Through long interviews with five outstanding male educational leaders, the authors share their stories and primary lessons on leadership development. The stories portray leadership as being perceived primarily as an evolutionary process characterized by family and teacher nurturance, community and spiritual centeredness, and responsive caring. This study aims, primarily, to share the stories of these exemplary leaders. Secondly, the researcher hopes that the findings and conclusions might contribute to the discussion on how such responsive and effective leaders evolve. The researchers emphasize the celebratory purpose of the study, and caution against generalizations to leadership theory.