Jacqueline A. Caiola

Jacqueline A. Hodgins Caiola 1949 - 2025 PORTLAND - The family of Jacqueline A. Hodgins Caiola is heartbroken to announce her passing on May 26, 2025, after a long illness. Born in 1949 to George T. and Teresa J. Hodgins of Brewer, Jackie was the eldest of four children. She was a proud graduate of John Bapst High School, Class of 1967, where she was a standout athlete in basketball, softball, and cheerleading. Her loud cheerleader clap and piercing whistle weren’t just high-school talents—they remained with her throughout her life, a playful yet powerful reminder of her spirited nature. Jackie’s passion for physical education led her to the University of Maine at Presque Isle, where she earned her bachelor’s degree in 1971. It was there she met Michael [Mickey] Caiola, her partner in the required folk and square dancing class for physical education majors. Mickey likes to claim he won her heart on their first date, when he took her to the Mapleton dump to shoot rats by the light of his car headlights. But Jackie always said she was smitten when she saw that, despite his late Saturday nights, he never missed Mass on Sunday mornings. The two were married on July 3, 1971, in Brewer. Soon after their daughter, Krista, was born, Mickey and Jackie moved to southern Maine, where they established their family and forever home in the Back Cove neighborhood of Portland. Their son, Michael, arrived in 1978, completing the close-knit household they cherished for decades. A dedicated educator, Jackie inspired generations of children for 46 years. She taught physical education at Presque Isle High School, Mahoney Junior High School, St. Joseph Parish School, Holy Cross School, Cathedral School, St. Patrick School, and St. Brigid School, retiring in 2016. She planned and executed the most epic field days, which became the highlight of every school year. She was always delighted to cross paths with former students, greeting them with genuine joy and excitement. Nothing made her smile quite like hearing, “Hi, Mrs. Caiola - I loved your gym class!” Beyond the classroom, Jackie served as a camp counselor at Waynflete Sports Camp and held part-time jobs over the years at Shaw’s Northgate, L.L. Bean, and Donatelli Variety. She coached youth basketball and Little League softball and was the team mother and chaperone for the 1993 sports exchange program with sister city Shinagawa, Japan. Even in retirement, she remained active in her community, working at Portland polling places during elections. Jackie took great pride in her expansive flower garden and loved sitting in the backyard with Mickey for morning coffee—often declaring, “Mickey makes the best coffee!” A cup of tea was more than just a drink to her; it was an invitation to share good company and conversation with friends and relatives. She enjoyed frequent walks and deeply valued the time spent with her walking companions. Jackie’s competitive spirit came alive at the bowling alley, and she was nearly unbeatable at Scrabble, always producing a clever, high-scoring word. Jackie and Mickey loved spending time on the water, celebrating milestone birthdays and anniversaries with memorable voyages—whether aboard a sailboat or a cruise ship. She never turned down a boat ride on Forest Lake, a sip from a “tall blonde” (always with a lime), or a good beat—music always made her dance. Her cooking brought warmth and flavor to every family holiday, with unforgettable dishes like her signature Thanksgiving stuffing and her lobster-laden seafood chowder on Christmas Eve. Many beloved traditions were started by Jackie—thoughtful, festive touches that are now remembered and carried on by the family who loved her so dearly. Jackie was affectionately known as “Diddy” to her five grandchildren. When they were babies, Diddy showered them with singsong love — “I love you a bushel and a peck / a bushel and a peck / and a hug around the neck.” She was a thoughtful gift-giver, a master of back scratches, and quite possibly the first person they ever heard utter a well-placed swear word. Diddy cheered loudly at every sporting event, clapped proudly at dance recitals, and never missed a theater performance. She was predeceased by her parents and her beloved brother, John R. Hodgins. Jackie is lovingly remembered by her devoted husband of 53 years, Michael Caiola of Portland; her daughter, Krista Henderson (Joseph); her son, Michael Caiola (Rachel); and her treasured grandchildren, Griffin, Lydia, and Stella Henderson, and Greta and Adeline Caiola. She is also survived by her sisters, Mary Ellen Palmieri and Elaine O’Connell (Kevin); sisters-in-law Linda Hodgins and Maryann Barter (Ronald); goddaughter Amy Larrabee Merrill, godson Owen Palmieri, as well as her niece and several nephews who held a special place in her heart. Visiting hours will be held on Friday, June 13, from 5:00-7:00 pm at A.T. Hutchins, 660 Brighton Avenue, Portland. A celebration of Jackie’s life will be held on Saturday, June 14, at 11:00 am at St. Pius X Church, 492 Ocean Avenue, Portland, followed by a reception at Bruno’s Restaurant & Tavern, 33 Allen Avenue, Portland. The family would like to express their heartfelt gratitude to the staff of Fallbrook Woods and Compassus Hospice Care for their care and support. Memorial donations can be made to: St. Brigid School, 695 Stevens Avenue, Portland, ME 04103.

Jacqueline A. Caiola

August 4, 1949 - May 26, 2025

Explore Obituaries &
Upcoming Services