Top left: Not your typical steakhouse fare—watermelon salad, pumpkin seed pesto, polenta croutons, chicken skin vinaigrette. Top right: Billy the Kid is a pasta carbonara with a silky sous vide egg sauce and tons of fresh herbs. Left: Bar food gets elevated with buffalo fried quail, celery root slaw, Jackson hot sauce. Middle: The Bone Marrow and Cheddar Fondue is one of the Cowboy Steakhouse’s must-order starters. Right: The zabuton steak is an incredibly tender cut named after its shape, like that of a flat Japanese sitting cushion. (Photo, top left, top right and bottom left: annie fenn, md; Bottom middle and bottom left: cowboy steakhouse)

Published in Planet Jackson Hole By Annie Fenn, MD on May 24, 2016

Chef Paulie O’Connor converts Cowboy Steakhouse into a culinary powerhouse.

JACKSON HOLE, WY – Before I tell you about the Million Dollar Cowboy Steakhouse’s new chef and revamped menu, I should probably mention that steakhouse fare is not my cup of tea. Overpriced steaks, unimaginative dishes, gloopy overdressed salads, and throngs of tourists seem to be the norm, especially in Jackson. In general, I find the whole steakhouse experience to be disappointing and the food ho-hum.

But when I learned that Chef Paulie O’Connor had taken over the kitchen at Million Dollar Cowboy Steakhouse, I had to check it out. Not only did O’Connor take over the business aspect of things at the steakhouse, he is also on the business end of a spatula—in the kitchen on a regular basis. This promised to be a very good thing.

O’Connor, or Paulie as everyone calls him, has been a beloved local chef since his days cooking at the Old Yellowstone Garage in Jackson under owners Cinzia and David Gilbert. For almost six years, Paulie cranked out dozens of now legendary Italian dishes to a loyal troupe of locals, myself amongst them. I celebrated all of my birthdays there, watched my kids grow up from one all-you-can-eat Sunday pizza night to the next, and have fond memories of buying my nephew Alex his first legal drink at OYG’s bar (Campari, of course).

When OYG closed in 2007, Paulie took over as executive chef at Il Villaggio Osteria. Once again, we locals were treated to Paulie’s incredible Italian food—handmade pastas, thin crust pizzas, innovative antipasti, perfectly executed seafood and steaks, and homey Sicilian desserts. During his time at Osteria, Paulie was nominated for a James Beard Award as a semifinalist for Best Chef Northwest.

I figured if anyone could make me fall in love with a steakhouse, it was Chef Paulie. And so I checked my preconceived notions on the boardwalk, entered the Cowboy Bar amongst the throngs of men on guycation and dolled up women in Western attire, headed down the stairs to the basement and straight through the saloon doors of the Million Dollar Cowboy Steakhouse.

The restaurant was brighter than I recalled, yet still had that old Jackson feel of knobby pine and cowboy print upholstery. The first friendly faces to greet me were wine expert Jean-Paul Glaume and his wife Tilly, key staff members from Paulie’s OYG days. What a good sign that Paulie had gotten the OYG family back together after all these years.

Paulie’s big personality is evident on the Cowboy menu. It’s laugh-out-loud funny and has so many delicious possibilities it took my group of 10 women quite a long time to order. We wanted to try everything, from the Bone Marrow and Cheddar Fondue, served with wild mushrooms, buffalo bratwurst and crostini; to the Charred Baby Iceberg Salad; to the Billy the Kid, a bucatini carbonara with lamb pancetta, spring peas, black truffle, and a soft egg on top. There were vegetable side dishes that we loved, like the creamed spinach and the whiskey glazed carrots.

And there were steaks: wild game cuts, Allen Brothers prime beef cuts, and Snake River Farms Wagyu cuts. Some of the steaks are enormous, like the 18-ounce bone-in rib eye, big enough to share with four or five friends. “We are definitely pushing the boundaries by selling bigger steaks,” Paulie said.

My group chose to share two smaller steaks, the 10-ounce beef zabuton, and the 10-ounce skirt steak. Both were deeply flavorful and cooked to perfection. Since that dinner back in December just after the Cowboy Steakhouse reopened, I’ve been back with big groups, small groups, with my kids, on date night with my husband, and to the bar for a late night indulgence of foie gras and a glass from Glaume’s excellent list of wines.

On each visit it strikes me that the Cowboy Steakhouse staff just loves working with Paulie. In fact, mentoring young chefs is something he takes very seriously.

“It’s important the staff feels like they are really a part of it,” Paulie said. “We do a lot of tastings together to powwow over the dishes. A dish evolves when staff members get involved.” By the way: Diners can end their meal with good karma by ordering a Bucket of Beers for the kitchen staff off the dessert menu.

Chef Paulie is determined to make the new Million Dollar Cowboy Steakhouse a place where locals can feel at home. For all his old OYG fans, he hopes to have an OYG night once a week to bring back some of those classic Italian dishes. He’s renamed the bar The Den with its own nicely priced dishes like the Buffalo Fried Quail ($13), the Sweet Potato Falafel Burger ($17), and the Wagyu Steak Frites with Asian Chimichurri ($17). Soon he’ll be rolling out whiskey flights (three half-ounce shots paired with a small plate, like a foie gras scotch bonbon) and a Knife Club (buy a New West KnifeWorks culinary knife, get a discount on food or alcohol.)

Back in the days when Paulie was working at Il Villaggio Osteria and overseeing a number of restaurants for Fine Dining Restaurant Group, he admits he had a good position and a great boss in Gavin Fine. But a voice in his head kept telling him: “Don’t settle, don’t be afraid to risk everything and see what happens.” Now, as he juggles his multiple businesses—not just the newly wonderful Million Dollar Cowboy Steakhouse, but his OYG restaurant in Alpine, OYG catering, and his new venture at Caldera House in Teton Village coming this winter, I have to wonder if he’ll need to be cloned to keep it all going.

“I’ve been working for other people my whole life,” Paulie said, “but it’s more satisfying to be on my own. Each decision I make has a ripple effect on how my life goes.” And he constantly gives credit to his staff for all the great work they do.

It will take many more visits for me to try everything on Paulie’s extensive menu at the Cowboy. Next time I’ll probably order the Joe Pesce for old times sake—a throwback to the old OYG menu, Paulie prepares Corvina sea bass piccata style with a buckwheat salad, brocciolini and a Meyer Lemon Vinaigrette. I guess you could say Paulie has made a steakhouse fan out of me after all. PJH

The Million Dollar Cowboy Steakhouse is open daily from 5:30 pm. OYG in Alpine is open Thursday through Sunday and just started offering Sunday brunch. OYG catering is available for private dining, corporate events, weddings and parties.