Gregory is a Tenor 1. Gregory was a paid chorister in the Harvard University Choir. UChoir prepares and performs at weekly services at Memorial Church in Harvard Yard and special concerts, like C.P.E. Bach’s Magnificat, Menteverdi’s L’Orfeo, and the Brahms Requiem. Gregory was a soloist in Keith Hampton’s “True Light” in the 110th Annual Christmas Carol Service, C.P.E. Bach’s Magnificat, “6. Deposuit Potentes” in the 2019 Fall Concert, Orlando Gibbon’s “Great Lord of Lords” in Sunday service on Nov 17, 2019, and Joseph Haydn’s “The Heavens Are Telling” from The Creation, Hob. XXI:2 (1797–98) in Sunday service on Sept 8, 2019.

Before attending Harvard, Gregory sang in the Young People’s Chorus of New York City. With YPC, Gregory performed in the largest concert halls all over the world, including Carnegie Hall and Lincoln Center. With YPC, he traveled to the Dominican Republic, Switzerland, China, and Japan. He was a featured soloist on US national radio. He has appeared on national TV on CNN on Christmas morning, Ground Zero on 9/11, and Interfaith Service with Pope Francis at the 9/11 Memorial Museum. In 2011, YPC was a National Arts and Humanities Youth Program Awardee, and Gregory performed at The White House for President Obama. Additionally, Gregory premiered many new vocal compositions as part of the Transient Glory commissioning program.