Jamaal Myers making a lasting impact through advocacy and action

September 29, 2025

Opportunities can open unexpected doors.

Even if they are not the perfect fit, they might lead to connections, skills or experiences that shape the future.

Twenty years ago, when Jamaal Myers' uncle encouraged him to apply for an internship with the GraceKennedy Jamaican Birthright program, he had no idea what to expect.

Established in 2004, the summer program assists with broadening the horizons of second and third-generation Jamaican students between the ages of 18 and 25 residing in the Diaspora who are pursuing undergraduate or post-graduate studies with a Grade ‘B’ average or higher.

“I didn’t know what it was about and why I should apply,” Myers said. “The only reason I did so is because my uncle suggested I do it.”

Meeting selection panellist Pamela Appelt, Canada’s first Black woman Citizenship Court judge, before the internship was a big turning point in how he viewed the opportunity.

“That was the first time I encountered someone with influence,” said Myers. “Watching how she gets things done while staying true to herself really impressed me.”

Inspired by Appelt who used her influence to give back to the community, he was motivated to begin his own community work and eventually run for city council.

Since October 2022, Myers has been the representative for Scarborough North which is one of Toronto’s most diverse wards.

He is also Chair of the Toronto Transport Commission (TTC) that is one of the most important roles in shaping the city’s transportation future.

Myers leads the Board of Commissioners overseeing the TTC’s policy, planning and operations during a time when the organization is facing several challenges, including a funding shortfall and safety and security concerns.

To fully grasp the customers’ experience, he uses the TTC regularly to get a perspective that informs his decisions for the system.

“I can’t fix what I don’t understand,” the former Toronto Police Service 42 Division Community Police Liaison Committee member said. “It’s like being a chef who never eats in his own restaurant. I want to experience what our customers, visitors and employees go through because only then can I truly make it better. I see what works and what doesn’t.”

That mindset comes naturally to Myers who spent three years working the night shift, cleaning trains at Greenwood Yard.

“That experience gave me a real appreciation for the people doing that job,” he said. “Even though I worked during the summer, I know how tough it is year-round. I have a lot of respect for those workers. Now, I’m in a position to advocate for them and help ensure they can do their jobs safely.”

Named the best transit system in North America in 2017 by the American Public Transportation Association, the TTC has since faced growing challenges.

Despite these difficulties, Myers maintains that the system remains strong and capable.

“Our system has been underfunded for a long time, and we are now trying to dig out of it,” he said.

The Eglinton Crosstown Light Rail Transit (LRT) is among the projects Myers oversees.

Construction delays have created a nightmare for residents and business owners, many of whom were forced to close their stores.

“It’s going to make a big difference when it opens, but it opened my eyes to how these large infrastructure projects meant to serve and connect communities can actually tear them apart,” said Myers. “It was also very stressful driving along sections of Eglinton Ave. W.”

The councillor expects the Eglinton Crosstown will open next year.

Work on the 19.7-kilometre light transit line started in 2011.

“They are making progress,” said Myers. “Finch West LRT, however, is in much better shape because they are further ahead in testing.”

As one of two lawyers on city council, he brings added value through his legal expertise, analytical skills and commitment to ethical decision-making. His ability to interpret legislation, draft clear policies and resolve complex issues strengthens the council’s ability to serve the community effectively.

“Having that analysis and background allow me to understand deals, read contracts, ask tough questions and push back when I disagree because I have a solid base of knowledge to draw from,” said Myers who was raised in Toronto Community Housing in Scarborough by a single mother.

Former Ontario Environmental Commissioner and provincial Green Party deputy leader Diane Saxe is the other lawyer on city council.

Jamaal Myers makes a presentation to pannist Wendy Jones (Photo by Ron Fanfair)

Reflecting on his young political career, Myers pointed to his election to council three years ago as the highlight.

Running to retain her seat in the riding, Cynthia Lai died three days before the municipal elections.

After her death, the city announced that the election would proceed as if she had never been nominated. Although her name remained on the ballot, voters were informed she was no longer eligible. Any votes cast for her, including advance votes, were not counted.

Myers received 5,315 votes while Philip Francis and Virginia Jones got 2,755 and 2,333 respectively.

The night he won the elections remains unforgettable.

“I didn’t expect it to turn out that way, and I didn’t want it to,” said Myers. “After Cynthia passed away, I asked myself, ‘Why would God do that?’ I ran a hard-fought campaign. At the funeral, I saw her team and her family, and you realize this was a person who had her own hopes and dreams. I came into a situation where a lot of people voted for her, but it didn’t count. They were upset and felt cheated. Coming in, I was tasked with bringing the community together.”

Becoming the candidate for everyone took a lot of hard work.

“Through effort, being deliberate and honest, building genuine relationships and hiring staff with strong community connections to facilitate introductions, I was able to get the job done,” said Myers who brought forward the proposal to rename Rosebank Park in honour of Cynthia Lai.

