Deep Something

The Ballot-Box Bureaucrat: Why Electing Hillsborough’s Superintendent Is Bad for Business and Worse for Classrooms

September 23, 2026September 23, 2026 B. John 97 Views 0 Comments elected superintendent, Public Education, Hillsborough School Board, Local Governance, Tallahassee preemption, school referendum, Michael Owen

This entry is in the series 2026 Elections

This entry is in the series Education

This entry is in the series Florida Amendments and Referenda-2026

Imagine Tampa General Hospital announcing that it will now select its President and CEO through a countywide partisan primary. Picture candidates debating surgical protocols on debate stages, taking a full year off to solicit campaign checks from medical supply reps, and catering to partisan party bosses instead of patient care. No board of trustees would tolerate it, and no major health system would survive it. Yet that is the exact circus Tallahassee politicians want to bring to Hillsborough County Public Schools, the single largest employer in our community.

Proponents dress up the proposal in the language of parental rights and democratic empowerment. But under the current model, the superintendent answers to an elected, seven-member School Board every single day. If the superintendent mishandles district finances, botches bus routes, or mismanages schools, the board can act immediately. Under an elected system, that daily accountability vanishes. The School Board loses its supervisory power, leaving a single partisan politician in charge of a $4 billion budget and 220,000 students, answerable to voters only once every four years.

An even bigger problem is the smaller pool of candidates. Instead of searching the country for experienced school leaders, we would be limited to local registered voters. The best-performing states treat school administration as a professional job, while the only two states that still elect superintendents are not among the top performers.

Injecting culture-war primaries and campaign fundraising into our school system’s executive suite is a disaster waiting to happen. Read the full analysis on why turning school administration into a political prize hurts our students, undermines teachers, and destabilizes our local schools.

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Brittany Lyssy’s School-Board Training Network Deserves a Closer Look

September 21, 2026 B. John 146 Views 0 Comments Brittany Lyssy, Leadership Institute, Hillsdale College, school board politics, Hillsborough County Schools, Moms For Liberty, Bridget Ziegler

This entry is in the series Education

This entry is in the series 2026 Elections

Brittany Lyssy cites her work with the Leadership Institute’s School Board Leaders Program as part of her education-policy experience. A closer look at that program shows a national conservative network built around recruiting, training, and supporting school-board candidates, with direct connections to Moms for Liberty and to policy resources from Hillsdale College and the Heritage Foundation.

One connection deserves particular attention. Bridget Ziegler, an early figure in Moms for Liberty, served in leadership of the same Leadership Institute school-board program where Lyssy worked on communications, policy analysis, ethics, and governance. Public records do not show that Lyssy belonged to Moms for Liberty or adopted every position promoted within that network, but the institutional ties are clear enough to warrant scrutiny.

The larger question is what parts of that philosophy Lyssy would bring to Hillsborough. The full article follows the connections among the Leadership Institute, Moms for Liberty, Hillsdale, Ziegler, and Lyssy’s own policy background, then asks what voters should examine before deciding how much those ties matter.

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Josie Tomkow Discovers Homeowner Rights

September 21, 2026 B. John 95 Views 0 Comments Senate District 14, Josie Tomkow, campaign contributions, homeowners insurance, attorney fees, Florida insurance reform, Homeowner Claims Bill of Rights

This entry is in the series 2026 Elections

Josie Tomkow says she wants to create a Homeowner Claims Bill of Rights and make sure insurance claims are fully paid. This sounds reassuring, especially in a state where rising premiums and storm losses have made things tough for homeowners. There is just one awkward detail: Florida already has a Homeowner Claims Bill of Rights. Even more, Tomkow spent years voting for laws that made it harder and more expensive for policyholders to challenge insurers when claims were denied or underpaid.

Campaign records also show ongoing support for Tomkow from insurance companies, industry groups, civil-justice organizations, and a former Florida Insurance Commissioner who now works in insurance advisory.

So is this a real change of heart, or just a shift for campaign season? Her voting record, contribution history, and new promises make it worth taking a closer look.

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Let’s Run A Real Education Experiment

September 16, 2026 B. John 130 Views 0 Comments School Choice, Florida Schools, Education Funding, School Vouchers, Private Schools, Student Outcomes, Public Education, education policy

This entry is in the series Education

Florida spends about $9,335 per public-school student through its main funding formula. Average private-school tuition is about $13,800. So before we decide private schools produce better results, there is a question worth testing: what would happen if public schools had comparable resources?

