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Through the amplification of the voices of 10 Latino male youth in one New York City public high school, this qualitative study uses portraiture methodology to render visible the practices of one educator that his Latino male secondary students identified as successful in supporting their educational potential. Findings indicate the saliency of pedagogies that embrace failure as a requisite element of learning, leverage academic peer support and demonstrate a willingness to be vulnerable with Latino male youth. The resulting portrait also encourages consideration of how more explicit attention to students’ cultural and linguistic practices as well as the development of Latino male students’ sociopolitical awareness could further support the academic and personal growth of these young men.