Smitherman spent much time working with his father's business, Smitty's Haulage (later Sure-Way Transport).

[12] Smitherman was active in politics at Burnhamthorpe Collegiate Institute, where he was the high school's student council president.

[citation needed] In the 1999 provincial election Smitherman was nominated as the Liberal Party candidate for the riding of Toronto Centre-Rosedale.

Former Toronto mayor John Sewell was running as an independent candidate, and activists accusing him of splitting the left-wing vote with the New Democratic Party.

[14] In the legislature, Smitherman was nicknamed "Furious George" for his aggressive and often abrasive manner, and rose to become McGuinty's right-hand man and favourite "attack dog".

Under Smitherman's leadership, the Ministry of Health and Long-Term Care launched the Wait Times Strategy in 2004.

The new health care model was designed to reduce wait times for various procedures such as hip and knee replacement, MRIs and CT scans.

[20][21] However, Smitherman was criticized for ignoring calls for an independent investigation into C. difficile deaths in hospitals, and he was unable improve the lives of nursing home residents who were often forced to sit in soiled diapers for hours on end.

[23] On June 20, 2008, Smitherman was shuffled to the new Ministry of Energy and Infrastructure, a merger of two formerly separate government departments.

In April 2010, Smitherman's campaign manager, Jeff Bangs, resigned and was replaced by Bruce Davis, chair of the Toronto District School Board and a veteran of local politics.

This partisan endorsement led to speculation that Smitherman's political fortunes were connected with those of the Liberal provincial government.

Smitherman claims he was set up by Rossi's campaign and he said the young woman tried to hand him a paper questioning his work with youth before a debate.

After Labour Day, he made fiscal promises to freeze property taxes for a year and cut down on reckless spending.

He also serves on the boards of medical marijuana producer THC Meds Ontario Inc., drone maker Alta Vista Ventures and mining company Ceylon Graphite.

[41] Smitherman considered returning to politics and seeking the Liberal Party of Canada's nomination for a federal by-election in Toronto Centre but announced on July 29, 2013, "I won't be a candidate now.

I won't be contesting a riding in the 2015 general election or any other," as he prefers to prioritize "fun, family and finances".

[3] Smitherman had also expressed interest in returning to provincial politics and reclaiming his former riding of Toronto Centre in the 2018 provincial election, which was vacant following the resignation of Glen Murray, but faced resistance from the leadership of the Liberal Party which considered him an unsuitable candidate for the party's nomination due to his association with the eHealth scandal as well as his reputation for being difficult and temperamental, and threatened to disqualify his candidacy.

[44] In the face of this opposition, Smitherman decided not to pursue the Liberal nomination and instead focus on his municipal campaign.