Guido A. Maiolo

It is with heavy hearts that we share the passing of Guido A. Maiolo who left us on Wednesday August 20th, 2025 as his 88th trip around the sun approached.

Guido was the heart and soul of his family. To countless former players and just about anyone else who knew him, he was just “Coach.” And to coach, the three most important things were Family, Football and Faith.

Family First

Once Guido started his own family, he remained close with his parents and siblings. Family  get-togethers involved three generations piled into a two-family house in New Rochelle, NY where dad's sister’s family and parents lived. And it wasn’t just for special occasions. It was most weekends (outside of football season, of course.) There was always plenty of macaroni with red gravy filled with sausage, meatballs, spare ribs and pig skin, and homemade red wine served with a heavy hand regardless of age.

Plays (regular, not football) were rehearsed by nieces and nephews, and put on regularly. Football was played in the backyard dangerously close to Guido’s dad’s garden. His dad was known to threaten to stick his knife in the grandkid’s football if it went into his garden. One time they found out it wasn’t just a threat.

From his parents, Guido learned lessons of loyalty, faith, and resilience. Even when money was scarce, there was always plenty of food for family and whoever dropped in for a meal. Family and faith came first. Literally. You couldn’t eat breakfast on Sunday until you went to church. His siblings stood by each other through thick and thin, modeling devotion that Guido carried into his own life. He also had a soft spot for dogs, usually mutts, who were treated as family members, especially at mealtime. That love of animals lives on through his daughter, Christine, who always has a pack of dogs running through her home.

A Life in Football

Every season was football season in the Maiolo house.

He taught the importance of preparation, dedication, teamwork, the power of belief and accomplishing big things, but not at all cost. If you were going to do something, do it the right way. With class.

He convinced his players that they were champions long before the scoreboard said so. Guido helped shape boys into men, who would carry these lessons into their families, companies and communities. Many of his former players from his early days coaching in the Bronx, to his final coaching days at Ridgefield High School, CT, stayed in touch. He received a steady and truly endless stream of messages and visits from his former players thanking him for the life lessons and the immense impact he’s had on their lives. To say nothing of the messages the family has received since his passing.

Guido’s two sons, Mike and Brian, played football for him. He also coached his daughter Christine’s softball team. His lessons went beyond the field, shaping their character and values.

When Guido’s coaching days were over, he poured that same love and energy into his grandchildren, Matthew, Trevor, Kate, Gabe, Anna, Luca and Ava. He took on the role of playmate, ice cream distributor, and overall spoiler-in-chief. Despite multiple back surgeries and an ankle replacement, nothing could keep him from getting down on the floor to play with his grandkids. Guido even came out of retirement to help coach several of his grandkid’s football teams.

A Hug for Everyone

Coach greeted family, friends and strangers alike with a full-on hug…an open heart if you will. He welcomed his children’s and grandkid’s spouses as his own, as Steve Gardiner (Christine’s husband), Katherine E. Maloney (Mike’s fiance), Lisa Gajda Maiolo (Brian’s wife), and Mara Wagner (Matthew’s fiance) will attest. 

His secret weapon was his wife, Toni, who was happy to leave the spotlight to her husband. She was his rock when things got rocky on the gridiron. She was an amazing cook, made killer brownies, and always had a spread ready for the coaches after football games, despite her other full time job as a nursing executive at a private psychiatric hospital.

A Life of Faith & Service

Guido’s faith was central to who he was. He went to Catholic mass religiously. As importantly, he did his best to live a life that emulated his faith. He opened his heart and home to others, often in life-changing ways. One player from the Bronx lived with Guido’s family for a year when he had nowhere else to go, and he wasn’t the last. Guido tirelessly networked with college coaches across the country, making calls and writing letters until complete strangers became fast friends who ate meals and stayed in his house. So doors could be opened.

Roots and Legacy

Guido came to America when he was a young man from Nardodipace, Italy. Five siblings (Gabe, Ida, Al, John, Richard) made their way to the US with his youngest sister (Mary Lou) born in the United States. He is survived by his wife, Toni Calder Maiolo, daughter, Christine Maiolo Gardiner, and son’s Mike and Brian Maiolo, along with Guido’s brother, Al Maiolo, and extended family of Maiolo relatives.

Service Schedule

Family and friends will be received on Thursday, September 4, 2025, from 5:00 PM to 8:00 PM at Kane Funeral Home; 25 Catoonah Street, Ridgefield. A funeral mass will be celebrated on Friday, September 5, 2025 at 10:30 AM at Saint Mary's Church; 55 Catoonah Street, Ridgefield. Interment will take place privately. 

Contributions in Mr. Maiolo’s memory may be made to the ROAR (Ridgefield Operation for Animal Rescue) - 45 South Street; Ridgefield, CT 06877, http://roar-ridgefield.org.

The above obituary was composed by Guido's family.