This essay will discuss two educational programs to improve the living conditions of students from low income families that Pedro T. Orata conducted during the middle years of the twentieth century. The question this paper will investigate is whether Orata considered the people he was trying to help as being trapped by the conditions of poverty to the extent that they required the assistance of trained leaders to rise from their depressed circumstances. Although this paper is limited to the personal views of Orata, it may suggest something about the conceptions that progressive educators held about the problems of poverty in the first half of the twentieth century.