Sydney artist, Nigel Milsom, has won the AUD150,000 acquisitive Doug Moran National Portrait Prize—now in its 25th year—from behind bars. Milsom’s works channel the condition of loneliness or the singularity of the human experience—a sensation that may be all too familiar for the artist, who is currently serving a six-year jail sentence for robbery and assault he committed while on a drug binge in 2012.