“Playing It Well, The Life and Times of Jack O’Leary” is a book in two parts about a man who was born into poverty who rose to become a successful Engineer, an elected and appointed government official and a much exhibited Photographic Artist. It starts with Part One and his birth in 1932 and his early days on the streets of New York, his misspent early years, and his later service in the Navy during the Korean War, after which he spent 35 years in the Aerospace Industry, helping to put a man on the moon while playing a key role in assuring the nations defense. It tells the story of the tragic loss of a wife and son and the subsequent remarriage and raising a family on Long Island. Part one ends with his introduction to New York politics when he is enlisted to seek the Conservative Party nomination to run for Governor of the State of New York in 1966 leading to his eventual elevation to the highest levels of party leadership on Long Island in 1972. Part Two follows Jack’s adventures through the end of the twentieth century to the early years of the twenty first.