History Is Fun! Toronto's Mayors in Short
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History Is Fun! Toronto’s Mayors in Short

2006_10_15_city_hall.jpgNext month Toronto will be holding municipal elections, in which, statistically speaking, the vast majority of you reading these words will not bother to vote. So in honour of all 38 mayoral candidates, and to encourage you hipsters to get out and rock the vote, Torontoist offers a brief history of some of Toronto’s most interesting mayors. If your favourite is missing or misrepresented, please let us know.
Most Disgruntled Mayor
2006_10_15_mackenzie.jpg William Lyon Mackenzie (not to be confused with his grandson, William Lyon Mackenzie King, WWII Prime Minister and noted speaker with the dead) served as first Mayor of Toronto in 1834.
His historical significance lies largely in his feuding with the “Family Compact”, the clique of elite families that ruled Upper Canada at the time. After attacking them to little effect for years in his newspapers “The Colonial Advocate” and “The Constitution”, in 1837 he led the spectacularly unsuccessful Upper Canada Rebellion, which was easily and enthusiastically put down by government forces. Never one to learn a lesson quickly, Mackenzie fled to the United States briefly before forming a provisional Republic of Canada government on Navy Island in the Niagara River. The regime was never recognized by anyone, and troops soon squashed this endeavour as well. However, the support of many Americans for Mackenzie’s rebels almost sparked another war between the US and Great Britain.
In later years things calmed down, and in 1849 Mackenzie was allowed to return to Canada from the US, where he had been imprisoned. He served as a member of the Legislative Assembly of the Province of Canada from 1851 to 1858.
Read about more of Toronto’s mayors after the jump.

Most Dangerous Mayor
2006_10_15_rebellion.jpgJohn Powell was the 5th mayor of the city from 1838 to 1840, and the Rambo of early Toronto.
A member of the Family Compact that controlled the political life of Upper Canada, he played a key role in suppressing William Lyon Mackenzie’s rebellion of 1837. At the time he was alderman for the district bounded by Yonge, Bathurst, King and Queen, which as yet had no live music venues or coffee shops.
On December 4, the night that the rebels were planning an armed march on the city, Powell and another man decided scout to the north of Toronto, where there had been reports of rebel activity. Captured by Mackenzie and his rebels, Powell pulled out a hidden pistol, killed one of his captors, and fled to give warning to the government militia. Only a misfire by Powell’s pistol prevented Mackenzie himself from being shot.
Powell was widely admired for his commitment to violence and oppressive government, and was unanimously acclaimed as mayor by the city council.
Worst Sore Loser Mayor
Politics in Toronto in pioneer days was not a game for sissies. Henry Sherwood was 7th mayor of Toronto from 1842 to 1844 and a staunch supporter of the establishment of the day, as represented by the Orange Lodge. In 1841, Sherwood and the Tories (supported by the Orangemen) were defeated in an election by the liberal Reformers (not to be confused with the conservative Reform Party of the 20th century). In those days, if you were dissatisfied with the outcome of an election, the appropriate thing to do was to take action, and Henry Sherwood’s brother Samuel gathered a group of armed Orangemen at his tavern to attack the Reform victory parade. In the ensuing melee, one Reformer was killed, but no one was ever charged with the crime, and Sherwood was elected mayor the following year anyway. He later went on to become joint premier of the Province of Canada East.
Most Climate-Afflicted Mayor
William Henry Boulton served two terms as Mayor of Toronto, from 1845 to 1847 and again in 1858, so was technically both the 8th and 14th Mayor. Boulton is noteworthy because it was during his tenure that Toronto Island was formed when a storm washed away 500 feet of the isthmus that had connected it to the mainland. Without this event, future mayor David Miller would have had to find another issue to obsess over during the 2003 election campaign.
Most Mysterious Mayor
According to the record books, Warring Kennedy was the 28th mayor of Toronto from 1894-1895. However, in 1930, when Toronto Council passed a by-law restricting the wearing of bathing suits in public, newspapers quote “Mayor Warring Kennedy” as saying that “Our old by-law would allow people to go along the boulevard in their birthday suits.”
A plaque near Mt. Pleasant cemetery indicates that the prudish Kennedy was already an adult in 1873, meaning that he would have been at least 80 years old by 1930 and could possibly have been mayor for some 36 years. While his advanced age might explain his aversion to immodest clothing, the mystery of when and for how long he was actually mayor remains unsolved. Readers with insight into the question are encouraged to contact us.
Most Heroic Mayor
George Reginald Geary, 35th mayor of Toronto from 1910 to 1912, was an unremarkable lawyer and politician until World War I broke out. In January of 1915, at the advanced age of 42, he enlisted in the Canadian Expeditionary Force and was shipped to France. He served there for the remainder of the war, winning the Military Cross and the French Croix de Guerre for bravery. He later became a Member of Parliament for Toronto South, and Minister of Justice. Rather sadly, if you have $7750 to spare you can buy his medals.
