He was born in Beggs, Oklahoma, the son of a sharecropper, Herman quickly learned about hard work and the need to entertain himself when ever possible in order to forget that the hard work did not reflect in the pay!

When his family decided to migrate to Chicago, Herman, who was twelve at this time, put his dedication and hard work to task. Whether it was shinning shoes, delivering newspapers or any of the other twenty odd jobs Herman was constantly on the move.

In 1939 Herman’s brother Colvin introduced him to a friend who owned several taxi cabs and offered him a job washing the cars for a small wage. His hard work and dedication paid off as his boss began asking him to drive him home and take his taxi back to the garage. Herman took advantage of the responsibility given to him and found an opportunity to make an extra dollar. He figured while his boss was sleep he would drive the taxi. So long as the car was clean and the tank was filled his boss never complained. Herman built up enough trust in the other drivers that he began driving there cabs during there down hours as well. At eighteen he had saved up enough money to purchase his own taxi and license. One taxi cab became two, two became three, and three became a fleet of 40 taxi cabs that by 1944 would be known as the Roberts Cab Company.

His business savvy and hard work took a pause as Herman was asked to do his part in defeating Nazi Germany in World War II. When he returned from service in 1947 he didn’t just pick up right where he left off. His resolve and determination to be the best pushed him ever forward. Always thinking of ways to improve Herman installed two-way radios in all his cab, the first to do this in Chicago. He as well as other cab owners fought for minority drivers to have the opportunity to service all of Chicago. Today thanks in part to men like Herman, taxi cab drivers are allowed to travel all over the city of Chicago.

Herman wasn’t a twenty-four seven work-a-holic by any means. He did find time to socialize with friends and take part in Social Club events. As the events got bigger Herman saw the need for a more entertaining and profitable venue. In 1953 the Lucky Spot was born, a small lounge where his friends and associates could take a break from the hard day. After years of driving passengers to lounges and nightclubs and his experience with the Lucky Spot he began to envision a place where blacks could be entertained and relax on the South Side of Chicago in a way that no one had ever seen.

The Roberts Show Club was the epitome of black refinement. Established in 1954 Herman introduced the South Side of Chicago to entertainers such as Sammy Davis Jr., Duke Ellington, Dinah Washington, Count Basie, Gene Krupa, and Sarah Vaughn. The Roberts Show Club was famous for its Mambo and Cha-Cha nights and infamous for its Jewel Box Revue! As always his drive and desire to be the best allowed him to take risks on acts no one had heard of helping launch the careers of entertainers such as Redd Foxx, Della Reese, George Kirby, and Dick Gregory to name a few. Unlike the white only clubs downtown and on the north side Herman made a point to be all inclusive in his guests and his performers.

While the Show Club was flourishing there still were obstacles that a man of color faced. Segregation denied blacks occupancy in most first class hotels. Often Herman had to find homes and apartments to house his entertainers. He figured “If we can not walk through there doors I will make my own to go through”!

In 1960 on South Park Avenue on the South Side of Chicago Herman opened the first of six Roberts Motels. The response was immediate and so overwhelming Herman literally had lines of potential occupants. Reservations had to be made months in advance to secure a room. It didn’t take long for Herman to realize that he had not only discovered a market for a much needed service but that this had the potential to be a huge financial success. In December of 1970 Herman completed the first fully equipped black owned motel in the nation. The “500 Room” as it was known had many amenities including 250 rooms, a dozen suites, banquet facilities, conference rooms, travel agency, beauty shop, dinning restaurant, lounge, and what at the time was said to be one the most beautiful ballrooms in the nation. Herman was finally able to see the reflection of pay through his years of hard work and dedication.

Whether it is Taxi Cabs, Show Clubs, Motels, Bowling Alleys, Skating Rinks, or Oil & Gas Herman is forever working. To this day Herman still has all ten fingers and ten toes at work consulting, as well as, working his ranch and enjoying the dream.


ard. Always thinking of ways to improve Herman installed two-way radios in all his cab, the first to do this in Chicago. He as well as other cab owners fought for minority drivers to have the opportunity to service all of Chicago. Today thanks in part to men like Herman, taxi cab drivers are allowed to travel all over the city of Chicago.

Herman wasn’t a twenty-four seven work-a-holic by any means. He did find time to socialize with friends and take part in Social Club events. As the events got bigger Herman saw the need for a more entertaining and profitable venue. In 1953 the Lucky Spot was born, a small lounge where his friends and associates could take a break from the hard day. After years of driving passengers to lounges and nightclubs and his experience with the Lucky Spot he began to envision a place where blacks could be entertained and relax on the South Side of Chicago in a way that no one had ever seen.

The Roberts Show Club was the epitome of black refinement. Established in 1954 Herman introduced the South Side of Chicago to entertainers such as Sammy Davis Jr., Duke Ellington, Dinah Washington, Count Basie, Gene Krupa, and Sarah Vaughn. The Roberts Show Club was famous for its Mambo and Cha-Cha nights and infamous for its Jewel Box Revue! As always his drive and desire to be the best allowed him to take risks on acts no one had heard of helping launch the careers of entertainers such as Redd Foxx, Della Reese, George Kirby, and Dick Gregory to name a few. Unlike the white only clubs downtown and on the north side Herman made a point to be all inclusive in his guests and his performers.

While the Show Club was flourishing there still were obstacles that a man of color faced. Segregation denied blacks occupancy in most first class hotels. Often Herman had to find homes and apartments to house his entertainers. He figured “If we can not walk through there doors I will make my own to go through”!

In 1960 on South Park Avenue on the South Side of Chicago Herman opened the first of six Roberts Motels. The response was immediate and so overwhelming Herman literally had lines of potential occupants. Reservations had to be made months in advance to secure a room. It didn’t take long for Herman to realize that he had not only discovered a market for a much needed service but that this had the potential to be a huge financial success. In December of 1970 Herman completed the first fully equipped black owned motel in the nation. The “500 Room” as it was known had many amenities including 250 rooms, a dozen suites, banquet facilities, conference rooms, travel agency, beauty shop, dinning restaurant, lounge, and what at the time was said to be one the most beautiful ballrooms in the nation. Herman was finally able to see the reflection of pay through his years of hard work and dedication.

Whether it is Taxi Cabs, Show Clubs, Motels, Bowling Alleys, Skating Rinks, or Oil & Gas Herman is forever working. To this day Herman still has all ten fingers and ten toes at work consulting, as well as, working his ranch and enjoying the dream.