Cindy Stuart enters Hillsborough Commission race to challenge Joshua Wostal; Aileen Rodriguez vows to fight on

Former Hillsborough County Clerk of Court Cindy Stuart has entered the race for Hillsborough County Commission in District 7, where she is aiming to challenge incumbent Republican Joshua Wostal.

But Stuart won’t be the only Democrat in the contest. Aileen Rodriguez, who entered the race in January, has vowed to continue her campaign while lamenting Stuart’s entrance into the race just 11 days before the qualifying deadline.

“Over the last year, we’ve been showing up, listening to residents, and talking about the issues that affect working families every day,” Rodriguez said. “That mission hasn’t changed, and it won’t change because of a last-minute political decision.”

Stuart was first elected to Clerk of Court in 2020, after she served two terms on the Hillsborough County School Board. She served just one term as Clerk before losing in 2024 to Republican Victor Crist, who unseated her with nearly 51% of the vote in a year that saw losses for Democrats across the region.

Since leaving the Clerk’s Office, Stuart has served as a strategic advisor for GrayRobinson and runs a consultancy firm, Cindy Stuart LLC, where she works with clients on policy advocacy, fiscal management and more, particularly for nonprofits.

Stuart does not yet appear to have a campaign website or social media page.

Rodriguez, meanwhile, has been building support in her bid against Wostal, a conservative who often riles critics from the dais. Rodriguez already has support from several elected officials, including recent nods from U.S. Rep. Kathy Castor, state Sen. Darryl Rouson, Florida House Democratic Leader Fentrice Driskell, and state Reps. Dianne Hart-Lowman and Michele Rayner.

Several local elected officials are also endorsing Rodriguez, including Tampa City Council members Alan Clendenin, Lynn Hurtak, Guido Maniscalco, Luis Viera and Naya Young, and Hillsborough County School Board Members Nadia Combs, Lynn Gray, Karen Perez, Jessica Vaughn and Shake Washington.

Several former elected officials are also lending their support, including Betty Castor, Janet Cruz, Cheri Donohue, Adam Hattersley, Pat Kemp, Andrew Learned, Kimberly Overman, Alex Sink and Mariella Smith.

Rodriguez is a career public relations expert, having run her own PR firm, AR Public Affairs and Strategic Solutions, since 2009. She also worked from 2014 to 2017 as a senior manager of executive affairs for the Hillsborough County Aviation Authority.

Prior to that, she served as marketing communications director for the Helios Education Foundation and Communications Director for the 2012 Tampa Bay Host Committee for the Republican National Convention.

Rodriguez was previously registered as a Republican but changed her political affiliation in 2019, saying the GOP left her and no longer reflected her values as a Christian.

“Families are struggling with housing costs, traffic congestion, and the rising cost of living,” Rodriguez said. “Voters deserve leaders focused on solving problems, not politicians looking for their next opportunity.”

Without mentioning Stuart by name, Rodriguez blasted the former School Board member’s entrance into the race, arguing that “Hillsborough County doesn’t need another political comeback campaign,” but rather “leaders who are focused on what’s next.”

“This campaign has never been about me,” Rodriguez added. “It’s about the people who work hard every day and still struggle to get ahead. While others may be focused on political calculations, we’re focused on delivering results.”

District 7 is elected countywide, where Republicans hold a voter registration advantage with nearly 292,000 voters compared to nearly 273,000 Democrats. With another more than 217,000 independent voters, Rodriguez’s experience as both a Republican and Democrat could help bridge the voter registration gap by enticing moderate voters.

But Stuart may come with an advantage as an experienced fundraiser, and she’s shown before that she can draw support from conservatives.

Stuart raised nearly $128,000 for her most recent campaign for Clerk of Court, far outraising Crist. As of the end of March, the most recent date for which campaign finance reports are available, Rodriguez had raised just shy of $28,000, while Wostal had raised more than $119,000.

In 2020, when she was first running for Clerk, Stuart drew criticism from some progressive Democrats because she accepted endorsements from Republicans. Critics also called on Stuart to denounce negative mailers that attacked her Democratic Primary opponent Kevin Beckner.

Then, she had backing from the local Tea Party, Hillsborough County Sheriff Chad Chronister and Terry Kemple. That year, however, there was not a Republican on the ballot, so the race was decided in an open Primary.