Kessler, born in Crawfordsville, IN, grew up on Cape Cod and began playing trombone at age ten. He and his family moved to Chicago when he was 13, and a few years later Kessler became intensely interested in jazz. While attending St. Mary Center For Learning High School, he began taking lessons from Kestutis Stanciauskas (Streetdancer) in electric bass and jazz theory in the middle of the 1970s. In 1977 he formed the ensemble Neutrino Orchestra with percussionist Michael Zerang and guitarists Dan Scanlan and Norbert Funk. He spent a year in Brazil in 1980-81 and spent time studying off and on at Roosevelt University in Chicago; he and Zerang also formed a group called Musica Menta, which played regularly at local Chicago venue Link's Hall.
Kessler began playing double bass in the 1980s and it became his primary instrument when he was asked in 1985 to join the NRG Ensemble, who toured Europe and recorded for ECM Records under the leadership of Hal Russell until his death in 1992. In 1991, he gigged with Zerang and guitarist Chris DeChiata; in need of a hornist, they called Ken Vandermark, who had been considering leaving the Chicago scene. Kessler and Vandermark would go on to collaborate extensively on free jazz and improvisational projects such as the Vandermark 5, the DKV Trio and the Steelwool Trio. In the 1990s and afterwards he worked with leading Chicago musicians such as Hamid Drake, Fred Anderson, and Joe McPhee, and also with European musicians such as Peter Brötzmann, Mats Gustafsson, Misha Mengelberg, and Luc Houtkamp.