[10] When commissioner Willie Logan resigned after winning election to the Florida House of Representatives, Riley won a special election on November 2, 1982 to serve out the remainder of Logan's term (through April 1984) on the City Commission[11] defeating Stuart Susaneck, Vince Cooper, Gloria Giardino (wife of former mayor Candido Giardino), and George Lipkins.

[13] While mayor, he was able to balance the budget, began the process of developing a downtown district through rezoning, and completed the restoration of city hall.

[15] Riley's popularity suffered after he was accused of accepting a bribe related to the relocation of a flea market, overspending his expense account, and not paying his water bill.

[1] In November 1998, he unsuccessfully ran for one of three open seats on the City Commission[2][16] losing to incumbent Myra Taylor and newcomers, Bobby Bradley and Derrick Miller.

[20][21] In November 2018, he again ran for mayor but lost in a 4-way race against Rose Tydus, Dorothy "Dottie" Johnson, and Matthew Pigatt.