Born in Columbus, Ohio in 1985, Diehl grew up in a musical family as the grandson of pianist/trombonist Arthur Baskerville. Introduced to piano at age seven, Diehl first became interested in jazz while attending the Interlochen Fine Arts Academy Summer Camp. A prodigious talent, Diehl performed with the Columbus Youth Jazz Orchestra in his teens, and was a finalist in the 2002 Jazz at Lincoln Center Essentially Ellington competition, where he took home an "outstanding soloist" award. The following year, he accepted an invitation to tour with trumpeter Wynton Marsalis' septet and enrolled in Juilliard's then newly minted jazz studies program. During his time at Juilliard, Diehl studied with several luminaries, including pianists Kenny Barron and Eric Reed. Also during this time, he garnered several more accolades including winning the 2003 Jazz Arts Group Hank Marr Jazz Competition and Lincoln Center's prestigious Martin E. Segal Award in 2004. In 2006, a year before graduating Juilliard, he released his debut album, Mozart Jazz, on Japan's Pony Canyon label. The concert album Live at Caramoor followed two years later. Diehl then appeared on vocalist Cecile McLorin Salvant's highly lauded, Grammy-winning debut, 2013's WomanChild.
Also in 2013, Diehl released his sophomore album as a leader, 2013's The Bespoke Man's Narrative, on Mack Avenue. In 2015, he returned with his third studio album, Space Time Continuum, which featured appearances from saxophonist Benny Golson and others. The Vagabond arrived in 2020 and featured the pianist's trio with bassist Paul Sikivie and drummer Gregory Hutchinson. ~ Matt Collar, Rovi