It is with deep sadness that the family of Jack Gerrie Lee announce his passing on Sunday, October 26, 2025 just 3 weeks shy of his 78th birthday. After a long, hard battle with numerous illnesses, Jack passed peacefully in his daughter’s home with family surrounding him.
Jack was born on November 19, 1947 in Winnipeg, Manitoba, the son of Ying Cheng (Sam) Lee and Dorothy Davidson.
Jack was predeceased by his beloved wife Carol of 51 years in 2021. Life lost its spark for him on that day. Left to mourn, his daughter Lori (Rob) Holmes and their children, Melissa (Patrick) Raymer (along with Jack’s 1st great-granddaughter Eva), Josh and Julia; his son Jamie (LeeAnn) Lee; brothers James (Elizabeth) Lee, Jarvis Lee and sister Janice (Carl) Cope; brothers and sisters in law David George, Susan George, Linda (Clint) O’Dell; several nieces and nephews. And many longtime friends…
Jack will be forever remembered as a generous, hardworking man by his family and many friends he made through his years in Dryden and Florida. He loved his family deeply and was so proud of all their accomplishments. He was very proud of Lori getting her CA designation and of Jamie following in his footsteps in the insurance industry – especially when Jamie became Manager and then Director at Federated Insurance. Must have been in the genes!
Jack was born in Winnipeg, MB but moved to Coronach, SK at a young age. A few years later, he moved to Rock Glen, SK and from there he moved back to Winnipeg where he finished high school at Gordon Bell HS. Several years later Jack met Carol, fell in love and got married. After welcoming their daughter Lori into the world in 1970 they soon moved to Dryden, ON in 1972 for a great career opportunity for Jack with Skillen Insurance. Eventually, after many years of hard work, Jack would become president and majority owner of Skillen-Squire Insurance.
Son Jamie arrived in 1976 and that completed the family. The early years were challenging with both Jack and Carol working their office jobs and then taking care of the apartment building they lived in. Finally, they purchased their first home in Dryden in 1977 and then built their “forever” home in 1987 out on Thunder Lake.
His grandchildren were the light of his life. (One great memory Mom told was Dad driving out on a golf cart to find her during her ladies’ golf day to tell her that Lori was in labour and shouldn’t she get going to see her, Rob and the new baby – they lived in Southern Ontario and it would take some arranging but he was so excited he couldn’t wait until she got home from her golf round to tell her!) The grandkids were the recipients of his love, generosity and often unsolicited advice!
Jack spent countless hours (along with Carol) taking care of their beautiful property on Thunder Lake, puttering in his garage, golfing and curling with the “boys” (Barry, Bill, Bob, Nigel, Rollie and others) and enjoying a cold one with those same boys. After Carol retired in 2000, it wasn’t too many years later that Jack sold Skillen-Squire Insurance and fully embraced the retirement lifestyle, summers in Dryden and winters in Florida. They truly loved the warm climate and low maintenance of their Florida home and neighbours who became dear friends.
A Celebration of Life service will be held at Life Church in Claremont, ON, Friday, October 31, 2025 at 1pm Eastern Time. Visitation will be held the night before on Thursday at 6:30-8:30 pm, same location.
Should you wish to join us virtually, the zoom link is: https://us02web.zoom.us/j/223401040?pwd=NjZ5RlFUeFdadU84eVRXTnM2STQ0dz09
If needed, Meeting ID: 223 401 040 Password: 351463
If you would like to send a message to the family, please send to gerrie1147@gmail.com. If you wish, in lieu of flowers, please send donations to the Canadian Cancer Society.
Gone too soon, forever loved.
