R.J. Fleming's self-made rise from schoolyard fist fights in Cabbagetown to the mayor's office.
He was among the most popular mayors in the city’s history. Some suggested he was its best mayor. R. J. Fleming pulled himself up from austere origins on the strength of hard work and his proclaimed Christian convictions to become a business leader and municipal politician in the late 19th century. Then, in economic collapse, he lost it all and spent the first decades of the 20th century rebuilding his fortune. Through it all, he was said to be among the city’s most popular citizens. “[I]t might be stated without exaggeration,” the Toronto Star (October 26, 1925) proclaimed at the time of his death, “that to write his life is to write the history of Toronto for that period, so closely was Robert Fleming identified with the great events during that time.”
Of Irish extraction, Robert John Fleming—known to all as R.J.—was born on St. David Street on November 23, 1854. Growing up poor on the working-class streets of Cabbagetown, Fleming frequently got into schoolyard fights at Park Street School before dropping out entirely at the age of 12. Earning three dollars per week to help support his family, he worked as a stoker in the office of a coal and wood merchant. Ambitious, Fleming showed a shrewdness in business affairs. Once, when an unhappy customer returned to complain that her bundle of wood contained only 99 pieces instead of 100, Fleming immediately took the initiative to retrieve for her the largest stick he could find in the yard. The customer was satisfied and the merchant rewarded Fleming’s initiative with a pay raise.
(Above right: Portrait of R.J. Fleming by William James, 1906. From the City of Toronto Archives [Fonds 1244, Item 8002].)
After attending business classes in the evenings, Fleming struck out on his own by the mid-1870s, operating his own wood and coal company from a storehouse on Parliament Street. By the mid-1880s, the budding entrepreneur expanded into financial and real estate investments.
Later in life, the devout Methodist credited his success in business and life to his association with the church at an early age. “I was an energetic boy. I loved a fight. When a fellow had licked all the rest they used to bring him to me,” Fleming later recalled to a Toronto Star reporter. “That energy of mine needed direction and restraint. It might easily have been misdirected—might have carried me where some others have gone.” He added: “But the church got me and held me. It gave me good associates. It directed my thoughts into right channels.” Fleming’s Christian convictions led to his ardent, lifelong activism for the temperance cause. He affiliated with the Liberal Party largely because they were most likely to support alcohol prohibition than other political parties.
Still in his early 30s, Fleming was elected to city council in 1886 for the St. David’s ward (which included Cabbagetown) as a staunch and outspoken ally of Mayor William Holmes Howland, who shared his religious reformist zeal. Among his first proposals in office was an effort to reduce the number of liquor licenses in Toronto. Political veterans warned that his proposed bylaw would cost him votes—particularly among the Irish of his working-class ward. Standing firm to his social reform convictions, he succeeded in passing the bylaw in 1887 and remained so personally popular that he was returned to office in 1887, 1888, and 1889.
Although absent from City Hall in 1890 and 1891, he returned to active politics—with the support of the Liberal Party—in 1892 to run for mayor. On the campaign trail, the scrappy and articulate Fleming lashed out at the retiring mayor, Edward F. Clarke, and his hand-picked successor, Conservative candidate Edmund B. Osler. In speeches, he promised to “clean out the old gang at City Hall,” to implement fiscal restraint, and lower taxes. The 38-year-old won handily.
As mayor, Fleming refused the traditional garb of office—the silk top hat, white gloves, and frock coat—during council meetings. This was in keeping with the unpretentious, populist image the “People’s Bob” cultivated in his electoral campaigns. “The source of Fleming’s appeal was his knack for combining practical politics, reformist zeal, and an exuberant personality,” Gayle M. Comeau writes in the Dictionary of Canadian Biography. “His unquestionably ethical behaviour and kindly Christian aura won him the respect of many adversaries.” A supporter of the working man, once in office Fleming gave all municipal labourers a hefty 25-cents-per-day raise and instituted a minimum wage for public workers.
“Don’t vote for him. He’s a prohibitionist,” someone shouted at a rally during Fleming’s campaign for re-election in 1893, historian Donald Jones recounts in the Toronto Star (February 15, 1986). “I sure will,” came a shouted retort elsewhere in the crowd. “Thanks to him I can now afford more beers every day.” Fleming won re-election by the greatest majority in Toronto’s history, defeating the Clarke-backed candidate, Warring Kennedy.
In 1894 and 1895, Fleming again faced Kennedy in the mayoral election. But, with the city suffering hard economic times, he was defeated on each occasion. The latter campaign, which featured a rally or candidates meeting almost every evening, was so closely contested that Fleming lost by only 14 votes. In early 1895, public confidence in the Kennedy administration was badly shaken when an investigation by County Court Judge Joseph E. MacDougall uncovered unprecedented corruption in municipal government—including aldermen who’d tried to sell their votes on key issues—and other malfeasance dating back to 1891. Fleming was returned to the mayoralty once again in 1896 and 1897.
In a review of his mayoral career, the Globe newspaper assessed that Fleming had achieved more “good reform in a few years than all the mayors had over the previous ten years.” His crowning achievement was to preside over the first Board of Control meeting on April 24, 1896.
