MANSFIELD: The Winston I Knew: A Long Retrospective

Winston Willis (left) with jazz great Dizzy Gillespie

Both the Black Power and Black Pride movements were still in their nascent stages in the early ’60s when Winston Willis, a brilliant, enigmatic, and ultimately tragic, figure of Shakespearian proportions first burst onto the Cleveland scene, soaring across the local landscape like a bright, white-hot comet.

And as Shakespeare’s King Henry IV said, “… like a comet I was wonder’d at;” Indeed, some folks have always been keenly interested in the man and his legacy, but also like a comet, Winston Willis would too soon burn out and virtually disappear.

Sure, there had been black men of substance and means in Cleveland for generations, their wealth often due to the numbers rackets and/or the bar, barber/beauty shop, or barbecue joint … the “three “Bs” of black businesses.

But Winston — and yes, I was on a first-name basis with him — was a different kind of cat. He was truly a man for (actually, far ahead of) his time, and possessed copious amounts of audacity to go along with his razor-sharp mind and extraordinary skills — or was it, as some said, pure luck? — at the gaming tables.

A stage production entitled The King of Cleveland, An American Tragedy will examine Winston Willis’ life and times on Sat 2/1 @ 6:30pm at the Rainey Institute on E. 55th at Payne Avenue. It should be a very, very interesting and informative evening.

Hailing from Detroit (where in his early teens he allegedly got a paper route and soon organized his own team of neighborhood youth to deliver the Free Press and pay him a cut) he was supposedly on his way to California when he stopped in Cleveland to visit a relative and never left.

The reason I got to know Winston as well as I did (but which really wasn’t all that much; I was only on the periphery, not an insider) was because his sister Andrea soon followed him to Cleveland and married Willie Ross, a lifelong friend of mine from “down the way.” Willie and I lived on opposite sides of Scovill Avenue and attended school, hunted, fished and went to Browns games together — along with the rest of our little crew. After the marriage, Willie began working part-time for Willis, and his new wife and my first wife, Christine, became fast friends and remained so even after Andrea moved to southern California where she developed into a first-class writer. So yes, I was more privy than most.

I’m not sure if it was the craps or pool table that provided Winston with his early stake, but he was uncannily good on any kind of green felt. As the word in the ’hood goes, “he could shoot a good stick.” Carl Stokes was among the best one-pocket pool players in the city at the time and Willis could more than hold his own with more experienced players. While big bets make some pool shooters nervous, the bigger the bet, the better Winston played. Big money doesn’t rattle men who are confident they can always get more of it, and Willis was extremely confident.

Luck, however, not skill, has to play a huge hand in winning at shooting craps and Winston was so good some dudes even brought their own new dice, thinking that the ones in use in Winston’s after-hours joint (which was the classiest cheat spot between New York and Chicago back in the day) must have been loaded. They weren’t.

I was in the club the night Willis threw an estimated $40,000 out of a window. Yes, it’s true — I witnessed it with my very own eyes. Here’s what happened: Winston had been winning all of this dude’s money at the crap table for weeks, and that Friday night it was more of the same. When one of Willis’ henchmen whispered to him that the dude had robbed a bank earlier that day, out the window and into the alley all of the money went.

I kept my seat. I wasn’t about to run downstairs and scruff up my expensive alligator shoes scrambling around on the ground for money, not when I already had a pocket full of it. I quickly went back to snorting cocaine with the lovely young lass I was attempting to convince to leave her bum of a boyfriend and abscond to New York with me. Alas, I was not successful.


By the time the phenom first began buying up property along Euclid Avenue from East 105th Street to 107th in the early ’60s, the area had long since seen its better days. And while no one would have confused it with the Las Vegas strip, even after he transformed the street (unless they were very provincial), he did open a string of wildly successful businesses — restaurants, topless bars and a game arcade — that well-complemented the couple of movie theaters he’d renovated. He brought a touch of egalitarian class and excitement to everything he touched and the masses ate it up.

Winston truly had lightning in a bottle.

Virtually seven nights a week the strip teamed with people, mostly black, but occasionally some whites — and the area was pretty much crime-free, which no doubt surprised and confused the police. The fact was, people loved and respected what Willis had accomplished and the local knuckleheads feared the tough bouncers he employed. He knew how to keep order.

But it was those aforementioned movie theaters that would eventually turn him into a wealthy man. The first-run film distributors wouldn’t rent movies to Winston, and legend had it that he once barged into the offices of one of the companies with a gas can in one hand and a match in the other, threatening to burn the mother down. That certainly sounds like something like the Winston I knew would not be fearful of doing. There was nothing soft, weak or timid about him.

But their refusal to rent him movies turned out to be a blessing in disguise for the dashing and handsome young entrepreneur. When the U.S. Supreme Court ruled that pornography was no longer illegal, Winston began screening skin flicks in the two theaters he owned on Euclid Avenue, and it was rumored that eventually he had a string of 30 dirty movie houses in the eastern U.S. and Canada at one point. Their newness and novelty made them literal cash cows.

