Drummond moved to Canada in 1976 and was raised in Toronto's Jane and Finch neighbourhood. He attended high school at Runnymede Collegiate Institute, and is a graduate of the Radio and Television Arts program at Ryerson University.
Drummond was Citytv's crime specialist. He started out at Citytv as a security guard on Electric Circus in 1989. He has since worked as a teleprompter operator, floor director, studio cameraman, deputy chief of assignment, anchor of CityNews Streetbeat, and videographer for CityNews. During this time, he appeared in the Maestro Fresh-Wes music video "Let Your Backbone Slide" as the cameraman at the beginning sequences.
In 1995, Drummond was accosted by two Toronto Police officers in what the officers described as a "high-risk takedown", but which was characterized by outside observers as a racial profiling assault as there was no evidence that Drummond had done anything besides driving while black. The allegation of police misconduct was one of several which contributed to a wildcat strike by police officers in the summer of 1995; current Toronto police chief Bill Blair, a supporter of community policing models, was assigned to head the affected police division in response to the strike. The incident also reportedly contributed to Drummond's own decision to move from a technical to an on-air journalist's role with Citytv.
Drummond previously anchored CityNews at Noon and was later made anchor for another newscast, CityNews at Five. Due to the Citytv layoffs in January 2010, Drummond lost his anchoring job, but continued to work as the station's crime specialist. He left the station September 6, 2010.
- Ashante Infantry (2010-10-12). "Diversity on the dial: New CBC co-anchors Anne-Marie Mediwake and Dwight Drummond". Toronto Star. Retrieved 2010-10-12.