Teach Me to Be Generous tells the remarkable story of Regis High School, the Jesuit school on New York’s Upper East Side that was founded in 1914 by an anonymous donor as a school for Catholic boys whose families could not otherwise afford a Catholic education. Enabled by the philanthropy of the founding family for nearly a century, and now by alumni and friends carrying on that tradition of generosity, Regis has been able to provide tuition-free, all-scholarship education for its entire history. It also holds the distinction of being the first free-standing Jesuit high school in the United States, with no connection to any Jesuit colleges or universities. Regis High School’s unique story is told by an engaging storyteller and historian who has taught at the school for more than ten years. Father Andreassi offers captivating glimpses into the lives and daily experiences of Regis’s students and faculty while chronicling the development of the school’s educational philosophy and spiritual approach in its first century. Filled with entertaining anecdotes alongside wider historical context and illuminating statistical analysis, Teach Me to Be Generous tracks Regis High School through the decades of the twentieth century to the present day—from the generosity of a devout Catholic widow, through the Depression and World War II, to changes in demographics of the Catholic community and shifts in the landscape of Catholic education in New York City. During the school’s first few decades, Regis admitted thousands of Catholic boys, mostly from poor or lower-middle-class families, helping prepare them for success in college and leadership positions in the professions. Because of the closing of dozens of urban Catholic schools and the general decline of the quality of New York City’s public schools, in more recent years the school has faced the challenge of remaining true to its mission in offering an education to Catholic boys “who otherwise would not be able to afford a Catholic education.” Teach Me to Be Generous paints a vivid portrait of the first one hundred years of an exceptional institution and looks with hope and confidence to its future.