In Dining

The Five O'Clock Steakhouse is legendary on Milwaukee's dining scene, though it got it's start as a tavern in a different location.

Urban spelunking: Five O'Clock Steakhouse

It's time for Dining Month, presented by Deer District and its spooky Halloween-themed alter ego, Fear District. Throughout the month of October, we'll be serving up fun and fascinating content about all things food. The signature dish, however, is our 2019 Best of Dining poll, who's winners we will dish out all month long. Get hungry, Milwaukee!

In any city, there are a handful of culinary landmarks that have remained consistent across the decades and have become iconic symbols of the local culture. In Milwaukee, one of those places has long been the Five O'Clock Steakhouse.

Though it began life as a tavern, the Five O'Clock has long since become a respected leader in the Milwaukee dining world, for its top-notch food and evocative, retro supper club atmosphere.

This winning combination has not only made Five O'Clock Steakhouse one of the city's top – if not THE city's top – special occasions venue, it has won countless accolades here and beyond for the place, now run by Managing Partner Stelio Kalkounos.

Recently, the steakhouse took home its fifth straight victory in OnMilwaukee's Best of Dining readers poll.

Two of the main draws at the Five O'Clock: the bar and the steak. (PHOTOS: Facebook)

While the restaurant and lounge has long occupied its home at 2416 W. State St., that building is not the original home of the Five O'Clock Club, which began life as a bar.

The building in which Five O'Clock Club is located was built in 1909 on land that was previously occupied by a pair of homes by real estate developer August Dietrich (aka Diederich).

Born in New York City in 1858, Dietrich came to Milwaukee as a youth and attended Milwaukee Public Schools. In the 1890s, Dietrich moved into the real estate, fire insurance and loan business in the mid-1890s. He was also active in politics and the community, serving as an alderman in two districts.

Like many of his colleagues, Dietrich invested in the construction of commercial buildings which could be rented to tenants – both residential and commercial – and sold at a profit.

The store and flat building he hired architect Charles Tharinger to design at 24th and State Street was close to his home on North 28th Street.

Tharinger – who also designed this residence and this distinctive commercial building, among others – drew a red-brick structure with two stores flanking an entrance to the apartments above. A cornice runs along the tops of the storefronts and a pair of window bays capped with another cornice with brackets are the main features of the second floor. Each tripartite bay has an arched central window.

Two windows above the entrance to the apartments have Jacobean revival influenced window surrounds, and the masonry has a repeating projecting brick motif.

The building, which would house two stores and two apartments was constructed by mason R. Hoeppner and carpenter William Strack to erect the structure.

A 1934 floor plan found among city records.

A 1909 permit suggests that one of the retail spaces was to house a bakery. In 1910, a machinist named Carl Birschel opened a delicatessen in one of the storefronts, and operated there until 1919.

By 1920, William Schneider opened a pharmacy in the building which, by 1927, was run by Ben Porath, who lived upstairs. Porath died four years later at the age of 38, his shop by then renamed Ben's Drug Store.

In 1932, a grease trap was installed and a "Mr. Turner" opened a restaurant in the former drug store, but he was soon replaced by Alma Lapsley, who changed the name to Mother's Restaurant.

But that incarnation, too, would prove short-lived, as in 1933, JoAnn Clark first opened a restaurant and then a bakery. Over in the storefront to the east a Mrs. Drenka was operating her "Mrs. Drenka's Products."

With Prohibition repealed, taverns were opened everywhere in Milwaukee and Frank Murray moved his eponymous bar into the by-then vacant storefront in 1935 and operated for a couple years, before Frank Kelly took over the place in '38, rechristening it Kelly's Tavern. Mrs. Drenka was replaced by H.W. Weimer Co.'s tin shop.

When Murray closed, Adrian Traas took over and the era of the Five O'Clock Club begins on 24th and State.

The birthplace of the Five O'Clock Club was a long-gone tavern building at 1217 W. Galena St., now a barren lot overlooking the I-43 freeway (and, perhaps appropriately, Leinenkugel's 10th Street Brewery across the busy interstate).

When Prohibition ended in 1933, this place became Fellner's Tavern but by 1936 Bertha Mack and her husband had taken it over and renamed it the Five O'Clock Club.

"Your drink is on the house every afternoon at five, with Mack's compliments," declared a newspaper ad. "Come in soon, come in often. A delicious full course dinner, complete from soup to dessert, offering delicious chicken and steak."

The cost of that meal? Sixty-five cents.

By 1938, Adrian and Sue Traas were behind the bar at the Five O'Clock Club, and when they relocated to 2416 W. State St. later that year they kept the name. The old place, meanwhile became home to the Joe Deutsch Cafe, itself long-standing Milwaukee favorite.

Traas would remain until 1943, when John W. Cregar, who was no stranger to newspapermen, took over the bar.

