Although there's almost nothing known about The Rambling Man's past, it's implied that he was investigating Jack. As with the case with those who attempt to look into Jack and the murders/disappearances he commits, this resulted in a face-to-face encounter with Jack. The encounter managed to drive the man insane, becoming increasingly paranoid and reclusive, holding himself up in his shack where he awaited his fate at Jack's hands.
The Nightmare of Samuel Ward (Short story)
During Samuel Ward's nightmare, the private detective found himself inside The Rambling Man's shack. The place was covered in sketches, frantic writings, and newspaper clippings related to Jack. Samuel Ward witnesses the man contemplate suicide before the man noticed his presence. Seeing the the determination in Samuel Ward's eyes, the same determination he had before his encounter with Jack. Grabbing a hold of Samuel Ward, the man attempted to warn the startled detective against going any further. Before he could further explain himself, the man sensed Jack's arrival and urged Samuel Ward to hide. Once the detective was hid away, the man was confronted by Jack. The man attempted to plead for his life, but was silenced by Jack who lifted the man into the air by his throat. Slowly choking to death, the man desperately attempted to free himself from Jack's grip but was soon killed when Jack coldly snapped his neck. The Man's body was soon teleported away with Jack to an unknown location.
The Rambling Man is described in the original short story as a disheveled man possibly in his late-50s or early-60s. The man's skin is partially discolored due to his shut in nature, and his body is thin and gangly. His wild hair and scruffy beard are evidence to the man's lack of personal maintenance and his eyes are partially glazed over and wild with madness.
Nothing is known on the original personality of The Rambling Man. It's quite possible that he had the same obsessive drive as Samuel Ward since it's implied that he attempted to look into the murders and disappearances committed by Jack. After a face-to-face encounter with Jack, The Man was driven insane and is now a pitiful shadow of the man he once was. His mind ravaged by his encounter with Jack, The Man shut himself away from the rest of the world, covering the inside of his home with sketches and insane notes on Jack. Like his name suggests, his incessant ramblings to himself are just a few symptoms that resulted in his encounter with Jack. When Samuel Ward meets The Man in his nightmare, he witnesses The Man contemplate suicide, showing The Man's hopelessness and willingness to give up on life. Although insane, The Man is should to be able to reason, as is evident when he sensed that Samuel Ward shared a similar drive to uncover the truth and warned him against going any further.
- It's hinted that The Rambling Man was an actual person murdered by Jack, and Samuel Ward was witnessing a replay of his brutal murder.