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Meet the Florida school superintendent at the heart of the mask battle

Carlee Simon, the superintendent of Alachua County Public Schools, started her teaching career in Tampa Bay.
Dr. Carlee Simon, the Alachua County Public Schools superintendent, pictured in her office at the Alachua County Public School District Office on Tuesday, Sept. 21, 2021 in Gainesville. Simon stands firm behind the district's student mask mandate, which was issued just days after Ron DeSantis's order banning such mandates, making the district one of the first two (along with Broward) to do so.
Dr. Carlee Simon, the Alachua County Public Schools superintendent, pictured in her office at the Alachua County Public School District Office on Tuesday, Sept. 21, 2021 in Gainesville. Simon stands firm behind the district's student mask mandate, which was issued just days after Ron DeSantis's order banning such mandates, making the district one of the first two (along with Broward) to do so. [ DIRK SHADD | Times ]
Published Oct. 1

Fifteen minutes into the Aug. 17 emergency hearing, the superintendent’s voice, clear and even, cut through the ambient hiss of the conference call. Carlee Simon, head of Alachua County Public Schools, laid out her case to the State Board of Education for the mask mandate in her district.

As board chairperson Tom Grady peppered her with questions, Simon responded in the deliberate cadence familiar to those who have watched her on national news broadcasts or at local school board meetings. At times she paused, searching for the just-right words. She didn’t react when Grady repeatedly referred to her as “miss” instead of “doctor” or needled her about giving interviews to news outlets across the country.

Simon, who is 45 and began her teaching career in Tampa Bay, has become an unlikely main character in the battle over student masking in Florida and across the country. Less than a year earlier, she’d gone from university professor and public school advocate to the superintendent of the relatively small, 30,000-student school district. Now she’s appeared on CNN, been interviewed on NPR and written a defense of mask mandates for the Washington Post.

With her at the helm, Alachua County was one of the first two districts in Florida to institute mask requirements for all students and staff this school year, a move that defied the wishes of Gov. Ron DeSantis. Nearly a dozen other districts, including Hillsborough County, followed suit.

Simon’s stance on masks is both deeply personal and tied to her professional philosophies. After losing her first husband to cancer, she knows how illness and grief can rupture a family. She relies on the expertise of health professionals, and she believes public schools should prepare students to be civic-minded.

At the August hearing, Simon said she believed her district’s mandate fit within the state’s rule because it allowed for opt-outs: Kids with medical conditions could bring in a doctor’s note; others could apply for a state scholarship to transfer to a private or charter school without a mandate.

She also argued that schools had a responsibility to follow medical experts’ guidance, even if it meant defying the state — a position that irked State Board members.

“Do you expect that your kids in Alachua County are taught to follow the rules?” Grady asked.

“We teach critical thinking in our district,” Simon replied, “and we focus on whether rules are going to be beneficial.”

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Related: Board of Education criticizes Florida schools over mask mandates, mulls penalties

Simon’s defense of masking has evoked passionate responses. Critics have accused her of harming children and self-aggrandizing. Others have held her up as a champion for public health. Hours after the State Board hearing, Alachua School Board members praised Simon’s testimony before unanimously voting to extend the mandate into October.

The State Board hearing was just one skirmish in a battle that has involved more than a dozen districts, multiple court cases and the federal government. Though many medical experts say masking is an easy way to reduce the spread of COVID-19, efforts to require it in schools have deepened community divides.

Many of the state’s largest school systems have mask mandates, including Hillsborough and Miami-Dade counties. (Pinellas and Pasco have made masks voluntary for students and staff.) The state has moved to cut thousands of dollars in funding from the Alachua and Broward school districts in response to their mask rules and put several others on notice.

While the decision to continue extending Alachua’s mandate ultimately rests with the School Board, Simon will be the one to enforce the decision, which means she’ll be in the line of fire for any discontent it prompts.

“I just happen to be in that place with the ability to do what I think is right,” she said. “I can’t wait for other people.”

Kimberly Green, Program Services Specialist, on left, talks with Dr. Carlee Simon, the Alachua County Public Schools Superintendent, in the offices at the Alachua County Public School District Office on Tuesday, Sept. 21, 2021 in Gainesville.
Kimberly Green, Program Services Specialist, on left, talks with Dr. Carlee Simon, the Alachua County Public Schools Superintendent, in the offices at the Alachua County Public School District Office on Tuesday, Sept. 21, 2021 in Gainesville. [ DIRK SHADD | Times ]

A winding path to superintendent role

Simon grew up in Alachua County schools, where her mother was a special education teacher and her father a counselor. The conversations at the dinner table, she said, often revolved around public education — including “navigating a system that was bureaucratic and complicated and undermined sometimes.”

She had no intention of becoming a teacher, she said. But after graduating from the University of Florida with an architecture degree, she wanted to try something new for a year and got a job teaching woodshop at Hillsborough County’s Sickles High. A year later, she moved to J.W. Mitchell High in Pasco County, where she taught math for five years.

While teaching at Sickles, she met and fell hard for the head of the lumber department at the local Home Depot. They married soon after that, and the first of their three sons was born just before their first anniversary.

In 2005, they moved back to Gainesville, where Simon got a doctorate in educational administration and policy, and then to the University of Cincinnati, where she joined the faculty as an expert in school finance and law. Her sons were then in school, two of them with individualized education plans for dyslexia, and she found the special education system to be complicated and flawed. She started working with other parents to advocate for their children’s rights.

