This study, based on research into a youth empowerment initiative in Canada, examines the transformational power of youth grants for marginalised youth and their communities. The positive changes on individual youth included increased confidence and skills, as well as strengthened social interactions between youth, and involved adults and organisations. To leverage grant impact, we identify the critical role of creating accountability at multiple levels, promoting sharing among grantees, and fostering allies and system thinkers. The evaluation points to the potential of grants for changing community's perception that youth are incapable of fostering community youth development. In the field of human development, attention is increasingly given to the role cash transfers and grants can play in reducing poverty and boosting the resilience of communities facing adversity (Hanlon and others, 2010). Interestingly, little of the discussion about this simple yet powerful tool has spilled over into either the child rights or community youth development sectors. Many programmes for vulnerable youth living in disadvantaged communities still apply a ‘charity’ approach that downplays the active role young people can assume in strengthening their own well-being and the resilience of their communities. This article examines cash transfers through youth grants as a mechanism for marginalised young people to act upon ideas and issues of importance to them. The study draws on an analysis of YouthScape (YS): a youth empowerment initiative in which almost 200 youth grants were allocated in four Canadian cities over a three-year period. With increasing interest in youth-granting in North America, this evaluation on the impacts and enabling conditions of the grants advances understanding of cash transfers as an entry point for reconnecting socially excluded young people with key adults, and as a tool for building important life skills and reinforcing aspects of community resilience.