Leonard Douglas Gillespie

LEONARD (LEN) GILLESPIE, P. Eng., born October 23, 1929, in Toronto, died peacefully in Halifax on December 17, 2025. Predeceased by his parents, his wife Mary (Ryan), their eldest daughter Ann and his siblings Ken, Neil, Mary Hebert and Elaine Hary. He is survived by his children Laurie, Neil (Peggy) Meg (Eric), Kate (Corey), his siblings Joan MacIsaac, Laurie, and John, his grandchildren Kyle, Chris, Chloe, Adrien and many nieces and nephews.

Len grew up in Dorchester, NB during the Depression, and went on to marry Mary Ryan, a young teacher and the love of his life. Together they had five children and were married for 68 years. With her support he was able to complete a degree in engineering at the University of Toronto and then embarked on a career as a civil engineer, eventually setting up his own construction company in partnership with his youngest brother John.

He and Mary put their all into creating a stable, loving home for their children and supporting them unconditionally in all their endeavours. He took joy in all their achievements and always encouraged them to be the best they could be, cheering them on at all their games and performances and making sure they were well-equipped for everything they engaged in. He ensured his family was always safe and supported.

One of the earliest members of the Oakfield Golf and Country Club, he golfed into his 80s, and had not one, but two ‘holes-in-one’ to show for it. He had a lifelong interest in aviation and even piloted his own plane for some years. He loved classical music and reading.

Dad was highly organized and took on many “projects” – assisting his children with household repairs and automotive challenges. Dad would make up a checklist and coordinate - and when his dexterity became limited he continued to enthusiastically supervise.

Len lived a rich faith life, very active in the Roman Catholic Church and a daily Communicant for many years. In more recent years he nurtured his interior life with a routine of daily prayers and devotions.

To his dying day Dad always modelled the qualities he wanted his children to emulate. He was patient, compassionate, generous, positive, proactive, charitable, intellectually curious, and had a quick-witted, dry sense of humour. But most important to him were enjoying life and being kind. Dad always put his beloved Mary and his kids (and later grandkids) first but also maintained warm relations with his siblings as long as they lived.

We will all miss him immensely but as he said in a family Christmas card several years ago, “we will close out this year with renewed hope and the assurance that faith will make us whole again”. His funeral Mass will take place on Tuesday, December 30 at 10:30am at St. Stephen’s Church (6032 Normandy Drive, Halifax), with a short reception to follow.

In lieu of flowers please consider making a donation to the St. Vincent de Paul Society, a charity that was always dear to Dad’s heart.