Once an innovative burger and shake joint, Winstead’s is now a dying chain—or is it? Is nostalgia enough to keep the iconic KC restaurant open?
Winstead’s, home of the steakburger and one of KC’s longest-standing restaurants, is dwindling. Just seven years ago, the Midwest-born chain had nine area locations. Now, it’s down to two—the flagship on the Plaza and one at I-435 and Roe in Overland Park. Even so, you don’t have to wander too far to find a local who will happily vouch for Skyscraper shakes and a 50/50 side of onion rings and fries.
So, why is the chain’s future so precarious? Is the restaurant’s once-outstanding reputation strong enough to ensure its future, or will Winstead’s soon disappear?
As a KC native, I’m aware of the impact Winstead’s has had on the city, even if it wasn’t my family’s go-to diner. The restaurant’s hold on KC’s heart especially came into focus for me last year, when I was invited to talk about the best burgers in town with KC Shepherd’s Center’s Adventures in Learning program for older adults, which is described as a “lifelong learning program” on their website. I quickly opened the floor for comments (how many ways can I describe my love for smash burgers and mustard before eyes begin to roll?). Time after time, they mentioned Winstead’s. It was endearing to hear them fondly reminisce about visiting the burger joint back in the day, whether it was with their sorority sisters or for a birthday celebration. I wondered: What did Winstead’s have then that it lacks now?
“HOW YA DOIN’, HONEY?”
the waitress enthusiastically said before she took my order on a recent visit to the Plaza’s Winstead’s. The interior still has the classic ’50s diner vibe, but the ripped and worn mint-green booths combined with stained carpet give another meaning to the word “retro.” My husband, a Winstead’s fan since childhood, was delighted to be there. I, on the other hand, was curious to see if the interior would reflect the food. The waitress and her congenial disposition gave me hope.
Memorable waitresses helped set the tone when Kathryn Winstead and her family opened the first Winstead’s drive-in in Springfield, Illinois. The popular restaurant then expanded to Jacksonville, Illinois; Fort Wayne, Indiana; and Sedalia, Missouri. The fifth and most iconic location opened in 1940 on the Country Club Plaza (right when overlords Tom Pendergast and developer J.C. Nichols were in charge). The Plaza site was the first of the chain to be designed in the classic Streamline Moderne style and was not only a drive-in, but a restaurant, too.
Daniel Coleman’s 2008 biography of Kathryn Winstead reveals that “many diners enjoyed car-side service as well as the interior’s 10 booths and two counters. Drivers backed into parking spots and flashed their headlights to hail a Winstead’s carhop, who was sure to arrive quickly and might be propelled by roller skates.”
When Winstead’s first opened, it offered little more than beefy steakburgers. Fries and frosty malts weren’t added to the menu until 1957. But even with an extremely limited early menu, Winstead’s took off. It was so successful that the family eventually bought the Plaza location from Nichols.
In the ’70s, native Kansas Citian Calvin Trillin, the lauded food writer and New Yorker contributor, referred to Winstead’s steakburger as “monumental purity” and firmly claimed it the best in the world. Over the next several decades, Winstead’s restaurants popped up in Independence, Lee’s Summit, North KC, Lenexa, Overland Park and Olathe, among others.
But obviously, “the bigger, the better” concept didn’t pay off. The Haddad Restaurant Group, which bought Winstead’s in 1988, told the Kansas City Business Journal in 2018 that it planned “to double the number of its Winstead’s restaurants in the next three to five years,” despite the fact that multiple locations had already closed. The plan failed. In 2020, the company filed for bankruptcy and eventually liquidated. That year also marked the closing of the diner’s Leawood location, leaving only the two current locales.
What went wrong? I posed this question to a good family friend, Jan Harness, who remembers visiting Winstead’s as a child in the ’60s.
“The Winstead’s of my youth was better,” Harness says. “I wish they hadn’t expanded it locally. Going to the Plaza, to that original Winstead’s, was a treat that went beyond getting a burger and fries and the frosty malt. It was a special event.”
Is a trip to one of the two remaining locations still a treat? Online reviews are, well, spotty. Over the past 10 years, plenty of unsatisfied customers mainly complain about service and quality of food. On the other hand, for every negative review, there are positive and often nostalgic reviews stating the experience was just as diners remembered.
Sarah Hibbert, general manager of the Plaza Winstead’s, remains upbeat, crediting the great location and cheap prices to its continued success, even through the pandemic. Regulars, school field trips, late-night wedding catering and professionals on their lunch break keep the restaurant busy.
“Our customers come from all over, and we appreciate their dedication,” says Hibbert, who has been managing the Plaza location for four years. “Business is great, and this location will be around for many more years to come.”
When the friendly waitress took my order, it was a busy Friday evening. The place was packed, and the staff meant business—in a good way. A busser was consistently making rounds, and our waitress apologized for making us wait, even though we couldn’t have been there for more than seven to eight minutes before she took our order. My chicken sandwich wasn’t something that needs to be ordered again, but my husband’s steakburger with the works—ketchup, mustard, pickles, a whole onion slice and bacon—was greasy and satisfying. It was strangely better than the one I had gotten through the drive-thru just a few days earlier. The 50/50 side of onion rings and tots were nothing out of this world, but they were crisp, and, well, we ate the hell out of them. I will say my cherry limeade made me feel like a kid again. It was topped with a small scoop of green sherbert and a fresh-squeezed lime. Screw Sonic. This was great.
Maybe this will devalue me as a food critic to some, but I can still appreciate a spot that does it “just fine.” Nostalgia is a flavor, too, and I understood this well sitting in my ripped booth with a massive broken-down jukebox in sight and a table full of greasy fried foods that predate the health food movement.
But let’s get back to the big question: What does the future hold for Winstead’s?
With locations closing down left and right this past decade, my focus is on the Plaza site, the pillar of KC’s historic restaurant scene. Under Hibbert’s care, my experience was prompt and overall satisfying. And you can’t argue with substantial conveniences like 24/7 service, a drive-thru and the affordable, dirt cheap menu.
Winstead’s clientele is so loyal that there’s no need for any extremes like a rebrand. But the interior needs updating—some kind of “oomph” so it’s retro by design, not because it’s forgotten. Some TLC could do wonders to make a visit special again, a place where young Kansas Citians can create memories. I’m getting flashbacks to the 1989 film Field of Dreams: “If you build it, he will come.”
Is Winstead’s a dying chain? For all intents and purposes, yes. But, for now, nostalgia prevails. My guess: The odds are … 50/50.
