
These Toronto flags were all neatly lined up on the eastern side of Nathan Philips Square early Sunday morning. The Wikipedia description of the flag's origin and design says what needs to be said.
The original flag of Toronto was designed by Rene De Santis, a 21-year-old George Brown College student, and won in a 1974 competition held by the City of Toronto Flag Design Committee. After the city amalgamated in 1997, the City Council looked for new designs from the public, but did not approve of any. De Santis suggested minor modifications to the original flag, which was adopted in October 1999, to create the current flag. The flag displays the twin towers of the Toronto City Hall on a blue background, with the red maple leaf of the Flag of Canada at its base, representing the Council Chamber at the base of the towers. The shape of the space above and between the towers suggests the letter 'T', the city's initial.
Chris Bateman's 2012 blogTO post on the subject looks at the birth of the flags and different alternatives to this one.