A Scoundrel Within the Bounds of the Law
Someone at your organisation has read the policy more carefully than the people who wrote it. Not to follow it. To find where it stops.
The medieval Jewish rabbi Nahmanides had a phrase for this person: “a scoundrel within the bounds of the law.” Technically compliant. Morally absent. Does nothing wrong on paper. However everyone, including themselves, know they’re working against the spirit of the group.
You’ve watched this person in a meeting, quoting clause 14(b) while everyone else knew the point had been missed. Where do they come from? Are some just wired that way?
Some probably are. But the environment is built for that behaviour to thrive in. The more specific the rules, the more undergrowth is habitable for them.
The scoundrel is ancient
Jewish scholars identified this problem at least two thousand years ago. This story is used as illustration:
A man named Rabbah bar bar Hanan hired porters to carry barrels of wine. They dropped a barrel and broke it. Rabbah was furious. He seized their cloaks along with all their pay for the damage.
The porters went to a judge. The judge told Rabbah to give the cloaks back.
Rabbah protested. The law was on his side. He’d hired them, they’d broken his property, and he was entitled to compensation. By the letter of the contract, he was correct, the wine was worth more than their wages.
The judge agreed he was correct. Then told him to pay the workers their wages.
The reasoning wasn’t found in any specific clause. The judge pointed to a broader principle: act the way a decent person would act, or lifnim mishurat hadin. The contract covered property damage. It said nothing about whether it was fair to leave your workers standing there with no coats and no pay. The specific rule had a gap.
Rabbah followed every rule and produced an unjust result. The fix was a broader principle, one that sat above the specific rules: “Do what is right and good.”
How detail feeds the scoundrel
When a broad statement is followed by specific examples, the broad statement gets consumed by the specifics. A contract that says “I cover all losses, specifically fire and theft” sounds comprehensive. In practice, it covers fire and theft. The word “all” dies the moment you list examples, because the examples define the boundary. Anything not on the list is out.
This is why detailed policies feel thorough but behave badly. I touched on this in the previous article: added detail creates gaps, technical definitions, edge-case exclusions, clauses that contradict other clauses. Every specific clause defines what’s covered, and by omission, what isn’t. The scoundrel lives in the omissions.
Tax codes work the same way. The more detailed the code, the bigger the tax avoidance industry that grows around it. Accountants make their living in the negative space between clauses.
The modern legal world has a Latin phrase for this: Expressio unius est exclusio alterius. The expression of one thing is the exclusion of the other. List 50 things that are covered, and you’ve implicitly excluded the 51st. Jewish scholars got there centuries earlier.
Specificity invites evasion. Generality invites responsibility. Give someone a 100-page policy and the scoundrel looks for gaps. Give them a simple, short but broad agreement and everyone is left engaging with the spirit of the outcome itself. There’s nowhere to scurry.
What this means for organisations
Organisations with strong cultures need fewer rules. Replace culture with policy and you build the exact environment where people follow the handbook and miss the point. Over-governance is habitat for the scoundrel.
A 50-page volunteer handbook tells people exactly what they must do. It also signals, by implication, that anything not in the handbook is someone else’s problem. A broad, shared agreement about “this is what we’re about and how we treat each other” puts the responsibility back on the actually fully grown and matured humans to to engage with the spirit and purpose of the thing. There is no loopholes in shared values.
Civility precedes law. Character comes before policy. If the disposition isn’t there, no amount of detailed rules will fix things. And if the disposition is there, you don’t need 47 clauses to get people to behave well.
How many policies exist because someone once did something annoying, and the response was to add a rule? How many of those rules created their own new gaps? Would things be simpler if they could be replaced by a clear, shared understanding of what “right and good” looks like here?
Strong culture needs fewer rules for co-operation.