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I can think of cunning, devious, machiavellian – but none of those is exactly what I want. I’m wondering if there’s some other word I’m failing to think of.

7 Answers 7

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crafty, as per M-W:

clever at attaining one's ends by indirect and often deceptive means

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Are you looking for conniving?

It means, per Lexico/Oxford:

Given to or involved in conspiring to do something immoral, illegal, or harmful.

Apparently this word at some point in the past had a more passive meaning than it has today, suggesting merely going along with a pre-existing plan, as suggested in a comment below and explained in a usage note for "connive" in m-w.com. I've never in my life (in the U.S.) heard or seen it used this way.

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  • Would love an explanation for this downvote.
    – cruthers
    Commented Aug 22, 2021 at 16:30
  • It wasn't me who downvoted but the reason might have been that conniving is a bit passive - going along with things - and so only a specific subset of the wider attributes the question is asking about.
    – Nemo
    Commented Aug 22, 2021 at 18:52
  • Interesting theory. This isn't how the word is used any more. Will update.
    – cruthers
    Commented Aug 22, 2021 at 19:23
  • Here is a recent example of an article which uses the more passive meaning cbsnews.com/news/wheres-tough-britain-when-you-need-her The word is often used when saying that someone should aspire to higher standards - i.e. not just avoid actually doing bad things but make a stand and do not stand by and let others do bad things.
    – Nemo
    Commented Aug 23, 2021 at 11:04
  • @Nemo: Ah - excellent. I should add that I'm in the U.S.... I assume you're located elsewhere if you're acquainted with this use (assuming you had heard it used this way before digging up this quote)? I see that this quote comes from a prominent Tory who learned English in elite British institutions in the first half of the 20th century.
    – cruthers
    Commented Aug 23, 2021 at 14:07
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A perfect adjective describing this type of behaviour is "calculating".

(OALD) calculating adjective BrE /ˈkælkjuleɪtɪŋ/ AmE /ˈkælkjuleɪtɪŋ/ (disapproving)
​good at planning things so that you have an advantage, without caring about other people
♦ a cold and calculating killer
♦ I never realized you could be so calculating.
♦ She caught a coolly calculating glint in the other woman’s eye.

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Not an adjective, but a noun, "demagogue" fits a political context perfectly.

"a person, especially a political leader, who gains power by arousing people's emotions and prejudices. TFD

or are you looking for "crafty"?

(adjective) "Skilled in underhandedness, deviousness, or deception. TFD

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My offering is someone who is scheming, and Lexico has

schemer
NOUN

A person who is involved in making secret or underhand plans.

Macbeth is a schemer and plotter who is eventually undone by his own misdeeds.

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Perhaps duplicitous - someone who acts in two ways at different times, openly and secretly; often including deceitfulness and double-dealing. (OED)

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M-W thinks that

Probably the best fancy way to describe a liar is mendacious. It comes from the Latin word mendax, meaning “lying” or “false.” It is often used to refer to people who habitually lie.

More specifically, the definition is

given to or characterized by deception or falsehood or divergence from absolute truth (M-W)

I must say I also like dissembler, which, though somewhat dated, seems to pick up in our century:

a person who professes beliefs and opinions that he or she does not hold in order to conceal his or her real feelings or motives (FreeDictionary)

M-W defines the verb to dissemble as:

to put on a false appearance : conceal facts, intentions, or feelings under some pretense

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