The L.E.A.D. Program implements two Legacy Projects, annually: Power of Potential Youth Conference and Challenge Cup. Both events are planned, organized, and facilitated by teacher candidates with the goal of engaging in-risk youth in various capacities. Taking place in the fall, the Power of Potential Youth Conference allows local high school students to explore some of their options for life after secondary school through a series of presentations and workshops focusing on Financial Literacy, Healthy Active Living, and Career Exploration. Taking place each spring, Challenge Cup is an outdoor event that fosters leadership, character development, and self-confidence in local secondary students. Students participate in a series of physical activities throughout the day which focus on building team-work, community, and leadership skills. This chapter explores how both L.E.A.D. Legacy Project events support secondary students outside of the classroom. The planning and organization of both events will be explained.