It is possible that in the future there may be a conjuncture of mass retirement of existing principals with a teacher shortage. We examine a range of data sets to examine this proposition. We consider the age profile of principals and teachers, the expressed career preferences of young teachers and the trajectory of teacher supply. We also examine employment statistics from three major state systems to see existing patterns of application, promotion, and retention. We come to the tentative conclusion that the shortage scenario does have some justification.