Gustav Mahler’s impact on Leonard Bernstein’s career is undeniable. Empathizing with Mahler’s dual role as conductor and composer, Bernstein commented that both he and Mahler led double lives. Bernstein continued emphasizing his connection to Mahler, notably in an essay entitled ‘Mahler: His Time Has Come’. Ultimately, his appreciation of Mahler’s music spanned a lifetime and Bernstein eagerly advocated for recognition of Mahler’s genius. This chapter focuses on three events during Bernstein’s New York Philharmonic years that illustrate the importance of Mahler to Bernstein’s tenure: the 1960 Mahler Festival, the 1963 death of John F. Kennedy, and the 1967 Mahler symphonic recordings. Although these three events are in no way all-encompassing of Bernstein’s efforts to reintroduce Mahler to the world, they outline the trajectory of the New York Philharmonic throughout the 1960s and show how Bernstein educated and inspired his audiences to a new appreciation of an old composer.