Sherlock Holmes, Charles Augustus Milverton and the power of optionality

“The woman stood with her hand buried in her bosom, and the same deadly smile on her thin lips.
‘You will ruin no more lives as you ruined mine. You will wring no more hearts as you wrung mine. I will free the world of a poisonous thing. Take that, you hound, and that! – and that! – and that!’
She had drawn a little, gleaming revolver and emptied barrel after barrel into Milverton’s body, the muzzle within two feet of his shirt front.”

This is from Charles Augustus Milverton, perhaps my favourite Sherlock Holmes story.

Milverton is a man whose trade is the rumours and secrets of the wealthy and influential. Sherlock calls him “the worst man in London.” He blackmails and threatens to wreak havoc in the lives of his targets.

Why is it my favourite, aside from it being a classic example of the good prevailing over the bad?

The less obvious reason is that the character of Milverton is appealing, not for how he accumulates his wealth or the joy he gets from destroying lives, but for the pragmatism with which he deploys his knowledge.

Consider the latter half of this passage, emphasis mine: “No one knows where his grip may fall, for he is far too rich and far too cunning to work from hand to mouth. He will hold a card back for years in order to play it at the moment when the stake is best worth winning.”

When I first read that, I scribbled “optionality” in the margin.

An option is the right but not the obligation to use something. It’s “the weapon of antifragility” according to Nassim Taleb.

In Milverton’s case, the dirt he accumulated on high society was his option, his weapon. He solicited it from housekeepers and maids and gardeners and criminal “ruffians”, as Doyle so nicely describes them.

But he didn’t know exactly when the information would be valuable, but he knew it would be at some point in the future. So he purchased it. And when the moment came, he used it to extract the highest price (and inflict the most harm).

Milverton understood the point that Taleb made in Antifragile: “the option is a substitute for knowledge.”