Edna King and the Roaring Twenties

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Sue Bosman is a private detective who has spent a lifetime researching her family’s history and their connections to Milwaukee. To date, she’s assembled an impressive library consisting of newspaper clippings, documents and certificates, precious photographs, and oral histories that begin the 19th century. 

As a child, Bosman loved hearing her grandmother, Edna King, talk about the 1920s and the excitement of living in the Jazz Age. But as Bosman got older, she realized that Edna danced in several Milwaukee speakeasies and was friendly with gangster Al Capone and Yankee slugger George Herman “Babe” Ruth. “He always told me ask for Herman,” King once said. “That way he’d know it was a friend.”

Edna said she enjoyed bringing Ruth his drinks because he was a generous tipper. By the time she passed away in 1982, King had given her granddaughter enough material to write a book about the flappers and philosophers of the Roaring Twenties.

Shake the Chemise

In 1916, teenage Gilda Gray (nee Marianna Michalska) provocatively shook her chemise while singing in her father-in-law’s Milwaukee tavern. With her Polish accent she pronounced ‘chemise’ as ‘shimmy,’ “Gilda and my grandmother were good friends,” Bosman said. “They lived together for a while as kids and in 1918 they moved to Chicago and rented a small apartment at 1422 North LaSalle Street.” A newspaper publicity photo depicts them in bathing suits taking a ‘polar plunge’ into Lake Michigan. 

The voluptuous Gray became a movie star in 1919, epitomizing the freedom of women in the Twenties. In 1922 she generated a risqué song, “I Wish I Could Shimmy Like My Sister Kate.” “Gilda wanted my grandmother to come to Hollywood with her,” Bosman said. “Instead, Edna moved back to Milwaukee and worked for a gangster named Sam Pick.”

Notorious Club

Edna was hired as a dancer at Pick’s Blue Chip, a notorious club on Hawley and Bluemound Roads. She also married her first husband, Harold Siedelmeyer, who was a con man and bond thief. He hated that she was a nightclub performer in an environment where men drank and gambled. “At one point, Siedelmeyer kidnapped my grandmother and locked her a New York City apartment,” Bosman said. “Her parents had to go to New York and bring her back.” Edna became pregnant with Bosman’s father but left her husband because he repeatedly beat and abused her. “My dad had a tough childhood ... it just wasn’t very stable”, Bosman said. “Because Edna worked at night, she often left him with neighbors and relatives.” 

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Edna was working at the Blue Chip when a Chicago assassin fired a sawed-off shotgun at Pick outside the club. He recovered from the shooting and left his brother, Ed, to run the club. Pick opened an elegant roadhouse at 12600 West Bluemound Avenue, just west of the Milwaukee County boundary line. Edna’s sister, Lola King, worked for Pick, running the club’s hat check concession. 

Pick’s operation was an instant hit with judges, lawyers, visiting movie stars and other celebrities. The shows were on the first floor, and the gambling and girls were upstairs. Pick moved Edna to the club as a featured dancer where she got to know personalities such as actor Spencer Tracy, who remained a lifelong friend. Al Capone was rumored to have a financial interest in Club Madrid and occasionally Pick had Edna ride along to Chicago for bootleg liquor when the club ran low. Edna also recalled buying liquor from Dirty Helen Cromwell’s tavern on St. Paul Avenue.

Hattie McDaniel Worked Here

During one of their many conversations, Edna told Bosman she was close to Hattie McDaniel, a ladies’ room attendant. One evening McDaniel substituted for a performer who fell ill. She brought the house down with “St. Louis Blues.” McDaniel became a regular performer at the club for two years before taking a bus to Los Angeles. She made history as the first person of color to win an Oscar for her performance in “Gone with the Wind.” McDaniel later called Milwaukee “her springboard to Hollywood.” 

Sam Pick’s nightclub burned down in 1951. For the next 45 years the Sleepy Hollow motel occupied the site. The club’s gates remain on the property to this day. Pick died in 1970 and is buried in Spring Hill Cemetery within sight of the former Blue Chip. That section of Hawley Road was nicknamed “Undertakers’ Row” because of the half dozen speakeasies located near the graveyard. Bosman was 25 years old and a seasoned historian when her grandmother died. “I’ve got everything Edna left behind except for some sexy pictures of her in bloomers and a parasol”, she said. “My mother burned those years ago. I guess she wanted to sanitize the family’s history.” Still, Bosman is grateful for the stories her grandmother shared. “She was courageous to talk about her youth”, Bosman said. “I suspect there are many other people like her in family histories that no one knows about.”