Should You Pay A Blackmailer?

A good chunk of the TV and movies I watch fall into the crime or detective genres, and are set and/or made in the early to mid 20th century (roughly the 30s-50s). The Early To Mid Twentieth Century Crime Fiction Universe (ETMTCCFU) is not unlike our own in some important respects - e.g. humans are still bipedal apes - but make no mistake, it is a universe apart. For example, their version of Los Angeles is much rainier than ours; I'd expect their California is more concerned by flooding than drought, even.

Perhaps the single most salient difference is that the inhabitants of the ETMTCCFU are constantly at risk of being blackmailed. In that universe if you ever cheat on your spouse or skim off the top of the payroll ledger you can be sure some twerp with a camera saw you do it and wants you to pay cash for the privilege. I'd compare it to the ever-present danger of quicksand in cartoons from the 90s and early 2000s.

Now, imagine you've been caught in an indiscretion by said twerp. They promise they'll destroy the negatives/burn the letters/shred the documents/etc if you provide a one-time payment of money or favors (but usually money). What do you do?

Option 1: You could discreetly withdraw the .38 revolver from your top desk drawer (in the ETMTCCFU all desks have a .38 in the top drawer, I think that's where they grow) and shoot the blackmailer then and there. The obvious downside is that this makes you a killer, and no matter how well you cover your tracks you'll eventually be found out by Sam Spade or whoever and either get sent up the river to Sing Sing or die in a police shootout.

Option 2: You pay the blackmailer some amount of money that's treated as significant, but still sounds oddly low to modern audiences due to inflation. But they don't destroy the evidence, instead they insist on recurring payouts into the indefinite future. Maybe you go along with this for a while, but inevitably the only way out is the same as above: top desk drawer, .38, police shootout, etc etc.

There is of course a theoretical third option where the blackmailer is true to their word, but it's only theoretical and has never been observed in nature. Now here's the question: why does anyone in the ETMTCCFU ever pick option 2? In fact, why does anyone choose to become a blackmailer? It has a near 100% fatality rate!

I was prompted to think about this recently in the context of another related crime that's lot more common in our timeline - ransomware. They're both essentially holding data hostage, the main differences are the threatened penalty for noncompliance (revelation or destruction) and the occupational risk taken on by the perpetrator (it's a lot easier to stay anonymous and therefore physically safe as a ransomwarer - you can blackmail by literal mail in the ETMTCCFU, but you'll be traced eventually).

Consider the options available to a ransomware victim. They could not pay the ransom and just accept the lost data, or they could pay up; in the latter case, what's to stop the perp from reneging? Why wouldn't they respond that they've altered the deal, pray they don't alter it further, and actually they'll be needing even more bitcoins? Just like in the blackmail case, they have all the leverage! So again, why does anyone pick option 2?

And generally people do pick option 2. Paying ransomwarers is often the normal, reasonable choice in this situation.1. The answer, I think, is that in our real world the incentives for the data hostage taker actually favor honesty to a degree. Imagine if a ransomware group pulled this kind of stunt regularly - maybe they get some extra payouts from the first few targets, but at a point everyone knows the MO and stops playing along. "We got hit by Foo Group? May as well just wipe everything and eat the loss, or else we'll never get off the hook."

This even accounts for why known ransomware groups are a thing in the first place. Just like how people are more willing to buy from a vendor with a positive reputation for delivering a quality product efficiently, they're more willing to pay a ransomwarer with a positive reputation for not erasing data that's been paid for. So a hacker group is incentivized to build up a "brand" just like a business.

This doesn't apply to fiction because the purpose of blackmail there is generally a placeholder motive for murder. It's just a convenient reason for one person to kill another. Blackmail needs to end in death, or else Philip Marlow doesn't have a case. The laws of the narrative supersede the laws of economics.2

That leaves us with this advice: If you find yourself approached by a blackmailer, and also you're a chain-smoking crooked cop in Chicago in the late 40s, just shoot them. This isn't going to end well for you no matter what, but this way is at least cheaper. If you're approached by a blackmailer in our universe, however, you should ask them for some references before deciding what to do.


The actual ideal response is of course to have good backups and strong security so you're never faced with the choice at all. I'm just talking about cases where preventative measures have already failed and some sacrifice needs to be made.


Free idea for writers: ETMTCCFU-style setting where blackmail is still incredibly common but also subject to real incentive structures, resulting in "trusted" blackmail "firms" that operate like normal bureaucracies.