Winston E. Willis and 105th and Euclid: The Long-Hidden and Untold True Story

Aundra Willis Carrasco
19 min readMar 1, 2023


…a brilliant life cruelly interrupted and altered beyond human comprehension.


· “Winston Willis’ Miracle on East 105th Street

· “The Brave New World of Winston Willis”

Profile in OHIO Magazine (1980)

· “Winston Willis: He Wants His A La Mode”

· “Cleveland has never seen anything like him. Willis is an anachronism, and he would have it no other way.”

· “He is outspoken, residing and working in a community ill at ease with blacks who confront their morality.”

· “It’s his style, a combination of street theater, civil rights legalese, and screaming spoiled child.”

· “If Willis were white his financial ties would be with bankers. He is a shrewd, savvy, black entrepreneur.”

Profile in CLEVELAND Magazine (1980)

· “…as far as I’m concerned, Winston Willis is the most brazen, audacious son-of-a-bitch I have ever met.” — Cleveland Police Captain Carl Delau

Profile and Interview PRESSURELIFE Magazine (2019)

· The Miracle on East 105th: The Rise and Fall of Winston E. Willis’ Opportunity Corridor

My 2016 Screenplay

“This is a powerful story, and it should be told, but it’s so unbelievable we doubt that it would appeal to a mass audience. But good luck to you!”

Having been writing my brother’s story for over thirty years, I have heard or read, with immense measures of incredulity, some version of this statement. From newspaper and magazine editors, filmmakers, and studio heads, and politicians. The general consensus has been disbelief. Which often translated into “it’s not trendy enough”, or even “…this kind of thing doesn’t happen in this country.” But it does, and it did. I was there and I saw it happen. Furthermore, in response to any nonbelievers, I encourage you to read on, because if you yourself happen to be an outspoken individual of color who speaks out against racism and defends your constitutional rights in today’s political climate, it could also happen to you. My brother’s story is even more impressive because he first spoke out when he was a young man in the turbulent, riot-torn 1960s. Today, however, at the age of 83, although he appears to be a mere shell of his formerly fit, robust 6-foot-tall custom-made suited self, the essence of the man he was, and the uniqueness of his larger-than-life persona remains. His deep, resonant voice is still strong and unmistakably identifiable, and his face retains enough character to indicate that he is still in possession of a razor-sharp mind. Beneath the graying beard and the sunken gravitas of his cheeks is the once handsome visage of the former wunderkind real estate mogul who created a huge business empire during the early ’60s and fought like hell for decades to protect and keep it. Singlehandedly stepping out, completely alone, confronting his powerful racist enemies and demanding his constitutional rights. Needless to say, however, the David and Goliath clash has clearly taken its toll. If his story were to be conceptualized in the form of a blurb, it would read:

In the summer of 1968, in racially polarized Cleveland Ohio, a brilliant and charismatic young Black businessman wins a staggering Half-A-Million Dollars in cash in three-day craps shooting marathon. After wisely and immediately parlaying his winnings into building a wildly successful, first-of-its-kind Black business empire where no Black people had ever been welcome, he unwittingly sets into motion a city-wide enmity that results in his eventual economic destruction by a corrupt city government, police force and local judiciary.

Cleveland, a blue-collar town was, at that time, rated as the third most racially polarized and segregated city in the United States. The nation was awash in social unrest, civil rights and anti-war demonstrations; flower children; political assassinations; and riots. Within the Black community there existed a paradoxical scuffle in the pursuit of social change. From stoic, non-violent resistance and a multi-racial civil rights movement to stentorian cries for “Black Power!” and “Burn, Baby, Burn!” Although Winston was an acknowledged and outspoken disciple of Marcus Garvey and Malcolm X, his true allegiance was to economic empowerment and autonomous control of Black communities. At times lionized, but more often vilified in the local press, his personal philosophy and vision were often obscured by his penchant for showmanship, but there was always, at the heart of his deeds, an inherent and genuine compassion for his people and their welfare.

Winston first came to local prominence in Cleveland during this period of time. Several years prior to that, in 1953, our parents had joined in the Great Migration and moved our family from our home in Montgomery Alabama, and settled in Detroit. A lot of young people of that era seemed to linger in adolescence, but not Winston. He sailed right through his. When the average teenager’s world consisted of high school sports, hot rod cars, Prom dates, and Rock-N-Roll, Winston’s ever-growing entrepreneurial spirit led him elsewhere. After ending his formal education after the tenth grade, he sought and found immediate gainful employment. His knowledge of the floor covering trade that he learned from our father secured several entry-level positions in two tile stores, and later, in key management positions. During his teen years, Winston was fully invested in becoming a successful businessman. And he was thoroughly enraptured with the philosophy of Marcus Garvey and embracing the entrepreneur activist’s unification and empowerment of Negroes. His experience and his reputation in the floor-covering field soon led to the upper-level position that aligned him on a parallel track with fame and fortune.

