By Alison E. Preston[1]
If you could have dinner with any historical figure, who would it be? For Judge Charles R. Wilson, a lifelong Catholic who attended Catholic schools from elementary to law school, the answer is “easy”: Jesus Christ. Long ago, Jesus taught, “Blessed are the meek, for they will inherit the earth.” Matthew 5:5. I’ve always understood that teaching, correctly or not, as Google’s AI overview puts it, that “those who are humble, gentle, and patient, even in the face of adversity, will ultimately be rewarded and find true fulfillment,” and that living “a life of quiet strength and reliance on God”—“rather than seeking power through aggression or dominance”—“will lead to a lasting positive outcome.” For anyone who wonders whether living that way can yield not just heavenly but earthly success, look no further than Judge Wilson.
In one word of several lawyers who have described him to or around me, Judge Wilson is “elegant.” He is a tall, soft spoken, effortlessly dignified, black man with an incisive mind, a soothing voice and manner, and a disarmingly quick wit. Although Judge Wilson keeps his chambers in the Sam M. Gibbons United States Courthouse, home to the Middle District of Florida Tampa Division, where I interviewed him, he is not listed in the directory; you know he’s there only if you know he’s there. In his words, he is a “guest.”
And yet, before Judge Wilson took senior status on New Years’ Eve 2024, he was the most senior active judge, besides the chief judge, on the United States Court of Appeals for the Eleventh Circuit after a quarter century of service there. Even by the standards of that court, which hears countless consequential cases, Judge Wilson has heard particularly high-profile ones, including Bush v. Gore, the Terri Schiavo case, and the Elián González case. Before his Eleventh Circuit service, he served as a federal magistrate judge, the United States Attorney for the Middle District of Florida, and a Hillsborough County court judge. He credits that enviable career to hard work, perseverance, resiliency, relationship building, community service, and luck as Seneca is said to have defined it: “what happens when preparation meets opportunity.” Those virtues also contributed to his sterling reputation—one’s “most important asset.”
But that reputation and career were long in the making and hard won.
Although he dreamed of becoming an athlete, as many children do, from an early age Judge Wilson “more realistically” considered law. His father was a lawyer and his role model. Mr. Wilson had “hung out his shingle” (started a solo practice) in Pensacola, Florida, where Judge Wilson was born. He was separated from the next closest black lawyer, in Jacksonville, by roughly 350 miles or the combined widths of Alabama and Georgia. He tried all the Panhandle’s major desegregation cases, including the first one in Escambia County, which was eventually affirmed by a panel of the United States Court of Appeals for the Fifth Circuit that included Judge Elbert Tuttle. (“As both a judge and then chief judge of the Fifth Circuit, Tuttle . . . assured the effective desegregation of southern society.” Charles M. Elson, Remembering Judge Elbert P. Tuttle, Sr., 82 Cornell L. Rev. 15, 16–17 (1996)). According to Judge Wilson, his father, who died before it happened, never would have imagined that his son would later sit on the Fifth Circuit’s offspring court or that the Atlanta courthouse would be named for Judge Tuttle.
Judge Wilson moved to Tampa when he was seven because his mother’s family was there. His mother was a third-generation Tampa native. Judge Wilson ballparks his Tampa cousins at 100.
His family greatly valued education. His mother grew up in Catholic schools and wanted to put Judge Wilson in them, so he attended St. Joseph’s, St. Peter Claver, and Jesuit High School. Attending the latter was “like being a member of a fraternity.” Jesuit has its own bar association, and last time the Jesuit alumni who are now Tampa judges gathered for lunch, they numbered around 16. So strong is Judge Wilson’s connection with the school, so great its impact on him personally and professionally, that he decided to have his upcoming portrait ceremony there.
When he was applying to college, his dad took him to see only two schools: Georgetown and Notre Dame. As soon as Judge Wilson set foot on Notre Dame’s campus, he knew he had found a home away from home. At Notre Dame, Judge Wilson majored in what was then called Government and International Relations, now Political Science. In Judge Wilson’s days, Notre Dame was even better in football than they are now; they won two national championships while he was there. Perhaps because Joe Montana kept fit playing pick-up basketball with Judge Wilson. Perhaps.
Judge Wilson also attended law school at Notre Dame. That decision was “probably irrational,” which I took to mean for pure love of the school. But he tacked on a plenty rational factor: Attending a national law school instead of a Florida law school, even though he planned to return to Florida, preserved post-grad employment options.
