The Black-Haired Man, played by Michael Shamus Wiles, is another Syndicate-employed marksman. He first  appears in the season 5 finale, "The End", where he executes fellow Man in Black The Shooter.
The Black-Haired Man, portrayed by Michael Shamus Wiles, is a Syndicate operative who appears in the season 5 finale of the show "The End." He kills The Shooter, another member of their team.