Jack D. Bailey

Jack Dennigan Bailey, 90, of Lakewood, NY, passed away peacefully on January 13th, 2026, at home with family at his side.

Son of the late Dorothy and Clifford Bailey, Jack was born in Jamestown, NY and grew up in Celoron, NY.

Jack graduated from Southwestern Central High School, attended Jamestown Community College, and served in the National Guard. His first job was at the amusement park in Celoron when he was 10 years old, climbing the old wooden roller coaster checking for rotting boards, and taking the first ride of the day to ensure safety for the riders. An avid sailor his entire life, Jack bought his first boat at 14 with the money he earned delivering newspapers to half the village of Celoron. He had a boat on Chautauqua Lake for the next 70 years.

Married for over 55 years, he and his beloved wife Diane had a great life together. For years they went dancing every Friday night, and at 90, Jack still loved to dance with his wife. They sailed as often as they could, both here and in Florida at their Punta Gorda winter home, traveled extensively throughout Europe and North America, and enjoyed spending time with their wide circle of friends.

Jack's first business [besides the paper route] was Bailey Floral Supply, which he operated in Jamestown and Dunkirk for 20 years. Later Jack and Diane owned and operated Diane R. Bailey Antiques and Interiors in Chautauqua Institution for over 30 years.

Jack loved his community, the local environment, and the history of Chautauqua Lake. In his commitment to protecting the lake, Jack served as a member of the Board of Directors and the treasurer of the Chautauqua Watershed Conservancy. He also served as a board member of the Chautauqua Board of Utilities during the time that the water treatment plant was redesigned to become a highly efficient and effective facility.

Jack is survived by his wife Diane and five children: Mary Beth [David] Southwick, Marc [Elizabeth] Bailey, Kimberly [Larry] Sweet, Kristin [David] Carnovale, and Daniel [Peg] Hoard. His beloved grandchildren are Devon [Maria] Southwick, Matthew Southwick, Eric [Hitomi] Bailey, Christa Bailey, Molly [Joseph] Kostka, Emily Sweet, Corey Anderson, Zachary Carnovale, Rachel Carnovale, and Samuel Hoard. His treasured great-grandsons are Sullivan and Austin Kostka, and Noah Bailey. His great-niece, Amy Volfe, is also as beloved as a granddaughter.

Besides his parents, Jack is pre-deceased by his sister Mary Lou Bracey, his niece Jetta Wilson, and his granddaughter Katy Sweet.

A private service will be held for the family. No visitation will be observed.

Memorial contributions may be made to the Chautauqua Watershed Conservancy, St. Luke's Episcopal Church, or Chautauqua Hospice.