Herman Roberts: The Life & Times Of A Historic Business Man & Entrepreneur

Born in 1924, Herman Roberts moved to the south side of Chicago with his family from Oklahoma at the tender age of 12 years old. Chicago presented more realistic opportunities for finding work. Herman entered the workforce in the late 1930s washing cars for a cab company. 

The entrepreneurial spirit hit him at an early age, and he moved up quickly, by 15 years old he was driving his own cab. By 1944, he owned his own operation, the Roberts Cab Company. Mr. Roberts served in the army for a few years before returning to Chicago. In 1952, he established a small club called The Lucky Spot, which was located at 602 E.71st. 

Two years later he relocated to 6622 South Park Way, where he established Robert Show Lounge. The south side had other popular night spots at the time, but Mr. Roberts knew what they were missing: National acts. So, in 1957 along with a new venue and a new name Roberts Show Club. 

He figured a bigger venue would attract bigger acts…and he was right. From 1957-1961, Mr. Roberts booked the likes of Nat “King” Cole, Sammy Davis Jr, Count Basie, Sam Cooke, and Jackie Wilson to name a few. A lot of these acts weren’t allowed to perform at the European clubs, So Mr. Roberts made them feel right at home. 

The club eventually shut its doors in 1961, but that wouldn’t stop him from formulating another plan. After realizing how difficult segregation made it to house the black acts that came to his club, he decided to open his own motel. In 1960, he established the first Roberts Motel. 

It opened to such a demand he quickly opened four others. He also began to focus more on family, turning his once club into a bowling alley. In 1970, he opened his most notable motel to date, fully equipped with 250 sleeping rooms, twelve suites, two penthouse party suites, a restaurant, ballroom, travel agency and beauty parlor. 

He would continue to expand his motel business with acquisitions in Oklahoma and Gary, Indiana. Herman Roberts manifested his dreams by never giving up. When it seemed as if one door closed on him, two more would open. His life and achievements can be an inspiration to all of us.















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