The Troops to Teachers (TTT) program was created in 1994 to provide funds to recruit and support former members of the military as teachers in high-poverty schools. Most of the research on TTT participants has been positive, and leadership is often mentioned as an important factor in participants' successes. A number of these military veterans have moved from the classroom into school administrative positions. Initial research on these administrators based on the ISLLC standards has been positive. This multiple case study drew from interviews and surveys with 15 former military veterans currently administrating in K-12 schools to increase our understanding of the experiences and values that they bring to the classroom. It relied on Stake's (YEAR) case study methodology to surface findings. The five findings, presented in order of strength of evidence, include: 1) Participants' overarching leadership philosophy was taking care of the people. 2) The leadership that participants had witnessed in both the military and in education influenced their own leadership. 3) Not all of the participants utilized TTT. 4) Participants had classroom experiences that were consistent with previous research on new teachers. 5) The veterans' values as they relate to trust, delegating responsibility, accountability, and beliefs in service, merit future inquiry. These values, along with "taking care of their people", appear to be the commonality between the two seemingly incongruent cultures of the military and education. This study has implications for future research and educational leadership training both at the university and district levels.