Deep Something

Ken Gay’s Campaign For Hillsborough School Board Deserves a Much Closer Look

September 14, 2026September 14, 2026 B. John 73 Views 0 Comments

This entry is in the series 2026 Elections

Ken Gay brings nearly four decades of experience in Hillsborough County public schools to the District 6 School Board race. His long career gives voters plenty to respect. But a detailed candidate questionnaire offers a much fuller picture of the political and social views he would bring to the Board.

Gay identifies himself as a conservative Republican and has taken clear positions on school choice, transgender students, sex education, books, guns in schools, religion and the federal role in education. These are not assumptions about his politics. They come from answers Gay submitted himself.

His campaign finances add another layer. The campaign is largely self-funded, while a recently formed company called Faith in Policy has received a substantial share of Gay’s campaign spending. I took a closer look at Gay’s record, his own words and where his campaign money is coming from.

AI Image of choice schools and State Constitution

Featured Places Tampa Politics Society Education Crack Pots Business Economy

When “School Choice” Stops Meaning Public Education

September 13, 2026September 13, 2026 B. John 60 Views 0 Comments Florida Schools, Education Funding, Educational Equity, Education Vouchers, Henry Mack, Public Education, Public Schools, School Choice

This entry is in the series Education

Florida’s new Education Commissioner has said the state does not need to run schools at all. That raises a question that goes well beyond vouchers: what happens when “school choice” starts replacing the idea of public education itself?

Florida’s Constitution requires a system of free public schools. Yet an $8,000 voucher does not guarantee admission, does not guarantee a free education, and means something very different to a family that can add another $30,000 than it does to one that cannot. That is why the slogan “fund the student” leaves out so much.

At our Voices of Justice: Speak Up for Students program earlier this year, USF education policy professor Dr. Bill Black asked a simple question: “What is public in public education?” With Florida moving further toward publicly funded private education, that question deserves a much closer look.

General Featured Places Tampa Politics Election

Daniela Simic Has Been Preparing for This Job for Years

September 8, 2026September 8, 2026 B. John 136 Views 0 Comments District 2, Brittany Lyssy, Campaign Finance, Hillsborough County School Board, community leadership, Daniela Simic, classroom experience, teacher endorsements, Public Education

This entry is in the series 2026 Elections

Daniela Simic’s campaign is built around something school board races could use more of: deep experience with schools themselves. She has spent about 25 years in education, from the classroom to district leadership, with years of PTA and community work layered on top of it.

Her fundraising tells its own story. Simic and Brittany Lyssy have raised roughly the same amount from outside donors, but Simic reached that total through far more contribution transactions, a lower median donation, and broader support from individuals, educators, labor groups, and community organizations.

The race gives District 2 voters a clear factual comparison in background, donor base, and connection to Hillsborough’s schools. The full piece looks at Simic’s record, the people backing her, and the experience she brings to one of the largest school systems in the country.

Election Society Education Gay Issues County Commission Featured Places Tampa Politics

A Polite Version of Josh Wostal Is Still Too Much

September 3, 2026 B. John 124 Views 0 Comments Stacy Hahn, Neil Manimala, developer contributions, Wostal, Ron DeSantis, Hillsborough County Commission, Hillsborough School Board, Campaign Finance

This entry is in the series 2026 Elections

Stacy Hahn doesn’t sound much like Josh Postal. She’s thoughtful, qualified, and generally pleasant. But votes count the same whether they come with a scowl or a smile, and Hahn’s eight years on the Hillsborough County School Board show a record that’s much more conservative than her polished image suggests.

Hahn opposed letting voters decide on more funding for teacher pay, voted against defending that referendum when Postal and the County Commission tried to block it, rejected a Pride Month proclamation, and publicly aligned herself with Ron DeSantis’s political group. There are some exceptions in her record, but when it comes to taxes, LGBTQ recognition, sexual-health education, and DeSantis-era politics, the pattern is clear.

Now Hahn is running for the County Commission with a campaign mostly funded by construction, development, real estate, and government-relations groups—including businesses that have worked with Hillsborough County. These contributions don’t prove improper influence, but voters have a right to look at who is supporting a candidate and what choices that candidate might make in office. Dr. Hahn may be a more pleasant version of Josh Postal, but the real question is whether Hillsborough County needs another version at all.

Featured Places Tampa Politics Election Society Gay Issues Crack Pots

Ambition, Attendance, and the Race for HCSB District 2

August 31, 2026 B. John 161 Views 0 Comments Public Education, Hillsborough County, Tampa Politics, Hillsborough School Board, District 2, Brittany Lyssy, Local Governance

This entry is in the series 2026 Elections

When someone wants to lead a multi-billion-dollar school district, authenticity comes first. Brittany Lyssy’s campaign for Hillsborough School Board District 2 asks voters to believe that a family of five lives in a 680-square-foot, one-bedroom condo while also keeping a homesteaded home in Manatee County. From barely attending advisory board meetings to repeating national talking points, District 2 voters deserve real community representation, not a staged political act.

Featured Places Tampa Politics Legislature

When Tallahassee Called, Josie Tomkow Answered

August 27, 2026August 27, 2026 B. John 179 Views 0 Comments Tallahassee preemption, party leadership, Senate District 14, Josie Tomkow, Tampa Politics, Home Rule, local control, Hillsborough County

When Josie Tomkow had the chance to support local communities, she chose Tallahassee instead. This pattern appears throughout her House voting record: tenant protections, land use, infill development, vacation rentals, civilian oversight, worker rules, and school-board governance all go the same way.

This matters because Tomkow now wants to represent Senate District 14, which includes Tampa and Hillsborough County. But her record comes from somewhere else, and it raises an important question for voters here: when local needs clash with party leadership, whose side will she choose?

