Chef Paulie O’Connor got just what he wanted for his birthday.
His parents bought him a power saw to cut meat.
For O’Connor, presenting a delicious steak starts long before the meat hits the heat, though that step counts too. It’s about sourcing high quality beef and wild game meat, which can be expensive. In order to serve the quality he desires, without a price that makes diners faint, he’s performing as much butchering as he can to trim prices on the menu.
“Pretty much we are doing almost everything in house,” he said. “This just helps us kind of combat the costs.”
In another signal to diners that the Million Dollar Cowboy Steakhouse is about fine food minus the fancy airs, O’Connor has stripped away the white tablecloths. Instead, shiny, varnished wooden tables greet those who descend the stairs to the steakhouse hidden beneath the dancing feet of patrons at the Million Dollar Cowboy Bar. O’Connor leases the space and runs the restaurant independently from the bar.
Embracing the cave-like atmosphere, O’Connor said he’s going for a speakeasy feel. For me, the restaurant’s gnarled knotty pine pillars, cowboy-themed upholstery and overall western vibe offered a cozy oasis from all the cool, hard-edged modern interiors that tend to dominate fine dining. As a local, it’s easy to write off the steakhouse as a place for tourists. O’Connor wants to change that.
Locals who might not know O’Connor by name have surely savored some of his creations at Old Yellowstone Garage or one of the Fine Dining Restaurant Group’s establishments. O’Connor grew up in a large Italian family in Hudson Valley, New York, and earned a degree at the Culinary Institute of America Hyde Park.
In his more than two decades in the food and beverage industry, he has worked as corporate sous chef for Il Villaggio Osteria, Silver, Bin22 and the Q Roadhouse & Brewing Co. During his time at Il Villaggio Osteria, he was named as a semifinalist in the James Beard Foundation’s 2011 Best Chef Northwest category.
Before that, O’Connor worked as the chef at OYG in Jackson from 2001 until owners David and Cinzia Gilbert closed its doors in 2007 to move to Italy. With the Gilberts’ blessing and backing, O’Connor opened OYG in Alpine in 2015. Around the same time, he also took on the Million Dollar Cowboy Steakhouse.
Even with two restaurants already on his plate, he added another Herculean task — accepting the executive chef role for Caldera House at Teton Village, where he and his staff created the food for catering and concierge services, the Southcable Cafe and the dining room.
But now he’s downsizing, he said, to focus “a little bit more on my health and just one business.”
Last year, he closed OYG in Alpine and stepped away from the Caldera house. Now he’s pouring all of his foodie obsessions into the Million Dollar Cowboy Steakhouse, which explains a newly revamped winter menu. For OYG fans, keep checking back because lasagna might be showing up as a special or on the summer menu. O’Connor said it will be a more Bolognese-style dish with house-made ricotta.
“I got a strong passion for what I do,” O’Connor said of his drive to make as much as he can — from cheeses to sauces to stocks — from scratch.
The Italian-influenced steakhouse offers a wide range of choices from table shares and lighter fare — for a more affordable option — all the way up to a special reserve menu for high-end meats such as Japanese A5 wagyu grade 9-10 from Miyazaki, Japan (selling at $30 per ounce with a 3-ounce minimum). For that price, O’Connor will present diners with a certificate of origin for the beef, a paper documenting the life history of the cow along with its tongue print.
During a recent visit, our group started with the table shares. We passed around a wild game board ($19) with sausages made from pheasant and cognac, pickled vegetables and dried nuts and fruit. The chef’s selection of sausages were well portioned for sharing.
We took our server’s recommendation to try the boot kickers, jalapeño poppers stuffed with beef brisket, house-made pimento cheese, guanciale and poblano sauce for $16. The kickers looked big enough to share so a friend and I split one, a decision we both quickly regretted after sampling the spicy, savory sensation. So we “split” a second one. I love nachos, and the kickers reminded me of all the delicious flavors you find in a fancy nacho minus the risk of soggy chips.
For those ready to splurge, O’Connor offers a family style meal with his signature “John Wayne & Friends” — the butcher cut of the night served with salad, creamed spinach, smashed potatoes and ample Béarnaise (MP $225-$325) for up to seven people, depending on the heft of your appetite. Cuts can range from a 40-ounce porterhouse steak to a more than 60-ounce tomahawk steak, essentially a ribeye with a longer bone on it. Prices are not for the faint of heart.
“The big John Wayne steaks are a big seller,” O’Connor said. “We had a couple of steaks this year from the Snake River Farms that we sold for like 520 bucks, 60-ounce. ...There’s a clientele here that wants to come out and spend good money and eat good food.”
For single entrees, the menu offers cooked-to-order cuts of pasture-raised Allen Brothers beef ($36-MP) alongside domestic or international wagyu ($46), bone-in buffalo ribeye from Gillette ($69), and gamier fare like wild boar shank ($34) and Denver elk T-bone ($48).
I ordered the 6-ounce buffalo tenderloin ($49), cooked medium rare. The well seasoned meat proved inexplicably tender without any fatty feel.
For preparing steaks, O’Connor recently purchased new Japanese grills for the kitchen.
“We finish them on the Yakitori grills just so it gets that smoked flavor on the outside of the steak,” he said.
My buffalo tenderloin paired perfectly with a hearty red wine, selected by the server, from the restaurant’s diverse wine list. The bar also boasts specialty cocktails with house-made shrubs, syrups and tonics alongside whiskey flights. For those wishing to avoid alcohol, tasty mocktails are available, like a Prickly Pear Snap with pear purée, pomegranate juice and cinnamon syrup ($6).
Given O’Connor’s OYG acclaim, I’ll be back to try his latest twist on lasagna along with the Italian coarse polenta with mushrooms, pomegranate, vegan butter, red wine and thyme and the classic French onion soup ($13) with gruyère and a baguette from the local 460 bakery.
For the right family occasion, I might even inquire about the John Wayne.
For those with a hankering to try anything on the menu, the restaurant’s last day for the winter season will be April 4. ￼