John S. Aiello, Sr., a 36 year resident of Dutchess County, formerly of Port St. Lucie, FL and the Bronx, passed away on Thursday, September 11, 2025 at the Hudson Valley Hospice House in Hyde Park. He was 79.

Son of the late Salvatore and Angelina (Derasmo) Aiello, he was born in the Bronx on May 30, 1946. After graduating from Cardinal Hayes High School, John enlisted in the U.S. Army and served his country for several years as a member of the Army National Guard.

He worked as a stock trader in Manhattan for 42 years, retiring from Merrill Lynch in 2007.

John loved watching sports and was an avid New York Jets, Yankees, and Rangers fan. He also enjoyed reading. More than anything else, however, he cherished spending time with his family, most especially his grandchildren, who meant the world to him.

On November 25, 1967, he married Julia Cuccinello at Our Lady of Mercy Church in the Bronx. Julia survives at home in Poughkeepsie.

Additional survivors include his son, Richard Aiello & his wife Shannon of Poughkeepsie; his daughter, Lisa Aiello & her partner Janice Dillon of Wappingers Falls; his daughter, Mary Henry & her husband Thomas of Poughkeepsie; his daughter, Jennifer Rosenberg & her husband Brian of Hopewell Junction; his son, John Aiello, Jr. & his wife Ellen of Melbourne, FL; his grandchildren: Tyler Aiello, Dominic Henry, Demitri Henry, Justin Aiello, Antonina Henry, Julianna Rosenberg, Jakob Rosenberg, Meghan Aiello, GianCarlo Henry, and Joshua Rosenberg; his sister-in-law, Leola Aiello; his nephew, Mark Aiello & his wife Michele, along with their children Chiara and Luca; his sister, Angela Aiello; and countless other relatives and dear friends.

John was preceded in death by his parents as well as his brother, Louis Aiello, and his sister, Mary McCarthy. He was also predeceased by his faithful companion and "best dog ever" Lucky J. Dog.

Calling hours will be held from 1 to 5 p.m. on Sunday, September 14th, 2025 at the McHoul Funeral Home of Fishkill, Inc., 1089 Main Street, Fishkill, NY. A Mass of Christian Burial will be offered at 10:30 a.m. on Monday, September 15th, 2025 at St. Mary, Mother of the Church, 106 Jackson Street, Fishkill, NY.

In lieu of flowers, memorial donations may be made to Hudson Valley Hospice Foundation at www.hvhospice.org or Sparrow's Nest at www.sparrowsnestcharity.org .