Jays father was a professional football player, so sport was ingrained in his family's history. He pursued a career in hockey in the OHL with aspirations of making it to the NHL. After his hockey career, he earned a bachelor's degree followed by a master's degree. He subsequently embarked on a lengthy career in communications, working in television, publishing, and marketing. He raised his family in various locations, including Toronto, Oakville, and White Rock. His sons displayed a strong interest in athletics, participating in football, lacrosse, and hockey.

One of them followed in his footsteps by joining the OHL, and with an MBA in hand, he was set to play professional hockey in Europe that fall. The other earned a BA in marketing and found employment in Toronto's tech sector. Together, his sons owned Halcyon Restaurant, a euro-centric food establishment offering coffee, wine, and pizza in Toronto's Bloor-West-Village. He and his partner, who hailed from Toronto, relocated and constructed their dream home in Caledon, a setting that provided a taste of country living with a view of the city. They were enamored with their new home and all the opportunities it offered for exploration and enjoyment.