Robert H. Bailey

In Loving Memory of Robert Henry Bailey Robert Henry Bailey, affectionately known as “Bobby,” was born November 9, 1947, in Baltimore to the late Leon Harrison Bailey Sr. and Lucille Catherine Bailey. As the oldest of eight children, he embraced the role of big brother, protector, and leader throughout his life. Raised in Baltimore’s Cherry Hill and Howard Park communities, Bobby loved sports, roller skating, crabbing, music, and dancing; anything that brought family and friends together. He accepted Christ at an early age and was baptized at New Saint Mark Baptist Church, where he sang in the youth choir and marched with the White Hawks. He later joined Mount Pleasant Baptist Church, faithfully serving on the security ministry. After graduating from Frederick Douglass High School in 1967, Robert studied drafting at Morgan State College before answering the call to serve his country in the United States Marine Corps during the Vietnam War. He went on to build a strong career as a certified water sprinkler installer, at Bethlehem Steel’s shipyard, and at the Veterans Cemetery, work that deepened his appreciation for family and legacy. Every week during those years, he brought flowers to his mother, a tradition that reflected his deep devotion. He later continued serving others at a nursing home in Philadelphia. Like many veterans, Robert faced personal battles, but through faith, family, and the steadfast love of his parents, he found renewed strength. During this season he met Angela Holliday, whose love and support became a true blessing. On his 60th birthday in 2007, Robert and Angela exchanged vows, beginning 19 years of marriage. He often said he finally felt he had a complete family; Angela, daughters Laqreshia and Latoyia, and a son he lovingly raised as his own. Bobby had a fighter’s spirit and a protector’s heart much like his hero, Rocky. He was known for his sharp style: signature hats, fresh sneakers, and perfectly coordinated outfits. He cherished family vacations, holiday dinners, cookouts, and reunions, and stayed close through regular calls when distance kept him away. His deep voice and warm enthusiasm filled every room he entered. Robert leaves to cherish his memory and continue his legacy: his devoted wife of 19 years, Angela Bailey; his beloved children, Laqreshia, Latoyia, and Shawn who he lovingly raised as his own; six cherished grandchildren, Ciahnni, Aziyah, Zaheem, Cohen, Kamii, and Mason; six brothers-in-law, James, Charles, Thomas, John, Gregory, and Rodney; four loving sisters, Joyce BaileyPipkin, Patricia Bailey-Jones, Anita Bailey-Shields, and Barbara Bailey Edwards; along with a host of nieces, nephews, great-nieces, great-nephews, cousins, extended family members, and dear friends who will forever treasure his memory. He was preceded in death by his parents, Leon Sr. and Lucille Bailey; his brothers, Leon “Bey” Bailey Jr. and Steven “Kawee” Bailey-Muhammed; his sister, Linda Bailey-Cooper; and his mother-in-law, Odessa Holliday.

Robert H. Bailey

November 9, 1947 - May 14, 2026