In the annals of Toronto history, Stanley Street is very possibly its most notorious street ever. It was so ill-reputed that its modern incarnation bears no resemblance in look, character, and name to the past. Indeed, Stanley was not even the first name of the thoroughfare, and it was not the last either; it started as March Street and ended as Lombard Street. Its route ran a very insignificant half kilometre between Victoria and Nelson (now Jarvis) Streets. It is this lack of distinction in geography married with its very important social dynamics and multiple name changes that comprise Stanley Street’s story.
The road that became Stanley Street has existed for roughly two centuries, and its infamy began early in its life. Kristine Morris, a leading historian of the street in all its versions and layers, noted that March Street’s ill reputation as a ‘red-light district’ was present as early as the 1820s and 1830s. Another great departing point for the poor state of the street was indicated in an 1849 “General Report of the Cholera in Toronto” by the Board of Health:
“March Street (as you are well aware) is for the most part, composed of low, undrained, ill-ventilated wooden building, chiefly occupied by the poorest classes of society to be found in this City, and taking into consideration the habits of many of its people, and the crowded and filthy state in which many of them live, it is a matter of no surprise that more than double the number fell victims to the Cholera there than in any other portion of the City.”
The Globe, October 20, 1849

Credit: City of Toronto
There was also March Street’s very notable and negative association with Toronto’s Irish population. William Jenkins, a leading scholar of the Irish in Toronto, in describing the street’s demographic associations, wrote that the 1846 directory revealed that at least a quarter of the denizens of March Street were of Irish Catholic origin. This percentage would increase with time, reaching fifty percent and eighty percent. March was one of two major Irish Catholic enclaves along with Dummer (later named William and even later, St. Patrick Street). The Globe later recounted a myth it even labeled as ‘slander’ that the 1876 Police Station on nearby Court Street was so positioned because of the Irish on the street. Reports about the Irish Catholic contingent on the street were not particularly favourable in newspapers. As Jenkins has noted, The Globe “was ever vigilant in its crusade to improve the city by ridding it of immoral elements”. The bias against Irish Catholic Torontonians repeatedly came into focus on Stanley Street.
March to Stanley
It was this poor reputation that led to the renaming of March Street to Stanley Street by order of Former City of Toronto By-Law 153 on April 22, 1850. Its namesake was Lord Edward-Smith Stanley, the Colonial Minister and Prime Minister of Britain; his son also later lent his name to the Stanley Cup of hockey.
However, the prestige of the new name did not eliminate the stigma. It is a telling introduction to Stanley Street that in 1851, there were three taverns and twelve beer-houses on the street. It contained by far the most alcohol establishments in St. James’ Ward, tied only with busy Yonge Street. (A later report in The Globe in 1859 outlined a change to the licensing system which had taverns installed based on the recommendation of the area’s ratepayers; the writer suggested that Stanley Street would have a tavern in every other house in such a system.) The decade to come was filled with tales of drunkenness, death, assault, rows, robbery, fire, disease, murder, houses of bad repute, and more. And this was all contained in two city blocks.
The year 1854 was eventful with a range of interesting occurrences that demonstrated Stanley Street’s debauchery. In February, the body of Elizabeth Stanton was discovered in a stable behind the Forest Traveller’s Inn. Although an inquest was made, no wrongdoing was found. The death was ruled to have been “from the effects of cold and intemperance.” In another event in June, Police broke up “a general row” on Stanley Street while looking for four men, including “an idiot named Charley”:
“…The house was full of men and women in a beastly drunken state; the idiot, Charley had bitten a women’s leg and arm; the inmates were fighting upstairs, down stairs, in the beds, and in every place and corner they could find footing; blackened eyes were numerous and the unfortunate idiot’s face was covered with blood.”
The Globe, June 1st, 1854
When Police arrived, the individuals who were not too inebriated scurried away while others hid under beds. The four prisoners were arrested, and they had trouble staying in the cart on the way to the gaol. In July, the Mayor and other city officials visited Stanley Street to find another shocking scene. There was a house containing many stolen goods: iron, brass, lead, pins, needles, coats, shawls, axes, and more. Next, in October, two women, Bridget Judge and Catherine Slattery, were taken in by police for disorderliness. Bridget’s eye was discoloured, and both girls “were well versed in Billingsgate oratory” – that is, vulgar language. Bridget was found drunk near a tavern at Church and Stanley Streets. She reportedly began to argue with herself and “pummeled a fence most lustily.” They later found her tearing another woman’s hair out. Finally, in November, a fire swept through a tavern on the north side of Stanley Street near Nelson (Jarvis) Street. It was terrifying sight; the fire could have ravaged the crowded quarters of the street if not for the quick action of firefighters.