Her votes seem to answer. Even when another Hillsborough Republican voted no on a major preemption bill, Tomkow voted yes. So the question is not whether she can learn Tampa’s concerns. The question is whether she has already shown us who gets her vote when Tallahassee comes calling.

Featured Places Tampa Politics Election

Before We Choose Together

August 14, 2026August 14, 2026 B. John 218 Views 0 Comments Civic Engagement, Tampa Politics, Campaign Finance, political power, Democracy, voter influence, political access, community leadership, special interests, representative government

This entry is in the series 2026 Elections

We like to tell ourselves a comforting story about democracy: everyone gets one vote. The developer who can spend thousands on campaigns gets one. The teacher gets one. The restaurant worker gets one. The college student voting for the first time gets one. On Election Day, at least, the arithmetic is wonderfully simple.

But political power starts working long before Election Day. Candidates need money, introductions, endorsements, volunteers, organizations to support them, and people who can get them into the rooms where political relationships are built. By the time most voters start paying attention, a much smaller group may have already spent months deciding which candidates have the money, visibility, and standing to be taken seriously.

That raises a question I hadn’t fully considered when I wrote What We Choose Together: What needs to happen before the word “together” is really true? In Before We Choose Together, I look at money, access, community ties, and the kind of public officials who still answer the phone and talk with regular people. Our vote matters, but so does our ability to be heard before we cast it.

Featured Places Tampa Politics Legislature

Mike Suarez Knows Insurance. That’s Why I Have Questions.

August 7, 2026August 7, 2026 B. John 289 Views 0 Comments Campaign Finance, Insurance, Florida House District 64, homeowners insurance, auto insurance, Luis Salazar, PACs, Mike Suarez

This entry is in the series Florida Legislature

This entry is in the series 2026 Elections

Mike Suarez says his 30 years in insurance make him the best candidate to tackle Florida’s insurance crisis. With what homeowners and drivers are paying, that sounds like valuable experience. But his campaign finance reports show something else voters should think about: insurance-related interests are also the largest industry group I identified among his contributors.

That doesn’t mean anyone bought Mike Suarez’s vote. But it does mean voters have every right to ask a tougher question. If you’ve worked in an industry for decades and people connected to it give a lot to your campaign, whose interests will matter most when insurers and policyholders want different things?

Suarez wants voters to see his insurance career as a reason to elect him. That’s fair. But his professional and financial ties to that same industry deserve scrutiny too. Florida families don’t need another explanation for high insurance costs. They need someone in Tallahassee who will tell them exactly how their homeowners and auto insurance bills will go down.

Tampa Politics Legislature Featured Places

Who Governs Tampa?

August 3, 2026 B. John 243 Views 0 Comments Karen Gonzalez Pittman, Tampa Politics, Home Rule, Hillsborough County, Preemption, Florida Legislature, Local Government, Tallahassee, school boards

This entry is in the series 2026 Elections

Most people assume that when they elect a City Council member, County Commissioner, or School Board member, those officials have the authority to govern. In Florida, that’s becoming less true every year. Through a growing list of preemption laws, Tallahassee has steadily taken power away from local communities, often replacing local judgment with statewide mandates.

Representative Karen Gonzalez-Pittman’s voting record shows she has consistently supported that shift. From housing and neighborhood development to public schools and worker protections, her votes raise a fundamental question for District 65: should decisions about Tampa be made by the people who live here, or by politicians in Tallahassee? This first installment examines one of the most significant, and least discussed, changes in Florida government.

Featured Places Tampa Politics Election

Would This Resume Get the Job?

August 1, 2026August 1, 2026 B. John 277 Views 0 Comments Brittany Lyssy, Campaign Finance, Hillsborough County School Board, Hillsborough County Public Schools, School Board Election, Leadership Experience, Local Politics, education policy

This entry is in the series 2026 Elections

Would this resume get the job? That’s the question every voter should ask before electing someone to help govern the seventh-largest school district in the nation. Hillsborough County Public Schools oversees more than 218,000 students, employs over 23,000 people, and manages a budget exceeding $4 billion. If this were a private company, would this résumé earn a seat in the boardroom?

This article examines Brittany Lyssy’s publicly presented qualifications alongside her campaign finance reports, which show that, excluding a personal loan to her campaign, nearly four out of every ten identifiable donor dollars came from outside Hillsborough County. It’s not a partisan argument. It’s a hiring question. Before entrusting someone with one of the most consequential governing positions in our community, voters deserve to ask whether the experience matches the responsibility.

Featured Places Tampa Politics County Commission

Seven Checks. One Address. Nothing to See Here… Probably.

July 30, 2026 B. John 225 Views 0 Comments public transparency, development interests, local elections, Hillsborough County Commission, Donna Cameron-Cepeda, Campaign Finance, campaign contributions

This entry is in the series 2026 Elections

What if the most interesting story isn’t who gave to one candidate—but who keeps showing up in multiple County Commission races? That’s exactly what caught my attention while reviewing Donna Cameron Cepeda’s latest campaign finance report. One connected business network accounted for more than one-quarter of her campaign’s monetary contributions, and the same network also appears in Josh Wostal’s filings. There’s nothing illegal about that. In fact, businesses have every right to support the candidates they believe will best serve the community.

But campaign finance reports exist for a reason. They allow voters to see who is investing in our elections and to ask informed questions before casting a ballot. This article doesn’t accuse anyone of wrongdoing. Instead, it examines one business network’s unusually strong financial interest in Hillsborough County Commission races, and asks the question every voter should ask: Why are these races important enough to attract that level of investment?

← Previous