A runoff contest for a Hillsborough County School Board seat has turned sharply combative in its final weeks, with allegations flying between candidates Daniela Simic and Brittany Lyssy over campaign finances, vendor ties, and the future shape of district leadership. Neither candidate cleared 50% in the August primary, setting up a November faceoff for the District 2 seat that covers dozens of schools stretching from Hyde Park to Ruskin.
The race has drawn accusations and campaign scrutiny, according to the Tampa Bay Times. In the August 18 primary, Simic took more than 38% of the vote while Lyssy earned more than 36%, according to the Tampa Bay Times. Third-place finisher Chris Taylor, who collected 24.4% of the vote, was eliminated from contention, forcing the two front-runners into a one-on-one November runoff.
Two Very Different Resumes
Simic is a registered Democrat who spent 25 years in education, including a stint as Hillsborough's assistant superintendent for curriculum, while Lyssy is an attorney who once led the Tampa Bay Young Republicans and registered as a Republican in 2017, per WUSF. School board races are nonpartisan on the ballot, though the candidates have party affiliations. That nonpartisan label hasn't stopped the contest from functioning along familiar partisan lines, with Simic supported by the teachers' union and Lyssy receiving endorsements from police organizations and Republican officials.
The seat opened up this year after incumbent Stacy Hahn decided not to seek re-election, instead launching a bid for county commission, according to the Tampa Bay Beacon. The district itself spans 42 public schools, running from Hyde Park in Tampa down through South Hillsborough County into Ruskin, a stretch that mixes dense urban neighborhoods with fast-growing suburban subdivisions, as the Florida Trib reported.
An AI Vendor Contract Draws Scrutiny
Simic's day job has become a flashpoint in the campaign. She works as an account executive for MagicSchool AI, an education technology company that landed a $2.1 million contract from the Hillsborough County School Board in February 2026 to supply artificial intelligence tools to more than 7,000 local teachers, according to Florida's Voice. The board approved that contract months before the runoff, raising questions about the overlap between Simic's employer and the district she's seeking to help govern.
The candidates also split sharply on a separate, higher-stakes question appearing on the same November ballot: whether Hillsborough's school superintendent should become a partisan elected official starting in 2028, rather than remain an appointee chosen by the school board. Lyssy supports the referendum, while Simic opposes it and wants the board to retain its appointment authority, per the Tampa Bay Times. Hoodline previously reported on the push to elect the schools boss when state lawmakers and local officials first advanced the measure.
Competing Endorsements and a Fundraising Edge
The two campaigns have assembled starkly different coalitions of institutional backers. Simic has the support of the Hillsborough Classroom Teachers Association and the Tampa Bay Times editorial board, while Lyssy has been endorsed by sitting District 4 board member Patti Rendon, Hillsborough County Commissioner Joshua Wostal, the Tampa Police Benevolent Association, and Tampa Firefighters Local 754, the Florida Trib reported.
Money has followed a similar partisan split, though Lyssy holds the financial edge. Campaign finance reports through October 2026 show she raised roughly $92,000 in total contributions, compared to nearly $80,000 raised by Simic, per WUSF. Lyssy maintained that fundraising advantage throughout the campaign, the station's report indicates.
Public forum appearances have also become part of the back-and-forth. At a nonpartisan candidate forum hosted by the Tiger Bay Club at The Cuban Club in Ybor City in March, Lyssy was the only District 2 candidate who did not take part in answering questions on literacy, book policies, and school safety, according to the Tampa Bay Times. That absence came as the district has faced separate, ongoing public fights over library materials.
Both the District 2 runoff and the superintendent referendum will appear before Hillsborough County voters on the November ballot, giving residents a direct say not only in who represents their schools but in how the district's top administrator is chosen in the years ahead.