With his popularity and profile growing, a future run for mayor cannot be ruled out.

Myers downplays such ambitions at this time.

“Right now, I am focussed on being re-elected, but I don’t see myself being a councillor forever,” he said. “The higher you go, the more you can actually do for people. That is why I get excited about this job because you can make a difference in people’s lives. Nothing is off the table.”

Myers has come a long way in the last two decades.

In 2005, he was unable to apply for the GraceKennedy Birthright initiative because he was part of the Canada Exchange Scholars program at McGill University.

The following year, he became the first male student to represent Canada in the program conceived by then GraceKennedy Chief Executive Officer Douglas Orane while helping a family member, who was attending an American University at the time, fulfil his dream of scaling Jamaica’s famous Blue Mountains.

“We interviewed six young people and Jamaal was the strongest among the best field of applicants we have had since the program began,” said Pearson Burch-Smith who at the time was the Caribbean community consultant for GraceKennedy Remittance Service in the Greater Toronto Area. “It was a tough decision, but at the end of the day, he emerged as the top candidate because of his stellar academic and community achievements.”

Pearson Burch-Smith (r), who at the time was the Caribbean community consultant for GraceKennedy Remittance Service in the GTA, congratulates Jamaal Myers in June 2006 (Photo by Ron Fanfair)

Myers also impressed Appelt who was on the GraceKennedy Board.

“From the time Jamaal came into the interview, he caught my attention,” the Order of Canada recipient said. “He had a genuine interest to learn about his roots. He also talked to me about his background and his intention to go to school in England for a Master’s degree. After he got the internship, he invited me home to meet his grandparents, with who he was living, and I became friends with them.”

Preparing to pursue graduate studies at the London School of Economics & Political Science in England, he had already served four years in the Canadian Armed Forces medical unit and volunteered with Habitat for Humanity Canada which is a faith-based housing program dedicated to building homes in partnership with needy families.

Before the internship, he had been to Jamaica, his mother’s birth country, just twice, the last time being in 1996.

“I had a relationship with Jamaica through my family there, but this was me having my own relationship with the island,” he said. “It was an opportunity for me to get to understand the people, the politics and the business community.”

Through that internship, Myers gained valuable insights that influenced his career goals.

“Working as a junior currency trader was my first real exposure to the world of business,” he said. “At the time, the market was extremely volatile, and I witnessed many fascinating dynamics at play. That experience made me realize that I could pursue a business career, even without a formal background in it.”

That experience set the stage for Myers to become a corporate lawyer, though not without a few detours along the way.

After completing a graduate degree in 2007 in England, he spent 19 months as a visa assistant in the United States Consulate in London before moving back to Toronto.

“I was thinking about becoming a diplomat, but I didn’t do well in the test,” he said. “I also applied for some government jobs but was unsuccessful. I was not progressing in England, so I came back home to figure things out and that is how I ended up at the Law Society of Upper Canada as a Special Projects Co-ordinator.”  

Myers was part of a team that conducted a survey to understand why Ontario law firms were reluctant to hire articling students.

Communicating with lawyers daily made him realize that he could do this work himself.

While Myers completed law school in New York in 2013 and worked for nearly five years as an Associate at two law firms, he eventually realized that his true passion lay elsewhere.

A candidate for the United States Democratic presidential nomination in 2016, Bernie Sanders’ policies, which focused on real-life change and championing causes important to young people, deeply resonated with Myers.

“When I was out in Washington Heights collecting signatures to get Bernie on the ballot in New York against Hillary (Clinton), it was my first time getting involved politically,” he said. “Speaking to people and being active made me realize I could do this. People telling me I am good at it was also reassuring.”

In 2018, while back in Toronto and considering his next steps, Myers accompanied his grandmother to a doctor’s appointment. During the walk, she pointed out that she couldn’t cross the street safely to get the bus because there was no crosswalk.

“I could cross the four-lane road without a problem, but she couldn’t,” the Scarborough Business Association Director said. “If she couldn’t, then someone in a wheelchair, visually impaired people and children couldn’t either. That was a wake-up moment for me. I went to a community meeting to advocate for a pedestrian crossing there, but it still hasn’t been installed.”

That experience sparked Myers’ interest in how people access transit.

After almost four years as legal counsel with TD Bank, he entered the municipal elections race.

As you climb the ladder of success, you need others to help you along the way.

Myers’ mentors include University of Guelph Chancellor Mary Anne Chambers who introduced him to TAIBU Community Health Centre where he was appointed to the Board of Directors and later served as Chair.

“Jamaal’s journey has been grounded in his commitment to being of value to others,” she said. “He saw municipal politics as being closest to the kinds of services that people need for their day-to-day lives. I continue to watch him with admiration for the important work he is doing.”

Because of his involvement in the GraceKennedy Birthright program and his legal expertise, Chambers recommended his appointment to the Grace Foods Canada Board where he served for just over four years until his election to city council.