Gail Cherkasky, aged 81, of Claymont, DE, passed away peacefully on March 1, 2026, surrounded by members of her family. Born on July 28, 1944, in Philadelphia, PA, Gail was known for her accepting nature, humor, and class. She enjoyed cooking and entertaining. You would never leave her house hungry. Gail could spend hours laughing about nothing and everything at the same time with her dear friends and sisters. Gail always did the Sunday crossword puzzle, she loved Broadway shows and trying new restaurants. Gail was enamored with her niece’s dog, Trigger, a Pomeranian mix whose picture was always on her living room table.

After graduating from Temple University, Gail went on to earn her Masters degree in education from Arcadia University. She spent more than 30 years as an English teacher in Philadelphia, primarily at Strawberry Mansion High School, where she taught until 1999. Despite the challenges of teaching in an under-resourced school, Gail’s commitment and passion for teaching shone through, providing a safe and nurturing environment for her students, demonstrating her altruism and selflessness daily.

Along with her colleagues, she organized class trips to Disney World for students who otherwise would not have had a chance to have that experience, paid for through bake sales. Recently, a nurse at the hospital where Gail was admitted recognized her after nearly 50 years and remembered Gail as one of her favorite teachers from high school.

Following her retirement, Gail spent her time with friends, many of whom she had been close to for decades, and her life companion, Barry Brody, who predeceased her in 2024. Gail loved her family deeply and was a caring and reliable sister, daughter and aunt.

Gail is survived by her sisters, Lynne Karabinas and Robin McGrath, her nephews and niece, David and Douglas Karabinas, Jason McGrath and Aristea Karabinas-Gadow, as well as her nine great nephews and nieces. She is also survived by many dear friends and her devoted caretaker Manolo “Manny” Salinel. She was predeceased by her father, Emanuel Cherkasky, and her mother, Hilda Lipkin Cherkasky.

She leaves behind a legacy of resilience and compassion. Her impact will undoubtedly live on through the many lives she touched as an educator, mentor, and friend.

Services will be private and held at the discretion of the family. The Goldsteins' Rosenberg's Funeral Home is honored to be entrusted with the care and arrangements of Gail Cherkasky.