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(From The Wrecker by Robert Louis Stevenson and Lloyd Osbourne, Chapter XIV, published 1892)

Passage 224

“Guess so,” he said. “You needn't fool with it. There's nothing else but a lead-pencil and a kind of worked-out knife.”

I looked in the bag, however, and was well rewarded.

“Every man to his trade, captain,” said I. “You're a sailor, and you've given me plenty of points; but I am an artist, and allow me to inform you this is quite as strange as all the rest. The knife is a palette-knife; the pencil a Winsor and Newton, and a B B B at that. A palette-knife and a B B B on a tramp brig! It's against the laws of nature.”

“It would sicken a dog, wouldn't it?” said Nares.

“Yes,” I continued, “it's been used by an artist, too: see how it's sharpened—not for writing—no man could write with that. An artist, and straight from Sydney? How can he come in?”

“Oh, that's natural enough,” sneered Nares. “They cabled him to come up and illustrate this dime novel.”

We fell a while silent.

“Captain,” I said at last, “there is something deuced underhand about this brig. You tell me you've been to sea a good part of your life. You must have seen shady things done on ships, and heard of more. Well, what is this? is it insurance? is it piracy? what is it about? what can it be for?”

“Mr. Dodd,” returned Nares, “you're right about me having been to sea the bigger part of my life. And you're right again when you think I know a good many ways in which a dishonest captain mayn't be on the square, nor do exactly the right thing by his owners, and altogether be just a little too smart by ninety-nine and three-quarters. There's a good many ways, but not so many as you'd think; and not one that has any mortal thing to do with Trent. Trent and his whole racket has got to do with nothing—that's the bed-rock fact; there's no sense to it, and no use in it, and no story to it—it's a beastly dream.

I couldn't find any wording like this. Is 'too smart by ninety-nine and three-quarters' common usage in such a context, is it idiomatic or have you to take it literally? Especially the wording 'by ninety-nine and three-quarters' troubles me. 'What does it mean or what does it express there?

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    In other words, just less than 100 ways. This kind of thing will not be in dictionaries. Not everything is in dictionaries or findable. It's called literary writing. Here, speaking.
    – Lambie
    Commented Oct 26, 2023 at 18:38
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    This particular phrase is not a standard idiom, but other uses of "too smart by". "too smart by half" has become popular in recent years, and "too smart by far" was almost as common in the past. This seems like Stevenson's own variation on the theme.
    – Barmar
    Commented Oct 26, 2023 at 19:25

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This reminds me of a more familiar saying, "too clever by half." Also, "too smart for your own good" where over-confidence in one's scheme can cause an important facet to be overlooked and the plan falls apart. Or like a ship captain who cheats but gets caught when the 'perfect plan' unravels by a small oversight. It was only 99 3/4 thought-out.

https://en.wiktionary.org/wiki/too_clever_by_half#:~:text=(file)-,Adjective,to%20be%20unreliable%20or%20unsuccessful.

too clever by half

(idiomatic, of a person, plan, theory, etc.) Shrewd but flawed by overthinking or excessive complexity, with a resulting tendency to be unreliable or unsuccessful.

1914, E. W. Hornung, chapter 8, in The Crime Doctor: The poor devil was too clever by half, and made a big mistake for each of his strokes of genius.

1993 March 21, Robert Dallek, “Roosevelt Unbound”, in The New York Times‎[1], →ISSN: Historians generally agree that Roosevelt was too clever by half, and that he miscalculated badly in assuming that he had the political muscle to alter the size of the Court.

2011 April 28, David Prosser, “Did Barclays' own executives see the bank coming?”, in The Independent‎[2]: Still, the thing about being just a little too clever by half is that it tends to catch up with you.

2017 October 20, Katharine Murphy, “At least for once, don't let politicking kill off a workable energy policy”, in The Guardian‎[3], →ISSN: As Combet pointed out in 2009, that sort of too-clever-by-half politicking can get you into trouble. It can sink the boat you really want to sail.

Add-on: English Stack Exchange 2011 post on "too clever by half."

Origin of "Too Clever by Half"

In the chosen answer, this observation rings true: "If someone is too clever by half it often means they are irritatingly devious and manipulating, rather than actually very clever (the implication being that the speaker, and probably many others, see through the trickery)."

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  • Thank you very much for this detailed and informative reply. I much appreciate your help .
    – philphil
    Commented Oct 27, 2023 at 10:55

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