Hon. Charles Clevert and Celia Jackson pose for a photo during an event in February 2020 honoring Wisconsin's pioneering black lawyers.

April 20, 2022 – The notion of becoming a lawyer first entered Charles Clevert’s head one day as he sat in a courtroom watching future Virginia governor L. Douglas Wilder argue a case. It was the first step in a journey that ended with Clevert’s ascension to the federal bench. This year, Judge Clevert celebrates 50 years in the legal profession.

Growing Up Under Jim Crow

Clevert grew up in Richmond, Va. To support Clevert and his seven siblings, Clevert’s father worked as a truck driver. Clevert’s mother was the salutatorian of her high school but couldn’t afford college.

Richmond had served as the capital of the confederacy during the Civil War, and in the 1950s racial segregation remained the law of the land.

“I would see white water fountains and colored water fountains,” Clevert said. “White toilets and colored toilets. Hospital staff referring to white people by their last names – ‘Mister this and Mister that’ – and Black people by their first names.”

The apartheid system was enforced by acts both public and private.

Clevert said it was common to see Klu Klux Klan members barreling down city streets in pickup trucks flying Confederate flags.

And he remembers vividly the time he walked up to a store and held the door open for a white woman who was struggling to enter the store.

“She turned around and called me the N-word,” Clevert said.

Wilder was Inspiration

A young Black lawyer in Richmond served as a beacon of hope for Clevert.

“I was inspired largely by seeing Doug Wilder, then a young lawyer, in court, and seeing how he interacted with the court on behalf of his clients, and how he was able to make a huge difference in the lives of his clients,” Clevert said.

Wilder would go on to be elected Virginia’s first Black governor in 1989.

“Upon seeing [Wilder] and having gone to totally segregated schools, I aspired to become a lawyer to help make a difference in my community and in the lives of others,” Clevert said.

Course Correction

After graduating from Davis and Elkins College in West Virginia, Clevert was accepted to the University of Richmond School of Law.

A chance meeting at a seminar held at the University of Cincinnati College of Law in the summer of 1969 altered the trajectory of Clevert’s legal career.

At the seminar, Clevert met Professor Jerome Shuman, who would be teaching at Georgetown Law School that fall. Shuman was a Black lawyer who taught at Howard University and had analyzed school desegregation plans for the U.S. Department of Education.

Shuman convinced Clevert to apply to Georgetown.

“He walked my application through the process,” Clevert said of Shuman. “I was able to attend Georgetown as a result of Professor Shuman. I clerked for him my first year in law school.”

Like Wilder, Shuman showed Clevert how a lawyer could help improve the lives of his clients.

“He spoke of how he had dropped out of school, but ultimately returned to school and found that the law was a way of making a huge difference,” Clevert said.

“In particular, he felt that commercial law and real estate were avenues where Black lawyers could make a huge difference because there were not a lot of Black lawyers in those area of the law,” Clevert said.

Clevert planned to hang out his shingle in Richmond. But Shuman inspired him to aim higher.

“I was just thinking of becoming a neighborhood lawyer, like Doug Wilder," Clevert said. "But Professor Shuman opened my eyes to possibilties that I'd not thought about.”

From D.C. to Cream City

Another chance meeting was behind Clevert’s move to Milwaukee.

During Clevert’s third year at Georgetown, one of his study partners invited him to a Christmas party. At the party, Clevert met Michael Ash, a Milwaukee County deputy district attorney who was working at the U.S Department of Justice on sabbatical.

When Ash asked Clevert to come to his house for dinner, it didn’t take long for Clevert to answer.

“I’m a starving young law student and somebody’s going to cook dinner for me?” Clevert said. “I jumped at that chance as fast as you can imagine.”

I would see white water fountains and colored water fountains. White toilets and colored toilets.

During that dinner, Ash called Milwaukee County District Attorney Michael McCann and put him on the phone with Clevert. McCann invited Clevert to Milwaukee for an interview.

Only years later, during Clevert’s investiture as a federal judge, did Clevert learn that Ash’s call to McCann was part of a plan.