Credit: Toronto Public Library
There were further cases and examples of Stanley Street’s unfortunates in the coming years. In April 1855, a Duncan Fraser, 30 years old, was found in a garret “in a sad state of intoxication.” First, he was taken to the gaol, but as his health was suffering, he was taken to the General Hospital. There, he died. Anne McGrath, in December 1856, accused her neighbours and tenants, George and Mary Monk of assaulting her. The two women, Anne and Mary, got into an argument where each lady pulled the hair out of the other. The husbands were involved, and they too began to fight. It was such a bizarre situation that event the Police Magistrate of the Police Court, George Gurnett, found it difficult to sort through the facts that he dismissed the case outright. There was yet another quarrel the following month, this time between marital partners, in which Martin McGlenn struck his wife, Sarah, and then pursued her when she ran. She escaped into a neighbouring house, and in a fury, Martin threw a large stone in the window. He was fined for his angry outburst. Another family affair occurred in June when the Flynn family were all arrested for stealing goods. The children, Terence and Mary, 10 and 11 respectively, stole some boots and other items from John Bacon’s shop on Yonge Street. They were found in the family home on Stanley Street. The kids were committed to trial for larceny and the father for receiving stolen property.
The Orange Riot of 1857
A high – or more aptly, low – point of Stanley Street’s dysfunction came on July 12, 1857, when Irish Catholic and Protestant tensions led to a violent riot. A man named Devlin, an off-duty policeman, passed through the street at the corner of Church and Stanley. He was wearing an orange rosette – the emblem of the Orange Order (July 12 is Orangeman’s Day). Some observing Catholics took offense and ripped it off, spurring a crowd to gather and brawl to form between Catholics and Protestants. Police sped to the scene and broke up the riot, arresting eight or ten of them. They also stayed on scene to discourage another melee. However, after they left, another brawl broke out that night. Police returned and spent until four in the morning keeping the peace. For Devlin, the man who arguably started the provocation with his presence on the street, his arm was broken, and his face cut. Another constable, Ormsby, hurt his shoulder, helping Devlin. Six of the men that were arrested were let go with a large bail; the others went to jail to await trial.
At Police Court, the rioters were identified as William Corbett, William Kavanagh, Michael McMahon, Bartholomew Kearnes, James Kavanagh, Michael McMahon, Patrick Enwright, Michael Sullivan, Matthew Mahon, and Simon Cantwell and were brought on the charge of assaulting Constables Devlin and Ormsby. Constable Devlin did not appear in Court as he was seemingly tending to his injuries. A witness, Frederick Smith of James Street, deposed that he saw a crowd gathered on Stanley Street where they were bothering a Police Constable. Constable Ormsby then gave his deposition: he proceeded to the scene of the riot where he saw Constable Church with a prisoner. He took the prisoner and escorted him to City Hall and then returned to the street. There, he got into a brawl with Michael Kavanagh, who attacked him with a stone. Another witness, Orangeman William Mulholland, came in to help and heard some the Catholic men call out “to take hold of the d—d Orange b—r” and then tried to take his own Orange lily. He saw Constable Devlin emerge from a house bloodied. Another witness, John W. James identified Michael McMahon as “more violent than the rest”. McMahon lunged at another man and called “give me hold of the Orange “b—r”. He described a scene where stones were pelted at Police until the Constables got control of the scene and arrested the prisoners. With Devlin not able to be deposed, the prisoners were kept.
The next day, Police Court continued investigating the “disgraceful riot” by charging John Foley, who denied being involved. On the third day, the Mayor and Alderman O’Donoheo presided over the Court. More testimonies were heard, and a judgment was made. Michael Cavanagh, James Sulivan, Michael McMahon, Bartholemew Kearns, William Cavanagh, William Corbett, John Foley, and Michael Horan were committed to trial. The end to the violent July events were concluded at Recorder’s Court in November, when William and Michael Cavanagh, Michael McMahon, and Bartholomew Kearns were convicted of rioting.
