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05/24/2023 02:31 PMGerald “Jerry” Chester Pendleton Jr., age 91, of Madison, beloved husband of the late Roberta Katherine Pendleton, passed away peacefully on May 19 at Yale New Haven Hospital. Jerry was born on March 21, 1932, on an island he grew up on, and was so proud to speak of Islesboro, Maine. He was the son of the late Gerald Chester Pendleton Sr. and the late Miriam Hatch Pendleton.
Jerry graduated from Islesboro High School in 1950, and from the University of Maine, Orono, in 1954. After college, Jerry entered the U.S. Army for two years and was stationed in Belvoir, Virginia. He then went on to teach middle school social studies in Berwick, Maine, while also coaching basketball. Jerry returned to the University of Maine, Orono, where he obtained his master’s degree in high school guidance and counseling. In 1960, Jerry took a position as the first guidance counselor for Daniel Hand High School in Madison. Jerry was a guidance counselor at Daniel Hand High School for 40 years, retiring in 2000. This was his passion, and he dedicated countless hours to his students throughout the years.
In his retirement, Jerry enjoyed spending time with his family, driving friends to the airport, golfing, and visiting the Florida beaches. It was always a joy for him to run into many of his former students, who were amazed he still had his Maine accent.
Jerry and his late wife, Roberta, were married for 49 years and spent most of those years raising their five children in Madison: Dana (Michael) Sosensky of Clinton, Jerry (Sarah) Pendleton of Andover, Massachusetts, Julia (Ray) LeBrun of Sturbridge, Massachusetts, Michael (Linda) Pendleton of Clinton, and Katie (Kenton) Doyle of Medfield, Massachusetts. Jerry and Roberta had 13 grandchildren: Melissa (Trevor), Kelly (Dave), Megan, Tommy, Ellie, Annie, Allison (Jared), RJ, Katie, Matthew, Grace, Cullen, and Emeline; and one great-granddaughter, Emma. Jerry is survived by his siblings, Barbara Pendleton of Sarasota, FL, Andrea Pendleton of Islesboro, Maine, David Pendleton of Islesboro, ME, and Angela (Frank) Mazer of Cambridge, Massachusetts; his loving sister-in-law, Sally Pendleton of Wappingers Falls, New York, and his loving sister-in-law and brother-in-law, Gerry and Herb Lieberman of Greensboro, North Carolina, as well as many nieces, nephews, and cousins. In addition to his wife, Roberta, and his parents, Gerald and Miriam Pendleton, Jerry is predeceased by his sister Mary Susan; his brother Nicholas Pendleton, as well as aunts, uncles, and cousins.
Jerry had a very large and loving family and will be remembered for his devotion and the love he gave to all of us. We also wish to extend our gratitude to the staff and his friends at Brother Mike’s and Donahue’s restaurants in Madison, who welcomed our Dad in and went out of their way to make him feel special when he visited over the past ten years. You provided him friendship, kindness, and such compassion with each visit.
There will be calling hours from 4 to 7 p.m. Thursday, May 25, at Swan Funeral Home in Madison, and a Mass of Christian burial will be held at 10 a.m. on Friday, May 26, at St. Margaret’s Church in Madison. The burial will be private. In lieu of flowers, donations may be made in honor of Jerry to the Islesboro Community Center, 103 Pendleton Point Road, Islesboro, Maine 04848. www.swanfuneralhomemadison.com.