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I am quoting from the Memoirs of Sherlock Holmes, The Reigate Squires by Arthur Conan Doyle: "'There are some very singular points here,'said Holmes, smiling. 'Is it not extraordinary that a burglar - and a burglar who had had some previous experience- should deleberately break into a house at a time when he could see from the lights that two of the family were still afoot'. 'He must have been a cool hand'". I found the following sources:

  1. finedictionary.com which kind of doesn't fit in the context, and

  2. thesaurus.com which perfectly fits in the context, but I couldn’t find this meaning in any of several online dictionaries.

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  • Don't you think a burglar would need to be brave and 'not easily abashed' to break into a house when he could see there were people still awake? – Kate Bunting Feb 23 at 8:39
  • I am not sure I follow you, not easily abashed doesn't mean courage or boldness these are two completely different concepts – aissam Feb 23 at 8:42
  • merriam-webster.com/dictionary/abashed - not easily made to feel uncomfortable or disconcerted? Not such a different concept. – Kate Bunting Feb 23 at 9:09
  • We are definitely agreed as to the meaning of the word abashed or not abashed, the problem is that no burglar would feel shy or uncomfortable when he's about to burglarize a house. – aissam Feb 23 at 9:16
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    From the full subscription-only OED: hand 15b (colloquial, with defining adjective) Used to designate a person in terms of action or character. And for no less than three of their nine citations for the usage, the specific character attribute is that of being a cool hand. Given that, I would advise non-native speakers to be very careful about assuming they can use any adjectives here. A nervous hand? A shy hand? I don't think so! – FumbleFingers Feb 23 at 18:50
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It appears to be a dated, originally mainly a BrE expression:

Cool hand:

a cool, calm, controlled and competent individual:

  • 1840 [UK] R. Barham ‘Black Mousquetaire’ in Ingoldsby Legends II (1866) 210: A fact which has stamp’d him a rather ‘Cool hand’.
  • 1855 [UK] T. Taylor Still Waters Run Deep II ii: I’m a cool hand, I flatter myself, but, by Jove, she nearly threw me off my balance last night.

——-

  • 1936 [UK] N. Marsh Death in Ecstasy 143: He’s a very cool hand is monsieur.
  • 1965 [US] D. Pearce [title] Cool Hand Luke.

(GDoS)

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  • This is indeed the common meaning. The comments about abashed are relevant but not central to the meaning, which refers to the calm and considering approach to, and acceptance of, risk. – Anton Feb 23 at 10:05
  • BrE? The movie Cool Hand Luke was an American film (and set in USA) released in 1967. – Weather Vane Feb 23 at 14:19
  • @WeatherVane - I’m referring to earliest usages. – user 66974 Feb 23 at 14:21
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He's a person who keeps his cool, who is able to stay calm under pressure.

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A "cool hand" would be someone who can remain "cool" under pressure. Meaning under control. Cool -- the opposite of hot as in hot tempered. The "cool hand" can keep their hands from shaking even with the extra threat of discovery by an awake home owner. Sherlock believes that would be a very, very good burglar who could do that.

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