Family and Personal Life

Born in Jamaica, Jolly enjoyed an idyllic childhood, playing on his family’s 300 lush acres and long, natural beach. His father was a successful entrepreneur and his mother was the local justice of the peace. After graduating from secondary school, he became a clerk with the West Indies Sugar Company in 1953.

Jolly was accepted at the Ontario Agricultural College, at the University of Guelph, and began his studies in September 1955. Upon entering Canada on a student visa, he was forced to sign a document pledging that he would leave the country the day the visa expired. He later learned that only Black students had to sign the pledge, and so he became acquainted with Canada’s subtle, bureaucratic racism. He augmented his studies with two years at the Nova Scotia Agricultural College in Truro before completing his science degree at McGill University. Jolly wanted to remain in Canada but, due to immigration rules, he was forced to return to Jamaica upon his graduation in 1960.

Jolly became a secondary school teacher and then a nutrition scientist. In 1961, he was finally able to secure the papers necessary to return to Canada. He worked for a few months as a City of Toronto air pollution researcher and then secured a position as a biology teacher in Sault Ste. Marie, Ontario. In the spring of 1963, he met Carol Casselman. After a year in Sault Ste. Marie, Jolly accepted a position teaching physics and chemistry at Toronto’s Forest Hill Collegiate. Carol moved to Toronto to pursue her nursing career. She and Jolly were married in July 1965 and later had three children.


While enjoying teaching, Jolly earned extra income through the purchase of a Toronto rooming house (see Real Estate in Canada). He then bought a second one. In 1968, he opened the Donview Nursing Home and six months later the Tyndall Nursing Home. The success of his growing businesses led him to leave teaching and build a state-of-the-art nursing home that grew to 151 beds. His entrepreneurial spirit was seen when he discovered the large sum spent for his residents’ laboratory work and reacted by arranging for the consolidation of two private labs and the purchase of 51 per cent of the new company. Then, in 1990, Jolly observed that family members visiting his residents had difficulty finding nearby accommodation, so he purchased land and built a 65-room hotel that he called the Jolly Inn. A year later, he paid the fee to register the hotel as a Day’s Inn franchise. His businesses became international when he purchased a 120-bed nursing home in Dallas, Texas, and began a boat chartering company in Montego Bay, Jamaica. After two years, the profits from neither justified the headaches of running them from afar, so he sold them both.

Community Engagement

While becoming an increasingly successful businessperson, Jolly never forgot the student visa document he was forced to sign and the racial segregation he had experienced in Nova Scotia where, because he was Black, he could not attend an all-White church (see Racism). Later, Jolly met Toronto landlords who assured him on the phone that an apartment was available. However, those apartments became suddenly unavailable when he arrived to see them. When Jolly arranged for a White friend to visit the landlord, the apartment was available again. When buying his first house, the unwritten rules about where Black people could live in Toronto forced him to have a White friend pose as the purchaser while he pretended to be a contractor. He also found that some banks had more stringent loan conditions for Black entrepreneurs. Others bluntly refused loans for Black-owned businesses. Jolly believed it was his responsibility to do what he could to help fight for racial equality and social justice.

Jolly became the treasurer of the Jamaican Canadian Association (JCA). He learned more about racist organizations in Ontario such as the Western Guard Party that worked with the Canadian Ku Klux Klan to harass non-White people, spread racist propaganda and urge the government to restrict non-White immigration. In May 1972, the JCA’s headquarters was burned to the ground in a suspicious fire that many in the Black community assumed to have been deliberately set, but arson was never proved.

One of the targets of racist groups and individuals was Contrast, a Black newspaper founded in 1969 as the “eyes, ears, and voice of Canada’s Black community.” Its articles reflected the kaleidoscope of Black experiences in Toronto from the perspective of long-time residents and more recent arrivals from Caribbean islands (see Caribbean Canadians). In 1983, the paper was in financial trouble until Jolly saved it by infusing much needed capital. He became its owner and publisher. The paper remained free to readers even as Jolly increased it from 16 to 24 pages, made it more professional looking with new computerized type-setting equipment, broadened its range of articles, and improved the quality of its writing. He ran the paper for three years before selling it to Horace Gooden, another Jamaican-born entrepreneur.

Jolly was angry when he saw Black Canadian athletes applauded for earning medals for their country in the 1982 Commonwealth Games while those at home endured racist discrimination. He and some friends gathered leaders from Toronto’s diverse Black community and formed the Black Business and Professional Association (BBPA). He was its founding president. It supported and publicized the success of Black businesspeople and professionals, partly through the annual Harry Jerome Awards and scholarships (see Harry Jerome). Meanwhile, he personally funded scholarships for even more aspiring young Black people.

