This paper presents three stories-over-time of the secondary schooling experiences of New Zealand’s rangatahi Māori–or Māori youth. The stories span fifteen years of New Zealand schooling and are told from three perspectives: the experiences of the students as told in their own words; the voices of youth within the prevailing political contexts of government policy; and, the reframing and repositioning of researchers listening to the experiences of rangatahi Māori who believe they have succeeded as Māori. In reality, the stories are interwoven, however, in an effort to make sense of the various methodological dilemmas, risks, and entanglements across the three points of learning, we have endeavored to disentangle these different threads from the whole and follow these independent of each other. We then weave these threads together again, as we sense-make across this complexity to identify implications for other educators, policy makers and researchers.