[2] He was educated at Singleton and at age 15 followed his father into the railways service, starting as a junior porter or in the parcels office.
In September, 1949, he was appointed Commissioner for Road Transport and Tramways, and in May 1950, he was appointed Director of the Transport and Highways' Commission,[3] at a salary of £5,500, a position superior to that of Garside, who retired in February 1952, to be replaced by James Fraser's son Keith Aird Fraser who, however, died on 23 August 1952.
The newly elected Premier Cahill abolished the Transport and Highways Commission and appointed Winsor Railways Commissioner, at the reduced salary.
[5] Against his wishes, Neal McCusker (often misspelled Neil) was in July 1955 appointed senior executive officer.
After a series of accidents and service delays Winsor was on 31 July 1956 obliged to resign, replaced by McCusker.