From the beginning, Ralph Medina has based his District 1 City Council campaign on the idea that no one else in the race could match his level of experience.

Medina, 55, often points to his 35 years as a San Antonio firefighter, his stint as a zoning commissioner, and his long history as an entrepreneur and neighborhood activist to make the case that he’s uniquely qualified for the District 1 seat.

Experience often comes with baggage, however, and last month the Express-News reported that Chief Investments LLC, a company run by Medina, owed more than $14,000 to Bexar County in property taxes on a vacant lot the company owns.

Plaza de Armas has learned that this tax debt was only the most recent in a series of messy business hiccups that have dogged Medina over his career, with the state revoking licenses for his various companies five times over the last 14 years for failure to file franchise tax returns.

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