Born in Bridgeville in Sussex County, Delaware, to parents William Cannon and Margaret Ann Barker, Cannon attended the Pennington Seminary and the Dickinson Grammar School and pursued the Latin Scientific Course at Dickinson College for two years starting in 1866.

[2][3] He did not graduate but went into business with his elder brother, Henry Pervis Cannon, operating a large farm and establishing a canning factory in 1881.

[1] Cannon remained one of Delaware's largest landowners and progressive farmers, owning hundreds of acres of peach orchards.

[2][5] A member of the Republican Party, Cannon served as the first Lieutenant Governor of Delaware from 1901 to 1905.

[1] Cannon was a member of the Belles Lettres Literary Society and the Epilson chapter of Phi Kappa Sigma.