The city’s growth into a bustling industrial metropolis, Victor L. Russell explains in Mayors of Toronto (Boston Mills Press, 1982), strained the local government’s ability to administer and deliver necessary municipal services efficiently and with appropriate financial accountability. After numerous failed attempts in the 1880s and 1890s to institute more businesslike management of civic affairs, the reforms implemented by Fleming at the behest of the provincial government created an executive branch composed of the mayor and key standing committees to oversee the city’s daily business while remaining accountable to the broader city council.
Outside of politics, Fleming assumed leadership roles in several temperance organizations in the 1890s, including acting as treasurer of the Ontario branch of the Dominion Alliance for the Total Suppression of the Liquor Traffic, and holding regular temperance rallies at the city’s Horticultural Gardens. He was an early advocate of women’s suffrage, largely because he felt women would cast votes in support of the temperance cause.
Fleming resigned from public office partway through his fourth term as mayor, in August 1897, when his wealth was wiped out in a real estate collapse and he had to seek employment on the municipal payroll.
For seven years, he was the municipality’s Assessment Commissioner (with the additional duties of the property department after 1903), acquiring land on behalf of the city—particularly along the waterfront—that would eventually be worth millions. Earning $4,000 per year, Fleming’s request for a raise of $1,000 was refused, so he quit in December 1904. Before long he was general manager of the Toronto Railway Company with an annual salary of $10,000—and assumed board positions with several of industrialist William Mackenzie’s other companies.
As mayor, Fleming had favoured the strong regulation of private companies providing civic utilities—like public transportation, electric, gas, and telephone services. In an address to city council in 1896, Fleming insisted that aldermen “definitely and emphatically inform corporations doing business with and having agreements with the city that they must live up to their agreements in every particular, and no violation of these agreements will be allowed upon any considerations.” But during Fleming’s time in office—as during prior and later mayoral administrations—municipal officials found it difficult to force private companies to live up to the letter of their contracts. The Toronto Street Railway Company, for example, had been so unpopular with the public that, when its franchise expired in March 1891, the municipality took over streetcar operation—only to relinquish it to another private company (William Mackenzie’s Toronto Railway Company) mere months after discovering the headaches and hassles of operating public transit.
(Above right: Editorial cartoon of R.J. Fleming by Newton McConnell, ca. 1910. From the Archives of Ontario [C 301].)
“With public opinion aroused by unsatisfactory service [of utilities monopolies], the vote-getting possibilities of the issue of public ownership were not lost on astute politicians,” historians Christopher Armstrong and H.V. Nelles argue in Victor L. Russell’s Forging a Consensus: Historical Essays on Toronto (University of Toronto Press, 1984), “who quite naturally welcomed the opportunity to present themselves as the fearless guardians of the public interest.” By the early 20th century, it was clear to many municipal politicians that if companies wouldn’t adhere to their wishes through forceful enforcement of contracts and regulation—as Fleming had proposed—the logical solution was the public ownership of utilities.
As general manager of the Toronto Railway Company, Fleming became the defender of the status quo, drawn into seemingly endless conflicts pitting him against civic authorities advocating for public ownership, like Frank S. Spence and Horatio C. Hocken who were childhood friends from the city’s east end. Aldermen fought him for improvements to service and to add routes; community organizations fought him on the TRC’s plan to construct a streetcar line through the precincts of Old Fort York. Becoming the target of public scorn—and caricatured in editorial cartoons—as he cut service and refused vehicle enhancements to maintain the company’s profitability, Fleming nevertheless remained personally popular even as the company’s unpopularity led to the establishment of the publicly-owned Toronto Transportation Commission in 1921.
With a salary of $10,000, supplemented by his board positions with other companies owned by William Mackenzie, Fleming was eventually able to repay debts he’d incurred during the real estate crash a decade earlier. So he did, reimbursing the principal and interest to all who’d loaned him money. Some had since died, so he paid their widows and families. It was remarked that, whether up or down, Fleming never forgot his roots. Even as a wealthy and successful businessman, he remembered by name those who’d known him in more humble times. It was said that, late in life, Fleming was regularly accosted by well-wishers wanting to shake his hand whenever he walked down the street. Spurred by his personal popularity, Fleming ran for mayor a final time in 1923 and was narrowly defeated by Charles A. Maguire by only 840 votes. Liberal Party operatives would continue to encourage him to seek public office for the rest of his life, but after his defeat in 1923, he retired to private life.
To all appearances, Fleming led a modest lifestyle. He moved from a house on Parliament Street to a country estate at the northeast corner of St. Clair Avenue and Bathurst Street in 1902, ostensibly because his neighbours had complained about the livestock he was keeping in his backyard. In fact, Fleming was convinced that his children, some of whom had taken ill, needed fresh country air. The property, which featured a large house surrounded by gardens and orchards, was sold for $250,000 in 1923 or 1924 to be used as an orphanage before eventually becoming the campus of St. Michael’s College School.
Moving to a 1,000-acre farm called Donlands (located between Don Mills Road and the banks of the Don River, on the present-day site of Flemingdon Park), Fleming bred cattle until he suddenly took ill and died of pleurisy at home on October 26, 1925. The funeral for one the Globe proclaimed to be “one of the best-known and most personally popular figures in the city” was attended by thousands of Torontonians.
Other sources consulted: Mike Filey, Mount Pleasant Cemetery: An Illustrated Guide (Firefly Books, 1990); and Patricia Petersen, “The evolution of the board of control,” in Victor L. Russell, ed., Forging a Consensus: Historical Essays on Toronto (University of Toronto Press, 1984).