“I learned that Mike McCann had his eye on me because he had spoken with my constitutional law professor and had apparently talked with Mike Ash about possibly recruiting me,” Clevert said.

Plea Bargain Work Presaged Switch to ADR

After graduating from Georgetown in 1972, Clevert began work as a assistant district attorney in Milwaukee.

He soon found himself one of two lawyers assigned to shepherding felony cases through the plea bargain process. The other lawyer was William Sosnay, who today serves as a Milwaukee County Circuit Court judge.

Handling plea bargains bore fruit later in Clevert’s career, when he left the bench to practice alternative dispute resolution as a third-party neutral.

“It gave me an opportunity to help resolve disputes in a way that was consistent and in a way that was evenhanded,” Clevert said. “And it certainly has been an asset now that I am doing mediations.”

But Clevert said he missed trial work.

“I loved trials. Maybe it’s the thespian in me,” he said. “When I was in high school, I was in the drama guild and I loved to be in front of audiences. A jury was another audience, of sorts.”

The move to Milwaukee was good for Clevert’s personal life too.

He met his wife, Leslie, while she was working as a columnist for the Milwaukee Journal. She was the paper’s only Black woman journalist.

Broad Impact of White-Collar Crimes

In 1975, Clevert left the district attorney’s office to take a position as an assistant U.S. attorney for the Eastern District of Wisconsin.

He handled both civil and criminal cases. Many of the criminal cases involved business or white-collar crimes – crimes that Clevert came to realize sent out wider ripples than the crimes he’d prosecuted as an assistant district attorney.

I loved trials. Maybe it’s the thespian in me. When I was in high school, I was in the drama guild and I loved to be in front of audiences. A jury was another audience, of sorts.

“Commercial crimes live on in the sense that those people do not have the money that they thought they would have set aside for their retirements," Clevert said. "It may mean they have to go back to work; it may mean that their dreams can no longer be realized. A crime of, say, possession of marijuana, does not have the kind of broad and immediate impact on society.”

First Black Federal Judge in Wisconsin

In 1977, the federal judges of the Eastern District of Wisconsin appointed Clevert to the U.S. Bankruptcy Court for the Eastern District. At the age of 30, Clevert became the first Black federal judge ever appointed in Wisconsin.

Bankruptcy law is widely perceived as a dry and narrow area of the law. Clevert said he found bankruptcy law anything but narrow.

“People don’t realize that bankruptcy covers an extraordinarily wide range of areas and touches on civil law and sometimes criminal law,” Clevert said. “The issues in a bankruptcy court can range from real estate matters to tax issues to domestic disputes.”

And there were plenty of cases, Clevert said, that taught that bankruptcy was often not as dry as its detractors maintained.

For instance, a case that posed the question of whether a judgment for alienation of affections – a cause of action since consigned to history in Wisconsin – was dischargeable in bankruptcy.

People don’t realize that bankruptcy covers an extraordinarily wide range of areas and touches on civil law and sometimes criminal law. The issues in a bankruptcy court can range from real estate matters to tax issues to domestic disputes.

The bankruptcy petitioner had slept with another man’s wife. When the aggrieved husband sued for alienation of affections and won, the petitioner filed for bankruptcy to escape the judgment.

Clevert said the case was an example of the type of human drama that plays out in bankruptcy court on a regular basis.

“There’s a lot of emotion behind something like that. Somebody feels terribly wronged, and they have obtained a judgment as a result of that wrong and they want to collect on it. Then somebody files bankruptcy to get out of that debt.”

Second Chance for Debtors

Clevert said he also relished the chance to implement the bankruptcy code in a way that gave debtors a second chance.

“The question was the kind of issue that made bankruptcy and continues to make bankruptcy exciting,” Clevert said.

“It’s one that certainly challenges some of the notions that people have about what is right and what is wrong, in terms of obligations. Bankruptcy can touch on things such as people’s ability to get a fresh start, and why certain debts, say for student loans, are able to survive a bankruptcy.”

