Normally the council is allowed to decide which process to follow in each individual case; however, if the vacancy occurs after March 31 in the year of a regularly scheduled municipal election, then the vacancy must be filled by direct appointment as provincial law prohibits the holding of a by-election in the final six months of a council term.

Peter Leon considered registering as a candidate in the 2014 election following his appointment as an interim councillor in 2013,[13] but ultimately did not do so.

If a full byelection is pursued, however, then the winner of that by-election is not barred from running in the next regular municipal election.

[14] Unlike a city council seat, however, a by-election must always be held, unless the vacancy occurs less than 90 days before a regular municipal election.

Doug Holyday resigned from council in 2013 after winning election to the Legislative Assembly of Ontario in a byelection, and was succeeded by Peter Leon.

[15] Adam Vaughan resigned from council in 2014 to contest a federal byelection for the House of Commons, and was succeeded by Ceta Ramkhalawansingh.

[28] Over the next three decades three new wards were added, one each in the north, east, and west, as new areas were annexed to the City of Toronto.

Former East York mayor Michael Prue lobbied successfully for a third councillor to be elected from that ward, and this was implemented mid-term.

In 2000 a new ward map was devised based on the federal ridings (electoral districts) that covered Toronto.

[30] The first councils were dominated by two factions: the Family Compact and its loyalists; and the reformers under the leadership of William Lyon Mackenzie, Member of Parliament for York.

[32] After the defeat of the Upper Canada Rebellion in 1837, the reformers were marginalized, as several were executed for treason, and others, such as Mackenzie, went into exile.

The Tories were associated with staunch Protestantism, shown through membership in the Orange Order,[33] and support for the Lord's Day Act.

The pro-labour social democratic party found support in various working-class areas of Toronto and several of its members were elected to city council.

There was considerable communist support in the downtown areas covered by Ward 4 and Ward 5, especially in the heavily Jewish areas of Kensington Market and the Garment District around Spadina Avenue and further west along College and up to Christie Pits including what is now Little Italy.

With the beginning of the Cold War and staunch opposition from the other political groups, the communist presence quickly disappeared.

[citation needed] The character of Toronto politics began to change in the 1950s and 1960s as the Anglo Tory lock on power faded in the increasingly diverse city.

His religion was an important issue in the election, in which his opponent proclaimed himself to be running as "Leslie Saunders, Protestant".

The Reform faction arose in opposition to the urban renewal schemes that had been in favour in the previous decades.

Two key battles were over the proposal for the Spadina Expressway and the replacement of the Trefann Court neighbourhood with a housing project.

[41] The Reformers opposed the destruction of existing neighbourhoods and followed the urban theories of recent Toronto arrival Jane Jacobs.

The Old Guard supported new highways and housing projects, in part because of their close ties to the development industry.

The debate between the two groups became the central issue of the 1969 municipal election with mayoral candidate Margaret Campbell running on an explicit reform platform.

[citation needed] One example of the close ties was revealed in 1971; a conflict of interest case of alderman Ben Grys, who chaired the Buildings and Development Committee.

Grys then helped get rezoning for the area to allow developers to increase the number of units they could build, without disclosing his interest.

Crombie was mayor until 1978 and during his term, the city enacted a holding by-law to curb the development industry.

Eggleton negotiated the agreement to administer Toronto Island Airport, allowing scheduled airlines, but disallowing jets.

[citation needed] In 2010, Councillor Rob Ford won the mayoralty on promises to cut taxes.

This was overturned on September 10, 2018, after City Council and several private respondents challenged the law in Ontario Superior Court.

The judge found that the Ontario government erred constitutionally in making the change during the election campaign, thus depriving voters and political candidates of their "freedom of expression" rights.

The decision was ultimately upheld by the Supreme Court of Canada in Toronto (City) v Ontario (Attorney General).