This article features James D. Donnelly Jr., principal of James A. Green High School in Dolgeville, New York. Donnelly, recipient of the MetLife/NASSP 2004 National High School Principal of the Year, exemplifies the foresight to think ahead, the wisdom to collaborate with colleagues, the resolve to take a stand, and the courage to take risks. His accomplishments include: creating a successful College Now program that allows high school students to earn college credit through courses at Herkimer County Community College; helping in the development and implementation of a block schedule to include a stronger academic intervention component to the school and to better the instructional climate; forming a districtwide faculty observation-evaluation system; creating a framework for consistent teacher-staff development; and implementing curriculum coordination both horizontally and vertically. Donnelly attributes his success as a principal to his collaborative effort with everyone in the school district, from faculty members and students to the custodial staff and bus drivers. Looking ahead, Donnelly said that he will examine how to address the issue of generational poverty in his school and in public education in general.