In 1928, John Montgomery was very happy with his career as a motorcycle patrol officer. He spent most of his time patrolling along the St. Lawrence River while he was working out of Morrisburg as a member of the Department of Highways Motorcycle Patrol. This enjoyment of life and career were put to the test in 1928 when he broke his jaw and both legs while on-duty.
Although PC Montgomery had a long period of recovery, he did not request a change for an alternate line of work. He went right back to highway patrolling as soon as the doctor gave him authorization to do so.
In March of 1930, the OPP took over the duty of patrolling the highways and John was one of the eighty people that became members.
PC Montgomery was deployed out of Westboro, now known as Nepean, upon joining the OPP. He spent most of his career in Eastern Ontario. Montgomery only served for 16 short months once he was hired by the OPP. He was the fatality of a head on collision while he was following another vehicle.
On Friday July 31, 1931, John Montgomery passed away at the age of thirty-two. He was survived by his wife and their young son.