His concerns were borne out. Judge Wilson returned to Tampa and, despite his deep ties, struggled to find a job. He wanted to be an Assistant United States Attorney but did not get the job. He eventually secured a clerkship with then newly appointed Fifth Circuit Judge Joseph Hatchett. While awaiting Judge Hatchett’s confirmation, he worked for a few months as an assistant county attorney for Hillsborough County.
Judge Wilson clerked for Judge Hatchett just before the Eleventh Circuit split off from the Fifth Circuit. In Judge Wilson’s view, other than scaling up (double the appeals filed, double the clerks per active judge plus a chambers staff attorney, and a larger staff attorney office), the court then felt much the same as it does now. The number of active judges has remained a mere 12, so that scaling, Judge Wilson says, is a testament to technology and the increased efficiency it provides. Judge Wilson learned a lot from Judge Hatchett and thinks he models some things after his judge.
As hard as it may be to believe given today’s standards, Judge Wilson still struggled to get a job in Tampa, despite having clerked. Those were also the days, however, when Tampa was so small that a lawyer could know all the local judges, as Judge Wilson did, and all the judges were men. So, like his father, he decided to hang out his shingle. He signed up for the court appointed attorney list and tried jury trials in both federal and state court for every type of case under the sun, “whatever walked in the door.” Slowly but surely, he built his reputation as a lawyer. Serving in bar associations helped with that. He served as president of the Young Lawyers Section of the Hillsborough County Bar Association and was eventually elected to the Board of Governors of the Florida Bar Young Lawyers Division. In Judge Wilson’s eyes, bar service is critical to the success of both the profession and individual lawyers.
That practice and service got him noticed. One day Guy Spicola, then Chief Judge of the Thirteenth Judicial Circuit, pulled him aside and told him that he did a “good job” and should consider applying to serve as a county court judge. And that judge’s opinion meant something not only professionally but politically: He had served with the governor and had stayed connected to him. Judge Wilson applied, and he got the job.
From the county court Judge Wilson saw a federal magistrate judge vacancy, applied, and got that job, too. The district judges remembered him, he recalls, from his court appointed cases. When he applied for a position as a district judge, however, he did not get it—three times.
Then President Clinton assumed office and chose as his Attorney General another Florida lawyer: Janet Reno. By connection to her, Judge Wilson had the opportunity to become the United States Attorney for the Middle District of Florida, and he was prepared to meet it. So after long seeking and never getting an AUSA position, Judge Wilson became U.S. Attorney having never sought that position.
If forced to pick, Judge Wilson would say U.S. Attorney was his favorite job. The U.S. Attorney, of course, impacts the community, deciding who gets federally prosecuted and who doesn’t. He also had the chance there to work with people like Janet Reno and later Eric Holder during the Clinton administration. More broadly, the position allowed him to build and maintain many relationships, which is also one of his favorite things about the job he was next appointed to, this time for life: Eleventh Circuit judge.
Judging on the Eleventh Circuit was as Judge Wilson thought it would be after clerking. In fact, the court still had many of the same staff, and he sat on a panel with Judges Tjoflat and Anderson, who had been on the Fifth Circuit when he clerked. And the work, which he loves, was much the same. Judge Wilson particularly enjoys working on constitutional issues. The remedial statutes that were passed to solve problems particularly pervasive in the South fascinate him. And he appreciates that the court is a tremendously impactful circuit for the number of diverse, important cases that arise here. Judge Wilson’s views on his role as a judge are also timeless. He aims to be “decisive” and “keep [the] docket current.” “Sometimes a case is so close that you could go either way, and in that case, the most important thing to do is just decide. The parties are waiting on a decision and generally don’t care a lot about the nuances.” But it is equally if not more important to him “to decide cases fairly and decisively based on the facts and the law with no ideological predisposition.” He thinks Justice Lewis Powell (who also earned his reputation in bar associations) did that, and for that reason, he would want to get dinner with Justice Powell as well, if he could. Judge Wilson hopes he too is remembered for having done that.
