Bobby James Gayle

The Life of Bobby James Gayle, Sr. “Ole Bob” Bobby James Gayle, Sr. quietly departed this life during the early morning hours of January 1, 2026, at the home of his daughter, Tracy. He was born on September 26, 1952, to the late John and Margaret Gale. He was reared in Princess Anne and was the youngest of six children. Bobby received his education from Somerset County Public Schools, graduating from Washington High School in 1971. After graduating high school, Bobby moved to Dover, NJ and was employed as a machinist. Bobby lived in Dover for approximately twenty years. It was during this time that he met the love of his life, his late wife Yvette, after a visit to the home of his late sister (Virginia) in Providence, RI. Bobby and Yvette united in matrimony July 31, 1983, and were married for over thirty years until her passing in 2016. From this union, two children were born - Bobby, Jr. and Tracy. He was also the father of Darrin Simmons, Sr. Bobby and Yvette lived in Dover, NJ for a brief while until their return to Princess Anne, MD. Upon returning to Princess Anne, Bobby worked at Purity Bacon until its closure, after which, he became a licensed carpenter and worked in construction. He was often called upon to repair homes for the local community. Bobby became a member of Metropolitan United Methodist Church, where he served as a Trustee, custodian, and a member of the United Methodist Men. He also provided carpentry work for the church. After his health began to fail, he moved in with his daughter, Tracy, until his transition. Tracy and his brother Charles have many humorous memories of Bobby’s stories and adventures during his stay with Tracy. Bobby leaves to “celebrate his life”: his loving children, sons Bobby Gayle, Jr. of Killen, TX, Darian (Nanette) Simmons, Sr. of Milledgeville, GA and daughter, Tracy Gayle of Delmar, MD; brother, Charles Wright of Princess Anne, MD; grandchildren, Briana Wright, Tyrel Wright, Jr., Jonathan Colon, Jr., Darian Simmons, Jr., Evan, Amani and Amilliana Simmons and two great-children, Dae’Andre’ Fowler and Brielle Lucas-Carter and several nieces, nephews, cousins and a host of friends. A special thank you to his nurse Ruth and CNAs, Ashley, Angela and Kashmere. In addition to his parents Bobby was preceded in death by his loving wife, Yvette, brothers, John and Robert Gayle, Roland Jones, Sr., and sister, Virginia Butterfield. Bobby will be missed by his family and loving Princess Anne Community. Lovingly Submitted -The Family

Bobby James Gayle

September 26, 1952 - January 1, 2026