Robert Howard Gilman, 68, of Naples, FL, passed away on September 4, 2021. Bob was born in Boston, MA on January 2, 1953. He graduated from Marblehead High School and earned undergraduate, graduate and law degrees at the University of Pennsylvania. He practiced law at Reed Smith LLP in Philadelphia and was General Counsel for AmeriHealth Caritas until he retired in 2016. Bob enjoyed his retirement years playing tennis, golf and bocce at Quail Creek Country Club in Naples and Hidden Valley Golf Club in western Pennsylvania. He is survived by wife Monica Sullivan, first wife Cynthia Gilman, daughter Samantha Gilman (Ronald Jones, Jr.), Philadelphia, son David Gilman, Denver, sister Karen Walkey, Melrose, MA, stepdaughter Kathryn Murdoch and stepson Drew Sabatos. Bob was eagerly anticipating the birth of his first grandchild in early December. Contributions in memory of Bob can be made to CurePSP, 1216 Broadway, 2nd Floor, New York, NY 10001.