Raymond J. MacDermott Sr., 60, of Poughkeepsie, died unexpectedly on Sunday, May 9, 2021, at Vassar Brothers Medical Center.  Affectionately known as "Big Ray", he was born October 5, 1960 in Poughkeepsie, the son of Raymond Ralph MacDermott  and Catherine Messina MacDermott. Ray was predeceased by his father and his mother survives in Hyde Park.    A lifelong area resident, he was a self-employed contractor for many years until a disability forced him into an early retirement.  Ray's hobbies included playing poker, watching sports, and flipping houses. Although he loved his family with all his heart, his second love was Christmas cookies. He didn't meet many cookies he didn't like.   On May 24, 1986 in the Full Gospel Center, LaGrange, he married the former Tina Traficante. Mrs. MacDermott survives at home.  In addition to his wife and mother, he is survived by his son, Raymond J. MacDermott Jr., at home; sister, Carol Manning and husband, Patrick, of Arizona; sister, Sherri Corcoran, and husband, Mike, of Hyde Park; brother, Thomas MacDermott, and wife, Maria, of Staatsburg; brother, David MacDermott, and wife, Jeannine, of Pleasant Valley; brother, Ricky MacDermott, and fiancée, Gabriella Lombardi, of Dover; several nieces and nephews; aunt and uncle, Doris and Thomas Serino, of Poughkeepsie; and many cousins.   In addition to his father, he was predeceased by his maternal grandparents, Joseph and Alice Messina.  Cremation has taken place. Funerals services were private.  Ray's family respectfully requests memorial donations to the charity of your choice.   Arrangements were under the direction of Sweet's Funeral Home, Inc., Rte. 9, Hyde Park. To send an online condolence, please visit www.sweetsfuneralhome.com .