Fighting and rioting was common on the street as in August of the year, several young men were brought up for the “desecration of the quiet and sacredness of a Sabbath morning” on the “already distinguished street”. Naturally, they were at a tavern acting disorderly. They were having a rowdy time; a fiddle was playing, and they were dancing, drinking, and making noise. Police arrived to cease the party, but they were ignored. A fight broke out, and arrests were made. It also so happened that the tavern owner, Carey, was not licensed. He was not happy with the charge and threatened to “smash” the constables. All the parties involved in the riot were fined 20s, and Carey for his threats was to give security to keep the peace for six months.
In November 1858, Michael and Anne Plunkett, brother- and sister-in-law, were charged with running a disorderly house. Brothels were common on the street. Anne adamantly denied the accusation. It was said “she took a drop of drink now and then, but she defied anyone present to say they had ever seen her act in a disorderly manner. Mr. Gurnett warned her, to a round of laughs, “Then you have been a much maligned woman, for I have hard quite a large number of persons swear you were a bad woman.” Michael Plunket was sentenced to find bail to keep the peace, and she was let go because the gaol was overly crowded.
The Brook’s Bush Gang on Stanley Street
Stanley Street was also frequented by members of the notorious Brook’s Bush Gang. The ill-reputed group had their headquarters in a wooded area east of the Don River, but they also had their haunts in the city. The disorderly group terrorized Toronto in the latter half of the 1850s and early 1860s, so their association with shady Stanley was fitting. One Brook’s Bush denizen who made his presence known on Stanley Street was John W. Clyde. He was often violent, drunken, and disorderly. In fact, Clyde’s first appearance in Toronto’s Police Court was in June 1856 when he was noted as “a notorious character”—a description that appeared in several reports of him—and was arrested in a ‘low house’ on Stanley Street. He was fined 25c and costs and sent to gaol in default of paying. To add, he was drunk and assaulted the officer when he was apprehended. In July, Clyde was involved in the murder of a young Black man, Isaiah Sewell, in the bush. He did not commit the awful deed himself – actually, none of the gang members were directly implicated and punished – but the affair shed a dark light onto Clyde and the group as whole. In November of the year, Clyde brutally assaulted an “old man” named John Douglas on Stanley. He was fined 50s and costs and, in default, was sent to break stones.
Beyond Clyde’s attendance, Stanley Street was familiar to other inhabitants of Brook’s Bush. In October 1858, Mary Ann Pickley was amongst “a depraved lot” of females who were found in a house on Stanley – known as “a notorious den of iniquity” in which an infant was previously smothered. They were committed to gaol for a month. In December 1859, Mary Sheppard of the gang was found by police frozen to death on Sayer Street, where she was attending a dance. Police figured she was going to Stanley Street, which was noted as one of the ‘haunts’ of the group. The same month, Maurice Malone and Cornelius Leary stole the watch of John Ault on Stanley. Leary again found himself in trouble on Stanley Street in August 1860, this time on the receiving end, when Anne Reordan assaulted him with a potato masher. In April 1861, Ellen McGillick — one of the primary characters in the late history of the group — was found in a house on Stanley Street by Detective Colgan. McGillick was present during the murder of politician and newspaper publisher of John Sheridan Hogan in December 1859. McGillick was solicited by the detective to inform on the group; her testimony as a witness would be key in the subsequent trials in the murder.
The decade of the 1860s served no better to ease opinions of Stanley Street. In April 1860, two well known “rowdies” got into a fight after consuming a lot of “bad whiskey” in a low tavern on Stanley Street. The melee spilled onto the street where a crowd gathered. A constable went to stop the fight, but he too was pummeled. Another officer in the vicinity went to help and carried the rowdy men to City Hall Station. In June 1865, “three blossoms of iniquity from Stanley Street were arrested for disturbing the peace and quiet of the street “to an inordinate extent. The Globe noted Sundays were generally light work for the police but this trio thought they would be causing no harm. In December of the same year, a man named Wellesly Coats, entering a store on Church Street near Stanley Street, left his horse and wagon in front of the place. He placed a rug on the horse. When he emerged from the shop, the covering was gone. The assailants were Elizabeth Cadwell and Ann Finelly, aged 12, “both denizens of the notorious Stanley Street.”
