February 18, 2021 – The once-grand Roberts Motel complex hosted Chicago crime boss Willie (Flukey) Stokes’ 30^th wedding anniversary party in the winter of 1985 and was the sight of Flukey’s son, Willie the Wimp’s highly-publicized gangland slaying, a year earlier.

Hotelier Herman Roberts, a pioneering figure in the African-American business community, died this month at age 97. His once large and encompassing Roberts Motel compound on the South Side of Chicago served as the “county seat” for the Windy City’s African-American community, where the jazz was legendary, the bubbly flowed freely and Black entertainers, athletes and celebrities from all around the country came to play and perform.

The local gangsters flocked to The Roberts Motel as well, for a variety of reasons, both nefarious and social. Flukey Stokes, the South Side’s biggest pimp, numbers boss and drug kingpin, was a regular at The 500 Room, the nightclub and performance venue on the property. His organization was also known to use rooms at the motel for drug world meetings, multiple-kilo narcotics transactions and for stash spot purposes, per Stokes DEA file.  

Flukey Stokes had his January 1985 anniversary party at The 500 Room. The party with the $500,000 price tag was a glitzy and widely celebrated event, written up in Chicago gossip columns and chronicled in Jet Magazine. William (Willie the Wimp) Stokes, Jr.’s February 1984 murder at the Roberts Motel made national headlines and his burial served as the premise of a Stevie Ray Vaughan song.

Herman Roberts came to Chicago from Oklahoma as a boy with his family in the 1930s. As a young man and fledgling entrepreneur, he owned a taxi cab company, which he soon took the profits from and invested into his own hotel chain. Roberts opened nightclubs and bought real estate while expanding his “Best Roberts Motel” brand around Chicago and into out-of-state locales like Indiana, Iowa, Missouri and Oklahoma.

In 1952, he opened The Lucky Spot, a jazz club and juke joint on Chicago’s South Side. Two years later, Roberts took over a storefront down the street and debuted The Roberts Show Club, hosting the top Black performers of the day, icons such as Sammy Davis, Jr. Redd Foxx, Nat King Cole, Count Basie and Richard Pryor.

Roberts purchased the property adjoining the nightclubs and opened his first Roberts Motel in 1960. Five more Roberts Motel outlets followed over the next decade, culminating in 1970 when Roberts, after buying up the entire block, unveiled Roberts Motel No. 6, a palatial complex including 250 state-of-the-art rooms, 15 suites, a fine-dining restaurant, lounge, nightclub, beauty salon, ball room and travel agency. The nightclub on the premises was the fabled 500 Room.

Roberts himself eventually retired to Oklahoma where he bought a plot of land and struck oil. At the time of his death on February 1 of this year, his estimated worth stood at anywhere between $20,000,000 and $25,000,000.

Twenty-eight year old “Willie the Wimp” Stokes, Jr. was killed in a drug deal gone bad on February 21, 1984, gunned down as he entered a room at The Roberts Motel for what he thought was going to be a quality-of-goods tests in a pending bulk heroin purchase. Stokes, Jr. was buried in a $10,000 custom-made Cadillac coffin with $10,000 of cash in his hands and lap. Stevie Ray Vaughan’s version of his brother Jimmy and Bill Carter’s song, Willie the Wimp — inspired by a newspaper article penned about Stokes, Jr.’s funeral –, appeared on Double Trouble’s Live Alive album, released by Epic Records in the fall of 1986.

Less than a week after the Live Alive hit the market, Flukey Stokes was murdered inside his Cadillac limo in a power-play set-up by his bodyguard. Stokes, 49, was blown away with automatic weapon fire outside his girlfriend’s house on the late evening of November 19, 1986.

On January 9, 1985, Flukey had thrown his wife Jean an extravagant 30th wedding anniversary party at The 500 Room in The Roberts Motel, hiring The Staples Singers and The Chi-Lites, as the party’s entertainment. The couple re-made their marriage vows and exchanged 40-carat diamond rings.