Robert John Fleming, or as he known to most Torontians, R.J. Fleming, was the son of William and Jane Fleming. R.J.’s parents were poor Methodist Irish immigrants who settled first in Montreal and eventually moved to Toronto in the 1850s. The young Fleming was born on Stanley Street (now called Lombard St.) on November 23rd 1854. In the schools of Cabbagetown he won a reputation as a scrapper. He always liked a good fight. He once said “When a fellow had licked all the other boys in the neighbourhood, they brought him to me.” Fleming’s extraverted spirited character was already well established during his youth. In his formative years he also developed some political and religious views which he would ascribe for the rest of his life, such as: social reform, Methodism, temperance, and involvement with the Liberal party of Canada.
R.J. was educated at the local Park Street School, but he eventually left school at the age of 12 for a paid position as a stoker at an office. The young R.J. Fleming may have left school at a early age, but he remained ambitious and career oriented. He attended classes and business school at night when he wasn’t working. By his early 20s, R.J. had become a business partner with T.W. Elliott, retailer in the commodity market primarily coal and wood. R.J.’s business was located at 231 Parliament Street, the future home of the Cabbagetown Store. Before reaching his 30th birthday, R.J. left the commodity market and he began to invest in real estate and finance. R.J. Fleming amassed a substantial amount of wealth from investment and speculation in the Toronto 1880’s real estate boom. A sudden market downturn and a depreciation of property and a series of poor investments made the self-made business man face near financial ruin. He was eventually over time able to rebuild his finances and pay back all his creditors over a period of 15 years.
In 1886, R.J. Fleming was elected to city council as an alderman for the ‘wet’ ward of St. David’s ward. His term in public office lasted 3 years. While he was in office he introduced a by-law which reduced the number of pubs and taverns in the city from 224 to 150. This new by law was passed with the spirit of temperance in mind, and may locals of the period simply referred to the new by law simply as the “Fleming By-law.” Many Torontians felt that his reduction in tavern licences would reduce the likelihood of Fleming successfully winning a re-election bid in his predominately Irish ward. However, Fleming was re-elected, and thereafter was elected three consecutive times. In 1892 R.J. Fleming decided he was no longer content in just being an alderman, he wanted to become the Mayor of Toronto. Fleming ran on a platform of being a reformist who would “clean out the old gang at city hall.” His Irish wit and fighting temper was a great crowd pleaser during the election campaign. The 38 year old Fleming easily won the election, and immediately after raised the wages of all civic labourers. He said the workers have always been grossly underpaid for their services to the city. Fleming was re-elected Mayor in 1896 and in 1897. His popularity and appeal are undeniable, voters referred to R.J. Fleming as the People’s Bob. The praises for Fleming’s political work also came from the press, the Globe newspaper wrote that R.J. had accomplished a substantial amount of “good reform in a few years [more] than all the other mayors had in the previous ten years.” Fleming resigned suddenly and went back into real estate, only this time on the civic level as the Land Assessment Commissioner.
After a dispute over a wage increase in 1904, R.J. Fleming quit the Assessment Commission and became the general manager for the privately owned and run Toronto Street Railway Company. He worked as the General Manager for the T.R.C. from 1904 to 1921 and during this period, he was able to cut operational costs, by reducing the number of cars and routes used by the T.S.R.C. Fleming’s business savviness and charismatic character, along with his diplomacy were of vital value to keeping the Toronto Rail Company afloat during turbulent years by appeasing both shareholders and the workers who could have brought potential labour unrest. R.J. retired from the Toronto Street Railway Company in the early 1920s just before the 1921 merger between the the privately owned Toronto Street Rail Company and other transportation agencies in Toronto, which would eventually lead to the publically owned and run Toronto Transit Commission.
R.J. Fleming’s new found stability and wealth allowed him to re-locate his family outside of the city, on the north side of St. Clair along a ravine.The child of a immigrant family from Cabbagetown had gone from relative destitution to establishing himself among the social elites of Toronto and becoming apart of the country gentry living on the outskirts of Toronto. The rational for the relocation stems from Fleming’s belief in the healthy benefits that come from living in the country living. This massive 1,000 acre farm was named the “Donlands,” denoting the fact that the farm was near the Don River. In his later years at the Donlands farm he enjoyed animal husbandry, and he had many award winning Irish Hunters and was of the first Canadians to import Jersey cows from the Isle of Jersey. In October 1925 he caught a severe cold which developed into Pleurisy and on October 26th 1925 he passed away at his home at the “Donlands” family farm.