Webster was the last constable to ride a bicycle on his beat, and was the last Toronto policeman to wear a bobby's helmet and tight-necked tunic on duty.
One of the murderers he helped capture was Detroit gangster Arthur Lucas, who was one of the last two criminals executed in Canada before abolition of capital punishment.
In 1991, he published an autobiography entitled Copper Jack: My Life on the Force, co-written with mystery writer Rosemary Aubert.
His daughter, Rosemary Vodrey, was a senior cabinet minister in the Manitoba provincial government of Gary Filmon during the 1990s.
Veteran Toronto Star crime reporter Gwyn "Jocko" Thomas spoke at his funeral, and described him as a "superb police officer".