Soon after the move, Simon’s husband was diagnosed with cancer. He died in the summer of 2012. The loss reoriented how she saw herself and the world: She was the only living parent of three boys, the oldest not yet 10. Though she married again, the grief never left, and it has informed how she’s managed the pandemic as a superintendent.

“I know how horrible that can be,” she said, “and so I don’t want to be a part of, oh, you know, I have to expose people to COVID because the governor says so.”

In an email to the Times, DeSantis spokesperson Christina Pushaw criticized the media coverage of Simon and slammed Simon’s “dedication to muzzling kindergartners in violation of parents’ rights to make health and educational decisions for their own children.”

Simon moved her family back to Gainesville in 2018. Wanting to continue the advocacy work she’d started in Cincinnati, and dismayed that the schools were now largely segregated along race and class lines, she started showing up at Alachua County School Board meetings.

Her advocacy made her a familiar face by 2020. Still, it was a surprise when a board member mentioned her name during the district’s search for a new superintendent. The district has historically hired from within, and Simon’s predecessor spent 29 years there.

The board, on a 3-2 vote, hired Simon as interim superintendent in December.

She stepped into the office nearly nine months after the pandemic began. Like others around the state, the district was requiring students attending school in person to wear masks.

By spring, with student and staff case counts at a low plateau and vaccines becoming available, Simon — then the district’s full-time superintendent — suggested students may return to class unmasked in the fall.

The idea earned blowback. Parents of students with disabilities or underlying health conditions — some of the same parents she’d aligned with as an advocate — argued that their children would be endangered by a rush to return to normal.

The laptop, reading glasses and superhero water bottle belonging to Carlee Simon, the Alachua County Public Schools superintendent, in her office on Sept. 21, 2021 in Gainesville.
The laptop, reading glasses and superhero water bottle belonging to Carlee Simon, the Alachua County Public Schools superintendent, in her office on Sept. 21, 2021 in Gainesville. [ DIRK SHADD | Times ]

Praise and shame

Over the summer, DeSantis made it clear that he was done with coronavirus-related mandates, even as the delta variant spread and cases increased. On July 30, he issued an executive order halting school mask requirements.

Related: DeSantis issues executive order to halt school mask mandates

In the days that followed, two district employees died of the virus. Local doctors told the School Board that the number of children hospitalized with coronavirus had increased tenfold in a matter of weeks. Simon mandated masks for visitors and employees, and a day later, the board unanimously issued the student mandate.

“This is what it’s like to be members of a society,” Simon told students as she thanked them in advance for wearing masks.

Prescott Cowles, a special projects manager for the district’s pandemic-related efforts, said Simon would have loved to eliminate mask requirements this school year.

“I really don’t think she would have done it if we hadn’t sat on a call and the doctors said, ‘This is what we have to do,’” he said.

But Simon’s position has put her in the crosshairs of a vocal group of parents who don “Fire Carlee” masks at School Board meetings.

“She’s going around, interviewing on national television about how she’s defying the governor and this board is defying the governor, rather than serving the parents and the children of this community,” one parent said at an Aug. 17 School Board meeting. She said Simon was trampling on parental rights. “It’s unacceptable. It’s disgraceful. It’s shameful.”

In her Washington Post opinion piece, Simon wrote that she had been called “a monster, child-abuser, communist, fascist, idiot and other names not fit to print.”

At recent School Board meetings, sheriff’s deputies have had to remove citizens who screamed at Simon or the board.

“If you have no idea who I am, and you don’t want to know who I am, and you need someone to be angry with, then that’s the character, the role I take on in this situation,” Simon said.

She tries not to take anything personally, she said, and has found one-on-one conversations with her critics are often productive and amicable — especially when they stop talking about masks and start talking about how their children are doing in school.

Becoming such a divisive figure can’t be easy, but Simon is taking the “moral high ground,” said Steve Noll, a UF history professor who once worked with Simon’s parents and has known her since she was born. “When she’s on TV, she doesn’t act like a flame-throwing, bomb-throwing radical.”

The back-and-forth over masks has continued. The federal government launched a civil rights investigation into the state’s opposition to mask mandates, and it stepped in to cover districts’ financial losses from state-imposed penalties. Parents, school districts and others have launched legal challenges against the state’s rules against mask mandates. On Sept. 22, the state’s new surgeon general issued an order that more explicitly banned student mask mandates.

Related: Feds cover Broward school board salaries as fallout continues over masks

Simon believes Alachua’s mask mandate has worked. Infection rates among students and staff have dropped steadily since the second week of school. The number of students in quarantine dropped from more than 1,800 in late August to 655 less than a month later.

That may not be enough, said Michael Lauzardo, the deputy director of UF’s Emerging Pathogens Institute and a key adviser for the district on coronavirus protocol. He praised Simon’s courage on masks, but said it will take widespread vaccination, by mandate if necessary, to push through the pandemic.

The district has made no move to mandate vaccines, though it has offered incentives for staff who get vaccinated. Simon wants to see how parents respond when a vaccine for children under 12, now on the horizon, is widely available.

She said she will continue to follow her beliefs in science and communal good.

“I don’t want to do anything that I’m not proud of doing,” she said. “If I’m in a place where I’m letting go of my principles, I don’t want this job anymore.”

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