Creative Academy was an alternative high school program in the Newburgh Enlarged City School District, 60 miles north of New York City in the Mid-Hudson Valley region of New York State. The 86 students previously attended one of three junior high schools or the 2800 student Newburgh Free Academy, the only high school in the District. Selected students had potential and promise but were not succeeding in traditional school settings. They needed a smaller, more nurturing environment. The Academy's doors were open from 2002 through 2004. This qualitative research study addresses a fundamental problem facing educators in similar academic settings: How can teachers successfully meet the instructional and emotional needs of students who have experienced limited academic success in school? This study explores the critical relationship between staff, students, and parents. Interviews primarily with eight staff members and secondarily with five Creative Academy students and five parents form the basis of the study. Four broad themes emerged from a pilot study with the Creative Academy staff and students. Those themes are reflected in the following research questions: (1) What practices did teachers and support staff utilize to meet the educational and social needs of students at Creative Academy? (2) To what extent did the staff create and sustain an ethic of caring in their attempt to establish meaningful connections with the students at Creative Academy? (3) What tensions arose for faculty and staff of Creative Academy as they worked with children, families, and the larger educational community? (4) What did the program mean to the students at Creative Academy? Interviews with teachers, counselors, parents, and students were triangulated to achieve a balanced perspective about the Creative Academy experience. This study has implications for the development of small learning communities and recommends that attention be focused on the emotional needs of students including self-esteem, the need to be cared for, and interpersonal relationships of trust between teachers and students. It also identifies potential challenges and pitfalls when designing innovative initiatives like Creative Academy.