A photograph by Dave Decker showing Aileen Rodriguez speaking at the C. Blythe Andrews Jr. Public Library in Tampa, Florida, on July 9, 2026. Captured in a medium shot, Rodriguez stands smiling behind a microphone held with both hands, wearing a bright magenta pink blazer over a black-and-white floral print top, cat-eye eyeglasses, and a name tag reading "AILEEN RODRIGUEZ" pinned to her lapel against a light, plain backdrop.
Aileen Rodriguez at C. Blythe Andrews Jr. Public Library in Tampa, Florida on July 9, 2026. Credit: Dave Decker / Creative Loafing Tampa Bay

Break out las chanclas, Aileen Rodriguez is headed for the Hillsborough County Board of Commissioners after ousting incumbent “hostile” Josh Wostal.

With 95% of precincts reporting, Rodriguez has 56% of the vote, according to unofficial results from the Hillsborough County Supervisor of Elections.

This was a seat that Democrats really hoped to flip, and Rodriguez, a former Republican, handily advanced from the primary despite a late-in-the-cycle challenge from Hillsborough popular, and former Clerk of the Circuit Court Cindy Stuart.

Wostal, for his part, had made a name for himself with an impolite style of governance that often diluted the message when he was actually making good points (ie: his scrutiny of the Rays stadium deal, where he could only draw support from one other commissioner in a 5-2 vote that will put nearly $800 million in taxpayer money towards costs associated with the baseball team’s new stadium).

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This article appears in Oct. 29 – Nov. 04, 2026.

Read his 2016 intro letter and disclosures from 2022 and 2021. Ray Roa started freelancing for Creative Loafing Tampa in January 2011 and was hired as music editor in August 2016. He became Editor-In-Chief...