In this lecture, held at Pardes as part of the Tisha B'Av program 2015, Jennie Rosenfeld looks at two different Talmudic stories of leaders who sin – one is the infamous Elisha ben Abuya and the other has no name that we know of. We will use this analysis as a springboard for a more contemporary discussion of leaders who sin today; what we as a community can best do to prevent this and respond to it.