James E. Masiello

1959 - 2025

James E. Masiello
October 1, 1959 - January 21, 2025
James Edward Masiello Jr., age 65, of Westport, Connecticut, passed away unexpectedly on January 21, 2025, surrounded by his loving family.
Born on October 1, 1959, to the late Nancy (Figlar) Masiello and Jim Masiello, Jimmy grew up with a deep sense of loyalty and an unshakeable bond with those he loved. His childhood best friends, Ed Bona and Ed Malloy, remained his closest companions throughout his life, a testament to the lasting friendships he built and treasured.
Jimmy was a tough cookie to crack, but those who got to know him witnessed a heart full of love, especially for those who needed it most. Known for his larger-than-life sarcastic sense of humor and his unwavering integrity, Jimmy had a knack for making people laugh and feel welcome. His family was everything to him, and he proudly bragged about his three children to anyone who would listen. His love for them knew no bounds.
A man of many passions, Jimmy had a special place in his heart for old mob movies, homemade Italian meals (especially when he was the one cooking!), the beach and golf. He loved spending time with friends on the course, often boasting about his handicap, and he had a talent for making every round feel like a good time. A fantastic cook, he always enjoyed preparing a delicious meal for family and friends to enjoy, but also loved visiting his favorite restaurants to spend time with special people.
Professionally, Jimmy had an illustrious 28-year career in sales and marketing, where he achieved tremendous success and formed long-lasting business relationships worldwide. Most recently, he was self-employed as a retail liquidator, renowned for his incredible salesmanship. Jimmy had a unique ability to sell face to face with charm and humor, never taking no for an answer, but always making people feel good about their purchases. He was truly one of the best in his field.
Jimmy was predeceased by his brother, Mark Masiello, and his two beloved chocolate labs, Winston and Duke, who were always by his side-especially when it was time for a special treat from Carvel. He is survived by his three children, Michele, Alexandra, and James (Buddy); his sister, Marnie Masiello; many cousins, extended family, and friends, all of whom loved him dearly. He also leaves behind a devoted community in Westport, where he was a familiar and cherished presence. His infectious smile, contagious laugh, and sense of humor will be missed by everyone who had the privilege of knowing him.
A wake will be held at Harding Funeral Home, 210 Post Road East, Westport, Connecticut, on February 7, 2025, from 4:00 p.m. to 7:00 p.m. The funeral will take place at St. Luke Church, 49 North Turkey Hill Road, Westport, Connecticut, on February 8, 2025 at 11:00 AM, followed by a celebration of life at BJ Ryan's East, 1 Cove Avenue, Norwalk, Connecticut, at 12:30 p.m.
Donations can be made in his honor to the Mark Masiello '83 Memorial Scholarship at Fairfield College Prep www.fairfieldprep.org/giving or to World Central Kitchen www.wck.org
Jimmy's memory will live on in the hearts of his family, friends, and all who were touched by his kindness, humor, and love.