James Joseph Cleary, Jr.

James Joseph Cleary Jr, 88, passed away peacefully on December 26, 2025, surrounded by loved ones. Born on January 11, 1937 in Elmira, NY to Philomena Emanuel Cleary and James Joseph Cleary, Sr., James, nicknamed “Sonny”, the eldest of six siblings, he lived the entirety of his life in Elmira, Big Flats, and Montour, NY.

James attended St. Anthony’s Elementary School where he was a choir boy and played in the CYO basketball league. He also participated in the Elmira Small Fry baseball league wherein he scored the league’s first ever run in its’ inaugural season. He graduated from Elmira Free Academy in 1955, where he played baseball and earned a varsity letter in football while his future wife, Lois Arnold, was a cheerleader on the sidelines rooting him on. He met the love of his life while in Junior High School and they married on September 5, 1959, while James was attending SUNY College of Education at Cortland, where he graduated in June of 1961 with a Bachelor of Science in Education with a secondary specialization in mathematics.

Starting at a very young age, James worked many jobs beginning as a pinsetter at a local bowling alley and as a busboy/waiter at Moretti’s Restaurant. He mastered masonry work and became a math teacher at Horseheads Jr. High West, where he spent his entire teaching career from 1961 until his retirement in 1992. He was loved by his students, many of whom he regularly ran into in the area, and he was always genuinely interested in catching up on their progress in life. He was instrumental in helping to unionize his fellow teachers and his steadfast determination helped to earn them fair wages and benefits. He also enlisted the help of several of his fellow teachers in his summer construction business and later included his sons and their friends. It is nearly impossible to drive through the Elmira/Horseheads area without coming upon a sidewalk, baseball dugout, patio or one of his specialty fireplaces that grace many homes in the area. He built the first Pudgie’s Pizza shop on N. Main St. in Elmira and eventually joined his family’s famous Pudgie’s Pizza business, owning his own store in Hornell, NY for several years.

James was an avid hunter and fisherman and could always be found casting a line on Catharine Creek on April 1st, where he was traditionally the “unofficial starter”, a role that he would often use to his advantage to land the first fish of the season and was featured in the local paper more than once. He was also a devoted NY Giants and Notre Dame college football fan, tuning in for each game despite the frequent disappointment from his beloved teams.

James was always happy to engage in conversation and never met a stranger he could not lure into a friendly discussion. His moniker of “Sonny” was a true testament to his wonderful disposition; warm, radiant, and the bright center of those who orbited around him to enjoy his glow and positive outlook on life. He lived a glass is half full life despite growing up with many hardships as a youth, never once complaining but using every experience as a lesson in life. He never forgot about those who helped him overcome life’s challenges along the way. He was a renowned storyteller, only occasionally embellishing the facts but always keeping his audience wanting more. His laugher was heartier than anyone else in the room and if you were lucky enough to share a treasured glass of good scotch with him and listen to his many stories of life, the party could go on for hours.

James was very proud of his Italian and Irish heritage. Sharing many stories of growing up in “The Patch” surrounded by his large extended family. Sundays are for family and sauce. He enjoyed teaching his grandchildren how to make the perfect meatball.

James biggest pride and joy is the large family that he and his beloved Loie built together, adding six children over ten years with the last being born on their tenth wedding anniversary.

James always said the best decision he ever made in life was to ask for Loie’s help with a Latin class in which he was struggling. Thus began a high school romance with Loie as cheerleader to Sonny’s athlete and they would often exchange their “I love you” with the Latin phrase “te amo”. They married young at age 22 while James was still in college and shared 45 beautiful married years together until Lois passed from brain cancer on their 45th wedding anniversary, the day after Sonny finished re-reading to her the last of the many love letters he had written which she had kept as treasured items in her cedar chest.

James was the very proud and loving father to his 6 children and their partners, 17 grandchildren and 7 great-grandchildren. His greatest pleasure in life was spending time with his large and loving family who absolutely adored him.

He is predeceased by his wife, Lois Arnold Cleary, both his parents, his siblings, Michael Cleary, Francis Cleary, Charles (Pudgie) Cleary and Bernadette Cleary Tarntino.

He is remembered lovingly by his surviving children: Maureen Vollmer (Paul), James Robert Cleary, Kathleen Cleary (Stephen Sinopoli), Christine Downey (Peter), Elaine Curry (Richard) and Thomas Cleary as well as his 17 grandchildren: Jessica, Laura, Alicia, Marissa, Hilary, Monica, Michael, Alex, Zoe, Elizabeth, Daniel, Kevin, Ryan, Brendan, Elise, Annabelle, and Meghan, their partners, and 7 great-grandchildren. In addition, he is survived by his sister, Mary Margaret Cleary Poteat, sisters-in-law Lois Ann Wright Cleary, Eileen Arnold Maceri; brother-in-law Stephen Arnold and wife Emi, companion Maryann Eichenlaub, as well as many nieces, nephews, cousins and friends, too many to mention by name but all who were touched by his loving spirit.

A Mass of Christian Burial will be held for James on Friday, January 9, 2026 at 10:00 AM, St. Patrick’s Church, 604 Park Place, Elmira, NY 14901.

Donations: In lieu of flowers, the family kindly requests donations be made to the Arctic League, P O Box 113, Elmira, NY 14905