Career
He had met Reid while working on the Code of Professional Responsibility and they eventually became partners. Middleton"s brother Alexander participated in the surveying of the route for the Newfoundland Railway in 1889. Both Middleton and Reid had contracted with the Whiteway government of Newfoundland on June 18, 1890 to build sections of the Railway.
Sometime in 1892 he had a falling out with Reid and dissolved the partnership.
Reid went on to complete the Railway contract.