A Cesspool of Disease
In an episode akin to the cholera report some seventeen years prior, the middle of the decade very much brought out its poor state of health again. In the February 14, 1866 edition of The Globe, a full-page report was published entitled “Sanitary – Slums and Filth of the City – Public Health in Danger – Prompt Measures Required.” While the expose included many areas of Toronto, Stanley Street’s inadequate conditions featured heavily:
“Take that plague-spot of filth and misery, that cesspool of disease – Stanley street – and look at its back yards and closets, and you have but a sample of what can be seen in filthy other plague spots in the city.”
The Globe, February 14, 1866
The Globe took a tour of the street, highlighting first the rear areas of residences which were, in the newspaper’s observation, more fitting for animals than people. From Victoria to Nelson Street, there were at least 28 closets (ie. outdoor toilets) in a disgusting state “that it is hard to comprehend how any man, however low and degraded a social position, could eat, drink, and sleep within gun-shot of them.” The pig pens were also a health nuisance. Entering a house, the report noted how at least ten people were huddled in a room 12 x 14. The stove was red as the mid-day food was being prepared, a woman was cleaning linens, the walls were black, and the stench of the pig pen travelled into the home. In another home close to Nelson on the south side of Stanley street, the newspaper was in disbelief that another room used for all cooking, eating, and sleeping could be beside animals’ pens.
The Globe’s harsh depiction of Stanley Street was followed with a lighter take in March 1867. It reported that “Stanley Street has been exceedingly turbulent during the past few days.” Its tone was seemingly ironic in noting how “its prestige [was] on the wane” and labelling the street as a “happy spot.” The events included a row between females caused by a drunk man attempted to enter their homes, the sight of an ‘amazon’ welding a cleaver, a melee between two men and two women, and most interesting, a brawl between a ‘devoted wife’ and another woman who had captured the attention of the first woman’s husband.
The newspaper published yet another awful account of the street in December 1868 when a reporter documented his experiences on the street on Christmas Eve. It started with his interactions with a poor girl selling newspapers. Pitying her, he bought all of items and then accompanied her to her house on Stanley. There, he witnessed a domestic disturbance with the girl’s parents. The reporter continued to tour the street and its dwellings, painting a grim picture of its poor denizens:
“Over and over again we came across old women, who were rather comfortably situated, yet had no apparent means of making a livelihood of any kind. When questioned on this point some refused to give any reply; others prevaricated in the most transparent fashion; while others the reply was they kept lodgers who were all out.”
The Globe and Mail, “How Christmas was spent on Stanley Street”, December 18, 1867
The ‘Mayors’ of Stanley Street
If Stanley Street was a stage with these very dramatic performances, it fittingly had its own cast of characters. This was highlighted by its very own ‘mayor’: James Doyle. In the Robertson & Cook’s Toronto city directory for 1870, Doyle was listed as labourer living at 39 Stanley Street. In the 1871 Census, he was identified as an Irish Catholic. He had some colourful tales attached to his name. In March 1869, Doyle was accused of “once more” poking out the eye of Jerry Shehan, a labourer at 47 Stanley. In this latest occasion, the two men had a run-in while drinking at a bar. When Shehan left, the Mayor followed him and proceeded to assault him. Prior to this violent engagement, Sheehan and Doyle are also noted as assaulting each other in February 1865 and again November 1868, so they were very well known to each other. This opposition relationship was confirmed by Doyle in October 1870 when Sheehan was on trial for stealing a purse and Doyle deposed that he and Sheehan “were not on friendly terms.”

Credit: Library & Archives Canada
Doyle may have had enemies as another event in June had the Mayor’s home burglarized. Mrs. Doyle deposed that she woke to find a back window open, and her ‘bureau’ had been carried to the backyard, broken, and robbed of its contents. A gold chain, two silver watches, two shawls, a black jacket, two silk aprons, a pair of cuffs, and $34 in cash were gone. James Leary and Pat Kavannagh were arrested. In July 1870, Mayor Doyle was fined $20 or given one month in gaol for assaulting Frank Conlin on Church Street. Finally, Doyle was a witness in the trial of Robert Wagstaff for the murder of Margaret Chapman. Wagstaff belonged to the Brook’s Bush Gang. Wagstaff and Chapman were drinking at Doyle’s house on Stanley Street on the night Chapman drowned.
