This is the astonishing ranking of the Sherlock Holmes villains from my new book, Wherever Fact May Lead Me: A Ranking of the Sherlock Holmes Stories, every day till we reach the greatest villain. You can find the rankings on my website, and you can buy a copy of the book on Amazon.
Ranking the Sherlock Holmes Villains
Tier One: The Stars of Holmesian Villainy
These villains are recognizable for their ingenuity and, save for one, are extraordinarily powerful characters on the page. These miscreants are wily, awful, and heinous, and each is a worthy adversary of Sherlock Holmes.
10. “Holy” Henry Peters/Rev. Dr. Shlessinger and Annie Fraser, Lady Frances Carfax
The Australian pair are led by the husband, a fraudulent religious type in the vein of Keith Raniere, Ron Hubbard, and Peter Popoff. Henry Peters and Annie Fraser proceed with cunning and malice, and their machinations are clever. Peters and Fraser thwart Watson and Carfax’s knight in shining armor, Philip Green. Peters and Fraser nearly get the best of Holmes. The coffin trick is an brilliant one, and it takes Holmes quite a bit of time to figure out what is happening. If not for a chance remark, made off-hand by the undertaker, then Carfax would have surely gone all the way to the grave, instead of diverting course when half-way there. Holy Peters and Fraser also escape justice. Their plan is, more or less, a success. They have pawned some of Carfax’s jewelry, and so made a profit. They have escaped from their predicament without having committed a murder. No doubt, to rogues of their cloth, they will undertake similar escapades in the future, and hopefully then—if the good public has any luck—Peters and Fraser will caught, tried, and imprisoned.
9. John Clay aka Vincent Spaulding, The Red-Headed League
John Clay can reasonably be attributed to being lead villain in the first of many Holmes stories in which an elaborate ruse is created that draws a person from their intended place or occupation. This type of device is used again by “Killer” Evans in The Three Garridebs. And other stories’ plots derive from it: The Stock-Broker’s Clerk, The Resident Patient, and, to a lesser extent, The Adventure of the Dying Detective (in which Holmes’ ploy draws out the villain). But at the font of this wellspring lies John Clay. The originator of the Red-Headed League, Clay’s inventiveness must have caused the London reading public to marvel. Clay was as cool as ice when caught, and he retained his manners and diplomacy. In him, we find a villain whose cleverness is as great as, or nearly as great as, Holmes’, thus making him an admirable foil.
8. James Winter, aka Killer Evans, The Three Garridebs
If James Winter is Doyle’s American, gun-toting version of John Clay, then Winter is a superb variant. In fact, Winter is the best of all of Doyle’s American characters, partly because he has cleverness, and also partly because he does so little talking. Compared with John Clay, Winter is coarser, more violent, and less aristocratic. Yet it is Winter who nearly inflicts on Watson a mortal wound, and it is Winter (and not Clay) who draws Holmes’ most livid ire. Had The Three Garridebs been written and published before The Red-Headed League, I believe that it is likely that Winter would go down in literary history as one of Holmes’ greatest enemies, rather than being forgotten to all but the most ardent of Holmes enthusiasts. As it is, Time has seen the shadows grow long over Winter, while Clay has grown accustomed to an even and steady light.
7. Maria Gibson, née Pinto, Thor Bridge
Far and away the most committed villain on this list, Maria Gibson of Thor Place, Hampshire, is also perhaps the most calculating villain in the canon. Passionately in love, fanatically jealous, and wretchedly unhappy, Maria Gibson seeks to feed three birds with one scone. She hopes to deliver herself from her unhappiness, to ruin the happiness of the man who jilted her, and to destroy her romantic rival. She nearly completes the trifecta, and likely she would have if not for Holmes. Her method of suicide was absolutely matchless. In the very first line of the very first story, Watson says that Holmes refers to Irene Adler as “the woman.” It is this reader’s opinion that Maria, originally of Manaus, Brazil, surpasses Adler by a full length in the race to see which woman is the most formidable in the Holmes canon. Only (in my opinion) because Holmes hadn’t had Maria Gibson to compare Irene Adler with does Irene receive the vaunted title of the woman. But though Adler shines brightly, Maria Gibson scintillates. She is absolutely unwavering and wily, and the only reason that she does not rank as the premier villain on this list is that, thanks to her own actions, we do not get to meet her. Paradoxical it is: Maria is well regarded because of what she does, yet she cannot be regarded any better because of what she did. The sword cuts both ways, and a brace of pistols proves to be both Maria’s medium and her undoing.
