Hi all, I watched an episode of Haunted History (The Murder Castle) last night and they came up with an interesting theory.
Apparently H H Holmes dropped off the radar at roughly the same time that the Ripper murders happened...
Also (apparently) a handwriting expert says that Holmes' writing matches the "Dear Boss" letter...

As per usual, take all of the above with a (very large) grain of salt, but it has definite storytelling possibilities for a follow-up show if you have already run a "Jack the Ripper" show.

As you suggest, Geoffrey, it's a silly theory. Their methods were different. Their targets were different. And their personalities couldn't have been more different: Holmes wanted to stay out of the spotlight and quietly satisfy his desire to kill; Jack wanted nothing more than to play his deadly game of Cat & Mouse in the public eye.

Just a reminder that Haunted History isn't a documentary, it's sensationalistic TV. In my opinion, the handwriting analyst is just using it for 15 minutes of near-fame.

Hi Necromancer, I agree totally
The "Dear Boss" letter was always thought to have been a hoax by a journalist, in order to sell more newspapers, but our audience don't need to know that minor detail...