Elm Grove was the location of one of the Midwest’s most notorious speak-easy joints, Club Madrid. It was a popular hotspot that served fine food and offered a variety of musical talent and other acts, black market booze, gambling and prostitution.
It was built in the early 1920s at the start of prohibition. It was located in Waukesha County just over the Milwaukee County limits because there was no local police force in the area except for the county sheriff and the area was already well-known by gangsters. There was a dog racing track for illegal gambling (the location was near where Brookfield Square is today) and Al Capone had a house north of Bluemound Road just east of Brookfield Road (which still exists today on Capone Court).
Club Madrid was well-known and popular with Milwaukee’s elite. It was owned by Sam Pick and his brother Ed, gangsters originally from Chicago. In its day, the club was visited by everyone from politicians and gangsters to movie stars like Milwaukee native, Spencer Tracey whose visits to the Club Madrid where documented by Buck Herzog, a society columnist for the Milwaukee Sentinel.
The club offered live entertainment. Hattie McDonald, an Oscar winning actress was a popular performer at Club Madrid and worked there about a year according to her biography. McDonald then moved to Hollywood. Eventually, McDonald found her way into acting in movies. She is best known for her role as “Mammy” in Gone with the Wind for which she received the Oscar in 1940 for best supporting actress.
It was well-known that Sam and Ed Pick associated with gangsters including Al Capone who frequented the club. In 1928, Sam Pick was wounded in a shotgun attack on the corner of Water and Wisconsin Streets in Milwaukee. After prohibition ended, Club Madrid continued to offer fine food, entertainment, gambling and prostitution until another attempt was made on Sam’s life when a stick of dynamite was tossed into the club in 1951 which caused it to burn to ground. The fire was the end of Club Madrid. Sam moved to Michigan. No information on what became of his brother, Ed, is available.
In 1954 the Sleepy Hollow Motel was built on the site where the charred remains of Club Madrid still stood. Portions of the old Club Madrid were reused in the new structure including the stone walls that flanked the entrance to the club from Bluemound Road.