6. James Wilder, The Priory School
Wilder is a sort of one-of-one in the Holmes canon, and The Priory School is, in its own way, a very unique story as well. The bastard son of the Duke of Holdernesse, James Wilder’s misbehavior is purportedly the result of a spoiled upbringing. However, it seems that the strain of deviance is congenital. For Wilder’s father behaves no better than his son when it comes to protecting the welfare of his younger child. Rather than rescue the kidnapped child at once, the duke leaves his son, Lord Saltire, with Reuben Hayes of the Fighting Cock Inn—a man who is a known murderer. While neither Wilder nor the duke display the moral courage, care, or judiciousness requisite for men of their station, Wilder is proactively evil, and, as a man who kidnaps his own brother, finds himself in elite company on this list of villains.
5. Jonas Oldacre, The Empty House
I have a feeling about Oldacre that recalls ACT equivalency questions, viz.: that Jonas Oldacre is to Josiah Amberly as John Clay is to James Winter/Killer Evans. Just as Oldacre and Clay are the originals, Killer Evans and Josiah Amberly are their facsimiles. Curmudgeonly, miserly, cunning, and cruel, Jonas Oldacre takes out a decades-old vendetta on the unwitting son of a woman who spurned him. By faking his homicide and framing the innocent lad for his murder, Oldacre carries out an act so heinous that, even today—in our society which is somewhat inured to sensational scandal—would be jaw-droppingly, pearl-clutchingly extreme. It is no wonder that Oldacre’s venom has left him friendless, save for his housekeeper, and ready to begin a new life under an assumed identity. This is a man who is desperate to get away even from himself.
4. Colonel Sebastian Moran, The Empty House
Col. Moran is mentioned throughout the Holmes canon. In The Illustrious Client, Holmes puts him into the same sentence as Moriarty. Moran’s name is tossed into The Last Bow. He’s talked of in The Valley of Fear. He is described as a tiger hunter with the career of “an honourable soldier,” and as “the best heavy game shot that our Eastern Empire has ever produced.” More importantly, Holmes describes him as “the second most dangerous man in London,” indicating that, for Holmes, Moran is second only to Professor James Moriarty. Certainly the praise for Moran’s villainy is unstinting, and it is only left to the reader to determine whether such praise is well-placed or not. In my view, it is. Light years ahead of his time, the wily colonel uses a nearly silent rifle—an air rifle made by a blind German—to attempt to assassinate Holmes. Moran is only thwarted in his attempt by the brilliant maneuvering of Sherlock Holmes, who arranges to have a wax bust placed in his stead on the very night of the attempted murder. But the effort that Moran goes to, and the very high levels to which his match-play brings Holmes, suffice to render the colonel one of the worthiest and most dangerous villains in the canon.
3. Professor James Moriarty, The Final Problem
Certainly the most famous of all Holmes’ villains, Moriarty has a name that has entered the general public and has become associated with Machiavellian evil. Drawn superbly by Sidney Paget, Moriarty is the arch-criminal’s arch-criminal. He could as easily lead SPECTRE as he could replace Karla. His personality type: cunning, cold, scheming, and ruthless brings him in line with the greatest of the great villains. If only we had seen Moriarty’s successes more obviously, he could have grown in stature even further. As it stands, he’s referenced multiple times throughout the stories and the novels, always with respect, yet he never triumphs over Holmes as Baron Gruner, as Joseph Harrison, or as Irene Adler do. This reader wishes that Moriarty was the main villain in other stories, perhaps even a collection of stories, and that, from time to time, he would emerge victorious over Holmes, or at least draw even with him.
2. Charles Augustus Milverton, Charles Augustus Milverton
Perhaps my favorite Holmesian villain, Charles Augustus inspires antipathy. He’s an oily, despicable fellow with a false smile and a heart of ice. No character in Doyle’s literature is more aptly described. Milverton springs to life from the page, and one can easily imagine him, in modern times, plying his extortion trade and/or mucking about with America’s most majestic guarantees as he strives selfishly to make a name for himself in national politics. Milverton is truly abominable, and he possesses Falstaffian magnitude.
1. Dr. Grimesby Roylott, The Speckled Band
The rotten doctor, Roylott, is perhaps the most physically imposing of all Holmes’ nemeses, and he’s one of the most cunning as well. Armed with a dastardly mind, one working in tandem with such a powerful body that it can bare-handedly bend a fireplace poker, Roylott possesses a murderous temperament, a taste for the exotic, and an absolutely black ethical code. After killing one of his daughters, he beats and attempts to kill the other. Are spiders so loathsome as that? He threatens Holmes and attempts to physically intimidate him. Roylott goes so far as to modify a wing of his house to make it into a murderous chamber. The gall! If Holmes and Watson had fallen asleep during their midnight vigil, it is possible that Roylott would have succeeded in killing Holmes. As it stands, the supremely villainous doctor gets a taste of his own medicine that proves overpowering and sends him, hopefully, further down than a mere six feet below the soil.
