Madden and his former gang rival turned partner, Big Frenchy De Mange (George Fox DeMange), began to open or acquire some of the flashiest speakeasies and nightclubs of the era, most notably the legendary Cotton Club.
Madden purchased the Club Deluxe from former Heavyweight Boxing Champion Jack Johnson and reopened it a year later. Nightclub patrons flooded into Harlem from downtown Manhattan to catch performers such as Cab Calloway, Duke Ellington, Louis Armstrong, Lena Horne, Bill “Bojangles” Robinson and the Nicholas Brothers.
Madden and his partners, Big Bill and Big Frenchy, also muscled their way into a piece of the exclusive Stork Club, where the influential gossip columnist Walter Winchell held court and everyone who was anyone wanted to see and be seen. As a celebrity nightclub owner with ownership in more than twenty clubs, Madden became well-known and glamorized for his Prohibition-era activities. He also gained recognition for his revenge tactics and payoffs of City Hall.
