Thomas S. Monterosso

Thomas S. Monterosso CPA , 76, passed away peacefully on Friday, August 29, 2025, surrounded by his most cherished family. A man whose presence filled every room with warmth, laughter and unwavering compassion. Tom lived a life defined by love, generosity, and an unshakable drive to help others. Born and raised in New Haven, Connecticut, Tom's early years shaped the spirited and hardworking man he would become. After earning his credentials as a Certified Public Accountant, he built a long and successful career grounded in integrity, dedication and service. Yet, it was never just about numbers for Tom; it was about people. His clients became friends and every person he encountered was treated with respect, care and often an act of kindness they’d never forget. Tom believed there was no such thing as "can't." Whether it was helping a single mother quietly cover the cost of groceries or anonymously paying for the emergency treatment of a stranger’s beloved pet, he always acted from the heart. At one veterinary office, he is still remembered simply as "the gentleman who paid for the cat treatment." That was who Tom was at heart, selfless, quietly heroic and full compassion. He was a man of remarkable character and an unforgettable personality, vibrant, colorful and deeply loyal. Tom forged lifelong friendships and made it a point to always keep in touch, no matter the miles or the years. He instinctively knew when someone needed a hand, a hug, or just a heartfelt note, something he was known for giving often, filled with encouragement and wisdom. But above all, Tom was a family man. He was the beloved husband, partner and best friend to Cheryl, his soulmate and the love of his life. Together, they built a life of joy, intention and togetherness. From morning coffee in the “happy room” to working side by side at the office and coming home to the warm, cozy haven they created, their relationship was a model of true partnership. They shared everything; interests, values, laughter and a deep commitment to health, family and each other. Tom was a devoted father to Tracey, Jaime and Kristi pouring all of himself into guiding, encouraging and supporting them. With Tracey, he saw a reflection of himself. He was immensely proud when she earned her MBA and joined him at the firm, becoming not just his daughter but also a trusted right hand. He nurtured Jaime’s calling in healthcare, celebrating every milestone on her path to becoming a Nurse Practitioner. With Kristi he admired her academic achievements and cheered her every success, especially when she got her Advanced Masters, he was always encouraging her to chase her dreams. His daughters were his pride, his heart and his legacy. In times of uncertainty, they still ask themselves, “What would Tom do?” Tom’s joy only multiplied with the arrival of his grandchildren Peyton, Avery, Emma, Ethan, Anna, Benjamin Thomas, Willow, Ryan, Anthony, Christian, Kyle and Cameron. Being “Papa” was one of the greatest honors of his life. He celebrated every report card, every performance, every goal scored, or hurdle overcome. His handwritten notes, thoughtful, inspiring, and full of love became treasured keepsakes. His eyes lit up in their presence, and his love for them was fierce, proud and unconditional. Tom lived life fully and gave freely to his family, his friends, his community and even to strangers. His absence leaves a space that can never be filled, but his spirit lives on in every life he touched, every lesson he taught and every heart he inspired. Tom was also a great animal lover and dog dad to his boys Peanut, Bailey and Scooby. He is survived by his beloved wife Cheryl, his daughters Tracey (and husband Adam), Jaime (and husband Tim), and Kristi (and husband Ian) and his adored grandchildren. He also leaves behind countless friends and extended family who loved him dearly. He is predeceased by his loving mother Nicolasa. The family will receive friends Saturday from 1 - 4:30 p.m. at Sisk Brothers Funeral Home 3105 Whitney Ave. Hamden. In lieu of flowers the family asks that you honor Tom’s memory with a quiet act of kindness or a handwritten note to someone who needs encouragement just as he would have done or a donation to Yale New Haven Hospital’s Neurology Department, 20 York St. New Haven, CT. 06510