Gail Maloney (Gillespie), 67, of Enfield, Connecticut peacefully passed away on Sunday, January 16, 2022, at St. Francis Hospital holding her husband’s hand after a courageous battle following a sudden cardiac arrest on November 30, 2021. Gail is survived by her loving husband of 43 years, Jim Maloney, and three daughters: Erin (Andy) Nolin; Heather (Jeremy) Shapiro; and Stephanie (Ryan) MacGillivary, all of Enfield; brother Hugh (Pat) Gillespie of Grosbek, Texas and two sisters: Cathy Grissom of Gainesville, Florida, and Beth (Don) Curty of Winchester, Tennessee. She is also survived by two brothers-in-law: John (Kathy) Maloney of Enfield and Thomas (Sandy Libby) Maloney of Cromwell, and two sisters-in-law: Annmarie Maloney of West Hartford and Kathy (Raphael) Garbalosa of Bristol. Gail leaves behind her best friend of over 50 years, Janice Stewart, special cousins Janice and John McDevitt, close family friend Sarah Mayo, and her extra “kids” – Nicole Gatcomb, Eric Michaelian, Kristin Petig and Holly Broderick. Gail is survived by 20 nieces and nephews, along with many great and great-great nieces and nephews. Gail is predeceased by her parents Hugh (Henry) Gillespie and Agnes (Nancy Strathern) Gillespie, her older brother Robert Gillespie, and her in-laws, Thomas J. Maloney, and Rita (Ferrier) Maloney. Gail also leaves behind four “grand fur-babies” – Scarlett, Duncan, Ann, and Molly – all of whom she loved so much.
Gail was born in Jersey City, New Jersey on March 29, 1954, the youngest of five children. As the baby of the family, Gail was a bit of a wild child, often getting into trouble with her best friends Janice and David Summers. She was famously kicked off the school safety patrol in 5th grade for beating up David after he was rude to her. Gail grew up surrounded by dogs and cats while living in the country, which made her a lifelong animal lover. Her favorite childhood dog was Bluebell, a West Highland Terrier with a BIG personality.
She graduated from Egg Harbor High School in 1972, and then earned an associate degree in Psychology from Atlantic Community College. After her father got sick, Gail and her family moved to Arizona. Gail attended Grand Canyon College for one semester before she was asked to not return the following year. Something about offering the dean a drink from her wine bag on a dry campus. Gail then attended Arizona State University, where she graduated with a bachelor’s degree in psychology.
Arizona was a turning point in Gail’s life. She worked her way through college by managing a McDonald’s in the evenings. It was here that she would meet the love of her life, a young Airman named Jim Maloney, who was stationed nearby at Luke Air Force Base in Phoenix. The moment an angry Gail threw a very drunk Jim and their mutual best friend Steve Wyatt out of that McDonald’s lobby, a love story for the ages, was sparked. They were married on May 6, 1978, and Gail took on one her most important roles in life, that as military spouse and mother.
From there, Gail and Jim were sent to Pease Air Force Base in Portsmouth, New Hampshire in 1978, where they adopted a dog named Kelly I. Gail worked for Liberty Mutual for a few years in this time. In August 1981, Gail and Jim welcomed their first daughter, Erin. From New Hampshire, the family moved to Eielson Air Force in Fairbanks, Alaska in 1983. In October 1984, Gail and Jim welcomed identical twin daughters, Heather, and Stephanie. In 1986, the family made the trek from Fairbanks, Alaska to Champaign, Illinois, where Jim was stationed at Chanute Air Force Base in Rantoul, Illinois. Gail was a stay-at-home mom and devoted classroom mother for her children. During their time in Champaign, Gail started her own successful ceramic business in the garage of the little house they purchased on Kenwood Road, that gained community attention including a feature on the local news. In addition, Gail adopted two dogs, Kelly II – a mutt with a penchant for chocolate and Hall's cough drops, and a West Highland MacGregor II, the families beloved pets for 17 years and 11, respectively.
Gail was a natural teacher and used every opportunity to instill a love of learning in her children. Every road trip and vacation had to include an educational element, whether it be a museum visit or a stop at a Civil War battlefield, a tradition that continues even as her children approach middle age.

From Champaign, the family moved to Dover Air Force Base in Dover, Delaware. It was here that Gail made the decision to go back to school, at the age of 40 years old, to become a teacher. In 1996, Gail graduated with a master’s in education from Wilmington College, an achievement that made her whole family proud, and one that inspired her daughters to do the same. Gail began substitute teaching, including a few stints in her own daughters’ classrooms. In 1997, the family moved to Scott Air Force Base in Illinois, and Gail began her teaching career as a music teacher at Mascoutah Elementary School.
In 1999, after 25 years in the Air Force, Jim and Gail made the decision to retire and settle near Jim’s family in Connecticut. On the day the family drove in, Gail had an interview for a teaching position with Enfield Public Schools. With her family waiting in the car, Gail was offered a job as a 6th Grade Teacher at Henry Barnard Elementary School, where she would teach until moving to John F. Kennedy Middle School in 2016. Many of her colleagues turned in to lifelong friendships for Gail. She was many students’ favorite teacher, often getting recognized when out in the community. Her daughters are often stopped by former students who want to tell them the impact their mother made on their lives. She had a reputation for being tough but fair and was one of the most empathetic teachers to ever teach. She changed many lives, including one young man who came back from serving overseas to tell Gail that while he was in a war zone, it was her voice that got him through. Teaching was her one of her greatest joys. Gail retired medically in 2019, to spend more time with her family and focus on her health.
When the pandemic hit, Gail used her time in quarantine to give back. She was an avid seamstress and spent her free time making masks for health care professionals. She had surgery during this time, and each week a visiting nurse would come to treat Gail, they would leave with a bag of at least 50 cloth masks for the hospital
In 2011, Jim became an active member of the American Legion Post 80 in Enfield, and like with everything else, his family joined with him. In 2021, Gail was elected Senior Vice and Treasurer for the American Legion Auxiliary Unit 80, where she was a treasured member of the Legion family.
One of Gail’s final wishes is that people refrain from wearing black – fire-engine red, bright pink, lime green, or any other cheerful color is encouraged! The family will receive visitors on Thursday, January at Browne Memorial Chapels (43 Shaker Road, Enfield, CT 06082) from 4-7 p.m. On Friday, January 28th her funeral will begin at the funeral home at 10:00 a.m. and then travel in procession to East Longmeadow United Methodist Church (215 Somers Rd, East Longmeadow, MA 01028) for a 11 a.m. service. A reception will follow at the American Legion Post 80 Lower Hall (566 Enfield Street, Enfield, CT 06082) Due to the COVID-19 pandemic; masks are required at both the funeral home and the church. In lieu of flowers, donations can be made to the Gail Maloney Memorial Community College Scholarship Fund at the Hartford Foundation for Public Giving (10 Columbus Boulevard, 8th Floor, Hartford, CT 06106).
A larger celebration of life for all of Gail’s friends, family and supporters will be held on July 16, 2022, at the American Legion Post 80 Pavilion (566 Enfield Street, Enfield, CT 06082).