'Willie the Wimp and his Cadillac Coffin'

Illustration by Lauren Nassef

     Spencer Leak Jr. passed away at the young age of 56. In their obituary of the scion of the famous South Side funeral home family, my colleagues Violet Miller and Mariah Rush include a few of the high profile funerals A.R. Leak Funeral Home have held, such as for singer Sam Cooke, Rev. Jesse Jackson and drug kingpin William Morris "Flukey" Stokes.

     I had to wonder how many readers, 42 years after the fact, knew just what a wild display of the funerary arts that last send-off truly was. I plunge into it in my 2022 book, "Every Goddamn Day." Honestly, I was reluctant to do so. The man was a drug dealer, his funeral a garish display of the values that killed him. Told haphazardly, I could see it coming back to bite me.

     But it happened on a Feb. 28, and that date needed a story. Context was everything, and I tried to gingerly tell the tale with sympathy and understanding.

Feb. 28, 1984

     “Willie the wimp was buried today,” the song begins. “They laid him to rest in a special way.” 

     Yes, yes they did. 

     White organized crime is celebrated. The Godfather. The Sopranos. Black gangsters, not so much. The glorification of rap, true. But those are Black artists singing about a life they know, in theory. “Willie the Wimp” will be written by a Texan, Bill Carter, who saw the news story and was fascinated. It’ll become a minor hit for blues rocker Stevie Ray Vaughan. 

     “Southside Chicago will think of him often / Talking about Willie the Wimp and his Cadillac coffin.” 

      Maybe the street-level carnage, the tragic effect on ordinary Black lives, is just too great to pretty up. Italian American kids are not being cut down every day in every city by the mafia. Drug dealers like Willie do too much damage, take too many lives. He’s easily, gratefully forgotten. And yet, what a sight he was. 

     “With hundred dollar bills in his fingers tight / He had flowers for wheels and flashing headlights.”           

     The funeral happens today, just as the song says. Willie “the Wimp” Stokes Jr., the 28-year-old son of drug kingpin Flukey Stokes. At the South Side’s A. R. Leak Funeral Home. In a pink suit, propped up behind the wheel of a coffin made to resemble a Cadillac Seville, down to its wire-spoke wheels, and authentic grill, put on at a body shop. The headlights and taillights work. Enormous wide-brimmed gray hat on his head. To some, the effect may be more of a toddler’s play car than anything that would seem elegant to anyone who isn’t high on the drugs he sold. 

     To others, however, there is a pride in the ostentation, a definite respect. Jet magazine gives the funeral three pages and is not critical. It ends pointing out that his mother finds comfort in the send-off. “I think he would have really liked it because that’s the way he was,” she says. “He was flashy and he believed in style.” And this is definitely style, of a certain sort. 

     "He been wishing for wings, no way he was walking / Talking about Willie the Wimp and his Cadillac coffin.”