parked by the stairwell with the octo. The team quickly shuffled past to take a bite in a well-practiced flow. There were murmurs of approval and questions.
Octo can be tough, but the spiadino had a perfectly pliable chew, surrounded by whorls of smoke and spice. Was it the love or was it the discipline of studied cooking? In Sullivan’s hands, it’s indistinguishable.
I began to ask a question, and in it, I registered that I had been saying “octo” without realizing it, even though it had been rattling around my head since watching “Top Chef.”
“You’ve got me saying octo,” I said.
Sous chef Michael Murray turned to me and said, “You’re one of us now.”