After residing in our family home in Detroit for a few years, Winston struck out on his own at the age of 19 and landed in Cleveland where he established a string of small tile stores. Following those business ventures, he and his girlfriend, Charlene, opened The Jazz Temple, a coffee-house nightclub in the upscale University Circle area, directly adjacent to Case Western University. Ironically, it had been a chance meeting with his Jazz idol, Miles Davis, in Detroit that was the impetus for Winston’s moving forward with his long-time dream of opening a jazz club. The serendipitous connection occurred in Detroit in the 1950s and continued for several years during Davis’ appearances at the club. It was during this time that I moved from Detroit to Cleveland into Winston’s and Charlene’s large home and was employed as a waitress at the Jazz Temple.

As the Jazz Temple’s notoriety grew, it came to be considered by many world-famous jazz musicians and dedicated Jazz aficionados as the “Jazz Mecca.” But from the moment the club opened on the Euclid Avenue and Mayfield Road intersection, residents in the Murray Hill-Little Italy area let it be known that the club was not welcome. And with attempted intimidation by local law enforcement, some nights saw as many Cleveland police officers in attendance in the club as regular customers. These visits were routinely followed by unscheduled and unannounced police and fire inspections and bogus citations. The warnings were dire and persistent, and thereafter, months of ominous threats of violence and anonymous phone calls during and after business hours foretold of the coming end. Several famous acts appearing at the club refused to be intimidated initially, insisting on performing. But finally, after several thwarted bombing attempts, the frequency and intensity of the threats were followed by a tremendous after-hours explosion that completely demolished the Jazz Temple and its brief reign ended soon after. As reported in the local press: “Police were unable to find reasons for the bombing of the interracial house of jazz, but they found remnants of a bomb.” And the message was clear.

The destruction of the Jazz Temple was a devastating loss to Winston but not entirely a surprise. In spite of the temporary setback, the club’s demise was soon followed by the unbelievably fortuitous twist of fate. With the staggering amount of cash, Winston began purchasing commercial properties up, down, and around Euclid Avenue, and set about building his business empire. But in doing so, he unwittingly triggered the animus of a powerful racist cabal and set into motion a vicious racially motivated conspiracy. Why? Because as a young self-made millionaire businessman, he bowed to no one. And he fearlessly spoke out against racism in the Black community in Cleveland. Most visibly on gigantic billboards on his properties. Making powerful enemies along the way as he purchased a slew of properties in the previously restricted University Circle area. As business owners were fleeing the area at warp speed, Winston recognized an opportunity created by riot-induced white flight. So he set about purchasing properties and abandoned buildings. Remodeling and transforming them into successful businesses.

One man’s wilderness is another man’s theme park” as they say.

In rapid succession, he established restaurants, bars, Penny Arcades, adult and family movie theaters, office suites as well as convenience stores. Referred to in the local press as “an inner-city Disneyland”, the strategically located strip of land and buildings was jam-packed with twenty-eight wildly successful and thriving businesses up, down, and around Euclid Avenue and perched right in the middle of the Cleveland Clinic’s proposed wide-spread expansion project.

Winston’s 105th and Euclid

1973 view of a portion of Willis’s 105th and Euclid empire.

In the colloquial vernacular of the time, it was said that “Winston Willis was the man. He had class and he had bank, and he was fearless. He was the man that every Black man wanted to be, and every woman wanted to be with.” He rode around town in a brand-new Cadillac limousine, trailed by a brand-new Mercedes, which was driven by one of his bodyguards. The limousine chauffeur was a White man whose alternate function was as roving, substitute manager for Winston’s out-of-town adult movie theaters where a Black manager would not have been welcomed. During these years, local newspapers repeatedly characterized Winston as “The Black Howard Hughes”, “The Baron”, “The Pied Piper of Euclid Avenue”, “105th and Euclid’s Slick Young Landlord”, and “Mr. University Circle”. After several interviews with Winston, local reporters soon recognized that he was always good copy, and a lightning rod of controversy. He was eloquently articulate, well-read, and fearlessly outspoken.

