Bill Cowles, Orange County Supervisor of Elections, announces retirement effective Jan. 31

Bill Cowles, Orange County’s longtime Supervisor of Elections, announced his retirement Friday and said his last day in office will be Jan. 31.

Cowles, 69, was first elected in 1996 and plans to leave his post following the Special Election for House District 35 in January, ahead of the Presidential Primary in March. By that point, he will have overseen 96 elections and leaves office as the longest-serving person in the job’s history.

He sent a letter to Gov. Ron DeSantis and Florida Secretary of State Cord Byrd earlier in the day sharing the news. DeSantis is now tasked with appointing a successor to the seat, as Cowles’ term runs through 2025.

“It just felt like the right time,” Cowles said Friday.

He cited a desire to spend more time with his family in his resignation letter to DeSantis.

“The good news is when you look back at the staff we have here at the elections office, they have a total of 425 years of elections experience,” Cowles said. “They’re prepared, they know their job, they know what is ahead.”

Cowles, a Democrat, said he didn’t think he’d finish the term when he was most recently re-elected but wanted to see through a few final projects before leaving office, such as redistricting and an upgrade to the county’s voting systems.

His term was bookended by national election uproars, starting with the 2000 presidential election between then-Vice President Al Gore and Republican George W. Bush. Florida was in the national spotlight due to a controversial recount.

And his final presidential contest was in 2020 when former President Donald Trump falsely claimed he won the national race.

The turmoil – and distrust by some – surrounding elections wasn’t a factor in his decision, Cowles said.

“The political chaos is a part of the factor that is leading a lot of administrators to leave the elections process,” he said. “It’s not a key factor here. Mine is more of tenure and timing.”

Orange County Mayor Jerry Demings praised Cowles’ tenure overseeing elections in the county.

“While I’m saddened to hear of Bill Cowles’ retirement earlier than planned, he has earned that right,” Demings said in a statement. “He has been an extraordinary Supervisor of Elections and public servant. I will personally miss his steady hand in ensuring fair elections in Orange County.”

When Cowles announced earlier this year he wouldn’t run again, candidates began lining up for the coveted elected office.

Seven candidates have already filed to run. His annual salary is $193,419.

The five Democrats in the race are: Karen Castor Dentel, Dan Helm, Wes Hodge, Ricardo Negron-Almodovar and Michael Scott.

Joseph Haynes Davis is the lone Republican, and Cynthia Harris is also a candidate with no party affiliation.

Cowles didn’t weigh in on whom DeSantis should choose to replace him in the interim but noted he doesn’t have a chief deputy. Before being elected as Orange’s election supervisor, Cowles served as the office’s chief deputy.

“I’ll leave that up to the governor,” Cowles said. “There’s a dedicated staff here who will support whoever comes in here as a placeholder.”

DeSantis previously appointed Chris Anderson as Seminole County’s Supervisor of Elections in 2019, after the governor tapped his predecessor Mike Ertel to be his first Secretary of State.

Ertel resigned from the state position shortly after photos of him in blackface surfaced. Anderson since was elected to the office in 2020.

The Orange County office has 55 full-time employees and a roughly $15 million budget. The county has more than 795,000 registered voters.