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In Red-headed League from The adventures of Sherlock Holmes, a character named Wilson describes a weird sight of hundreds of red haired men crowding the area to Holmes. By his account he had been really shocked by this crowd, yet he says 'I should not have thought there were so many in the whole country as were brought together by that single advertisement.' By context I think he means he wouldn't've thought it, but I don't...understand the use of 'should not have' here..

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As the OED notes, this use of should is a colloquial expression of the "strong affirmation" of a statement. Here

I should not have thought ...

is the equivalent of

I definitely would not have thought.

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In our (chiefly British) English lessons in a German high school in the late 1970s we learned that shall and its past should are simply the first person forms of "will" and "would". I think this use has since then become rare, certainly in the U.S. The use has shifted towards or focused on assertion and moral obligation ("The plaintiff shall...", "I know I shouldn't").

In your example, an American Wilson of today would probably just say "I wouldn't have thought ...".

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  • As would a British Wilson. But perhaps not a Sir Humphrey.
    – Edwin Ashworth
    Commented Feb 19, 2016 at 11:12
  • I expect that use was somewhat rare even in the 1970s. Ngram.
    – Peter Shor
    Commented Feb 19, 2016 at 12:23
  • @PeterShor Entirely possible. The text books' texts may have been a decade old, easily, and reflected past use back then.
    – Peter - Reinstate Monica
    Commented Feb 19, 2016 at 12:25
  • And in high school German we were taught that sollen is exactly the same as should... the key concept being "obligation".
    – Spencer
    Commented Apr 20, 2017 at 10:37
  • @PeterShor For some reason the answer received an upvote today; I (re-?)visited your ngram and find it quite interesting. I probably had that lesson as a 12-year-old (Latin being my first foreign language) in 1976, in the later phase of its usage decline. But assuming that the book was essentially 10 years old and incorporated at the time of its writing a version of English two or three years old, it reflects a state of English that still very much used should as past tense of shall. Interesting how quickly that usage changed, in a bit more than a generation.
    – Peter - Reinstate Monica
    Commented Apr 10, 2022 at 0:30

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