This chapter addresses the educational experience of Puerto Ricans in New York City. In so doing, it explores (1) the results of the educational experience, as reflected in student achievement; (2) a number of theories often advanced to explain student outcomes; (3) the historical context and its effect on education; (4) the response of the Hispanic community to the problems in education; and (5) some ideas on how to improve the current educational situation. An important theme in this chapter is that within the educational system an educational dynamic has been institutionalized that involves a number of components in an assimilation dialectic. These components are the system (teachers, schools, and the values they try to inculcate) and the new entrants (students, parents, and their values and aspirations). These interact to create the results (educational outcomes and changes in the system).