The ‘office’ of the Mayor of Stanley had a successor in Daniel Dwan. Like Doyle, Dwan had his own misadventures. In 1878, it is reported that Dwan had a rivalrous relationship with a shoemaker named Michael O’Connell. There was one runin on Jarvis Street with Dwan wielding a stone and O’Connell a knife. In another fight, the shoemaker apparently badly assaulted the mayor, but the charge was dropped based on little evidence. In 1878, Dwan is listed as a labourer living at 85 Lombard (along with John Maley and George Maley). Dwan also had a wife named Bridget. After Daniel’s death, in 1883, Mrs Dwan was taken by Police “as a vagrant, having been wandering about the street in a destitute condition.”

Credit: Library & Archives Canada
A Final Name Change
In 1876, a breaking point seemed to have been reached concerning Stanley Street’s seedy character. In March, Alderman Wright introduced a bill to the City Council to change the name. “[Wright] explained that many respectable people would settle on the street, were it not for its name, which was associated with everything odious.” Then, on November 27, 1876, by order of By-law 764 “To Change The Names of Certain Streets In The City of Toronto”, as it had 26 years prior, the street received a new moniker: Lombard Street. There was a prestigious street of the same name in the centre of London housing the city’s financial heart. Hopefully, the association could rub off on the Toronto street. The Globe, however, was skeptical that a new name would make a street “smell a good deal sweeter”:
“The same cure was tried once before in the case of Stanley-street when its name was changed from March Street, with what success we all know. Nor are the same tactics likely to prove any more effective now. It is plain to every observer that Stanley-street has already begun to amend, and the rapidity of its progress will depend, not on the change of name to Lombard-street, but on the speed of which its present tenants and their rickety tenements disappear, and a better class of each take their place.”
The Globe, “Street Nomenclature”, December 7, 1876.
Indeed, The Globe continued to report on Lombard Street’s vices and the pointlessness of the renaming. In 1882, it derisively mentioned that a more appropriate new name would have been “Whiskey Avenue.” It questioned the existence of the slummy street in the middle of “the Queen City of the West” and labeled its denizens “of the lowest classes in the community.” In 1888, the newspaper reported again on “The Horrors of a Lombard Street Tenement. ” Although the article was yet another gloomy portrayal of the street, it did contain a hint of positivity: parts of the street were improving! In the next year, The Globe wrote:
“The name of Lombard is not unknown in the Police Court either, but still the street is improving – not, it is feared, because the residents have improved but because the old rookeries are being pulled down and their place is being taken by good business buildings.”
The Globe, January 14, 1889
By the end of the century, Lombard Street had a distinct identity than Stanley Street. Its rowdy denizens were just about gone. The old, shoddy buildings were razed, and factories and warehouses took their place. As Kristine Morris wrote: “Progress took care of what street name changes could not.” A look about the street today is jarring as there is no indication of what was once Toronto’s most notorious street.

Credit: ArcGIS
Cover image: Map of Toronto, 1855. Credit: Old Toronto Maps
Acknowledgments: This article builds upon the work of William Jenkins, Kristine Morris, and Katherine Taylor. Each has produced insightful histories of Stanley Street. Thank you also to Francesca Bouaoun of Toronto Archives for the aid in locating by-law 153.
Further Reading
Jenkins, William. Between raid and rebellion: The Irish in Buffalo and Toronto, 1867-1916. Montreal: McGill-Queen’s University Press, 2017.
Jenkins, William. “Poverty and Place: Documenting and Representing Toronto’s Catholic Irish, 1845-1890.” At the Anvil: Essays in Honour of William J. Smyth (Dublin: Geography Publications), 2012.
Morris, Kristine. “The Names of Lombard Street, Toronto: Not 1, Not 2, but 3, and Almost 4.” Lively Legacy of Lombard Street, October 31, 2023. https://lombardstreethistory.wordpress.com/2019/10/28/the-names-of-lombard-street-toronto-not-1-not-2-but-3-and-almost-4/.
Smyth, William J. Toronto, the Belfast of Canada: The Orange Order and the shaping of municipal culture. Toronto: University of Toronto Press, 2018.
Taylor, Katherine. “By Any Other Name …” One Gal’s Toronto, April 28, 2018. https://onegalstoronto.wordpress.com/2017/02/11/by-any-other-name/.


























































































