February 17, 2021 – The Wimp was anything but wimpy. And his goodbye was anything but small.

Chicago rackets prince William (Willie the Wimp) Stokes, Jr. was killed in a drug deal gone bad on February 24, 1984 at the iconic Roberts Motel on the Windy City’s South Side, ending the life of a rising star in the underworld right as he was coming into his own as a gangster. Stokes’ burial proceedings made national news and inspired a song made famous by guitar legend Stevie Ray Vaughan.

The Roberts Motel, a sprawling complex with a restaurant, lounge, nightclub, performance venue, ballroom, banquet hall and swimming pool, was the epicenter of African-American culture at the time in Chicago. According to the police report, Willie the Wimp was ambushed as he approached one of the motel’s suites for what he thought was going to be a quality-check on a shipment of heroin he was negotiating the purchase of on behalf of him and his father.

Willie the Wimp, 28, was buried in a $10,000 custom-made Cadillac coffin with $10,000 of cash in his hands and lap. Stokes was dressed in a pink-colored three-piece suit and fedora and wore a diamond pinky ring on his right hand. The coffin featured a vanity Illinois license plate with the letters W.I.M.P. on it.

Willie the Wimp’s dad, the flamboyant Willie (Flukey) Stokes, Sr., ran the South Side Chicago dope and pimp game of the 1970s and first half of the 1980s. He was well known in the Windy City media for quippy banter, high-living and a loud fashion style. His ritzy January 1985 30th wedding anniversary party was written up in Jet Magazine and had musical performances by The Chi-Lites and The Staples Singers.

“I’m off to Las Vegas to shoot dice, I’ll see you all when I get back,” Stokes told the press corps gathered outside the Cook County Criminal Court in August 1986 following charges in a first-degree homicide case against him getting tossed.

State prosecutors had charged Flukey Stokes with putting out a murder contract on South Side pharmacist Robert Ciralski because Ciralski discontinued his black-market quinine business. Quinine was purchased in bulk by Stokes and other drug bosses in Chicago and used to cut their powder narcotics. Chicago Police believed Stokes and another South Side drug lord named Charles (King Arthur) Ashley issued the contract on Ciralski’s life. Ciralski was gunned down outside his home on August 1, 1984.

Flukey Stokes’ days were numbered himself though and the plotters were from within. The debonair 49-year old kingpin was murdered in a power play orchestrated by his own bodyguards, shot to death in the backseat of his Cadillac limousine on November 19, 1986.

Just three days earlier, Epic Records released rock god Stevie Ray Vaughan’s album Live Alive with his version of Bill Carter’s Willie the Wimp, written after Carter and his wife read a news story chronicling his killing and funeral. Vaughan’s brother, Jimmy, got a co-writing credit on the song. Stevie Ray Vaughan died in an August 1990 airplane crash.