Present attempts to transform the meaning and purposes of schooling through a radically reformed notion of leadership are examined in this paper. The first part presents a framework that explains the mechanisms through which school cultures are produced, reproduced, and transformed: pedagogy, curriculum, assessment, and discipline. The first puzzle of culture and leadership involves cultural formation and cultural difference. The paper refers to the cultural battles that occur under the umbrella of the pursuit of modernity; the transformation of social structures increasingly dominated by industrialism, capitalism, surveillance, and control; the shifts in cultural formation and production that result; the battle between lifeworld and system; the dangers of a commodification of culture and the emergence of repressive regimes of power and of a political economy of truth that, among other things, is produced and transmitted under the control of a few great political and economic apparatuses. These are battles that effect both individual and collective futures. Because schools are centrally concerned with such futures, school leaders must understand these issues and the ways in which they are articulated through the school's message systems. The second puzzle involves purpose and practice in the school. Alternative implications of current attempts to refashion the four message systems are described. The third puzzle examines leadership as a moral question; choices made by educational leaders are historical in that they change history and are judged by history. (Contains 12 references.) (LMI)