The comparison gets more complicated because public and private schools often operate under different rules. Public schools serve students with widely different needs, provide transportation and specialized services, and operate under statewide testing and accountability requirements. Private schools receiving voucher money have different admissions, staffing, testing, and service obligations.

Research does not provide a simple answer that one system always produces better outcomes. Some private-school and voucher programs show gains, others show little difference, and some have produced worse academic results. Once researchers account for differences in family income, parental education, previous achievement, and other factors, much of the apparent private-school advantage can shrink.

So the essay proposes a thought experiment: fund public schools at something close to average private-school tuition while keeping their public obligations intact, or run the test in reverse by asking voucher schools to educate students for the voucher amount under comparable standards. Maybe the real difference is not public versus private education. Maybe it is what happens when one kind of school is simply better funded.

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Some Things Should Not Be Run for Profit

September 15, 2026 B. John 168 Views 0 Comments Education Funding, Educational Equity, School Vouchers, Public Education, education policy, public good, School Choice, Florida Schools

This entry is in the series Education

What if the biggest mistake in Florida’s education debate is assuming schools should work like ordinary businesses?

Markets reward efficiency, control costs, and give consumers choices. Public education has a different job. It has to serve every child, including the student who needs far more support, the student who needs advanced opportunities, and the student whose family could never afford to buy those services on its own.

That is why I think the debate over vouchers and school choice has to go deeper than whether competition can improve some outcomes. The real question is whether K-12 education should be organized around market incentives at all.

In this essay, I look at what happens when we confuse efficiency with public duty, and why some things may work better when the goal is not profit, but making sure everyone is served.

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

September 14, 2026September 14, 2026 B. John 266 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

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When “School Choice” Stops Meaning Public Education

September 13, 2026September 13, 2026 B. John 171 Views 0 Comments Public Education, Public Schools, School Choice, Florida Schools, Education Funding, Educational Equity, Education Vouchers, Henry Mack

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.

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Whose Choice Is It?

September 12, 2026September 12, 2026 B. John 155 Views 0 Comments Wealth Transfer, Public Education, School Choice, Florida Schools, Vouchers, Education Funding, Teacher Shortage, Educational Equity

This entry is in the series Education

Florida calls it school choice. But choice for whom?

An $8,000 voucher may open doors for a family that can add another $10,000 or $15,000. For a family that cannot, the same voucher may leave those doors closed. And even when the money is there, private schools still decide whom they admit. That raises a harder question than the slogan suggests: whose choice is it?

In this essay, I look at what public education was created to do, what Florida is changing, and why the stakes go far beyond schools. Drawing on our March Voices of Justice: Speak Up for Students program at Hyde Park United Methodist Church, including insights from USF education policy professor Dr. Bill Black, I argue that public education is one of the few institutions designed to give every child a claim on shared public wealth. Weakening that promise risks hardening the very class divisions public schools were built to overcome.

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A Polite Version of Josh Wostal Is Still Too Much

September 3, 2026 B. John 204 Views 0 Comments Hillsborough County Commission, Hillsborough School Board, Campaign Finance, Stacy Hahn, Neil Manimala, developer contributions, Wostal, Ron DeSantis

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.

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Ambition, Attendance, and the Race for HCSB District 2

August 31, 2026 B. John 203 Views 0 Comments Local Governance, Public Education, Hillsborough County, Tampa Politics, Hillsborough School Board, District 2, Brittany Lyssy

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.

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What Is the Money For?

August 25, 2026 B. John 171 Views 0 Comments billionaire philanthropy, generosity, economic inequality, Jeff Bezos, Andrew Carnegie, public good, wealth and power, moral responsibility, billionaire wealth

This entry is in the series The Stoics

A single mother stops at a traffic light and hands five dollars to a homeless person. Jeff Bezos pledges $10 billion to fight climate change. Bezos will accomplish far more with his gift. Yet the mother may have given up something she needed.

That distinction sits at the heart of my latest essay. The world’s richest people possess more money than they could spend across several lifetimes. Their fortunes keep growing while the planet warms, public institutions weaken, and millions struggle to survive. Their philanthropy does useful work, though it rarely costs them any comfort or power.

So what is all the remaining money for? The answer takes us through the Gilded Age, the widow’s offering, other religious traditions, private bunkers, life extension, and the strange belief that enough wealth can free someone from the fate shared by every human being.

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