[1] Sutton was working as a photographer when he registered for the Union Army draft during the American Civil War.

[4][5] He was later involved in several other business ventures, including owning apartments and commercial buildings, working as a real estate broker, and operating a lumber dealership.

[6][7] He also took part in civic activities, including joining the volunteer fire department's Hook and Ladder Company Number 1, of which he served as auditor.

[11] Sutton defended himself in a trial before the city recorder and won a dismissal of the charges and return of his liquor.

[11] In January 1869, he was found guilty on four counts of selling liquor at the City Coffee House, and paid an $80 fine.

[15] In August 1873, law enforcement officers searched his home in the early morning hours and discovered a workman leaving the premises with two jugs of liquor.

[16] Upon entering Sutton's basement, they found him packing bottles of whiskey for transport and observed him emptying a washtub and another container.

[18] In 1889, a search of his barn uncovered a secret tunnel with a concealed entrance in the cellar, which led to a hidden storage room.

[19] As Vermont began to market itself as a tourist destination, the prohibition on alcohol sales was subject to lax enforcement.

[20] For example, by the 1890s Urban A. Woodbury, the owner of Burlington's Van Ness House hotel, was openly serving alcohol.

[34] In September 1886, Sutton was an unsuccessful candidate for the Vermont Senate, placing fourth in the race for three at-large seats.

[35] In March 1887, Sutton was an unsuccessful candidate for mayor, losing to Republican William W. Henry by a vote of 1084 to 769.

[42] Sutton was the Democratic nominee for mayor in March 1898, and defeated Republican Hamilton S. Peck by a vote of 1351 to 1312.

[43] His term was marked by a contentious relationship with Burlington's Republicans, who opposed many of his initiatives, including suing to prevent the police chief Sutton appointed from assuming his duties.

[47] Motions and appeals kept the case active until March 1904, when the State's Attorney of Washington County declined to prosecute and the charge was dismissed.