Robert Kennedy’s transformation from a conservative investigator to a liberal politician is a political legend. Kennedy started his career investigating corruption in labor unions—a bastion of liberal support. His career, and life, ended while campaigning for president as a champion of the poor and opponent of injustice. His brother President John Kennedy’s assassination is often cited as the origin of Robert Kennedy’s transformation. By examining Robert Kennedy’s anti-juvenile delinquency efforts, this project demonstrates that his commitment to fighting poverty started as Attorney General and before his brother’s death. I also show how Robert Kennedy’s insistence on local solutions to juvenile delinquency differed from the solutions offered by other liberals. I use congressional testimony, his books, and archival sources from John F. Kennedy Presidential Library to examine Robert Kennedy’s views on juvenile delinquency and poverty. This research challenges the dominant narrative that Kennedy’s political reorientation was solely sparked by the death of his brother President Kennedy. It also highlights an often under discussed topic—how Kennedy differed from other liberals of his time.