He joined the then Metro Toronto Police in 1964 as a beat officer and became a homicide detective in 1978.

Prior to becoming police chief, Boothby was the unit commander or superintendent of 52 Division, the division that covered much of the downtown business and residential area from Spadina to Jarvis, the Lake to south of Summerhill.

He was instrumental in beginning a dialogue between the lesbian and gay communities and the police force; a force that had a violent history in dealing with the gay and lesbian community especially after the bathhouse raids of 5 February 1981.

Boothby's rise to the chief's post was seen as a change from the style of William J. McCormack, but he had a difficult time with the Toronto Police union president Craig Bromell.

His management style was seen by some as soft and was suspected to contribute to his departure from the force.