Maddox was indicted on December 12, 2018, on 44 charges, including racketeering, bribery, extortion, bank fraud and wire fraud, in an FBI investigation into corruption that played a key role in Democrat Andrew Gillum’s campaign for Florida governor.

[4] Maddox was suspended from the Tallahassee City Commission following the indictment and subsequently replaced after the appointment of Commissioner Elaine W. Bryant, Ph.D. on December 31, 2018.

In 1990, at the age of 22, Maddox ran for the Florida House of Representative's 10th district, but lost the Democratic primary by 32%.

Described as a "rising star" by Vice President Al Gore, Maddox spoke at the 2000 Democratic National Convention.

Maddox attempted a run for Attorney General of Florida in 2002, but lost to future Orlando mayor Buddy Dyer in the Democratic primary.