At 18 years, and after completing secondary school, he was eagerly pursued by several football clubs including St Kilda and Essendon.

He was ideally suited to Australian Rules football due to his stature; six-foot tall, weighing 12 stone and extremely agile.

At six feet tall (183 cm) and twelve stone (76.2 kg), Thurgood possessed qualities that made him a versatile key position player: he was extraordinarily fast, a superb mark, and very nimble and agile.

During his stint there he topped the WAFA goal kicking list on three consecutive occasions between 1895 and 1897, helping the side lift premierships in the first two of those years.

[31] While contemporaries noted that Thurgood was slower, heavier and less keen, he produced his finest performance in the 1901 VFL Grand Final against Collingwood when he kicked three of the side's six goals and was a major contributor to Essendon's victory.

[31] In 1902, Thurgood received a three match suspension for striking St Kilda players Mick English and Alf Trevillian.

[32][33] Football historians Michael Maplestone and Stephen Rogers determined that "Goodthur" was most likely Fred Mann,[34] while official VFL/AFL player statistics reflect this view.

[35] In 1902, there were widespread allegations that he had 'laid down' against Collingwood in the Grand Final, which Essendon lost by 33 points, a heavy margin for the time: in disgust, Thurgood demanded, and was refused, a clearance to the Magpies, whereupon he decided to retire.

He ran a number of successful horses, including Amazonia, which won the Bagot Handicap in 1921 and was placed third in the Melbourne Cup that year.

[39] He owned a stock and station agent business with premises in Flinders Lane[40] In 1912, he registered as a bookmaker and was given space in the elite “Paddock Reserve” at Flemington racetrack.

[41] He enjoyed modest success with racehorses; a horse named Choi took out the Cantala Stakes in 1919, while another, Amazonia, was placed 3rd in the 1921 Melbourne Cup.