Willie the Wimp (and his Cadillac coffin)

Inspiration can come at you from so many ways. For me it sometimes comes in the form of a digression in a book that sticks in my head – I wonder why no-one has told THAT story, till I go chase down the rest of the tale. Sometimes something comes from a conversation you’ve had with someone else.

Sometimes the teenage you is looking through second hand cassettes in a 4 for $5 bin. You are planning to spend the afternoon hand writing a legible copy (I did not get my first computer till I was 22) of a university essay on Shakespeare’s ‘Measure for Measure’ from your completely illegible notes – and you may as well grab a seat in the AV lab, borrow a cassette player, and listen to a little music while you work. Among my picks that day was Stevie Ray Vaughan’s ‘Live Alive’, and on that album a cover song with a back story that has always fascinated me. I find the following quirky. I don’t intend any veiled commentary on society, no judgment or praise. I could make the point funerals are for the living, they often reflect the needs and wishes of those left behind, and why I think, most of the time that is OK – but I’ll leave it to you all to join any dots you see fit. I really just mean this as a quirky tale that found its way to me many moons ago.

Willie ‘Wimp’ Stokes jr. was a notorious figure among the underworld of Chicago’s South Side. Though at the time of his passing, Jet magazine listed him as a ‘flamboyant gambler’, and gamble he sure did – it would be reported later that he was a drug dealer working for his alleged kingpin father, William ‘Flukey’ Stokes. If one is thinking back to the Macks from my Christmas podcast, that is OK – I used a photo of Flukey to represent what a modern day mack looked like. One February night in 1984, Stokes Jr was gunned down on his way to a motel on the South Side. Though nowhere could I find any indication that anyone was arrested for the murder, it is to be noted the murder happened at a time when cheap crack cocaine was starting to flood the streets in many US cities, and a number of young gangsters were suddenly looking to elbow into the business – in spite of the few kingpins who had dominated the narcotics business for years. Stokes Jr, just 28 at the time, left a wife and five children behind.

William ‘Flukey’ Stokes snr.

Willie ‘the wimp’s father, Willie ‘Flukey’ Stokes, was also something of a flamboyant gambler – at least on his income tax forms he claimed most of his money came from gambling. He owned a pool hall – and was, at the time of his own death, reputed to be the owner of as many as 40 drug houses, employing around 200 people in his organization. Like his son he cut a flamboyant figure – silk suits, diamond rings with carat counts into the dozens – a taste for Cadillacs. Flukey, for all the damage his ‘gambling’ did in his community was beloved by most – he was well known in the neighborhood for acts of kindness to the elderly (bringing turkeys to pensioners) the poor (no strings attached financial assistance to many needy folk who approached him for help), and the unfortunate (helping re-house a family whose home had caught fire). All the same, at the time of his own death Stokes Snr was facing murder, conspiracy to murder and racketeering charges. He was also thought to be bringing in a million dollars a week from his drug houses.

So when Willie the wimp is gunned down, Flukey put on a funeral which caught the imagination of a number of journalists. There laid out in all his finery was the younger Willie – propped up at the wheel of a Cadillac coffin. Before Willie the wimp had been loaded into the coffin it had been taken to a local panel beaters, and had a genuine Cadillac front grille and boot added to it. Working front and tail lights were installed. A plastic windshield, a big floral steering wheel, a dashboard were added, as were four wheels to the chassis. All up it is believed the coffin, modelled after a 1984 Cadillac Seville, cost Stokes Snr around $7,000. It also had a vanity licence plate W.I.M.P. Willie himself was dressed in a hot pink three piece suit with a matching tie, a rather pimping looking hat, and a giant diamond ring just like his father wore. He went driving into the great unknown clutching what most newspapers report as a wad of $100 bills, and Flukey’s own biography claimed to be $1,000 notes.


When interviewed about the funeral Flukey advised “He (Wimp) had a brand new Cadillac every year for the past eight years or so… Furthermore, one year I was in debt and he sold his Cadillac to help me out, so I owed him one”. Willie the Wimp’s mother Jean added “I think he would have really liked it because that’s the way he was. He was flashy, and he believed in style”

Two years later Flukey Stokes would make the news again, after spending $200,000 on a lavish party to celebrate the 30th anniversary of his wedding to Jean. They hired the Staples Sisters and Chi-Lites to play, and Flukey threw $50 and $100 bills to the guests at one point in the night. It has always astonished me the party was held at the South Side motel where Willie the Wimp was gunned down. Not long after Flukey himself would be gunned down. Having just been acquitted of attempting to kill a rival drug boss, he was killed in a hit organized by his own bodyguard, on his way back from a night at the movies with his girlfriend.

One morning Texan musician and songwriter Bill Carter is reading the local paper, when an article grabs his attention. He shows it to his wife, and co-writer Ruth Ellsworth, commenting “This isn’t a column, it is a song”. That morning, on their two mile drive to the studio the songwriting partners have a song out of it, and cut the track that day. In the studio, Carter’s friend The Fabulous Thunderbirds Jimmy Vaughan, who lays down guitars on the track. Jimmy called his brother, blues legend Stevie Ray Vaughan that night, raving about how good a song Willie The Wimp (And His Cadillac Coffin) is. SRV agreed, adding the song to his live set. And that folks is that tale of Willie the Wimp Stokes.

1 thought on “Willie the Wimp (and his Cadillac coffin)

  1. Pingback: The New Colossus | Tales of History and Imagination

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