After being educated in local schools, Swearingen attended Mercer University in Macon, Georgia, graduating with his Bachelor of Laws degree in 1899.

[2] He served on the court until 1913, when he successfully ran for mayor of Jacksonville, defeating Socialist Thomas W. Cox with over 92% of the vote.

[4] Swearingen sought reelection in 1915, though he faced three challengers in the Democratic primary: businessman Rudolph Grunthal, physician Charles Johnson, and former mayor J. E. T. Bowden.

Seeing Swearingen's efforts in cracking down on Jacksonville's red light district, Catts appointed him to finish the remaining 3 years of West's term.

Despite making use of his spy network from Jacksonville, Swearingen was unable to combat rum runners coming from Cuba and the Bahamas.

Swearingen faced the Speaker of the Florida House of Representatives Cary A. Hardee and State Senator Lincoln Hulley in the Democratic primary.