Donald Howard Bailey, Sr.

Donald Howard Bailey Sr., affectionately known as Don or Pop, passed away on February 1, 2026, in Easton, Maryland, due to medical complications at the age of 61. Born on November 15, 1964, in Annapolis, Maryland, he was a family man who devoted his life to his children and was often heard bragging about how proud he was of all of them. He had a loving nature and was known for his humor, big heart, and authenticity. He was a master of conversation, knowing no strangers and effortlessly engaging with everyone. In his early years you could find him roaming the streets of Annapolis with his brothers, hanging out at Gino’s. He was also very passionate about golfing and loved being on any course with his friends. Donald spent his professional life as a painter and contractor, a career through which he met many individuals who transitioned from clients and colleagues to friends and family. His work was not just a job but a means to connect with people and build lasting relationships. In the most recent years, he found a new sense of pride and joy in his 6 grandbabies. He was recently attending Eastpoint Church with his family and friends where he was rebuilding his faith in God. Donald also had a passionate involvement in hockey, often found cheering the loudest for his grandchildren and the Easton Icehawks at their games. He was known as “Pop” by many coaches, players and parents at the rink. Donald is survived by a loving family: his siblings, Cindy Parks, James Elmer Bailey, and Melanie Slaughter; his children, Donald Bailey Jr., Tiffany Cantler, Sara Brown, and Justin Bailey; and his cherished grandchildren, Jonny (Bubba) Brown, Bailey Brown, Bella Cantler, Brett Bailey, Sophia Cantler, and Josiah Bailey. He was preceded in death by his parents, Ray Charles Bailey Sr. and Frances Bailey (Stokes), and his brother, Ray Charles Bailey Jr. The viewing will be held on Sunday, February 8th from 2-4 pm and 6-8 pm at Fellows, Helfenbein & Newman Funeral Home, 200 S. Harrison Street, Easton, MD. The funeral service will follow on Monday, February 9th at 10 am at the Talbot County Community Center. The Fellows, Helfenbein & Newnam Funeral Home in Easton, MD, is assisting the family during this difficult time. Donald's life was a testament to his strong character and the deep connections he fostered throughout his years. He will be remembered fondly and missed deeply by all who knew him. In lieu of flowers, donations can be made to “Eastern Shore Hockey Association” or the family welcomes support toward funeral expenses. https://www.gofundme.com/f/support-for-pops-funeral-expenses-dx48c?attribution_id=sl:3177a330-0114-4dec-b9dbfb58722bfcb4&lang=en_US&ts=1770152124&utm_campaign=man_sharesheet_dash&utm_content=amp17_ta&utm_medium=customer&utm_source=copy_link

Donald Howard Bailey, Sr.

November 15, 1964 - February 1, 2026