[1] Eskelin has resided in New York City since 1983 and has led numerous international touring ensembles while participating as a sideman or collaborator with many of today's most forward-thinking composers and improvisers.

Eskelin has maintained lasting musical associations with Joey Baron, Mark Helias, Gerry Hemingway, Marc Ribot, David Liebman, Han Bennink, Sylvie Courvoisier, Bobby Previte and Daniel Humair among others.

Musicians from New York often passed through Baltimore to perform on the weekly Sunday afternoon Left Bank Jazz Society concert series presented at the Famous Ballroom.

Early performances as a leader took place at various jazz clubs such as "The Bandstand" and "The Closet" run by saxophonist and entrepreneur Henry Baker, who had a long history in the Baltimore music scene having known Lester Young, Cannonball Adderley, Miles Davis, Red Garland, John Coltrane, Clifford Brown and many others.

Also in 1979 Eskelin encountered bay area saxophonist Mel Ellison who was performing in Baltimore for an extended engagement with trumpeter Ted Curson's group.

[7] In an effort to deepen his understanding of be-bop Eskelin attended nightly informal jam sessions for several years at a local club called the "Star Cafe" on 23rd Street and Seventh Avenue in Manhattan.

During the summer of 1984 Eskelin joined organist Jack McDuff's band (which featured guitarist Dave Stryker and drummer Joe Dukes) on a regular engagement at Dudes Lounge in Harlem.

Laying the groundwork for these explorations were studies with saxophonist David Liebman which led to informal jam sessions and eventually a working professional relationship.

This group, featuring Parkins on accordion and electronics and Black on percussion released "Jazz Trash" in 1995 and followed up with a dozen recordings over the ensuing decade and into the 2000s primarily for the Swiss-based Hat Hut label.

In the liner notes to "One Great Day..." (the band's second release) Eskelin explains that the fractured and sometimes incongruent nature of his experiences as a musician coming up in the 1970s and 1980s finally came together in a manner that made sense and could be expressed in a unified musical language with this ensemble.

Throughout the first decade of the 2000s Eskelin focused primarily on his group with Andrea Parkins and Jim Black, touring and recording, occasionally augmenting the band with additional musicians such as vocalist Jessica Constable, keyboardist Philippe Gelda, cellist Erik Friedlander, tubist Joseph Daley, guitarist Marc Ribot and bassist Melvin Gibbs.

During this time Eskelin also continued launching new projects of his own (leaning towards complete improvisation) such as "Vanishing Point", a group-improvised recording from 2000 with Mat Maneri (viola), Erik Friedlander (cello), Mark Dresser (bass) and Matt Moran (vibraphone).

[8] Trio New York incorporates standard material from the Great American Songbook (much of the repertoire being inspired by his mother, organist Bobbie Lee) in a freely improvised setting.

Eskelin remarked that he was interested in exploring the "expressive range of the saxophone that is perhaps most associated with its beginnings" and that his objective is to "bring that type of lyricism to the language of contemporary improvised music.