Following the Money Behind Josie Tomkow

This entry is in the series 2026 Elections

Campaign finance is so complicated that most voters give up before they get to the interesting part. That may be part of the point. Josie Tomkow has a regular campaign account and two political committees, with millions of dollars coming from business groups, health care interests, developers, insurers, political committees, and party organizations—often with names that don’t reveal who is really behind them.

Insurance stands out. About $92,500 came from companies, organizations, and people involved in property, auto, and casualty insurance. That’s notable on its own, but it’s even more interesting since Tomkow is now running as a candidate who wants to reform insurance, even though her voting record shows support for laws that reduced legal protections for policyholders. Her version of insurance reform has, at times, looked suspiciously like an aid package for the insurance industry.

There’s also at least $94,500 from donors directly connected to data centers, cloud computing, energy, or the infrastructure behind them. Add in big business and development money, plus $50,000 from Publix, and the donor list gets even more interesting. Maybe Publix just expects Tomkow to buy a lot of groceries. The rest of us might want to keep an eye on where the money goes.

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Kathy Castor Voted Against Hurricane Relief 11 Times? There’s Much More to That Story.

This entry is in the series 2026 Elections

Kathy Castor voted against hurricane relief 11 times, supposedly blocking $151.43 billion in federal disaster assistance. That’s the accusation circulating in an article from West Orlando News, courtesy of the National Republican Congressional Committee. Eleven votes. More than $151 billion. You can almost hear the ominous music playing behind the next Republican campaign commercial.

There’s just one problem. When you examine the actual congressional records, the story begins to fall apart. The article counts votes against massive spending bills covering everything from FEMA to immigration enforcement, along with a procedural vote that had little to do with disaster relief itself. Apparently, voting against a bill containing dozens of provisions means you oppose every dollar in it. Congressional voting records are wonderfully useful things, particularly when you select only the votes that support your accusation.

Here’s what the article conveniently forgot to mention. Castor voted FOR $6.4 billion in FEMA disaster funding in 2011, FOR $15.25 billion in emergency disaster assistance in 2017, and FOR legislation providing $29 billion to FEMA following Hurricanes Helene and Milton in 2024. That last bill passed 366–34. Every single vote against it came from a Republican. Funny how that little detail escaped the article’s attention.

The NRCC is entitled to campaign against Kathy Castor. Voters are entitled to know what Congress actually did. We’ve examined the votes, the bills, and the facts the original article left out. Before accepting the claim that Castor repeatedly voted against hurricane relief, read the full article. The congressional record tells a much different story, and the facts are considerably less flattering to the people spreading this accusation.

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When Four Times the Votes Doesn’t Mean Four Times the Support

This entry is in the series Daily Douche-Bag
This entry is in the series 2026 Elections

Josh Wostal has a unique way of measuring political influence. When people said Hillsborough County doesn’t treat Tampa fairly, he noted that he got far more votes than Tampa’s mayor and at-large City Council members. That sounds impressive until you consider the size of the electorate and voter turnout.

Wostal ran in a countywide November election where 486,230 people voted. Tampa’s at-large council members won their seats in an April runoff with only 25,913 voters. If you compare each candidate to the people who voted in their election, Wostal’s supposed advantage goes away. In fact, some of the votes he mentions came from Tampa residents. So, Hillsborough County is bigger than Tampa. Who would have thought?

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Jackie Toledo and the Curious Case of Local Control

This entry is in the series 2026 Elections

Jackie Toledo is now seeking a seat on the Hillsborough County Commission, where local officials decide on growth, infrastructure, public safety, and county policy. This makes her time in Tallahassee especially interesting, because she repeatedly supported laws that limited what counties and cities could decide for themselves.

Toledo supported state intervention in areas like impact fees, occupational licensing, utility policy, and even local police budgets; Toledo backed state intervention in matters normally handled close to home. In one case, Tallahassee could even review and overturn a local decision about a police budget.

There is a certain irony in spending years helping state government restrict local author

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Cool Classrooms and Common Sense: Why Hillsborough Must Renew the Half-Penny Promise

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

Florida summer heat is not theoretical. It is a relentless physical reality. Anyone who expects children to concentrate on algebra or reading in an eighty-eight-degree classroom with a dead air conditioner and water dripping into plastic buckets has never spent an afternoon inside an aging Florida school building. You cannot build academic excellence when students and teachers are simply trying to survive the humidity.

Hillsborough Referendum 3 asks voters to renew the half-cent sales tax for another ten years to pay for air conditioning, roof repairs, and security at schools. Opponents talk about tax fatigue, but this is not a new tax. It keeps the same rate as in 2018. If it ends, your grocery bill will not go down, but school maintenance will lose $120 million a year.

The results speak for themselves. Since 2018, the Half-Penny Promise has funded over 750 projects, including air conditioning upgrades at 177 schools, all overseen by an independent Citizen Oversight Committee. Tourists pay about a quarter of the cost, and over $716 million has gone to local contractors and workers in Hillsborough County.

While the state Capitol stays busy manufacturing political culture wars and diverting public funds into private vouchers, local communities must take care of their own. Read the complete breakdown on why renewing this capital surtax is an investment in our kids, our local workforce, and our neighborhood schools.

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Trading Four Votes for One: The Cynical Math Behind Hillsborough’s Commission Power Grab

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

If someone came to your door and offered to trade four hundred-dollar bills for a ten-dollar bill, you would quickly close the door and check your security cameras. That is exactly the kind of deal behind Hillsborough County Charter Referendum 2, a Tallahassee plan that would undo forty years of balanced local government.

For forty years, Hillsborough has used a mix of four district commissioners and three countywide at-large commissioners. This lets every voter choose four out of seven seats, giving people a say in the majority. Referendum 2 would end this system by expanding the board to nine and removing all at-large seats.

Think about what this means for your representation. You would go from voting for four commissioners to just one. You would not be able to vote for or against the other eight, even though they decide on taxes, infrastructure, and big development projects. Single-member districts encourage commissioners to trade favors for their own areas and ignore countywide needs like Port Tampa Bay and regional transit.

Tallahassee politicians love to lecture local communities about neighborhood control while quietly shrinking our democratic leverage from afar. Read the full commentary to see why trading away four seats for one is a bad trade for Hillsborough taxpayers, and why we must vote No on Charter Referendum 2.

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

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

This entry is in the series 2026 Elections
This entry is in the series Education

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

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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Josie Tomkow, Insurance Reform, and a Trail Worth Following

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

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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