Prohibition was repealed in 1933, but already by July of that year, George Gebhard, Cregar's partner in the Sunset tavern at 1129 N. Van Buren St. (which had also been located at 1214 N. Jackson St.), had advertised that he had "dissolved partnership with John W. Cregar ... (and) will not be responsible for debts after this date, July 25, 1933."

(PHOTOS: Courtesy of Cami Cregar)

The following year, Cregar paid his $200 license fee, but was then denied a license by the Common Council after neighbors' complaints about the bar. When he applied for a refund of the fee, it was denied. Cregar's suit was being used as a test case and more than 200 similar cases were waiting to see how the judge would rule before filing their own suits.

The suit was dismissed, with the judge ruling that, "Even though Cregar was qualified to operate a tavern, the council ruled that under the statues, he was not entitled to a license. A license to sell intoxicating liquor is a privilege to be enjoyed with the conditions are complied with. Society has a right to protect itself and help sobriety, peace, comfort and happiness of the community, and to demand reasonable regulations, and such right is tantamount to the private rights of the individual."

Cregar's bar became Dominic Maggio's barber shop. And beginning in 1944, Cregar and his wife Nina ran the Five O'Clock Club, being the last owner before Wilmer "Bill" Coerper took over in 1948 and lent his surname to the business for the next half-century.

Coerper expanded into a former belt store next door, adding the dining room, in 1950 and the upper-level Alley Cat Lounge soon after.

It was during the Coerper's years that the business grew into a legendary Milwaukee eatery, thanks to its great steaks, classic supper club relish trays and dark, mysterious atmosphere.

It's a place that has, in more recent years, won accolades from Saveur magazine, the Travel Channel, Thrillist and others.

Before his death in 1991 Coerper himself was, for decades, one of the big draws, in addition to the food and classic decor.

A pair of early 1960s renderings for exterior signage.

According to long-time customer Karin Gundrum, "Old man Coerper would stand guard at the hostess' spot keeping track of the comings and goings of everyone in his restaurant. For those of you who have never had the chance to meet Mr. Coerper, he was a man of small stature, gruff, with a full head of snow-white hair.

Coerper's around 1963. (PHOTO: City of Milwaukee)

"Even with his petite frame," she wrote in a memory she submitted as part of a contest, "he would boss around those waitresses like there was no tomorrow. It was funny to watch the constant herding of his waitstaff."

Later, Coerper's son Ted would take over the family restaurant.

In 2004 the Kalkounos family, which owns some steakhouses in suburban Chicagoland, bought the place.

George Kalkounos was born into a family of farmers in Pyrgiotika Nafplion in southeastern Greece, according to his son, Stelio.

The family came to America in 1966, stopping first in Brooklyn. George, says his son, "moved to Wisconsin to pursue opportunities in the restaurant and cheese businesses," before moving to Chicago in 1975, where he opened a number of restaurants and event halls.

"Quite an achievement for someone with a third grade education," says his son.

"In 2002, my father's cousin Sam, heard a rumor in the restaurant community that Ted Coerper was thinking of selling," says the younger Kalkounos.

"He pushed my father to begin discussions with the Coerper's. My father immediately began pursuing the opportunity. Many other entrepreneurs were interested, but Ted (Coerper) preferred to sell it to another family business."

Kalkounos says that Ted Coerper remained a fixture at the restaurant.

"Over the last few years of Ted's life, he was a regular and loved seeing the place busy and growing."

Coerper died in 2017 at the age of 83.

A few years ago, Kalkounos – who is passionate about the history of the Five O'Clock and of restoring as much of it as possible – asked customers for their memories, and garnered an impressive response, including photographs from a 97-year-old customer who had held her wedding there decades and decades ago.

"It is amazing to see how Five O'Clock Steakhouse has been ingrained in customers' lives for generations," Kalkounos told OnMilwaukee. "We received stories of birthdays, proposals, weddings, acts of kindness and even one story of college roommates stealing leftovers."

Around the same time, an old mural, signed by painter H.J. Scharwick, was uncovered in the bar area.

The mural (seen in then and now side-by-side images above), which shows a nude female figure with its arms around the neck of a black winged horse – both rising up from a cloud – had long been rumored to be hidden behind the mirrors on the walls of Five O'Clock bar.

Kalkounos had it restored.

Some Alley Cat lounge images, including the organ Chubby Neiland played.

A few years earlier, Kalkounos – who is also a musician – reopened the Alley Cat Lounge, initially launched in the as a VIP room – where local organ star Chubby Neiland could often be heard, among others – bringing live music back to the space, which had closed in 1970.

Still the pinnacle of supper club steakhouses in Milwaukee, the Five O'Clock Steakhouse is also packed full of delectable history.

"My family took over this legendary business 15 years ago and have since passed it down to me, so there's pressure to maintain the standards, and manage its growth," says Kalkounos.

"I feel it's my duty to protect this Milwaukee landmark and help guide it through the next 30 years. The amazing thing is that we are experiencing record increases in covers and sales without compromising who we are. It is an honor to be the current steward of a thriving business that's over 70 years old in the same location here in Milwaukee."


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