Born in Israel in 1987, Maestro began playing piano at age five and excelled, eventually graduating from the Thelma Yellin High School of Performing Arts in Givataim, Israel. During this period, he won the Jazz Signs National Jazz Ensembles Competition in 2002 and 2003, and earned scholarships from the America-Israel Cultural Fund for jazz piano. After high school, he attended Berklee College of Music's five-week Summer Performance Program in Boston. Although he was offered a scholarship to attend Berklee, he declined and instead joined bassist Avishai Cohen's trio with drummer Mark Guiliana.
With Cohen, he toured and made his recorded debut, appearing on Gently Disturbed and Sensitive Hours in 2008. Aurora followed in 2009 (the year Maestro relocated to New York City) and Seven Seas in 2011. A year later he issued Shai Maestro, the debut album of his trio featuring bassist Jorge Roeder and drummer Ziv Ravitz, for Laborie Jazz. Over the next two years, Maestro's trio toured the world, sharing stages with artists like Chick Corea, Tigran Hamasyan, Esperanza Spalding, and others. In 2012, he returned with his sophomore trio album, The Road to Ithaca. This was followed by Untold Stories in 2015 and The Stone Skipper in 2016. He then joined Theo Bleckmann for the singer's 2017 album, Elegy. In 2018, Maestro made his ECM debut with The Dream Thief, featuring bassist Roeder and drummer Ofri Nehemya. For 2021's Human, Maestro expanded his trio to include American trumpeter Phillip Dizak, with whom he had played on numerous New York bandstands. Working at Studios la Buissonne with producer Manfred Eicher, the group cut ten Maestro originals and a reading of Duke Ellington's "In a Sentimental Mood." ~ Matt Collar, Rovi