Youth Liberation Army (YLA) is a youth-led grassroots organization advocating for school abolition and addressing issues most concerning young people in schools and communities. YLA utilizes adult ally trainings to invite educators to work toward liberatory education. The transformative organizing practices of YLA are examined through a youth activism framework to discuss how young people and adult allies may collaborate to disrupt systemic injustices in schools and communities. Findings from a critical qualitative Project in Humanization are shared to examine the power and purpose of an adult ally training facilitated by YLA in a conventional teacher education program (TEP). Through critical listening and dialogic spiraling, reflections and implications on intergenerational collaboration are provided by a researcher-teacher educator and a participant-youth organizer. The dynamics between YLA, teacher candidates, and a teacher educator highlight the significance and possibilities of intergenerational collaboration when youth organizers are welcomed into TEPs as co-educators.