A writer and social justice advocate, Jackson was raised in Northeast Portland and arrested on drug charges in 1996 while attending Portland State University. In prison, he discovered a passion for literature, going on to earn graduate degrees in writing. His debut novel, The Residue Years, won major literary awards, and in 2021 he won the Pulitzer Prize in Feature Writing for his reporting on the killing of Ahmaud Arbery. He continues to visit prisons and youth facilities as part of his advocacy work.