A Republican, Cheney represented African American clients during the segregation era and supported voter registration drives during his U.S. Senate campaign in the era of white supremacy supported by the Democratic Party in Florida and across the south.

Efforts to register African Americans resulted in the Ocoee massacre.

He was a Supervisor for the United States Census for Florida in 1900.

He was the United States Attorney for the Southern District of Florida from 1906 to 1912.

[3] Cheney received a recess appointment from President William Howard Taft on August 26, 1912, to a seat on the United States District Court for the Southern District of Florida vacated by Judge James William Locke.