Scenario: Detective hunt!

[MorphyVSFischer]

Dick Tracy, The Question (Post Crisis, Vic Sage), Rorschach, Sherlock Holmes, and The Shadow are all dropped in a random spots in modern day NYC. They must all find and kill each other while staying within the city bounds.

Rules: I am aware there are some versions of the Shadow with supernatural abilities but for this he does not.

2) Everyone gets standard equipment to start but may make use of the city around them if they wish.

3) No outside interference of any kind.

[Powerboy]

Dick Tracy, The Question (Post Crisis, Vic Sage), Rorschach, Sherlock Holmes, and The Shadow are all dropped in a random spots in modern day NYC. They must all find and kill each other while staying within the city bounds.

Rules: I am aware there are some versions of the Shadow with supernatural abilities but for this he does not.

2) Everyone gets standard equipment to start but may make use of the city around them if they wish.

3) No outside interference of any kind.

Assuming this is Holmes from the original source material, he's going to be operating under an extreme handicap in that he has no knowledge of modern technology. Physically, he's well with the limits of a real life human. I don't remember much about Dick Tracy other than the radio watch or whatever it was. But the Shadow seems kind of a ringer here. Even in his non-telepathic versions from the earliest books, he still has invisibility (regardless of whether it's telepathy or a skill, it still allows him to be unseen in situations where, for all practical purposes, it's a power). His physical abilities are certainly on the Rorschach level. I'd say the Shadow takes this rather easily.