Shai Maestro started on classical piano at five. Three years later, an 8-year-old in Israel heard Oscar Peterson's Gershwin Songbook for the first time, and that was the record that turned him toward jazz. Keith Jarrett came into the picture not long after. Both names still show up whenever Maestro talks about where his ear comes from.

He won Israel's "Jazz Signs" national jazz ensembles competition twice, in 2002 and 2003, while still a student at the Thelma Yellin High School of Performing Arts in Givatayim. The America-Israel Cultural Fund backed him with jazz piano scholarships from 2004 through 2010. Somewhere in that stretch he attended Berklee College of Music's five-week summer performance program and was offered a full scholarship. He turned it down.

What happened instead is the story most people tell first when they talk about him. Bassist Avishai Cohen heard Maestro play, still in his late teens, and pulled him into his touring trio alongside drummer Mark Guiliana. Cohen already had one of the most respected ears in Israeli jazz by that point; he didn't hand a touring seat to a name, he handed it to a teenager at the piano. Maestro's recorded debut with the group arrived on 2008's Gently Disturbed and Sensitive Hours, followed by Aurora (2009) and Seven Seas (2011). Four albums, and a young pianist's real education happening on stage every night rather than in a classroom.

He stepped out as a bandleader around 2010, forming a trio with bassist Jorge Roeder and drummer Ziv Ravitz (Ofri Nehemya has since also filled the drum chair). Their debut, Shai Maestro Trio (2012, Laborie), was followed by The Road to Ithaca (2013, Laborie), Untold Stories (2015, Motéma), and The Stone Skipper (2016, Sound Surveyor). Three labels in four albums. Then, in 2018, came the jump that mattered most: ECM Records, the German label that has spent decades defining a spare, exacting sound through Keith Jarrett, Paul Bley, and Chick Corea. Signing there put Maestro's name in that same sentence.

His first ECM record, The Dream Thief (2018), was followed in 2021 by Human, ten tracks that include a closing cover of Duke Ellington's "In A Sentimental Mood" featuring trumpeter Philip Dizack. The cover matters: it's proof he can sit inside the jazz standards tradition on purpose, not just orbit around it.

Before The Guesthouse, Maestro made a quieter turn: Solo: Miniatures & Tales (2025, Naive), his first record entirely alone at the piano, no trio, no guests.

The Guesthouse, out March 6, 2026 on the Naive label, breaks the pattern again. It's his most collaborative record yet, built around Rumi's poem of the same name, using the image of a guesthouse with an open door for musical guests to enter freely. MARO, Michael Mayo, and Immanuel Wilkins all appear. For the first time, Maestro wrote his own lyrics and worked electronics into the sound. Reception has split: one review called it "a brave and distinctive artistic statement," while another argued the record is missing a central core beyond the lyrics and the added instrumentation. Both readings are worth knowing before you press play, because this is not a safe record and it doesn't try to be one.

Five labels, eight albums as a leader, and a stylistic range that runs from ECM's spare standards-rooted trio work to Naive's electronics-and-lyrics experiment. Nearly two decades after a bassist heard a teenager play and changed his life, Shai Maestro is still the one changing his own sound, record by record.

Maestro names Oscar Peterson and Keith Jarrett as his earliest and most direct influences, going back to age 8. Reviewers reach for a different comparison once they hear his ECM records: Keith Jarrett again, but also Paul Bley and Chick Corea, the three pianists whose names are inseparable from ECM's own aesthetic under producer Manfred Eicher. American pianist Brad Mehldau is also frequently named as a stylistic peer, particularly for the lyrical, narrative quality both players bring to trio improvisation.

His own sound sits on a lyrical, narrative core: a strong sense of storytelling inside a solo, built on sophisticated odd-meter writing and a rhythmic imagination that keeps the trio format from ever going stale. He treats jazz tradition as something to build on rather than repeat, which is the throughline connecting a standards-rooted ECM record like Human to a genre-crossing experiment like The Guesthouse.