In Pursuit of Freedom: The Life of Joshua Glover

Slavery existed in the United States from its founding in 1776, a continuation of the enslavement of African and Indigenous peoples from the early British colonies. Slavery in America persisted until emancipation in 1865, 31 years after the abolition of slavery across the British Empire, including Canada. 

Little is known of Glover’s time as an enslaved man prior to New Year’s Day in 1850, when he was purchased by Benammi Stone Garland at the St. Louis Courthouse Auction in Missouri. Slave auctions could permanently separate enslaved families when sold to different slave masters. At the auction, Glover was publicly stripped of his clothing to be examined for any health issues or signs of punishment and he likely had to verbalize his marketable skills to potential buyers.

After being purchased, Glover was transported to Garland’s farm. Along with five other slaves, Glover carried out a variety of work including animal care, wood splitting, land clearing, cultivation, harvesting, and driving wagons. Glover’s knowledge of the land likely contributed to his successful escape from Garland’s farm in the spring of 1852.

During Glover’s escape he travelled approximately 550-650 kilometers to Racine, Wisconsin, arriving by the summer of 1852. Upon arrival, he chose the surname “Glover”, and was hired at the local sawmill owned by Duncan Sinclair, who provided him with a wage and living quarters. For two years, Glover lived and worked in Racine. 

On March 11, 1854, everything changed. Glover’s friend Nathan Turner betrayed his location to his former enslaver, Garland. Acting in accordance with the Fugitive Slave Act of 1850, Garland travelled  to Racine to ambush Glover in his cabin with the help of an officer and marshall. The struggle that ensued resulted in Glover sustaining severe injuries and his imprisonment in the Milwaukee County Jail. 

News of Glover’s capture sparked outrage among local abolitionists who, despite the risks to themselves, demanded Glover receive an expedited and fair trial. With their demands unmet, the crowd of frenzied sympathizers broke through the jail walls and doors using pickaxes and a battering ram, freeing Glover. 

Glover was escorted to a horse-drawn wagon enabling him to quickly leave town and distance himself from slave catchers pursuing him. He was brought to Waukesha, Wisconsin, continuing his journey on the Underground Railroad. Glover, still healing from his wounds, was transported, hidden, and provided for by several abolitionist families in the area until a ship to Canada became available in Racine. Their efforts and protection helped to secure Glover a new life free from the threat of slavery.

Glover likely arrived first in Collingwood or Owen Sound, Ontario, and further journeyed to Etobicoke. He first settled in the Islington community, joining Etobicoke’s 39 other Black residents in the population of 2,900. Soon after his arrival, Glover began working for Thomas Montgomery, a local landowner and savvy businessman. 

Thomas Montgomery is perhaps best known as the proprietor of Montgomery’s Inn, a large stone building built in 1830, located on the then-bustling Dundas Highway in Etobicoke. Montgomery’s Inn served as the centre of the community, providing both locals and travellers a place to eat, drink, and sleep, along with hosting social events and meetings.

In addition to his inn, Montgomery owned a 400-acre parcel of agricultural land located between Bloor and Dundas Streets. This is where Glover was employed. By the end of his life, Montgomery had amassed over two hundred pieces of property in Ontario and had an estate valued at $154,000. 

Glover worked as a general farm labourer for the Montgomery family for over thirty years, performing demanding tasks including cultivating land, harvesting crops, splitting wood, and fence building. He also grew his own crops on the acre and a half of land that came with the one-story home Grover rented from Montgomery in Lambton Mills around 1870. 

Glover was married twice, both times to women from Ireland. Glover’s family enjoyed a relatively standard 19th-century, rural, working-class lifestyle. Glover participated in recreational activities in his free time, such as attending the Annual Agricultural Association of Upper Canada fall fair in 1858. Although Glover was free to make his own choices, those choices were likely limited or impacted by discrimination due to both his race and his interracial marriages.

Black citizens were legally recognized as equals in Canada; however, social stigma and systemic racism were widespread, resulting in segregation and prejudice. The Ontario Common Schools Act of 1851 fostered a segregated school system with Black students banned from attending public schools. Segregation was also prominent in other social institutions including church services. Although there are no records of Glover’s specific experiences of racism, it undoubtedly impacted his life in Canada. 

Glover continued to work with the Montgomerys until his early 60s. In 1884, Glover was accused of stabbing a white man and was charged with the crime of “wounding with intent.” William Montgomery came to Glover’s aid, providing him with new clothes for court and access to the family lawyer, who did not charge for the case. Throughout the trial, many notable members of the community defended Glover, and the charge against him was reduced to wounding without intent. He was sentenced to only three months in prison. 

In January 1888, Glover was admitted to the York County Industrial Home in Newmarket, a home for the impoverished and destitute. Commonly referred to as the county poor house, industrial homes served as a last resort shelter for those who were unable to care for themselves. Poverty was considered a moral failure of the individual and, due to this ideology, the conditions in these crowded homes left much to be desired. In his final days, Glover would have been required to work in the home’s vegetable gardens to earn his care and lodgings.

Glover died six months after being admitted to the York County Industrial Home. William Montgomery was notified of Glover’s death via telegram on June 4, 1888, which asked if he would take the body. The following day, Montgomery travelled to the home to collect Glover’s remains; however, due to an administrative error, his body had already been donated to the Toronto School of Medicine. Montgomery then travelled to Toronto’s medical schools in search of Glover, but despite his efforts, he never recovered the body. Glover is now buried at St. James Cemetery in the University of Toronto’s medical research memorial plot.

Glover lived in Etobicoke for more than 30 years after spending half his life enslaved in the United States. He was able to make the escape many Freedom Seekers could not due to their circumstances.

Glover’s story was featured in multiple abolitionist newspapers across both the United States and Canada. Articles shared his and other’s experiences of enslavement and journeys to freedom, bringing awareness to the abolitionist sentiments swelling across North America. The aftermath of his arrest and inhumane treatment in Racine and Milwaukee was a factor in the state of Wisconsin declaring the Fugitive Slave Act of 1850 unconstitutional in 1854. 

A song sharing Glover’s fight for freedom was commissioned by Toronto History Museums and produced by Kardinall Offishall as part of the City of Toronto’s Awakenings project. Watch the Freedom Heights (A Song for Joshua Glover) lyric video that summarizes Glover’s adversity and resilience.