John Edward Conway Jr.

In Loving Memory of John Edward Conway, Jr. (1959-2026)

It is with heavy hearts that we announce the passing of John (Jay) Edward Conway, Jr., who departed this life on January 12, 2026, at the age of 66, after a courageous battle with cancer. A man defined by his unwavering work ethic and profound love for his family, Jay's legacy is one of enthusiasm, warmth, and quiet strength.
Born in Kingston, NY, on June 9, 1959, to John and Dorothy Conway, Jay was the eldest son in a lively household. He grew up in Ridgefield, CT, where his childhood was filled with cherished moments - from the exhilarating ski slopes of Stratton Mountain, VT, to idyllic summers at the Lakeside Field Club on Peach Lake in NY, alongside his beloved siblings. After graduating from Ridgefield High School, he pursued higher education at Western New England University and Western Connecticut State University.

In 1983, Jay embarked on a distinguished career with PHH, where his diligence and financial acumen propelled him forward. He began in Connecticut and, in 1994, relocated his family, sons John and Thomas and his devoted wife Susan to Toronto, Canada, to assume the role of Senior VP of Finance. He was a proud and hardworking businessman who found deep satisfaction in his professional accomplishments.

Above all, Jay was most proud of his three sons. John E. Conway IV and Thomas M. Conway, from his marriage to Susan (Cascio) Conway, and Ryan M. Conway, from his marriage to Ella (Chow) Conway, were the greatest joys of his life. He cherished each of them profoundly. With all of his boys, he discovered a special connection through sports. Countless hours were spent discussing games—not to create athletes, but to impart timeless lessons of focus, accountability, and hard work. He taught John and Thomas to ski on the slopes of Vermont and shared laughter on the golf course. He cheered for them at their football games, coached John's regional basketball team, and shared the tradition of early morning hockey practice with Ryan.

Later in life, Jay settled in Oakville, Ontario, to begin a private consulting career. There, he married Ella (Chow) Conway, and together they welcomed their son Ryan, a tremendous blessing who brought immense joy to Jay's world. Of course they relished in the great Canadian sport of hockey, but Jay wasn't limited to teaching Ryan skills only on ice. He was influential in Ryan's studies, especially his public speaking - a talent that proved invaluable to Ryan as an attorney in Toronto. Together they worked on many of Ryan's English assignments - most notably, 'What to do with your hands when speaking.' Tragically, Jay was predeceased by Ella after her own brave journey with cancer, but not before proudly watching Ryan complete law school and pass the Bar.

In his leisure time, Jay's love for the golf course was surpassed only by the camaraderie he shared with his brothers, Matthew and Michael, at Dlhy Ridge. Always competitive on the ski slopes, the men found great joy on the greens as well. The debate continues on who could ski the steepest slopes and hit the longest drives.

Jay's spirit lives on through his three sons, John E. Conway IV, Thomas M. Conway, and Ryan M. Conway; his six loving siblings: Maureen Burns (Peter), Matthew Conway (Lisa), Ellen Conway Hill, Michael Conway (Paula), Catherine Racz (Ed), and Patricia Iannetta (Rudy), as well as eighteen nieces and nephews and five great-nieces and nephews who will miss him dearly.

Interment will be held privately.