Nonetheless, storm clouds were gathering on his horizon. One of the more attractive topless dancers was overheard saying, “I hope his dick is as big as his ego.” She would never find out since Winston favored women of a different class.

After being warned not to, Willis opened a nightclub called the “Jazz Temple” at the foot of Mayfield Road, right off of Euclid Avenue. However, the mafioso, ever watchful for any black incursion into Little Italy, warned him to shut down the immediately popular nightspot. He didn’t, and in the early hours of one Sunday morning, a dynamite explosion silenced the music permanently.


Winston Willis was truly self-actualized in every sense of the word. He’d built his empire in the true, time-honored American tradition of hard work, cunning, booze and vice. However, the Establishment has never been a respecter of the nouveau riche — especially if said rich are black. He was sorely testing the patience of those opposed to black progress, whose numbers were legion.

Some say the city administration of Mayor Ralph Perk used the expansion of Cleveland Clinic as a ruse, as an excuse to take the brash upstart’s prosperities that dotted Euclid Avenue and put him out of business. Others said that Sam Miller had a hand in it. But the truth was, it probably was a combination of people and factors that ultimately led to Winston’s downfall.

One thing was for sure: The throngs of blacks enjoying themselves in an entertainment district built just for them didn’t sit well with the powers that be. A hidden part of our ugly American past and culture is that whites felt — and to a degree still feel — they should control when, where, how and indeed, even if, blacks enjoy themselves. There probably wasn’t a comparable, entirely black-owned, entertainment district anywhere in the U.S.

But the desire to control black bodies didn’t end with the enacting of the Emancipation Proclamation; it’s just that subtler forms of control were developed and are currently employed by those still fighting the Civil War. For those opposed to black progress, it will never be over.

But I digress.

Nonetheless, Winston’s arrogance — the same arrogance that he displayed when he built the Jazz Temple at the edge of Little Italy — kicked in and he decided to fight City Hall. Another inkling of his overblown sense of self-importance (almost to the point of being delusional) was the signs he had painted on the marquees of his theaters blasting white folks. While the words that called the Establishment out for its racism were, for the most part, accurate and true, he probably didn’t need his taunting visage painted alongside of the damning indictments. What should have been a business/legal battle turned into a very personal one for the courageous iconoclast who loved nothing better than “tickling the bear.”

In all probability Willis was low-balled; no way was he going to be offered fair market value for his property. But had his thinking been clearer, he would have seen the writing on the wall and made some moves. The Establishment had the all-powerful weapon of eminent domain on its side. He simply could not have won against it, even had he been white.

There were a couple of sharp young black lawyers in town at the time, James Willis and John Carson, who probably could have negotiated a decent — or at least better — financial outcome on Winston’s behalf. But he elected instead to fight “the man” and seemed to relish doing so. He wasn’t interested in settling; he wanted complete victory. But in the end, in the biggest gamble of his life, he lost it all. The W.O. Walker Building now stands where his empire once existed.

In this age of hero worship, it’s indeed easy to romanticize the saga of Winston Willis, and we black folks need and can use all of the inspiration we can get. But as far as I know, Willis wasn’t a philanthropist to any degree. He wasn’t fighting for black voting rights; he wasn’t demanding better schools or even handing out free turkeys to the poorer folks of the neighborhood at Thanksgiving. His goal as far as I could tell was to advance black accomplishment only to the extent to which it applied to him — increasing his wealth. He never mentored, encouraged or assisted other blacks in becoming successful businessmen, at least that I am aware of.

But time has a way of rearranging some facts, while adding or subtracting others, and I’m sure Andrea (who probably played a major role in writing the stage production) has a somewhat different view of her brother than the one I recall. But as Oscar Wilde once quipped, “Autobiography, like patriotism, is the last refuge of a scoundrel” … which is why it’s taking me so damn long to write my own.

From CoolCleveland correspondent Mansfield B. Frazier Frazier’s From Behind The Wall: Commentary on Crime, Punishment, Race and the Underclass by a Prison Inmate is available in hardback. Snag your copy and have it signed by the author at http://NeighborhoodSolutionsIn


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One Response to “MANSFIELD: The Winston I Knew: A Long Retrospective”

  1. Jamie Lamka

    I worked for Winston in 1971 for about 6 months or so, opening theaters and bookstores in various towns and cities. 2 other white guys and I traveled to the various locations to lease them, because in most of them, they wouldn’t lease commercial property to black people. It was quite the experience for a naive college guy, which was the nickname Winston and the rest of his crew called me. The other man I remember well was Elmer Turner, vp of the company. Elmer was the man who hired me and we became good friends during my time with the company. It was one of the most amazing and eye opening experiences of my life, and a great insight into black culture from the inside. I google Winston every once in awhile to see what’s up with him. An amazing man!!!

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