Deep Something

Rainy Days and Blue Tarps: Why Hoarding Billions in Tallahassee Won’t Protect Hillsborough

September 22, 2026September 22, 2026 B. John 165 Views 0 Comments Tallahassee preemption, Florida Amendment 1, Budget Stabilization Fund, rainy day fund, Hillsborough County, state budget

This entry is in the series 2026 Elections

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

Tallahassee politicians often present Florida Amendment 1 as basic common sense. After all, who would argue with saving for a rainy day? But there’s a big difference between keeping an umbrella handy and locking away billions while your ceiling is falling in.

If you drive through Hillsborough County, you’ll see blue tarps still on roofs from storms years ago. Homeowners are struggling with high insurance costs, classrooms have broken air conditioners, and stormwater ditches need repairs. Yet Amendment 1 would require up to $750 million a year to be set aside in Tallahassee until the fund reaches 25 percent of general revenue.

Florida already has a fully funded emergency reserve at 10 percent. Forcing billions more into storage isn’t smart budgeting; it’s a way to cut local spending now so politicians can brag about a big balance later. Read the full essay to see why we should fix our roofs before Tallahassee builds another vault.

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

September 21, 2026 B. John 218 Views 0 Comments Leadership Institute, Hillsdale College, school board politics, Hillsborough County Schools, Moms For Liberty, Bridget Ziegler, Brittany Lyssy

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 128 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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Whose Voice in the Committee Room? Michael Owen, Insurance Cash, and the Squeeze on District 70

September 20, 2026September 20, 2026 B. John 124 Views 0 Comments Property Insurance, Campaign Finance, Michael Owen, HB 4027, HB 4029, Hillsborough County

This entry is in the series 2026 Elections

Michael Owen sits where Florida’s property insurance laws are shaped: the House Insurance & Banking Subcommittee. His campaign finance reports also show substantial support from insurance companies, insurance political committees, agents’ groups, and lobbyists. The article examines that money alongside the choices he has made in office.

Owen has shown no shortage of legislative ambition when Hillsborough County government is involved. He sponsored HB 4027, which puts an elected school superintendent before Hillsborough voters, and HB 4029, which would substantially restructure the County Commission. Both measures passed the Legislature and require local voter approval.

That leaves a harder question. With homeowners still confronting steep insurance bills, what has Owen used his seat on Insurance & Banking to do for them? The campaign money does not answer that question by itself, but it makes his legislative record worth examining closely.

This article follows the money, looks at where Owen has chosen to spend his political capital, and asks what those priorities tell District 70 voters about whose concerns are getting attention in Tallahassee.

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Wisdom: Whittling Away at Uncertainty

September 20, 2026September 20, 2026 B. John 127 Views 0 Comments decision-making, uncertainty, judgment, self-knowledge, experience, Stoicism, Reflection, wisdom

This entry is in the series The Stoic Virtues

This entry is in the series Journey Through Stoicism

How do we know when we are wise?

I have been thinking about that question because wisdom may be the hardest Stoic virtue to define. Courage, justice, and temperance all give us something concrete to work with. Wisdom feels different. We rarely have all the information we want, yet life still requires us to decide, act, adjust, and sometimes admit we were wrong.

In Whittling Away at Uncertainty, I look at some decisions I would make differently today, a new job I am about to begin, and what experience has taught me about research, judgment, and knowing when enough information is enough. Wisdom may not be about certainty. It could be learning how to make the best decision we can, then having the courage to begin.

Scales of Justice weighted to Insurance Companies

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Josie Tomkow, Insurance Reform, and a Trail Worth Following

September 18, 2026 B. John 210 Views 0 Comments Campaign Finance, Insurance Reform, homeowners insurance, Florida insurance, attorney fees, David Altmaier, Josie Tomkow, Florida Legislature

This entry is in the series 2026 Elections

Florida homeowners have heard “insurance reform” so often that the phrase almost deserves its own ZIP code. But behind that label were years of very real changes to what happens when an insurance company denies or underpays a claim and a homeowner has to fight back.

Josie Tomkow voted yes, again and again, as Florida changed the rules around lawsuits, attorney fees, assignment-of-benefits claims, and insurer liability. Those laws may sound technical, but their effect can be painfully simple: even when policyholders have a valid dispute, taking an insurer to court can now carry more financial risk.

Then there is the campaign money. Tomkow’s contribution records show recurring support from insurers, insurance-industry organizations, civil-justice reform groups, and people tied directly to Florida’s insurance-policy world, including former Insurance Commissioner David Altmaier. This cycle alone, at least $2,500 has come from three interests closely connected to this issue.

No, campaign contributions do not come with thank-you notes for specific votes. But voters are entitled to look at the money, look at the voting record, and decide for themselves whether the two tell a story worth following.

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Let’s Run A Real Education Experiment

September 16, 2026 B. John 157 Views 0 Comments Public Education, education policy, School Choice, Florida Schools, Education Funding, School Vouchers, Private Schools, Student Outcomes

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 220 Views 0 Comments education policy, public good, School Choice, Florida Schools, Education Funding, Educational Equity, School Vouchers, Public Education

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 336 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.

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When “School Choice” Stops Meaning Public Education

September 13, 2026September 13, 2026 B. John 233 Views 0 Comments Education Vouchers, Henry Mack, Public Education, Public Schools, School Choice, Florida Schools, Education Funding, Educational Equity

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 219 Views 0 Comments Education Funding, Teacher Shortage, Educational Equity, Wealth Transfer, Public Education, School Choice, Florida Schools, Vouchers

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.