Award-Winning Legend Larry’s Comes to Milwaukee
From Sheboygan corner bar to nationally recognized chicken wings.
Legend Larry’s. Photo by Michael Horne.
A visit to Buffalo is as likely to include an order of chicken wings as a trip to Milwaukee is to include beer.
Twenty-five years ago, the inaugural National Buffalo Wing Festival was held in the “Queen City of the Lakes.” That same year, Legend Larry’s opened in Sheboygan as a corner bar with fresh—not frozen—chicken wings bathed in homemade sauces.
The 2026 event drew about 30,000 people to Buffalo. More than 20 restaurants competed in a variety of categories, including Hot, Sweet Heat, BBQ and Traditional Medium.
Legend Larry’s, which will soon open an outlet in Milwaukee, entered the four categories listed above. It took the blue ribbon in the first three mentioned, and a bronze in the fourth. The restaurant has entered the contest since 2005, when its Traditional Medium captured the first prize, and is now the most awarded restaurant in contest history.
Today, the restaurant offers about a dozen sauces, ranging from mild BBQ to extra-hot DOA, plus a few seasonal offerings. It is the hometown favorite in Sheboygan and Sheboygan Falls. Folks laud its sauces in Manitowoc and Green Bay. And now the Legend is on its way to the Cream City, where it is expected to open in early October in the space formerly occupied by Balzac at 1716 N. Arlington Pl.
A Quarter Century of Winging It
Legend Larry’s LLC was incorporated on Sept. 12, 2001, and the original restaurant opened less than a month later. It was run by Larry Schaefer and his wife Tammy. Son Dane was then 17 — the perfect age for a kid to learn the ropes of the family business, and for the folks to get some work out of him. Sister Amber Willis is also involved. Father and his two children were at the Milwaukee location on a recent afternoon in the remodeled restaurant.
Dane and his sister sat at one of the wooden tables lining the north wall of the space. Large television screens were hung throughout the room. It is likely that they will be broadcasting sports games (and maybe “Jeopardy!”) in the near future. The bar has a pass-through window from the kitchen and rustic paneling above the coolers. There are two pinball machines and a number of “Amusement Only” gambling machines. It has a jukebox and an ATM. The plan of operation calls for four garbage cans inside. A fifth will doubtless be needed to accommodate all of the losing pull-tab tickets that will emanate from a vending machine that hangs on a wall.
There were details still to be done here. Milwaukee Tool equipment was arrayed on a table, but no workers were to be seen. That’s because this family gets a lot of work done themselves. If you scrimped and saved, spending 15 years driving a truck to open your dream business — you bet you’re not going to waste any money.
Dane is the spokesperson for the operation. He says there is no beer list yet, but 15 tap lines are ready to be filled. You may be assured the distributors will come a-calling. He is excited about the potential of the adjacent patio in season and about the location in general. The menu will feature the full range of sauced wings, along with sandwiches. “In Sheboygan Falls, we have sandwiches and salads. There will be no salads here,” he told Urban Milwaukee.
A pair of eyes glances from the kitchen pass-through window. They belong to the Legend himself, who is in the kitchen area hooking up various items of equipment like soap dispensers and things of that sort. Already installed are four commercial deep fryers, each with a 75-pound capacity. That’s a lot of wings. Dane expects three people to staff the kitchen during peak times. He has already hired some floor staff; Amber was holding interviews during the visit. She says she is impressed with the quality of the applicants.
Coming Soon!
Society retains its taboos, and there is a big one involving asking a restaurant owner when the place is finally going to open. They’ve been shelling out $4,200 monthly rent on their lease, which runs to 2032 for the 2,520-square-foot space, so there is an incentive. You can’t have Sheboygan people subsidizing the operation here. The best guess is early October, once the place is fully staffed, stocked and trained — and passes its final inspections for a certificate of occupancy.
The 99-seat-capacity restaurant plans to serve until midnight. According to its license application, it expects 21% of sales to come from alcohol and a hefty 74% from food, with entertainment providing 3% and merchandise 2%. It will accept cash and electronic payments.
The landlord, Julilly Kohler, who built the Passeggio in 1997, was able to hold out for a quality tenant. She adamantly would not entertain any plans to turn the location into a club, but wanted to retain it principally as a restaurant. Nor would she accept national chain operations. But helping a family expand their business organically is quite appealing to her spirit. However, as I recall, the place was originally outfitted with Kohler plumbing fixtures. Imagine my shock and horror when I encountered an American Standard toilet in the spacious men’s room.
Legend Larry’s will join La Masa, King Crab Shack and Apollo restaurants in the Passeggio complex.
A Funny Connection
We learn from Dane Schaefer‘s website https://daneschaefer.com/:
CREATIVE SIDE
That Time I Did Comedy
If you’ve seen the Manitowoc Minute, I’m lurking in a few of those videos. I produced Charlie Berens‘ first statewide tour, built his first website, designed early merch and stickers, helped write some sketches, and co-wrote a Green Bay Packers parody of Old Town Road that picked up a lot of traction from Packers fans.
We also co-created Card Sale, a card-based party game we Kickstarted together. It exists. It’s genuinely fun at parties.
I suppose there will be room on the bar shelf for some Berens Old Fashioned Brandy.
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