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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Two Campaigns, Two Very Different Funding Models

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

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.

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