Dr Pickersgill was born in Annotto Bay, Jamaica where he completed his secondary school studies. He is a U.S. trained Orthodontist and completed his doctoral program in Dentistry and post-doctoral studies in Orthodontics at Howard University in Washington, D.C. He also holds a post graduate diploma in Dental Public Health from the University of Toronto. Dr Pickersgill has practiced privately in Cleveland, Ohio, Mandeville, Jamaica and currently practices in downtown Toronto. His hobbies and interests include soccer,cricket, reading and politics.