Black History Month Spotlight on Winston Willis: A Forgotten Local Hero

Aundra Willis Carrasco
6 min readFeb 19, 2024
The recently released book featuring Winston Willis’ 1982 billboard statements on his theater marquee.


Continuing its sweeping elimination of Black people’s community.

Loss of Sears, Big blow to Blacks.”




“The most vocal critic of the Cleveland Clinic, however, was area businessman, Winston Willis. Willis was unquestionably the most successful black entrepreneur to emerge out of the post-Rebellion tumult…His empire stood directly in the way of future plans for Cleveland Clinic expansion…Refusing to sell out, Willis became a persistent thorn in the institution’s side. He constantly criticized the Clinic in interviews with the local press and erected huge billboards on his properties lambasting the Clinic’s failure to supply adequate health care for the poor and its destruction of area businesses…”. — Daniel R. Kerr, Historian and author of Derelict Paradise: Homelessness and Urban Development in Cleveland Ohio (2011).

The local newspaper’s caption below the book’s cover photograph is misleading. As are the words Final blow — The last protest of Winston Willis…”. The unlawful seizure and destruction of his business empire in 1982, as evidenced in the background image, was in no way the final blow. There would be many more blows to come. But Winston Willis was and still is innately a fighter to his core, and his billboard statement on his theater marquee was in no way his last protest. As described in the recently released Winston Willis: A Memoir, his is a remarkable story about an exceptional Black man who rose to local prominence in Cleveland during the turbulent, riot-torn 1960s and became a millionaire commercial real estate mogul. Only to suffer the racially motivated thefts and destruction of his entire business empire. Written by the most attentive witness to his controversial life, his sister, yours truly, Aundra Willis Carrasco, I document the decades-long fight my brother waged against a corrupt, racist cabal that targeted him, weaponized the local judiciary against him, stole every one of his properties without compensation and gifted the land to the internationally renowned medical metropolis, the Cleveland Clinic. Where today, the majority of the Clinic’s buildings on the main campus are illegally occupying properties that Winston was never paid for and still owns.

After creating a wildly successful business empire on 105th and Euclid in the 1960s, it was made clear to Winston that such a visible symbol of thriving Black prosperity was not welcome in the dominant White community. His newly refurbished intersection was affectionally referred to as “Black Wall Street” and “Black Folks Downtown” and “An inner-city Disney Land”. But white inhabitants in the racially polarized city frequently expressed their displeasure by referring to Winston’s group of businesses as “an eyesore”. Soon, Winston unwittingly became the target of a powerful group of White racist demigods who were determined to remove him and his hundreds of employees from the area they considered their “cultural oasis”. Throughout years of constant police harassment, bogus fire inspections, countless arrests, and incarcerations as well as decades of epic courtroom battles, Winston fought back with all the legal power his money could buy. 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 possies.

During this volatile time, the local Black newspaper, the Call & Post ran a scathing editorial, “Fire Inspections As Weapons” about the city’s continuing harassment, saying: “It is unfortunate when city workers are forced to carry out their normal duties as a means of effecting the policy and prejudices of higher-ranking officials. It is to the worker’s credit that they have attempted to do their job with a minimum amount of political or racial prejudice. That does not excuse the higher-ups from blame for fomenting a plot against Willis. Their motives need examination.” Citing another reason for the continuing hostility, “It is a generally accepted fact that Willis has refused to make payoffs to anyone for any reason.”

With the levying of these 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 directed them to build 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. Gargantuan in scope, looming high and mighty from the most visible side of his recently purchased building, he had, at last, seized the Constitutionally guaranteed right to be heard so long denied him in the courts. His initial posted comments were bold, fierce, astute, nettlesome, and provocative, exhibiting both a fierce intellect and a sense of moral outrage at the judicially sanctioned racism being abided and protected in the local courts. But to his institutional University Circle neighbors, the statements were explosive and intolerable. But being a man of tremendous political courage and personal integrity, Winston courageously called out city and judicial officials, exposing the corruption and lawlessness he encountered in local courtrooms while defending his property rights. He publicized the City’s and Cleveland Clinic’s patently illegal attempts to seize and take his lands and properties and remove him and his businesses from the University Circle area. Though he was clearly exercising his constitutionally guaranteed right to free speech, the White establishment elite viewed his billboard statements as intolerable. Setting into motion a vicious vendetta that continued for decades.

But soon the billboards 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. Reacting to a controversial local case in which a White man had gotten away with the murder of a Black man, his billboard posed the question:


The community billboard, as it came to be known colloquially, quickly became the featured attraction for neighborhood residents in the Black community and patrons of Winston’s numerous business outlets on the block. The copy was changed every two weeks and was soon elevated to folklore status. But the statements infuriated the local government officials and sent them into a vengeful rage. Nevertheless, it is fair to say that long before the ubiquitous advent of social media, Winston Willis created his own platform for expressing his concerns for the Black community in Cleveland. Thereby creating his very own social network. As a result, however, doing so eventually cost him dearly. As his powerful enemies’ rages intensified, they devised a judicial bear trap for Winston from which there could be no escape. After surreptitiously spiriting him away and jailing him so that he could not stop the grotesque and lawless activity, the entirety of Winston’s business empire was illegally seized and destroyed, while the Cleveland Clinic awaited the gifting of the properties. And in the aftermath, a brilliant and promising life was interrupted and altered beyond human comprehension.


Winston Willis: A Memoir” is available at:

(Photo source: Cleveland Public Library Main Center for Local and Global History. PD Photographer: James Gayle/Jimmy Gale Photography).