Henry was born on November 10, 1966, in Miami Florida, to the late Willie B. Osby and Willie Bell Osby. Affectionately known as, "Redd", he was a dedicated Miami Dolphins fan.

Henry was preceded in death by father, Willie B. Osby, mother, Willie Bell Osby; sisters, Lois Osby and Stephanie Osby; nieces, Deborah Osby and Angel Moore; nephew, William; two grandchildren.

He leaves behind to carry on his legacy: devoted wife, Philana K. Osby; and four children, Dominique Osby (Pewee),

Davasia Evertt, Erykah Kendrick, and Tyrail Kendrick. His memory will also be held dear by his seven aunts; two sisters, Brenda Cade-James, and Sandy Myers; as well as his mother-in-law. Henry's family also includes a host of nieces, nephews, great-great-nieces, great-great-nephews, cousins, and friends who will remember him with love and admiration. Henry will be deeply missed by all who knew and loved him. His warmth, kindness, and special bond he shared with his family will be remembered.