Jon Nathaniel Loveless was a former Starfleet Commander and Maquis cell leader. Loveless and his younger brother, Jason were born on a Federation colony near the Cardassian border.
He entered Starfleet Academy in the mid-2350s, where his charisma and natural leadership abilities earned him the respect of his peers and underclassmen, including Ben Bartholomew.
Loveless resigned his commission in the late 2360s and became one of the founders of the Maquis resistance. During that time, he befriended Davin Andersen. In 2370, he met Bartholomew at Starbase 47, and eventually convinced him to join the Maquis. (Star Trek: Pendragon: "Children of the Burning Heart", "The Good Fight")