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For five years, Leonard sang with the Manhattan School of Music Children’s Chorus. She also attended the Joffrey Ballet School. She is a graduate of the Fiorello H. LaGuardia High School of Music & Art and Performing Arts. She earned her Bachelor and Master of Music degrees at the Juilliard School, where she was a pupil of Edith Bers. She has also studied with Marilyn Horne, Brian Zeger, Warren Jones, and Margo Garrett. She is a 2005 winner of a Marilyn Horne Foundation award. She is a recipient of a 2006 Licia Albanese-Puccini Foundation Award. She was also chosen as a recipient of a "Movado Future Legends" award in 2006.
In New York, Leonard has performed with the Chamber Music Society of Lincoln Center and with the Juilliard Opera Center. Her first appearance with the New York Philharmonic was in a concert version of Leonard Bernstein's Candide, and she later sang the part of the Squirrel in L'enfant et les sortilèges in concert with the orchestra and Lorin Maazel. In February 2007, Leonard made her professional operatic stage debut as Stéphano in Roméo et Juliette. In September 2007, she made her Metropolitan Opera debut in the same role. Leonard made her debut with Santa Fe Opera as Cherubino in 2008. Her commercial recordings include a DVD recording for Euroarts as Dorabella in the 2009 Salzburg Festival production of Così fan tutte. In February 2011, Leonard made her Vienna State Opera debut singing Cherubino in Le nozze di Figaro.
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