Most Lovably Eccentric Mayor
Thomas Foster, 40th mayor of Toronto from 1925 to 1927, was born to a poor family and became very wealthy through investments in real estate. His nickname in public life was “Honest Tom”, and he was something of a character, once holding a contest to find the woman who could have the most children in 10 years. As mayor he was known for his willingness to turn up and take care of repairs on his tenant’s properties in person.
2006_10_15_foster_memorial.jpgLate in life he traveled to India, and was inspired by the Taj Mahal to build a memorial near his family home in Uxbridge Ontario in 1935. He lies buried there today, Uxbridge’s premier tourist attraction. After his death his will included bequests for birds in Toronto, needy newsboys, and an annual picnic for inner city schools in Toronto.
Mayor Least Welcome on College Street
Ralph C. Day served as 46th mayor of Toronto, Ontario from 1938 to 1940. A veteran of World War I, on his return he founded a funeral home in Toronto, which serves dead folks on the Danforth to this day.
In 1939, when Canada went to war with Italy, the federal government interned Italian-Canadian men as enemy aliens. The following year, Day explained to the press that families of the interned men, many now without any source of income, would be ineligible to receive welfare because “This country is at war with Italy and Italians cannot very well expect us to spend money for war purposes for the purpose of maintaining alien enemies.”
Mayor With Most Interesting Command of the English Language
Allan Lamport, known by the strikingly unoriginal nickname of “Lampy”, was 50th Mayor of Toronto from 1952 to 1954. As mayor, he unsuccessfully fought Toronto’s Blue laws which forbade most activities on Sunday. In the 1960’s, a more reactionary Lampy attracted attention with his opposition to Yorkville’s hippies, once asking a hippie delegation to City Council (sure, it sounds weird now…) “Why don’t you people take baths? How do you go unwashed and have dignity?”
Perhaps Lamport’s most lasting legacy will be his famous malapropisms, including;
“All this progress is marvelous… now if only it would stop!”
“It’s hard to make predictions – especially about the future.”
“I’m lost, but I’m making record time.”
“I spent a week in Montreal last weekend.”
“We’ve got to act wisely and otherwisely.”
“Let’s jump off that bridge when we come to it.”
“We have to choose between collapse and ruin.”
“What you’re telling me is a matter of major insignificance.”
“I am a man of sound prejudice.”
“Canada is the best country in the nation.”
First Multicultural Mayor
Nathan Phillips, QC, 56th mayor of Toronto from 1955 to 1962, was the first Jewish mayor of the city. In fact, he was the first non-Protestant mayor ever, and also the first in the 20th century who was not a member of the Orange Lodge.
Today, he is known by most Torontonians as the square in front of City Hall where Gord Martineau spends his New Year’s Eves.
Tiniest, Perfectest Mayor
David Edward Crombie, 56th Mayor of Toronto, occupied City Hall from 1972 to 1978, a virtual eternity in Toronto municipal politics. As his success implies, he was immensely popular, and had a reputation as a reformer, opposing developers and favouring policies to make the city more livable.
During the 70’s, he was frequently referred to by media as “the tiny, perfect, mayor”, although the specific origins of the phrase seem to be lost in the mists of recent history. Later he served in several cabinet posts for Tory governments under Joe Clark and Brian Mulroney, but the nickname “tiny, perfect, Minister of Indian and Northern Affairs” never really caught on.
Most Female Mayor
June Rowlands was Toronto’s 60th mayor from 1991 to 1994, and the first woman ever to hold the post. Apart from her gender, which she really had no control over, she is most remembered for prohibiting popular band “The Barenaked Ladies” from playing at a City Hall function. At the time the press claimed that she had imposed the ban because she felt the band’s name was sexist rather than just irritating and cutesy. It later emerged that the decision had been made by a hyper-sensitive City Hall staffer, and that Rowlands had had nothing to do with it. She was defeated in 1994 by Barbara Hall, the second woman to become mayor.
Most Embarrassing Mayor
2006_10_15_lastman.jpgWhat can anyone say about Mel Lastman?
The once and future furniture salesman who rose to become 62nd mayor of Canada’s largest city is a controversial and enigmatic figure. Mayor of North York from 1972 to 1997, he was elected the first mayor of the amalgamated megacity of Toronto in 1997, and reelected in 2000. An outspoken man, his public gaffes were frequent, ranging from threatening to kill reporter Adam Vaughn for reporting on his wife Marilyn’s shoplifting arrest to speculating about being boiled alive by natives on an official visit to Kenya. The reasons behind his self-assigned nickname “Bad Boy” were clarified in 2000 when it emerged that he was the father of two illegitimate adult sons, from a 14 year relationship with an employee at his Bad Boy furniture chain.
Lastman did succeed in establishing a reputation on the world stage; when he announced that he would not run for reelection in 2003, the BBC ran a story with the headline “Canadian gaffe-prone mayor to retire”
Mayor With the Most Interminable Wikipedia Entry
Seriously. Current mayor David Miller’s entry runs to over 13,000 words (including footnotes), implying a level of detail in which only the most dedicated Miller groupie could possibly take an interest. If you start reading now, you may finish before the election on November 13.