Complex sentence: He supported his family through working as a long-haul trucker, and had been doing this since around the late 1980s until his eventual apprehension by law enforcement authorities in 2008.
Split into simpler sentences: He supported his family through working as a long-haul trucker and had been doing this since around the late 1980s. His twenty some year long career as a long-haul trucker was abruptly ended when he was apprehended by law enforcement authorities in 2008.