Christopher Bailey Obituary
Published by Legacy on Aug. 29, 2025.
Leo Tolstoy penned that nothing can make our life, or the lives of other people, more beautiful than perpetual kindness. If Chris' journey could be defined by a personal goal, it would be to treat others with genuine kindness. From his family to his classmates to his coworkers to his community, a kind man is a phrase people could easily use to describe him, as it was a characteristic that came so naturally, even if he tried to mask it behind sarcastic banter. He often wished for the world to be a kinder place, where people were treated with fairness and respect. Although no one is perfect, if Chris had a choice to leave behind a legacy, it would be for the world to adopt the motto, "be kind."
Born in 1962, Chris entered the world as Rupert and Gloria's third child and the baby brother of his two oldest sisters. It's a role he didn't have much time to enjoy, for he became big brother to Shawn in 1964. And remained the big brother from that point forward, at times the protector, but at other times an instigator who awaited the response from the rest of the family. The latter would also make him a victim of his siblings' attempts to level the score. The greatest example of this was when Chris, naively, was convinced by a sibling, who will remain nameless, to lick the metal swing set pole because it looked like a candy cane. By the time everyone else laughed at a similar scene in A Christmas Story, Chris had lived to tell the tale, and so did his tongue. Throughout his life, Chris would recount stories from his upbringing, woven with elements of the truth and a side order of fiction. Not only could these tales elicit laughter, but his role as the teller of TALL tales was born.
Besides being a kind and compassionate man, Chris was an amateur comedian whose stage was a room of willing listeners waiting for the punchline. From George Carlin to Howard Stern to Jerry Seinfeld, Chris loved to laugh and to make others laugh, too. He would use his unwitting and often unwilling siblings, his friends, and his community as subjects and could bring people to tears. Not only did Chris' laughter liven up the room, but his laugh was also contagious, especially when he was mischievously mocking his brothers and sisters. He may have just missed his life's calling, for large families and small towns are often ripe for joke-telling.
Although born and raised for a short time in Ogdensburg, Chris and his siblings became Morristown Central School Green Rockets in 1966. Little did he know that one of his older sister's classmates would become the love of his life several decades later. At Morristown, Chris participated in many activities and sports, but one of his favorite classes was art. He produced drawings and sketches both in high school and college, many of which he has shared with his children. A talent worthy of praise, Chris simply enjoyed showing his creativity in this medium.
For years following high school, Chris lived his life seeking adventures, experiencing some ordeals, but valuing his role as son, brother, dad, friend, employee, and community member. He LOVED Morristown and the family homestead on Gouverneur Street. He LOVED the lazy days of summer, hanging out with his friends, listening to music, and savoring the St. Lawrence River. He LOVED the holidays, especially Halloween, when family and friends would gather to celebrate. Even though he was out of the area a few times in his life, his heart always brought him back to the place and people he loved the most. Chris was quick to tease his family and friends, but he genuinely appreciated having them in his life. He may not have outwardly shown this appreciation when he was younger, but he knew his life was richer because of the people he loved whom he loved in return.
Even though they didn't connect romantically as elementary students at MCS, Chris and Sandy eventually fell in love and married on October 9, 2010. For the last 15 years, they shared a common love for their children and grandchildren, the community of Morristown, and the creative energy they both possessed. Chris found in Sandy his one true love, his best friend, and his confidante. They traveled to the Carolinas, especially enjoying their time at the Outer Banks, and sought out unique destinations, like haunted hotels. They created a home where guests were always welcome, and music added to the ambiance. Whether it was in the garagemahall or the mancave, Chris was very proud of the expanse of his musical catalog, having spent decades building and organizing it all alphabetically. He loved sharing his passion for music with fellow music fans and attempted to "school" his children in the classics, as he ranked them.
A. Ray said, it does not matter how long you are spending on the earth, how much money you have gathered, or how much attention you have received. It is the amount of positive vibration you have radiated in life that matters. Chris spent his life finding ways to radiate his kindness, compassion, love of music, sense of humor, and creative nature with others. And for those of us who knew him, this is what mattered most.
Chris is survived by his cherished wife, Sandra (Woodcock) Bailey of Morristown, his daughter and daughter-in-law, Alexandra (Bailey) and Charlotte Robinson, of Lansing, Michigan, his sons, Ian Bailey of Ogdensburg, and Gavin Bertrand of Buffalo. He also leaves behind his father, Rupert Bailey of Morristown and his siblings and their families: Herb and Cindy (Bailey) Holmes, daughter Bailey, John and Susan (Bailey) Schofell, sons Tom and Wesley, Shawn Bailey, daughters Emily and Macy, Scott Bailey and Jennifer VanTassel, his brother Tim's children Aidan and Iris, Donald and Andrea (Bailey) Bertrand, children Amanda, Joe, and Karissa, Dan and Sandra (Bailey) Chambers, daughters Morgan, Linzi, and Natalie. John and Damie (Bailey) Evans, son Jack and his half-sister, Darcy Demers and her husband, Paul. He is also survived by his mother-in-law, Pat Woodcock, his stepchildren & grandchildren: Abe and Jamie Blasko, daughter Delaney, Bill and Christianne Blasko, son Owen, Michael and Shanna Blasko, and Josh and Jolene Blasko, son Zeb. He also leaves behind aunts, uncles, and cousins on both the Bailey and Langley sides of the family. Besides his family, he leaves behind many friends, especially his longtime friend and fellow Class of 1980 Green Rocket, Jim Smithers, and his wife, Carol (White) Smithers.
Chris was predeceased by his mother, Gloria (Langley) Bailey, his youngest brother & fellow music fan, Timothy Bailey, his favorite partner in crime, comedy, and mischief, John Hess (after whom his son, Ian, is named), his father-in-law, Lyle Woodcock, his brother-in-law, Jamie Woodcock, and aunts, uncles, and cousins from his large extended family.
Arrangements are under the direction of Frary Funeral Home and Cremation Services. Online condolences may be shared at https://www.fraryfuneralhome.com/
In Celebration of Chris' Life, family and friends will gather at the Morristown Fire Hall, Morris Street, on Friday, September 5th at 6:00 pm. For those wishing to contribute a dish to share, it can be dropped off to Karen Madill at the Firehall just prior to the event.
Memorial donations, in place of flowers, can be made in Chris' name to the Summer Concert Series, in care of the Morristown Gateway Museum, PO Box 231, Morristown, NY 13664 [https://www.morristowngatewaymuseum.org/] or the Morristown Volunteer Fire & Rescue, 200 Morris Street, Morristown, NY 13664.
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