Deep Something

Trump Wants the Midterms to Be About Trump

August 26, 2026 B. John 146 Views 0 Comments Republican incumbents, MAGA Inc., campaign advertising, voter accountability, Democratic politics, Donald Trump, Cost of Living, 2026 midterms

This entry is in the series 2026 Elections

Donald Trump has looked at a 34 percent approval rating and reached a comforting conclusion: Americans have not seen enough Donald Trump. His super PAC is preparing midterm ads built around his record, his speeches, and clips of Trump praising Trump. Apparently, the nation has suffered from a shortage.

The ads will tout stock-market highs, factory output, falling overdose deaths, and other signs of the “Golden Age.” Families will still see grocery bills that keep climbing, gasoline near $4.09 a gallon, and a job market that lost ground in July. The Dow Jones Industrial Average has yet to buy anyone’s groceries.

Trump wants voters to treat the midterms as though his name appears on every ballot. They should accept the invitation. Then they should ask every Republican incumbent whether Trump’s record belongs to them too, which votes lowered costs back home, and why the greatest economy in history remains so difficult for most people to find.

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Ambition, Attendance, and the Race for HCSB District 2

August 31, 2026 B. John 182 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.

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A Polite Version of Josh Wostal Is Still Too Much

September 3, 2026 B. John 149 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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Daniela Simic Has Been Preparing for This Job for Years

September 8, 2026September 8, 2026 B. John 206 Views 0 Comments classroom experience, teacher endorsements, Public Education, District 2, Brittany Lyssy, Campaign Finance, Hillsborough County School Board, community leadership, Daniela Simic

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.

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

September 14, 2026September 14, 2026 B. John 235 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.

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 107 Views 0 Comments Josie Tomkow, Florida Legislature, Campaign Finance, Insurance Reform, homeowners insurance, Florida insurance, attorney fees, David Altmaier

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

September 20, 2026September 20, 2026 B. John 70 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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Josie Tomkow Discovers Homeowner Rights

September 21, 2026 B. John 48 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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Brittany Lyssy’s School-Board Training Network Deserves a Closer Look

September 21, 2026 B. John 47 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.