Jonathan Peter D’Michael Gregory, 38

Dec 19, 2020

Jonathan Peter D’Michael Gregory, 38, of Onset, passed away on Thursday December 10, 2020 at Tobey Hospital. Jonathan was born in Wareham, the son of Michele M. Semple of Wareham and the late Albert “Butch” Gregory.  

He attended Wareham Public Schools and graduated from Wareham High School in 2000. Jonathan loved to cook and he worked for many of the area’s restaurants. He was also a Recovery Coach, helping and giving back to his community.  Jonathan was focused and proud of his steps to recovery. He was the first to help a neighbor, a hard worker and loving father.  

He was an avid sports fan who had been following the WWE since childhood and the National Basketball Association. He enjoyed music (especially Wu-Tang), a good peanut butter sandwich, a losing season for the Dallas Cowboys but more than anything he loved to make you smile, tell a joke or reminisce.  

Jonathan was the loving father of Hailie Swider-Gregory of Onset and Kailie Sylvia of Wareham. He was the brother of Tammi Semple of Minnesota and Nicole Miceli and her husband Philip of Wareham. He was the uncle of Destiny, Chloe and Giselle, all of Minnesota and Danielle, Sasha, and Gwendolyn, all of Wareham. He was also survived by many loving aunts, uncles, relatives, his girlfriend Elisa Callahan and her daughters, Aria and Seraphine, friends and his recovery family. He was the cousin and best friend of the late Charles “Bear” Semple.

Funeral Services will be private at this time and a celebration of his life will be held at a later date. To leave a message of condolence for the family please visit 

In lieu of flowers the family asks all to offer a random act of kindness in Jonathan’s memory.  

Funeral arrangements are in the care of Wareham Village Funeral Home 5 Center St. Wareham, MA.