Gerald (Gerry) Francis O’Connell of New Canaan, CT, Nantucket, MA and Sanibel, FL died November 27, 2025, surrounded by his incredible wife of 61 years Judith Ann (Papp) O’Connell and his loving family.
Gerald Francis O’Connell https://hoytfuneralhome.com/tribute/details/1952/Gerald-O-Connell
Gerry was born on October 17, 1938, the second son of Desmond Henry Sr. and Rosemary McGough O’Connell in Plainfield, NJ. The brother of predeceased Desmond H. O’Connell, his wife Roberta O’Connell and Timothy E. O’Connell, his husband Larry Little. Father to Kevin M. O’Connell, his wife Dianna, Julia (O’Connell) Bossidy, her husband Michael, Patrick M. O’Connell, his wife Robin, Megan (O’Connell) Marciano, her husband Lance, Colleen (O’Connell) Bailey, her husband Troy and Erin (O’Connell) Hoffman, her husband Mitch. He is survived by his 21grandchildren, Michael, his wife Emma, Edward, his wife Annie, Madeleine her fiancé Justin, Josephine, Ryan, Quinitin, Courtney, Katherine, Emery, Shea, Brinley, Isabella, Christina, Nicholas, Teresa, Conor, Reagan, Brendan, Maddox, Brody and Cole as well as two great grandsons James and Graham. Gerry was loved profoundly by his family and left nearly everyone he encountered with gratitude for their time with him.
Gerry spent his early years in Fanwood and Westfield, New Jersey. He then lived in Winnetka, Illinois and attended New Trier High School, where he was a proud member of what he claimed to be “the best high school football team ever.” Gerry graduated from John Carroll University in Ohio in 1961 with a BS in Economics. He then earned his master’s in business from Loyola University in Chicago, where he met his future wife Judy in the summer of 1959. Gerry joined the Army and served from 1961-1963 with the final rank of 1st Lieutenant. Gerry and Judy were married on November 14, 1964, in Chicago, and lived in Riverside, IL, and Ann Arbor, MI before finally settling in 1980 to their beloved community of New Canaan, CT.
Gerry’s successful career in technology had him involved with 12 different companies over the years, where he was supported by venture capital firms and his own investments. As Gerry stated in an interview years ago, “My resumé looks like a schedule for a commuter train that stops at all stations.”
Gerry was a very active member in a variety of charities and community organizations; New Canaan Sports Council, Chairman of the New Canaan Board of Education, New Canaan Men’s Club, and coached multiple New Canaan youth football and softball teams. Gerry particularly cherished being part of the St. Aloysius community and working on Emmaus retreats over the years. He was active with the Fresh Air Fund, and along with Judy volunteered at the New Covenant House, where they served meals at the soup kitchen for 40 years. Gerry and Judy were active as alumni and donors at the Jesuit Universities: John Carroll University and Loyola of Chicago.
Gerry was a spirited golfer where he valued camaraderie more than some of his score cards. He favored golf rounds on Nantucket, as well as sitting under an umbrella at the beach with family, and his Annual Lobster Bake on island. He was a huge sports fan, especially Michigan football, but his favorite events to watch were those in which his children and grandchildren were the participants. He was so proud to cheer on his family in sports, music, and theater.
Gerry was a courageous Catholic. His faith was the bedrock on which he built his life. He modeled this strength by consistently choosing the harder right instead of the easier wrong. He was generous with his time and practiced the Jesuit mission of serving with and for others. He shared these beliefs with his beautiful wife Judy. Gerry loved his wife beyond measure, regarding her with endearing admiration as his unwavering companion. He adamantly would state that marrying Judy was the greatest decision he ever made, and he was grateful for every day they shared.
A wake will be held December 3, 2025, at Hoyt Funeral Home, 199 Main Street, New Canaan, CT from 4-8pm followed by a funeral Mass at St. Aloysius Catholic Church 21 Cherry Street, New Canaan, CT on December 4, 2025, at 11am. For live streaming please click the link. https://boxcast.tv/view/funeral-mass-for-gerald-f-oconnell-yho28e5md5yzi87ytogq
A reception will be held after services at Roger Sherman Inn 195 Oenoke Ridge Road, New Canaan.
For online condolences please visit www.hoytfuneralhome.com
[This obituary appeared on the Hoyt Funeral Home website.]
Gerry’s wonderful life is reflected in the lives of his large and loving family. He and Judy were constant attendees at all their children’s and grandchildren’s games and always modeled good sportsmanship and appropriate behavior. His legacy, whether measured by his faith, his family, his principled business career, or his contributions to his hometown, is secure. Astronaut James Lovell wrote, ‘I’m not a very religious person, but when I looked at the earth itself, I started to wonder why I am here – how to figure out what I see, and then it sort of dawned on me that God had given mankind a stage on which to perform. How the play turns out is up to us. Gerry deserves an Oscar.