Jaye passed away peacefully, surrounded by her cherished husband William Crossland “Billy,” her sons Jackson “Jake,” Samuel “Sam,” and William “Will,” daughter-in-law Brooke, and her faithful dog, Sadie.
A passionate and creative supporter of family, friends and community, she spent her life serving the public, representing her community with fierce determination and unbending principle, and creating and implementing major events to bring people together, foster arts and culture, and drive economic growth.
Amidst her many accomplishments, nothing eclipsed the love she held for her "four boys.” Jaye was not just their guiding light; she was a pillar of strength and support, a cherished fun and funny "Momma" to Jake, Sam and Will, and an ever-present best friend and partner-in-everything to Billy for 42 years. She was their leader in play, infusing their lives with laughter and love. Her passion for celebration and meticulous attention to detail ensured no achievement went unnoticed and no occasion unmarked.
Born in Orangeville, Ontario, to John “Jake” and Shirley Robinson (née Jackson) on a special day that coincided with her father's birthday, providing Jaye and Jake a unique and unwavering bond. She is survived by her mother, Shirley, and her siblings Elizabeth “Brandy,” Robin, Kelly, and John.
Jaye was raised on a small farm in a close-knit community near Grand Valley, Ontario. Memories from life on “The Farm” are filled with apple picking and cider pressing, maple syrup harvests, tending the large vegetable garden where each year the green onions spelled out a new message, and traversing the waters of the “the Mighty Irvine” creek that flooded the laneway each spring. It was here, with the one-room “Little School House” community centre just down the road, that Jaye inherited, from both Jake and Shirley, a strong sense of community service, celebration, and collective fun that she carried throughout her personal and professional life.
Jaye's formative years were a testament to her diverse talents and passions, and perhaps a sign of things to come. At school she was student council president and class valedictorian. She was an active curler, while her artistic side found expression in competitive tap and jazz dancing. Summers were a split between her Jackson grandparents in Grand Bend and her Robinson grandmother and 21 cousins in Waupoos.
As a young girl, she was affectionately known as J.J., but upon arriving at the University of Guelph, she decided that henceforth, she would be known as “Jaye,” and it stuck. She thrived in the university culture, and this is where her passion for community began to shine. She was Residence Hall President, then Vice President of Activities for the campus-wide Central Student Association. As Vice President, her leadership skills and passion for organizing events became evident as she orchestrated numerous on-campus activities, including Frosh Week, Homecoming, Winterfest, the Community BBQ and weekly live concerts. The following year, she was elected President – a full-time position representing all 20,000 students.
Following university, after spending some time travelling throughout Europe and Asia and taking time to study French at Sorbonne and Laval, Jaye's professional career began in the events and protocol office of the former city of North York. She quickly rose through the ranks and eventually became Director of Events for the City of Toronto when North York and the other five Metro Toronto municipalities amalgamated into the “Mega City” in 1998.
Jaye’s innovative approach merged arts, culture, and economic development, resulting in the founding of many of Toronto’s current iconic initiatives like Nuit Blanche, as well as Summerlicious and Winterlicious, which were originally designed to help Toronto’s struggling restaurant industry in the wake of the SARs crisis. Her Moose in the City initiative, which generated international attention and raised money for charity, involved placing 326 moose around the city that were decorated by local artists. The Celebrate Toronto Street Festival was designed to bring the city together after the amalgamation in 1998 by transforming five major intersections along Yonge Street into a world-class, free one-of-a-kind festival. The festival attracted more than one million revelers each year with 12 stages and more than 1,200 performers. Toronto’s Millennium Lights New Year’s Eve Celebration was Canada’s largest millennium celebration and attracted over one million people to Toronto’s waterfront. Her other events included Cavalcade of Lights, Live with Culture, Winter City, Summer in the Square and many more. All of these events showcased Toronto's vibrant culture and generated significant economic benefits for the city.
Jaye also played an active leadership role in the festivals and events industry, serving as President of Festivals and Events Ontario for five years and developing a national certificate program and special events course at George Brown College. In 2000 she was inducted into the Festival and Events Ontario Hall of Fame.
In 2010, Jaye's commitment to public service led to her election as Toronto City Councillor for Don Valley West, a role she cherished for 14 years. She proudly represented her community, which encompassed the neighborhoods where her parents and grandparents once lived.
Jaye advocated for transparent governance and evidence-based decision-making. She championed hundreds of motions addressing planning reform, road safety, public transit, congestion management, environmental initiatives, improving Toronto’s fiscal health, and protecting trees and green spaces. She created a number of brand new parks in Don Valley West and revitalized dozens more. She worked on protecting and expanding Toronto’s tree canopy by strengthening the tree protection by-law. She was a steadfast supporter of environmental and sustainability initiatives, including strategies to reduce single-use plastics and textile waste.
Serving as Chair of Public Works and Infrastructure from 2014 to 2018, she introduced the City's Vision Zero Road Safety Plan and Long-Term Waste Management Strategy. As Chair of the Toronto Transit Commission from 2018 to 2022, Jaye secured record-setting investments in public transit and spearheaded environmental initiatives, such as expanding the TTC's electric bus fleet. As a strong advocate for arts and culture, she was a member of the Art Gallery of Ontario Board of Trustees, the Canadian Film Centre Board of Directors, and the Toronto Symphony Orchestra Board of Directors. Most recently, she led Toronto's preparations for the FIFA World Cup in 2026 and advocated to bring a professional women's soccer team to the City of Toronto.
Jaye was a beloved leader and mentor to her staff, both former and present, and will be deeply missed at City Hall.
If you were lucky enough to meet Jaye, or more likely see her in action, you would have experienced a kind, caring, creative, inclusive, fun, and funny individual – a visionary with an unprecedented passion for her community. She will be dearly missed, but her legacy will live on.
A Celebration of Life took place on Thursday, May 30 at Yorkminster Park Baptist Church. The livestream is available online.
In lieu of flowers, please consider a donation to the Toronto Region Conservation Authority (https://foundation.trca.ca/donations/) in Jaye’s name and help keep Toronto green.