Several years prior, the city’s two reigning institutional Goliaths, University Circle Incorporated (UCI) and Cleveland Clinic Foundation had joined forces and initiated plans to form an alliance to create a sprawling medical-educational metropolis and become one of the most dominant medical facilities in the world. But the Hough Riot in 1966 and the Glenville Shootout in 1968 brought their plans to a screeching halt. Included in this mega-billion-dollar project was a far-reaching and prodigious plan to expand the world-renown Cleveland Clinic’s campus and connect it with Case Western Reserve University and University Hospitals, essentially creating their own private driveway. The only “temporary obstacle” to their master plan was Winston’s strategically located strip of land and properties with his twenty-eight wildly successful and thriving businesses perched right in the middle of the proposed expansion project.

Having successfully “handled” such “temporary obstacles” with little resistance in the past, the powerful consortium’s expectation was for similar results. But little did they know. They would be in for a fight with a young Black man who quickly proved to be a formidable force and anything but “handleable”. And to further complicate matters, Winston had exhibited remarkable business acumen and a unique flair for acquiring commercial real estate, and he also owned and controlled several other businesses and key parcels of land up and down Euclid Avenue, the city’s main thoroughfare. Not only was young Winston in their way, he was also a fearless and unique presence in their previously racially restricted community. At first, the locals in the area were cautiously curious and intrigued by this young Black man who had the audacity to speak his mind and demonstrated that he had the capacity to think for himself. However, Winston was still considered an intruder, and no effort was spared in letting him know he was unwelcome, and they increased their efforts at trying to force him out. Engaging, in concert, in a pattern of illegal activity for the purpose of erasing visible Black prosperity. They prevented further growth of his business empire by doing everything in their power to trap him in poverty, far away from any possibility of future success. They wanted him gone. But with every attempt to remove him and his growing business empire from the University Circle area, he gave as good as he got, challenging his opponents, confronting them with his constitutional rights, and employing all the financial and legal resources that his increasing wealth could buy to hold onto his properties. He let it be known in no uncertain terms that he wasn’t about to be removed without a fight. And what a fight it was.

As the enmity escalated, the state of Ohio, acting through the county prosecutor’s office and the city police department; began an endless course of harassment, police raids, bogus citations, arrests, bad faith criminal indictments, fires of suspicious origin, and illegal break-ins. Whenever he challenged any of this illegal conduct in the courts, the judicial authorities would stay their hands, declining his requests for injunctive relief and dismiss the action. Not even the team of high-priced lawyers he retained could call off the vengeful posse. With the levying of these bogus inspections having become a blood sport, and with no other legal recourse available to him, Winston took full advantage of his First Amendment privileges and mounted a public forum. Utilizing his skillful in-house construction crew and a talented artist, he erected a large, very visible billboard on the side of his building overlooking Euclid Avenue, the main thoroughfare for suburban commuters to Cleveland’s downtown financial center. Initially utilizing the newly erected structure as his own personal platform and bully pulpit, he exposed, protested, and criticized what he believed to be the rampant practice of racism by local city officials and so-called philanthropic institutions. Soon the billboard became the talk of the town. A tourist attraction, and ultimately an embarrassment to the establishment and the staid University Circle community. Following several weeks of posting personal interest assertions, he recognized the overall benefit of also publishing Black American interest propaganda as well.

The man and his billboards.

Long before there was Facebook and Instagram and Twitter and TikTok, Winston was erecting huge billboards on his Euclid Avenue properties and publishing provocative statements exposing the racism he was encountering from city officials and the local judiciary. Looming high from his tallest buildings in an area that was constantly bustling with round-the-clock activity, his fearless voice was being echoed and heard. Exposing and challenging the city’s ongoing pattern of systemic racism and oppression, he spoke out on behalf of the Black community. Thereby creating his very own social network. His voice soon became a clarion call to the unheard. Not only to his Black neighbors but also to other local communities as well as the hundreds of men and women he employed in his popular, thriving businesses.

Living in Cleveland at the time, as well as working in several of my brother’s 105th Street and Euclid Avenue businesses, I was an eyewitness to most of what happened. Often assisting him during court hearings. What I saw with my own eyes was clear and undeniable evidence of a local judiciary literally weaponizing the law against Winston. Over the years, Winston and his high-profile, high-priced lawyers fought mightily in local courts with every imaginable legal strategy and remedy available. But after all the years of corruption, property thefts, illegal seizures, and gun-point evictions, attempts on his life, threats against his children, wrongful imprisonments, fires of “unknown origin”, and flat-out judicial corruption, the City of Cleveland/State of Ohio finally succeeded in illegally taking every single one of Winston’s wholly-owned properties — without a dime of compensation, just or unjust, and gifting them to the Cleveland Clinic. Leaving him penniless and living in abject poverty while the Clinic illegally occupies properties that he still rightfully owns.

