• Ed Brown

My Flemingdon Park: The Life of Robert Fleming, The People's Bob

The placename Flemingdon is a portmanteau, derived from combining portions of two words: Robert John Fleming, Toronto's 27th mayor, and Donlands Farm, his vast landholding. Who was Robert J. Fleming, where exactly was Donlands Farm located and how did a neighbourhood come to bear his surname?


In late October 1925, a freak autumn blizzard battered the city. The mercury dipped to a forty-year low. Outside Timothy Eaton Memorial Church on St. Clair Avenue, nothing could deter thousands of mourners who lined the sidewalk waiting to file past the coffin of beloved former mayor Robert John Fleming, encircled by deep banks of flowers, lying in state.


The service about to commence, mourners arranged themselves in pews. Observers noted something amiss. As expected, Fleming's large family, his widow Lydia, eight of nine surviving children and his numerous grandchildren occupied the first pews. However, in a break from protocol, dignitaries and the wealthy — including Mayor Foster, provincial court judges and business elites — were relegated to the rear of the sanctuary.


Immediately behind the grieving family sat farmhands, stablemen, herders, and teamsters employed at Donlands Farm and Fleming's other property in Pickering, as well as other 'ordinary' citizens.


In life, R. J. Fleming put family and working-class people before status. Known affectionately as the People's Bob, a moniker bestowed upon him decades earlier by an adoring public, Fleming never lost sight of his humble beginnings.

R.J. Fleming was first elected mayor in 1892

Flemings haled from County Tyrone, Ireland and immigrated to Montreal, then Toronto in 1850 to escape the Great Famine. Robert was born in a dilapidated house on Stanley Street (now Lombard St) on November 23, 1854, before moving to St. David's Street in the impoverished Irish enclave of Cabbagetown. He attended Park Public School. A scrappy, good-humoured, hearty fellow with a twinkle in his blue eyes, years later he reminisced to a reporter, "I was an energetic boy. I loved to fight. When a fellow had licked all the rest, they used to bring him to me."


Dropping out of school after sixth grade, he began clawing his way out of poverty, tending furnaces in an office on Parliament Street. His $2 a week wage helped support his large family of ten siblings. An earnest teenager, he attended business school in the evenings. Around 1874 he and a partner founded a profitable coal and wood distribution business. A few years later, he sold his portion of the company to his partner and successfully entered the city's booming real estate market.


From the beginning, Fleming believed in doing one thing at a time and doing it well.

In 1879 Robert Fleming married Margaret Breadon. The couple chose to remain close to family in Cabbagetown.

A decade of personal upheaval commenced.


Two years into marriage, the couple had a daughter, Rebecca. Margaret was pregnant again two years later, this time with a son, Everett. Weeks after giving birth, Margaret died from complications related to the delivery. At the same time, an unexpected market downturn saw Fleming lose much of his wealth. In 1886 he was elected to city council as an alderman. Two years later, the widower married Lydia Orford.


He was 32 years old.


Fleming would be elected alderman for three terms, then mayor of Toronto for the first time in 1892 (elections occurred annually). He proved himself a man of high ideals. Admired by the populace, he advocated for the poor, supported women's rights and challenged lax liquor laws. He initiated a living wage for civic employees. Unpretentious, he refused to don the silk top hat, white gloves and frocked coat mayors traditionally wore to Council Meetings.

Robert and Lydia on their wedding day

He quickly became known as the People's Bob for his down-to-earth manner.


Winning the 1893 mayoral election by the largest majority in the city's history, Mayor Fleming continued residing in Cabbagetown. His broad appeal caught the attention of the national media, earning him nationwide recognition and respect. He would be elected mayor four times.


Robert and Lydia had a total of eight children plus Rebecca and Everett from Fleming's first marriage. (Everett died unexpectedly at eighteen from a heart ailment.) Through hard work and determination, R.J.'s finances rebounded. The Flemings were affluent but never ranked among Canada's wealthiest. They moved into a large home on a sprawling rural property near Bathurst Street and St. Clair.


Near the end of his final term, Fleming resigned from the mayoralty and became the city's assessment commissioner. After this, he became general manager of the Toronto Street Railway Company, the precursor to the Toronto Transit Commission. His annual salary in 1910 was ten thousand dollars. He remained in the job for nearly two decades.

His keen eye for real estate saw Fleming purchase Donlands Farm, a thousand-acre farm northeast of Leaside, from William Maclean when the former newspaper baron and Member of Parliament put the farm on the market in 1922. Fleming had acquired a farm in Pickering years earlier.

Donlands Farm, east side of Don Mills Road, north of Wynford Dr

Donlands Farm covered a vast area. Referencing present-day geography, the farm stretched from approximately St. Dennis Drive north to Don Mills Shopping Centre at Lawrence Avenue; Leslie Street east to the Don Valley Parkway. The property boasted three homes. The Flemings resided in the largest, built in 1825. The fourteen-room two-story brick and stone dwelling stood east of Don Mills Road, between Wynford Drive and the current C.P.R. underpass.


Approaching seventy, Fleming declined offers to run in provincial and federal elections, preferring a retired life at Donlands as a gentleman farmer attending to hay meadows and fields of rye. He bred prize-winning Irish Hunters and was the first to import and breed authentic Jersey cows from the Isle of Jersey.


Three years into retirement, R.J. Fleming died unexpectedly in his bed at home at Donlands.

Mount Pleasant Cemetery

Over the next quarter-century, some of Fleming's adult children and grandchildren would reside at Donlands. The farm's reputation for champion husbandry became world-renowned. In the late 1940s, the property north of the C.P.R. tracks was sold to developers designing to construct the community of Don Mills.


Land south of the tracks became Flemingdon Park.


On the bitterly cold morning of Robert J. Fleming's funeral, raw winds blowing across fields of fall wheat under a pristine blanket of white, his family held a private wake and memorial service in their home. Before noon, the funeral procession bearing the coffin of the scrappy, industrious and compassionate R. J. Fleming inched south on Don Mills Road, passed the spot where, thirty-six years later, developer William Zeckendorf would cut a ribbon establishing a neighbourhood bearing the former mayor's name.

Thank you Jason Fleming and Katie Stuart for their contributions


Additional material from Mayors of Toronto, Volume 1 1834-1899, Victor Russell, 1982;

Polly of Bridgewater Farm, Catharine Fleming McKenty, 2009,

Toronto Daily Star, Feb 17, 1922, pg.1; Oct 28,1925, pg.1

Photographs used without permission


Ed Brown lived in Flemingdon Park at 58 Grenoble Drive from 1969-1991


edbrownwriter@gmail.com