Something different about judging, however, from his days clerking with one other co-clerk is that, as an active judge, Judge Wilson had four clerks (now three) and a staff attorney, who was functionally a fifth clerk. Judge Wilson loves having clerks and building a chambers community. Although he looks foremost for writing ability, law school success, and “people he would be comfortable working with for a year,” he consciously hires many clerks from Notre Dame (about 45) and Tampa to give back to communities that shaped him and matter most to him. He and his clerks eat lunch together every day. Bonding with his clerks and watching them bond with each other both during the term and later in life are some things Judge Wilson enjoys most about the job. He considers himself a lifelong mentor to them and follows their careers. As he often reminds them and indeed reminded me during our interview, “our reputations are inextricably intertwined.”
To paraphrase what Judge Wilson tells his clerks about judicial writing, it is a means to an end, not so much an end itself. He says he writes for the parties and the district judge, “not for Twitter.” That said, he still enjoys it. Dissents are fun “because you don’t need to convince anyone of your position and you have freer rein to write as you want to; you can get a bit sharper when the case calls for it.” He is particularly proud of his dissent in Nelson v. Campbell where he opined that a death row inmate could use the Eighth Amendment and Section 1983 to challenge Alabama’s procedure of cutting to bypass collapsed veins during execution. 347 F.3d 910, 913–14 (11th Cir. 2003). The Supreme Court agreed and reversed 9-0. Nelson v. Campbell, 541 U.S. 637 (2004).
Although Judge Wilson thinks advocates’ writing the court sees is generally good, he shared some advice. Briefs should be brief (ideally two to three best issues), trustworthy, and accurate. Pay attention to proper grammar, punctuation, and spelling; if it’s off, that undermines the trustworthiness of the brief. Don’t assume judges know anything about your case. And the facts and procedural history should be set forth chronologically, from the filing of the complaint or indictment to the notice of appeal, to provide useful context. Sometimes, he observed, he will start with the district court’s order before turning to the briefs.
The importance of briefs is underscored by how few cases (only 15-20%) go to oral argument. But if you get oral argument, Judge Wilson says, it is probably because judges have questions, the issue is important or of first impression, or the court needs to clarify circuit precedent. To be prepared, then, is to come ready to answer questions, not to regurgitate briefs.
Incidental benefits to the court also flow from oral arguments. The judges, normally scattered across Florida, Georgia, and Alabama, and connected by memo, try to get together during sittings and to maintain collegiality that way. Local judges will volunteer to host visiting judges and their clerks, sometimes even for dinner at their homes. Judge Wilson’s favorite sitting location is Montgomery because of its history and southern food. When there he visits local attractions such as the civil rights museum, state capitol building, and the church where Martin Luther King, Jr. was ordained.
When not judging, Judge Wilson can be found enjoying his family and hobbies. He has always appreciated his wife and daughters’ support and understanding of the sacrifices that his public service has required, such as restrictions on political contributions or less pay over the years compared to private practice. He is proud that both his daughters are lawyers like him and his father and that they each hold a degree from Notre Dame. Speaking (again) of Notre Dame, Judge Wilson loves watching Notre Dame football—every game—while texting with friends and classmates, and he goes up to South Bend once or twice a year. He serves on the Advisory Council for Notre Dame Law School and otherwise volunteers for bar programs. He loves to read, particularly biographies, and recently read The Warmth of Other Sons about the Great Migration. He also considers himself a “foodie.” Although he diplomatically declined to name names of favorite Tampa restaurants, he said he loves Italian food and Wright’s cake, specifically chocolate alpine with a scoop of vanilla ice cream. But when asked whether he would rather be able to only eat Wright’s cake or watch Notre Dame football, he picked Notre Dame, albeit with a grimace. He loves things that make Tampa: Gasparilla (he ran the 15k for 25 years straight and stopped only a few years ago), Ybor City and its history (“it’s what gives Tampa its culture”), the Florida State Fair (especially the corn dogs and cotton candy), and the Strawberry Festival. And now that he has taken senior status and will drop to 50% of his active caseload, he looks forward to relaxing on the beach in Northwest Florida.
True to form, Judge Wilson focused his parting thoughts on service and responsibility. He reminds lawyers that it is a privilege to practice law and that they have a duty to serve their communities. Communities depend on young lawyers because they are well educated, have a lot of energy, and can correct injustices. And, in his view, the most satisfied lawyers are those who give back.
If that’s true, Judge Wilson is surely supremely satisfied.
[1] Alison E. Preston is a Deputy Solicitor General in the Florida Solicitor General’s Office. A Tampa native with a lawyer for a father, she long hoped to clerk for Judge Wilson on the Eleventh Circuit and did during the 2019 term.
