This paper tells the remarkable and compelling story of Leonard Covello, a ground breaking progressive educator who worked tirelessly to shape public education in New York City during the first half of the 20th century. Covello was the founding principal of Benjamin Franklin High School (BFHS) in East Harlem in the 1930s. The author invites everyone to explore a little known part of the past and frames a critical discussion about what the future might be. The major objective of this study is to examine Covello's work within the twin frameworks of educational leadership and progressivism. It begins by providing a biographical sketch of Covello and then explores his professional and personal philosophy and the way that these played out in his roles as educational and community leader, sociopolitical activist, and community ethnographer. It then examines BFHS as a new paradigm for educational institutions, with an emphasis on its pioneering work in developing student leaders, engaging in community activism, and promoting intercultural education. Finally, it looks at the larger implications of Covello's work in an era of increased emphasis on testing and standardization. By looking back to Covello's work, the author locates the problems of our present situation in schools' retreat from a core progressive goal--the development of social capital within students and community members. (Contains 3 footnotes. Introduction written by Patrick Shannon.)