Dine in Style

When he was young, Paulie O’Connor’s dad told him there are two career paths that will always be in high demand: mortician—because everyone dies—and the food industry—because everyone eats. He chose food.

Recently, O’Connor has taken over the Million Dollar Cowboy Steakhouse that resides below the iconic bar. The restaurant has gone through many owners, and has featured several different genres of food, ranging from Mexican cuisine to burgers.

Now, O’Connor is changing the menu and the atmosphere again, creating what he calls a “speakeasy steak house with a modern twist.”

O’Connor grew up outside of Albany, New York, and attended the Culinary Institute of America near New York City. After graduating, he headed west to work in Park City, Utah, and then opened an Italian restaurant with his cousin called Stoneground Kitchen. After a year and a half, he was ready for a new adventure.

“I came up here for a vacation for a couple days and then really fell in love with the place,” O’Connor says.

The chef put in his time at Jackson restaurants, working for Calico, Old Yellowstone Garage, Il Villaggio Osteria, Bin22, and Q Roadhouse. After more than 10 years moving up in the local culinary scene, he took some time to decompress and travel for eight months, working short stints at restaurants in Connecticut, San Francisco, and Seattle along the way.

When he returned to Jackson, he started Old Yellowstone Garage Catering, opened a restaurant of the same name in Alpine, Wyoming, and recently took over ownership of the historic Million Dollar Cowboy Steakhouse in downtown Jackson.

“I am trying to re-brand everything as a speakeasy steak house because we are underground,” he says. “We just renamed the bar area ‘The Den.’”

Entering the Million Dollar Cowboy Bar, the scene completely transforms as one steps downstairs into the steak house. The aesthetics morph from classic cowboy to mountain chic. O’Connor describes the menu as classic steak house with a modern twist, but he’s modest about the creativity in his food.

“As soon as you want to stop learning in the profession you're in, then it’s time to retire. There is always something to learn as a chef.”
Paulie O'Connor

The restaurant offers large cuts of prime meats and wild game with innovative sauces, appetizers, sides, and salads. It features poppers made with duck, citrus cream cheese, bacon, and tamarind barbecue sauce. There is also a take on the classic iceberg salad, made with pickled egg, shishito peppers, and deep-fried braised pork belly cut up like croutons.

O’Connor spends the Jackson off-seasons traveling the world to meet new chefs and discover creative and delicious new dishes to introduce to Jackson. He is constantly focused on innovating and learning.

“As soon as you want to stop learning in the profession you’re in, then it’s time to retire,” he says. “There is always something to learn as a chef.”