Henry Richard Mastrianna

The family of Henry Richard Mastrianna known and loved by many as Hank, Red and Poppy is deeply saddened to share that he passed away on December 31, 2025. He was surrounded by his family and was talking until the end about his children’s sports and shenanigans.  His family told him how grateful and thankful they were for the love and support he provided. Subsequently, he raised his right arm several times, eyes focused on the heavens and peacefully passed.

Henry was born on December 22, 1929, in Waterbury, Connecticut to Steven (Pappy) and Mary (Gommy) Sullivan Mastrianna. He was the grandson of Michele and Carmella (Martone) Mastrianna of Caiazzo and Frigento, Italy and Joannes (originally Szalaman) and Maria (Kochiss) Sullivan of Plavnica and Kozelec, Slovakia.

Henry graduated from Leavenworth High School in 1947. Henry served in the Army during the Korean War from 1951-1953.  Following graduation, he joined the family’s petroleum contracting business, Steven Mastrianna and Sons, Inc., where he serviced numerous gas stations across Connecticut representing brands such as Arco, Chevron, Exxon, Gulf, Mobil, Texaco, and Mobil. He would reminisce about the ninety-two Waterbury gas stations that they served.

 When he returned home, he met the love of his life, Judith Leary. They married in 1955 and went on to share an extraordinary 55 years together until Judy’s passing in 2011. They raised their family in Middlebury, CT. Since 1993, he resided in Siesta Key FL enjoying many years with family and friends.

Hard work and integrity were everything to Henry.  He dedicated his time to various organizations, including supporting Holy Cross High School’s capital campaign, coaching Middlebury Little League and girls’ sports and serving as an usher at Saint John of the Cross Church.  

His loyal support for his grandchildren will remain treasured memories. He loved talking to them regarding their professional pursuits in aviation, engineering, HVAC, and teaching. He recently wanted to go on work calls with his grandson. We will miss the day-to-day conversations and if there was only a phone line to heaven.

He traveled extensively and recently went on an Italian trip with a group of family and friends. He was able to revisit his ancestral towns, and we all had so much fun! Not to mention the stories!

He is survived by his four children, Elizabeth, Leslie, David and Paul and his eight grandchildren, Daniel, Erin, Colin, Elizabeth, Colleen, Steven, Brendan and Michael, and several great-grandchildren. He also leaves brothers Steven and Thomas and sister Mary. He was predeceased by his brothers William and Robert.

Burial in the spring will be private at Middlebury Cemetery.

Prospect Memorial/The Palmerie Family Funeral Home is honored to care for Henry and assist his family during their grief journey. Please leave your condolences, memories, and words of comfort for his family on Henry's Tribute Wall on this page. 

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