Robert Edward Penn was born in Rockville Centre, New York on July 22, 1943 to William Charles and Jacqueline Penn Romano. He was one of five children (William, Robert, Sharon, Dave and Linda).

He joined the US Air Force in 1961 and was stationed in Amarillo, Texas. Bob, however, was best known for his work as a Police Officer. He had a 'one mile beat' in Harlem, New York. He enjoyed sharing stories from this time and they were always interesting. He was honored for his heroic act of saving a man from a fire in a high-rise apartment that was vacant. He also was proud of a young boy he met in Harlem that eventually became a Sargeant for the Police Department.  He retired after 20 years of service.

Bob was an avid golfer who, upon retiring, did what any reasonable person would do: he went right back to work…at a golf course. He spent his days at Van Cortlandt Park Golf Course in the Bronx, where he played daily with friends and occasionally let them win (or so he claimed). A devoted dog lover and lifelong Yankees fan, Bob believed in loyalty—especially to teams that tested it regularly.

Bob passed away in Texas, a place he grew to appreciate—though not quite enough to root for the Rangers. His loyalty to the Yankees remained intact, even deep in enemy territory.

Bob was a great brother and uncle. He was survived by Sharon (Hugh) and Linda as well many nieces and nephews.