Ford attended Scarlett Heights Collegiate Institute in Etobicoke. He dreamed of becoming a professional football player, and his father paid for him to attend special camps of the Washington Redskins and the University of Notre Dame. After graduating from high school, Ford went to Carleton University in Ottawa to study political science. He made the football squad, but did not play in any games. He left Carleton after one year to return to Toronto and did not complete his degree. After Carleton, he started a sales job at Deco. After Doug Ford Sr.'s death in 2006, the Ford family retained ownership of Deco Labels through the Doug Ford Holdings corporation. Ford, alongside his brothers and their mother was a director of the company.
Ward 2 is located in the north-west corner of the city in the former city of Etobicoke. The ward's population of over 50,000 in 2006 was 53% composed of immigrants, the largest group being South Asians. It is mixed in nature with 40% of dwellings being single-family detached homes and 35% being high-rise apartments. It is also known as an area that has seen gang violence, including six murders in 2000.
In June 2006, Ford spoke out against the city donating $1.5 million to help prevent AIDS, arguing that most taxpayers should not be concerned with AIDS. Ford publicly apologized for the comments in May 2010 during his mayoral campaign after his opponent, George Smitherman, called Ford's character into question over the remarks. At a council meeting on March 5, 2008, Ford stated "Those Oriental people work like dogs", a remark he later formally apologized for but stating that he meant it as a compliment.
Ford suffered from alcohol and drug addiction for many years. After the death of his father in 2006, Ford's abuse grew and led to public episodes of intoxication, followed by public denials. His episodes were symptomatic of alcohol and drug addiction. His episodes were reported in the media widely and attracted much condemnation. Ford's abuse led to him being stripped of much of his powers as Toronto mayor and he later entered drug rehabilitation.
On April 15, 2006, Ford attended a Toronto Maple Leafs hockey game at the Air Canada Centre. According to a couple nearby, Ford was intoxicated, using profanity, and insulting people. The couple then sent a detailed complaint to the City of Toronto. When confronted about the episode three days later by a National Post reporter, Ford initially denied having been at the game, but later admitted it. "I'm going through a few personal problems, but it doesn't justify, you know, getting drunk in public and pretty well acting like an idiot if you ask me."
The death of Rob Ford's father, Doug Ford Sr., in September 2006 due to cancer has been pinpointed as the time period when Ford transitioned to crack cocaine in addition to alcohol. A convicted heroin dealer who used to supply Ford's sister Kathy recalled a party with Ford around that time. According to reporter Robyn Doolittle, Ford would come home at night and drink heavily, use hard drugs or prescription pills.