Yotam Silberstein grew up in Tel Aviv and started on guitar at ten, playing rock and blues before jazz entered the picture. At fifteen he was accepted into the Thelma Yellin high school for the arts, where he studied jazz with Walter Blanding and Amit Golan. He served three years in the Israel Defense Forces as a musical director, arranger, and lead guitarist, and at twenty-one won Israel's "Israeli Jazz Player of the Year" title with his own trio, a win that landed him a booking at the Umbria Jazz Festival in Italy.

His recorded debut, The Arrival, was cut in July 2003 and released the following year on Fresh Sound New Talent, credited to the Yotam Silberstein Trio: guitar, bass, and drums with players he'd known since high school. The album's reception opened up touring across Europe and the Middle East.

In 2005, a scholarship brought him to The New School in New York, where he began studying with Barry Harris and Kurt Rosenwinkel. Saxophonist James Moody discovered him not long after, and for years Silberstein built his reputation the way most serious New York jazz careers get built: as a sideman first. He worked with the Dizzy Gillespie All-Stars, trumpeter Roy Hargrove, clarinetist and saxophonist Paquito D'Rivera, and singer Ivan Lins, and shared stages with bassist Christian McBride, pianist Aaron Goldberg, and drummers Gregory Hutchinson and Eric Harland. The New York Times took notice, describing a guitarist playing "in a cutting tone" with "heady original tunes that seem to tug the straight-ahead jazz tradition in new directions."

As a leader, his catalog runs eight albums since Next Page (2009, Posi-Tone), his first American recording, made with organist Sam Yahel, saxophonist Chris Cheek, and drummer Willie Jones III. Resonance (2010) and Brasil (2011) followed in close succession, the latter his first deep dive into Brazilian jazz, cut with guests Toninho Horta, Roy Hargrove, and Paquito D'Rivera. The Village (2016), built around a "global village" concept spanning Middle Eastern, Spanish, Argentine, and Brazilian material, earned 4 1/2 stars from DownBeat. Future Memories (2019) brought in bassist John Patitucci, who returned in 2024 alongside tenor saxophonist George Coleman and drummer Billy Hart for Standards, Silberstein's eighth leader album and his first devoted entirely to jazz standards repertoire, pulling from Miles Davis, Rodgers and Hammerstein, Victor Young, and Tommy Flanagan. A second volume, Standards, Vol. 2, followed in April 2025, drawn from the same studio sessions.

In June 2026, Silberstein released Duets, a full album co-billed with bassist Ron Carter, arguably the most recorded bassist in jazz history. Conceived as a tribute to Carter's own duo recordings with guitarist Jim Hall, the album was recorded at Rudy Van Gelder's studio in Englewood Cliffs, New Jersey, tracked on December 4th, Hall's birthday, deliberately. Eight tracks split between standards and two Silberstein originals, "Blues For Brother Malone" and "Rain Again."

He is now on faculty at The New School's School of Jazz and Contemporary Music, the same program that first brought him to New York two decades earlier, and opened a Patreon for lessons and playlists in January 2025.

Silberstein's playing is rooted in bebop and blues, the vocabulary he absorbed studying with Barry Harris in New York, layered with the musical folklore of South America, North Africa, and the Middle East, an inheritance of growing up in Tel Aviv and later immersing himself in Brazilian material for albums like Brasil and The Village. Reviewers and the New York Times alike have singled out a "cutting tone" and original compositions that push at the edges of straight-ahead jazz tradition rather than simply restating it. His Standards and Standards, Vol. 2 records, by contrast, show a player equally comfortable inside the jazz standards canon, working with a rhythm section (Patitucci, Hart, and guest George Coleman) drawn from an older generation of the music's own history.