Although federal funding has been provided to add mentoring to youth development programs for decades, we still lack knowledge about the impacts of mentoring on youth outcomes. This research seeks to fill a gap by documenting youth outcomes from an enhanced mentoring approach for urban Boys and Girls Clubs (BGC) in the Southeastern United States delivered by paid staff who serve as mentors through group activities and 1:1 interactions with youth. We perform logistic regressions of secondary data from a cohort of BGCs to understand the relationships between enhanced mentoring and youth outcomes related to program retention, behaviors, and academics. We find the presented approach has a significant relationship with retention with those mentored being 1.92 times more likely to return the following program year. Mentored youth also experienced higher expectations from staff and were less likely to be involved in a physical fight with peers.