Two memories stand out to Jimmie Pearson from the early ‘90s at Botten Field Junior High School in Jefferson County. Pearson was the school’s principal at the time, and Bill Cleveland was one of his social studies teachers and coaches.

The first was seeing Cleveland’s mom, who was ill at the time, at every basketball game and football game Cleveland coached. “That stuck with me that (she cared) enough about family members that she would do that,” Pearson says. “My family was young at that point, and I said (if we only) can be close to how his family interacted.” He quickly learned that Cleveland embodied his mother’s relentless dedication not just to his own family but to the whole community of a family.

The second was watching when the teams Cleveland coached had to sit and wait for the gym to come available for practice. Rather than just letting the students talk or play, he would get them to study up until their practice time. “That was phenomenal to me,” says Pearson, the current Homewood Middle School principal. “I could see at that time he would be a leader.” Plus, “If his kids needed something, he’d go to their house,” Pearson continues. “He took it on as a personal badge of honor to help people, and he kept up with them as they went off to college.”

And the same Mr. Cleveland the teacher Pearson knew in 1994 is the same Dr. Cleveland the Homewood City Schools superintendent today—a “family man who cares about the kids,” he says. “He has touched my life in a special way. Even though he is younger than me, I looked up to him by watching that. And that’s translated from being a superintendent to a teacher to a community member.” For Pearson that looks like Cleveland dressing up as Elvis one minute, being a guest speaker in a social studies class the next, leading a board meeting the next, and coming to a sporting event the next.

In fact, Jimmie Pearson says Cleveland knows more kids at HMS than he does. “When he comes into the building, he’s five-ing them, he’s hugging them,” Pearson says. “He knows their parents and some of their grandparents. He went to school with some of their relatives and knows their background. He’s talking to them like it’s his daughter or son since he knows them. It’s such an outstanding trait.”

There’s no doubt that there’s no superintendent quite like Dr. Cleveland, so it was a bittersweet moment when he announced in February he would retire on June 30 after 12 years as a student in the school system and 12 as its superintendent and that he planned to join LEAN Frog Business Solutions as the vice president of sales and operation. And it was an equally poignant moment in mid-March when Cleveland decided to temporarily delay his retirement to lead the school system through the COVID-19 crisis—a decision telling of the character countless students and parents and students in Homewood have seen him live out with equal parts compassion and action for years.

Former HCS superintendent and current grandmother of five Homewood students Jodi Newton recalls hiring Cleveland to be the principal of Homewood Middle School just as they were finishing construction of its new building in 2004. “I remember that he was so energetic and optimistic,” she says. “We walked the school that was under construction, and he seemed enamored with it. I thought he had a good balance of appreciation of music and sports, and a strong grounding in academics.” Plus many of the Homewood parents had been his peers growing up, and Newton notes, he has an “incredible sense of humor.” (Or in HMS teacher Steve Sills’ words, “He’s a straight up trip. He’s a ball of laughs.”)

But what Newton remembers most from that first year is the first day Cleveland first walked into the new building with students midway through the year. “I remember…how excited (the students) all were and what positive influence he seemed to have with them,” she says. “He had only known them four months and he knew their names, he knew something about them and their families, and he seemed to have such a great personal connection with so many different students.”

Current HCS Director of Student Services Cristy York, then a HMS teacher, vividly calls to mind the initial impression Cleveland made as a leader that year too. “I just remember being so appreciate of how in charge of it he was and how much ownership he took,” York recalls. “He really took care of the teachers and made (the move) as seamless and organized as possible. He calmed everyone’s nerves about the move and made it was easy as possible for us.”

After the move, the part of that school year that York will never forget is the final faculty meeting. For it, Cleveland donned a tuxedo with tails and had a piano rolled out on the stage in the lunchroom. And then he broke out in song—and not just any song but one he’d written about different things that had happened with faculty and staff that year. “It was absolutely hysterical,” York remembers. 

Even when Cleveland became the school system’s assistant superintendent and then superintendent 12 years ago, he joined in on the HMS PTO Sports Challenge each year where faculty play eighth grade students in basketball. “You could always count on Dr. Cleveland to come lace up,” Sills says. He’d take shots from half court and make them—and the kids were amazed. After all, Cleveland, a fierce University of Kentucky basketball fan, is a as competitive as he is caring.

And even as superintendent, Cleveland would often help serve lunch in school cafeterias or pick up a broom, and when “Snowmageddon” hit in 2014, he was sweeping snow and spreading sandbags, not waiting for maintenance workers to do it. He wasn’t above any of it.

Sills has example after example of how Cleveland is “the type of guy that makes everyone feel special.” Sills’ oldest daughter Makiyah graduated from HHS last year, and Cleveland still regularly texts him to ask how she’s doing and tell him he’s keeping up with her track scores at UAB. On Sills’ desk sits a handwritten note Cleveland gave him after his eighth grade football team won the metro championship two years ago—a memory also marked by Cleveland joining him on the sidelines during the game. “He’s very intentional about making sure he sees what you do,” Sills says.

Homewood City Schools talks a lot about every student reaching their full and unique potential, but Sills knows Cleveland really means it. “I hear his voice in the back of my head often when I am teaching or coaching, (telling me) to get every ounce of hard work that he or she has out,” Sills says. “He’s challenged me.”

Not only that, but Sills has seen Cleveland sit at the hospital during a faculty member’s child’s surgery—just one marker of his constant care. “He just loves people,” Sills says. “The person he is transcends race, gender, socioeconomic status. He is a man for the people.” And, according to Sills, his “people” want to be for Cleveland too. “When teachers get teacher of the year awards, we are a reflection of our leader and our leadership,” Sills says. “That’s our way as a school system of paying him back. He won’t look at it like that, but we want to make him look good.“