Roberto Estacado was a hitman during World War II. He was assigned to kill a man known only as Logan. Logan was in France at the time in a pub when Estacado arrived offering to buy him a drink. While Logan did not know of Estacado's ability to wield the darkness he knew his reputation as a killer who never missed. Logan proceeded to refuse the drink and departed. Estacado later found Logan and attempted to shoot him but Logan caught the bullet. Realizing this was no ordinary mark Estacado proceeded to unleash his dark power upon the unsuspecting target. Despite being momentarily surprised Logan cut his way through the dark creatures until he reached his target.
Roberto faced Logan with the Canadian mortally wounding Roberto. It is only by sheer luck that the Darkness Entity was able to survive as Roberto did not survive the encounter himself.