He was a member of Thelonious Monk's regular group from 1970–1975, and also worked extensively with other musicians such as Charles Mingus, Dizzy Gillespie,[3] Clark Terry, Lionel Hampton and B.B.

King,[5] after which he worked as a freelance musician in the New York City area and toured with bands led by Howard McGhee, Clark Terry, and Dizzy Gillespie.

[8] In the 1970s, Jeffrey served on the music faculties at the University of Hartford, Rutgers University,[5] Jersey City State College along with leading his own Octet consisting of Paul (Tenor Saxophone), Alex Foster (Alto Saxophone), Sam Burtis (Trombone), Artie Simmons (Trombone), Oliver Beaner (Trumpet), Jim Roberts (Piano), Mattifias Pierson (Bass) and Chuck Zeuren (Drums).

The band members were Paul Jeffrey on tenor sax, Thelonious Monk Jr. on drums, Richard Davis on acoustic base, and Jack Wilkins on electric guitar.

In 1983, Jeffrey joined Duke University as Artist in Residence and Director of Jazz Studies, positions he held until he retired and became Professor Emeritus in 2003.