Today, after decades of state-sanctioned illegal seizures and property thefts motivated by institutional racism, the glory days of 105th and Euclid are just a memory. And the ever-expanding imagery of Cleveland Clinic’s main campus has replaced what used to be called an “Inner-City Disneyland”, and “Black Folks’ Downtown”. But underneath the colossal, hulking medical towers is a skeleton in Cleveland’s closet. A sizeable piece of the American dream. And I submit that this area is also a crime scene, and justifiably should be wrapped in the official bright yellow tape routinely used by law enforcement at crime scenes. The long unpunished crime took place at this location in 1982, and it is one of the most criminally underreported stories in Cleveland history. The 24-hour bright lights and R&B music on Winston’s 105th and Euclid were dimmed a long time ago, and all of the buildings have been destroyed, leveled, and replaced by Cleveland Clinic's main campus structures. Many of which are illegally occupying land that Winston still owns and has never been compensated for.

From 1968 until 1982, Winston E. Willis waged a mighty battle in defense of his constitutionally guaranteed property rights. That is his story. But ultimately, this is the story of the triumph and tragedy of a Black man whose public criticism of racism in Cleveland sent his adversaries into a rage and cost him everything. What started out in the 1960s as a mildly adversarial rift between a brilliant and charismatic young Black businessman and Cleveland city officials soon escalated into a full-scale war that lasted for decades. A war that he could not win because in this country, the lethal combination of systemic racism and the insatiable lust for power and its corrupting influence are insurmountable.

The Cleveland Clinic is the city of Cleveland’s crown jewel, and its controlling influence is widespread. The planned sprawling multi-billion-dollar medical metropolis is now a reality, dominating the Euclid Avenue corridor and continuing its ever-widening and far-reaching expansion. But the mammoth steel-and-glass superstructures cannot hide the true history and the vivid memories of those who were there. The ones who remember Winston Willis as a young, charismatic Black American citizen who, with youthful exuberance, and verbal joie de vivre, dared to venture into and triumph in a racist community without compromise or apology. Believing wholeheartedly that the American dream was his to have. But such was not the case in Cleveland.

For the past four decades, in the city of Cleveland Ohio, my brother has waged a mighty war against corrupt local government officials and courtroom manipulations that led to racially motivated property thefts and the destruction of his vast business and real estate empire. He fought and he fought. And then he fought some more. Today, at the age of 83, he is still fighting. Even knowing that he is virtually powerless against the reigning elitist band of power brokers and institutional giants. Where are the custodians of justice? The interpreters of the Constitution? The defenders of the rule of law? Where is the national outrage that something like this could’ve happened in the United States of America?

Although many of the actors and participants in the cruel and often violent crimes against my brother are no longer alive, there are city and government officials and agencies that are complicit in the cover-ups. But it is one of the miracles of modern American entrepreneurship that during the turbulent 1960s, one lone young Black man had the courage and insight to penetrate Cleveland’s previously racially restricted University Circle area and create a thriving business empire. It is even more miraculous that after decades of life in the cross-hairs of vicious politically powerful White racists, he continues to fight to protect his rights. Winston has endured an obscene amount of grotesque, racially motivated punishment at the hands of corrupt city and government officials and local judiciary tantamount to a modern-day lynching. But he fought back mightily. Never giving up until his politically powerful enemies laid a judicial trap for him that he could not escape. In spite of it all, he would not give up the fight. He fought and he fought and he continues to fight. Witnessing his David and Goliath struggle, inspired by the strength of a life-long bond created in childhood, I was propelled to join him in team formation that led to more epic courtroom showdowns and confrontations than I can count. But we were powerless against the assembled machine of corruption we were up against. So, I shifted my focus, and for the past thirty years, I have tried to position my brother’s story at the forefront of public consciousness by writing about it. His lifelong aspiration and vision of the American Dream was cut down, killed, and destroyed in its infancy. This was a travesty of justice. An egregious wrong that must be righted.

There is a legal expression, one that’s used in the law, “make one whole”. Which means to return the injured party who was damaged back into the position that he/she would have been in without the fault of another, and/or to pay or award damages sufficient to place the injured party in an otherwise favorable condition.