Serving as a bankruptcy judge also enabled Clevert to rule on corporate bankruptcy petitions – rulings that often helped people resurrect businesses and keep jobs in the community.

For instance, Clevert handled the first Chapter 11 petition by Excalibur, a company that manufactured a luxury car in West Allis, and the first Chapter 11 petition by Gander Mountain, the outdoor recreation products and services store headquartered in Kenosha County.

The benefits of shepherding Gander Mountain through Chapter 11 bankruptcy reached beyond the Eastern District of Wisconsin, Clevert said.

“It touched the lives of so many individuals who worked in those stores across the country.”

A Brief Retirement

In 1996, President Bill Clinton appointed Clevert to the U.S. District Court for the Eastern District.

Clevert served as the court’s chief judge from 2009 to 2012, when he assumed senior status. He retired from the bench in 2017.

It didn’t take long for Clevert to realize that he missed both the law and helping people. So he became a mediator and arbitrator with JAMS (a mediation and arbitration service).

“I love people, and ADR gives me a chance to make a difference in a different way, than say handling criminal cases, where very often the cases result in the people being incarcerated,” Clevert said.

I had a role model in Doug Wilder. So many others, as a result of Judge Jackson’s appointment, will have a role model at the pinnacle of the legal profession. It says, ‘Look – there is no limit to what you can aspire to.’

Serving as a third-party neutral also allows Clevert to give back to the profession by helping the next generation of lawyers.

“I am able to stay involved in the law and decide disputes, and I can also help lawyers in terms of preparing for some of the arguments they may have in cases,” Clevert said.

“I do neutral analysis and handle some moot-court-type situations. I also have the chance to do some mentoring of young lawyers as part of my work.”

Changes Since 1972

Clevert said that two of the biggest changes he’s noticed during his five decades of practice are lawyers’ comportment and the increasing prevalence of lawyer advertising.

“It’s really disturbing how all too often, people become personal in their attacks on others in the civil arena,” Clevert said.

When he became a lawyer, Clevert said, advertising by lawyers was rare.

“Now, advertising is ubiquitous. It was almost unheard of when I began practicing.”

A third change is an increase in the number of women lawyers. When he attended law school, Clevert said, only 2% of his class were women.

It was an era when many women lawyers faced hostile workplaces, both across the nation and in Wisconsin.

“I have good friends who have become judges who have told me about their experiences, and they’re very distressing,” Clevert said.

‘No Limit to What you Can Aspire To’

Clevert spoke to InsideTrack the day after Judge Ketanji Brown Jackson’s appointment to the U.S. Supreme Court was confirmed by the U.S. Senate. She will become the first Black female justice in the Court’s 230-year history.

Clevert said Jackson’s elevation to the highest court in the land will serve as an inspiration for a new generation.

“I had a role model in Doug Wilder. So many others, as a result of Judge Jackson’s appointment, will have a role model at the pinnacle of the legal profession. It says, ‘Look – there is no limit to what you can aspire to.’”

Clevert also said that Jackson’s appointment will have an effect beyond the legal profession.

“It also says to others, ‘I shouldn’t just stereotype individuals because of their skin or because of their background or because of their gender.”

‘I Can’t Imagine Walking Away From the Law Entirely’

The tenor of the Judge Jackson’s confirmation hearing is likely to renew calls to reform the U.S. Supreme Court and the federal judiciary.

Clevert’s experience on the federal bench makes him wary of one of the more commonly discussed reforms – ending lifetime tenure for federal judges.

“Judicial independence is so critical,” Judge Clevert said. “If a person is beholden to political whims or momentary changes in attitude, their fealty to the law can be shaken.

“I think judges should be able to make decisions based upon their honest belief in what the law says or what the law requires. If a judge is looking over her shoulder all the time, and feeling she might not retain her position for making a decision that is right and appropriate under the circumstances that will shake the foundation of the law.”

Clevert said he does see a day a when he’s no longer working as a mediator and arbitrator, “but I can’t imagine walking away from the law entirely.”

When he does retire, Clevert said, he looks forward to honing his golf game, which he admits could use some work.