Born in Portland, New Brunswick, the son of William A. Chesley and Mary Ann Algee, Chesley received his education at the schools of St. John and at the Albert County Grammar School.

During that time, an act was passed by the Legislative Assembly of New Brunswick for the purpose of appointing three commissioners to prepare a scheme to unite Portland with the city of St. John.

A vote was taken in the Spring of 1889, and the scheme of union, submitted to the people, was carried by a large majority, Portland and St. John becoming one corporation.

He was warden of the County in 1891 and 1892, and at the by-election of 1892 for the riding of City and County of St. John, on the retirement of the current MP Charles Nelson Skinner, who was appointed to the office of Judge of Probate, he was acclaimed to the House of Commons of Canada.

[1] On Mr. Skinner's resignation, October, 1892 This article incorporates text from The Canadian album: men of Canada, Vol.