The question then becomes: How can Winston Willis be made whole again when everything he worked so hard for all of his adult life has been taken away from him? His livelihood. Every one of his businesses. Millions of dollars worth of property. His personal belongings. Family memorabilia. An entire fleet of automobiles, limousines, and service vehicles. Office and restaurant equipment. His pets! His gardens. His health. His autonomy? The very fabric of Winston’s identity was ripped away, and he now lives out his dotage in abject poverty in the shadow of his former empire. Considering what my brother has endured over several decades, I also know for a fact that he is not the only Black person who has suffered the thefts of his properties. He is simply the only one who fought back. There are many other Black families who have also been victims of wrongful governmental takings of their land and property, and understandably, they may not have had the financial resources or legal representation that Winston had at one time. So, they just suffered their losses in silence and went away.

I have been asked numerous times over the years why I have continued my decades-long pursuit of justice for my brother, and the answer perhaps lies in our upbringing. Winston has always been my big brother protector, my defender and my strongest ally, and my closest confidante at times. As children growing up in pre-civil rights movement Montgomery, Alabama, the third and fourth of our parents’ five children, we were similar in temperament and personalities, and he was my closest sibling. As his pesky little sister who dogged his every step, I observed Winston’s transformation from docile altar boy to truth-seeker-challenger. A force of nature. Of course, as a child I was unaware of this. He guided me around the restricted landscape that our early childhood encompassed, and over the years he has remained an integral part of my life. Evidence of the bond created in childhood growing ever stronger has been revealed over the years with each new chapter of our lives. He has been a constant presence of boundless generosity and support and broad shoulders to lean on when needed. I never imagined that he would someday be the one in such desperate need of help.

After having suffered the loss of everything he had worked so hard for all of his adult life, and being reduced to living in soul-crushing poverty, my brother reached out to me for editorial and research assistance, and I complied immediately and wholeheartedly, working side by side with him as he prepared his legal cases. Countless research hours at libraries, both legal and public. Accompanying him in and out of courtroom after courtroom, as he continued trying to save his last building and defend his property rights. Confronting and dealing with the corruption of local government officials, judges and lawyers. It was a hellish ride through Cleveland’s corrupt judicial system, and my brother’s heroic efforts to defend and save his rightfully owned properties were admirable. But witnessing the way the local judiciary in Cleveland manipulated and weaponized laws against him, I felt even stronger in my determination to expose the sordid and downright criminal manipulations. And in 2007, when Winston’s petition to the United States Supreme Court was initially accepted and docketed, only to be denied three months later, I decided to utilize the power of the Internet and social media to tell my brother’s story. So, here we are.

In final analysis, I never imagined or even considered the remote possibility that it would be left to me to complete this journey that my brother began decades ago. Perhaps I’ve been holding on to memories and images of our childhood when he guided me safely around the perimeters of the restricted landscape that our early childhood in Montgomery Alabama encompassed. Or when he tutored and help me with my math deficiencies, or in later years, educated me in the intricacies of the workings of the law. Or when we joined forces in a two-person team and faced off against a corrupt judiciary in countless Cleveland courtrooms. As a writer, I envisioned the two of us engaging in oral arguments at the United States Supreme Court and winning. And then descending the white marble steps, jubilant and triumphant. Hand in hand. But the truth is what it is. Several decades have flown by and we are both in our dotage with most of our lives in the proverbial rear-view mirror. But even though, at the age of 83, he can no longer do the extraordinary things he once did as a young man and is not immune to the indignities of old age, he is still Winston. My big brother. And he is still fighting. And I will continue this fight on his behalf when he cannot.

To Make Him Whole Again:

In spite of all that has been taken from him over several decades, as well as the numerous fraudulent foreclosures and subsequent illegal gun-point evictions, I am fully aware that those crimes are not likely to be prosecuted or even adjudicated after the passage of so many years. However, I believe very strongly that the following must be considered in order to provide some semblance of recompense and to make him whole again:

· Winston’s loss of revenue from his businesses for over 40 years.

· Deprivation of heir property rights and generational wealth due to Winston’s children and grandchildren, which is their birthright.

· Punitive damages for wrongful incarceration while his properties were being seized and destroyed in 1982.

· Relocation benefits due to a federally classified dislocated person as guaranteed by the Uniform Relocation Assistance and Real Property Acquisition Act (URA).

In Thomas Jefferson’s writings on a personal right to property, he stated the following:

“By nature’s law, every man has a right to seize and retake by force his own property taken from him by another by force or fraud… It was long retained by our ancestors. It was a part of their common law, laid down in their books, recognized by all the authorities, and regulated as to circumstances of practice.”

External Links:

Winston E. Willis — Wikipedia

The Winston Willis Empire — Instagram

The Miracle on East 105th: The Rise and Fall of Winston E. Willis’ Opportunity Corridor

Radio WOVU-95.9 — The Winston Willis Project