Deep Something

Votes-Money Infographic for Wostal Campaign

Follow the Votes. Follow the Money.

October 5, 2026October 5, 2026 B. John 78 Views 0 Comments Hillsborough County Commission, Campaign Finance, zoning, development interests, Josh Wostal, land use, Homes by WestBay, Hillsborough growth

This entry is in the series 2026 Elections

Josh Wostal likes to remind people that he represents voters across Hillsborough County. Some of those voters have shown up at County Commission meetings, asking commissioners to slow development in their neighborhoods. In several cases, Wostal voted the other way, even when county planning officials recommended denial or found the proposed development inconsistent with the comprehensive plan.

Then there is the money. Builders, developers, construction firms and land-use interests have contributed substantial sums to Wostal’s political operation. In at least two cases, contributors or business networks tied to his campaign also had development matters come before the commission. None of that proves why Wostal cast a particular vote. It does give voters a reason to look closely at who funds his political operation and what happens when development interests come before him.

And those residents standing at the podium asking him to listen? They are countywide voters too.

Featured Politics Election

Two Campaigns, Two Very Different Funding Models

September 29, 2026September 29, 2026 B. John 157 Views 0 Comments Brittany Lyssy, Campaign Finance, Hillsborough County School Board, Daniela Simic, Leadership Institute, political committees, District 2

This entry is in the series Education

This entry is in the series 2026 Elections

Campaign finance reports can be tedious, but the District 2 numbers tell a fairly simple story. Daniela Simic’s campaign is driven much more by individual donors and smaller contributions. Brittany Lyssy’s campaign relies far more heavily on large checks, businesses, and political committees. Her latest filings also include direct support from a Hillsborough County Republican organization in a race that is formally nonpartisan.

There is another layer. Lyssy also chairs a separate political committee bearing her name, while part of the education-policy experience she cites comes from the conservative Leadership Institute’s school-board program. That same program has featured Bridget Ziegler in a leadership and training role.

The full article strips away the financial-report clutter and examines who is funding these two campaigns, the political networks surrounding them, and the very different professional backgrounds the candidates would bring to the Hillsborough County School Board.

Featured Politics Election Legislature

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

September 20, 2026September 20, 2026 B. John 128 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.

Scales of Justice weighted to Insurance Companies

Economy Featured Places Tampa Politics Election Legislature

Josie Tomkow, Insurance Reform, and a Trail Worth Following

September 18, 2026 B. John 222 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.

Election General Featured Places Tampa Politics

Daniela Simic Has Been Preparing for This Job for Years

September 8, 2026September 8, 2026 B. John 352 Views 0 Comments Public Education, District 2, Brittany Lyssy, Campaign Finance, Hillsborough County School Board, community leadership, Daniela Simic, classroom experience, teacher endorsements

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.

Tampa Politics Election Society Education Gay Issues County Commission Featured Places

A Polite Version of Josh Wostal Is Still Too Much

September 3, 2026 B. John 264 Views 0 Comments Hillsborough School Board, Campaign Finance, Stacy Hahn, Neil Manimala, developer contributions, Wostal, Ron DeSantis, Hillsborough County Commission

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

Before We Choose Together

August 14, 2026August 14, 2026 B. John 298 Views 0 Comments Tampa Politics, Campaign Finance, political power, Democracy, voter influence, political access, community leadership, special interests, representative government, Civic Engagement

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 355 Views 0 Comments Florida House District 64, homeowners insurance, auto insurance, Luis Salazar, PACs, Mike Suarez, Campaign Finance, Insurance

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.

Election Featured Places Tampa Politics

Would This Resume Get the Job?

August 1, 2026August 1, 2026 B. John 369 Views 0 Comments education policy, Brittany Lyssy, Campaign Finance, Hillsborough County School Board, Hillsborough County Public Schools, School Board Election, Leadership Experience, Local Politics

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 265 Views 0 Comments Hillsborough County Commission, Donna Cameron-Cepeda, Campaign Finance, campaign contributions, public transparency, development interests, local elections

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?

Featured Politics Election Society Education

Hillsborough School Board District 2: The Choice Between Proven Dedication and Outside Ambition

May 13, 2026May 13, 2026 B. John 986 Views 0 Comments Campaign Finance, Local Governance, Tallahassee Influence, Education Leadership, Public Education, Hillsborough School Board, District 2, Chris Taylor, Brittany Lyssy

Is a seat on our local school board up for grabs by the highest out-of-county bidder? For months, the District 2 race was a focused contest between candidates with deep, functional ties to our classroom, including professionals like veteran educator Chris Taylor, who has spent years in the trenches of our district. Chris understands student achievement because he has managed it from the front lines, and his commitment is rooted in the actual lives of the students he has taught and the teachers he has led. His vision is focused on stability, inclusivity, and the professional integrity our schools need to thrive.

In sharp contrast, the late entry of attorney Brittany Lyssy introduces a jarring shift toward outside influence and corporate-backed interests. While Chris Taylor’s support is local and organic, an analysis of Lyssy’s campaign finance reports reveals that nearly 45% of her total donations—excluding personal loans—flow from outside Hillsborough County. Backed by Tallahassee-based PACs and out-of-county law firms, her candidacy suggests an agenda more beholden to a state-level political machine than to our community. Hillsborough deserves a board member whose only “client” is the child in the classroom, not a strategist using our schools as a policy laboratory.