In August 1988, Jolly became a founding member of the Black Action Defence Committee (BADC). Its goal was to stop police harassment of Black citizens and the frightening regularity of police officers exonerated after shooting young Black men. The BADC wrote articles, staged demonstrations, lobbied politicians, and helped victims’ families. The Ontario government responded to a May 1992 riot that followed a peaceful protest organized by the BADC with an investigation that revealed and confirmed the depth of Toronto’s systemic anti-Black racism.

FLOW 93.5

Jolly observed that among the problems faced by Black youth in Toronto were the divisions within the Black community and a feeling of isolation as a minority within a predominantly White city. Part of a response to the problems, he decided, might be the creation of a Black-themed radio station that would play a range of Black music while offering Black voices and perspectives. He gathered other Black leaders and businesspeople and, in 1988, became the founder, president, and chief executive officer of Milestone Radio Inc. He then led the effort to obtain the city’s one available radio frequency from the Canadian Radio and Television Commission (CRTC) in 1990. The first question he and his colleagues were asked by the all-White CRTC commissioners was, “… what is Black Music?” Jolly and the others quickly understood that race was an issue and that their application would be, as he said later, tossed in the trash can as soon as they left the room. The license was granted to a group proposing a country music station. Several years later, another frequency came available and Jolly led another expensive and complex effort to earn it. The Canadian government sabotaged its own process by stating in advance that the frequency would go to the CBC. Finally, 12 years after first applying to the CRTC, a third application was successful.

In February 2001, Jolly’s FLOW 93.5 began broadcasting an energetic mix of hip hop, reggae, jazz, R&B, and gospel. Instead of having to tune in to American stations, Black youth heard themselves reflected and their tastes respected over the airwaves in their own city. As the station became increasingly successful, Jolly increased the power of its range so that it reached 6 million listeners across southern Ontario. While a financial success, the station maintained its broader mission by promoting emerging Black artists, providing journalism scholarships for Black youth, staging free concerts, and supporting Caribana, the annual celebration of Caribbean-Canadian culture. Given the racial makeup of the region, 60 per cent of FLOW’s listeners were White. This meant that more than just Black listeners were learning of the presence and vibrancy of the diverse Black culture that was a part of the Canadian mosaic. Jolly happily helped other Black music stations to form, first in Calgary and then elsewhere. After five years on the air, FLOW 93.5 was chosen as Canada’s best contemporary radio station.

Legacy and Significance

In his 70s, and pleased with the impact the radio station had made and that Black music had become mainstream, Jolly sold FLOW 93.5 in 2011. He also sold his nursing homes. Jolly’s first marriage ended in divorce. He later met long-time partner, Janice Williams. They travelled extensively including to South Africa, where he had made generous donations to Nelson Mandela’s African National Congress to support its actions that helped end the state-sanctioned discrimination called apartheid (see Nelson Mandela: A Soft Spot for Canada).

Jolly’s business acumen and community engagement was recognized through numerous local and national awards. Each recognized his dedication to his community and country and to the idea that Canada and Canadians will be better when there is justice for all through the creation of a more equitable, non-racial nation whose reality matches its international image and the principles for which it stands.

Honours and Awards

  • 125th Anniversary of the Confederation of Canada Medal (1992)
  • YMCA Council of Advisory Governors Appreciation Award (1993–1995)
  • Certificate of Appreciation Award, African National Congress (1995)
  • President’s Award, BBPA Harry Jerome Awards (1996)
  • Excellence in Business, African Canadian Achievement Awards (1998)
  • Award of Honour, Black Action Defence Committee (1998)
  • Award of Recognition and Commitment, Jamaican Canadian Association (1999)
  • Award of Excellence in Recognition of Black History (2000)
  • Special Achievement Award, Canadian Urban Music Awards (2000)
  • Queen’s Golden Jubilee Medal (2002)
  • Award of Appreciation, National Association of Black Female Executives in Music and Entertainment (2002)
  • President’s Award, Black Action Defence Committee (2003)
  • Honorary Alumni Award, University of Toronto Black Alumni Association (2005)
  • Award of Appreciation, Consulate General of Jamaica (2007)
  • Urban Leadership City Soul Award, Canadian Urban Institute (2008)
  • BBPA, Educational Foundation for Children’s Care Canada and Metro Fay Award of Recognition for ongoing sponsorship of the Annual Martin Luther King Celebration (2009)
  • Award of Dedication and Contribution, BB PA (2010)
  • Lifetime Achievement Award, African Canadian Achievement Awards (2011)
  • Queen Elizabeth II Diamond Jubilee Medal (2012)
  • Dr. Anderson Abbott Award for High Achievement, Ontario Black History Society (2013)
  • Toronto Book Award (2017)