Ambition, Attendance, and the Race for HCSB District 2

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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When Tallahassee Called, Josie Tomkow Answered

When Josie Tomkow had the chance to support local communities, she chose Tallahassee instead. This pattern appears throughout her House voting record: tenant protections, land use, infill development, vacation rentals, civilian oversight, worker rules, and school-board governance all go the same way.

This matters because Tomkow now wants to represent Senate District 14, which includes Tampa and Hillsborough County. But her record comes from somewhere else, and it raises an important question for voters here: when local needs clash with party leadership, whose side will she choose?

Her votes seem to answer. Even when another Hillsborough Republican voted no on a major preemption bill, Tomkow voted yes. So the question is not whether she can learn Tampa’s concerns. The question is whether she has already shown us who gets her vote when Tallahassee comes calling.

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Who Governs Tampa?

This entry is in the series 2026 Elections

Most people assume that when they elect a City Council member, County Commissioner, or School Board member, those officials have the authority to govern. In Florida, that’s becoming less true every year. Through a growing list of preemption laws, Tallahassee has steadily taken power away from local communities, often replacing local judgment with statewide mandates.

Representative Karen Gonzalez-Pittman’s voting record shows she has consistently supported that shift. From housing and neighborhood development to public schools and worker protections, her votes raise a fundamental question for District 65: should decisions about Tampa be made by the people who live here, or by politicians in Tallahassee? This first installment examines one of the most significant, and least discussed, changes in Florida government.

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The Price of Political Playacting: Michael Owen’s Assault on Hillsborough Schools

This entry is in the series 2026 Elections

Hillsborough County Public Schools, the seventh-largest district in the nation, is facing a top-down assault disguised as “local accountability.” State Representative Michael Owen’s House Bill 4027 calls for a referendum to eliminate our professionally appointed superintendent in favor of a partisan elected office. The schools are already governed by an elected board of education. This change is not about transparency; it is a calculated effort to force a toxic culture-war agenda into our local classrooms and strip our school system of seasoned, professional leadership.

The structural fallout of this power grab is devastatingly clear. Instead of an experienced educational administrator focused on student performance, our district risks being handed over to a political partisan. Under an elected model, policy decisions on curriculum, budgeting, and student safety will inevitably bow to the need for campaign survival, turning every fourth year into a multi-million-dollar reelection spectacle. This essay shows how Owen’s legislative overreach, paired with his habit of distorting local facts for political points, threatens the shared institutions our children rely on.

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Josie Tomkow’s Record Shows Tallahassee Comes First

This entry is in the series Florida Legislature
This entry is in the series 2026 Elections

Florida Republicans love to talk about freedom, but their voting records often tell a very different story. Over and over again, Tallahassee politicians have voted to take decision-making power away from local communities, local governments, and local school boards. Josie Tomkow’s record in the Florida House is a clear example.

Tomkow is now running again against Brian Nathan in Senate District 14, asking Tampa-area voters to send her back to Tallahassee. But when she served in the House representing Polk County, she repeatedly voted for state preemption over local control, including on housing, zoning, infill redevelopment, civilian oversight, and public schools.

That matters here. Tampa and Hillsborough County deserve representation rooted in this community, not another vote for Tallahassee control. The question for voters is simple: if Tomkow voted this way in the House, why should anyone expect her to vote differently in the Senate?

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Tallahassee Keeps Telling Local Communities to Sit Down

This entry is in the series 2026 Elections
This entry is in the series Florida Legislature

There is a word in Florida politics that sounds dry enough to cure insomnia but is quietly reshaping life in our communities: preemption.

Preemption is what happens when Tallahassee tells local governments they are not allowed to solve local problems. In recent years, the Legislature has used it to block local worker protections, weaken local control over zoning and development, and shift more decisions away from the people who actually live with the consequences.

My latest article examines this growing pattern, including Florida’s ban on local heat protections for outdoor workers, recent development bills that override local planning, and the legislators who keep voting to shift power away from communities and into the state’s hands. This is not just a procedural fight. It is about whether local democracy still means anything when powerful interests want it out of the way.

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2022 Election – Hillsborough County Board of County Commissioners District 1

This entry is in the series 2022 Election

I had one of the most interesting candidate conversations I think I have ever had around this race. I had a long conversation with Scott D. Levinson, the Republican running for the seat. This is where it got interesting. He seems to be very socially progressive, to the point I eventually said, “Scott, you need not be telling people this. You may get kicked out of the Republican party. But the thing is, Harry gave me an appointment when he was a member of the City Council and heard me out on some contractor behavior issues we were having in the neighborhood.

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2020 Election – Hillsborough County Board of Commissioners District 6

This entry is in the series 2020 Election

This has Republican Sandy Murman seeking to unseat Democratic incumbent Pat Kemp. This is a tough one for me. Sandy Murman panders, moves from office to office as she’s termed out, and serves only developers. On the other hand, Kemp, who I contributed to, has refused to return calls and messages, so I won’t be voting for either candidate.

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2020 Election – Hillsborough School Board District 7

This entry is in the series 2020 Election

This is a county-wide seat and the only school board race I vote in this round. Lynn Gray, the incumbent, is being opposed by Sally Harris who previously served on the board and was voted out. Harris served in 2017 and 2018 as Chair of the Board of Education, but her entire tenure was pretty lack-lustier. Given the challenges that will be faced by the district in 2021 and into next year, that’s just not going to cut it. I talked to Lynn Gray this time and in her previous election. She has over 40 years of classroom and school administrative experience and is involved in the schools as more than just a member of the board. She shares my concerns about the loss of funding to for-profit charter companies. So, for all those reasons, I’m going with Lynn Gray for Hillsborough School Board District 7.

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2020 Election – Hillsborough County Commission District 1

This entry is in the series 2020 Election

Democrat Harry Cohen and Republican Scott Levinson are vying for this seat. I did not get a call from Levinson, but I did hear from Harry Cohen. In fact, that’s not the first time we’ve talked. Cohen is a policy wonk. He makes sure he knows what he’s talking about, and he will have thought through any proposals he makes, and he takes the long view. So for Hillsborough County Commission District 1, I’m recommending Harry Cohen.

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