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"His failure to register was not knowing and willful."

This may seem like a stupid question, but does the sentence above mean he was not knowing and not willful, or not knowing and willful?

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I think this is the first time I've ever upvoted three answers to a question in rapid succession. Obviously knowing and willful is effectively a "stock phrase" in legalese, but without punctuation to establish this it's not obvious how to parse the sentence without prior familiarity or more context. –  FumbleFingers Nov 18 '11 at 18:45
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One should probably say "not knowing but wilful" or "neither knowing nor wilful", but if it is a legal term... –  Stephen Nov 18 '11 at 19:13
    
For seriousness... NOTTTTT! –  Thomas Eding Nov 18 '11 at 21:38
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It's ambiguous. English speakers don't generally write phrases like this because they're ambiguous. Scanning the first few pages of a Google books for "not large and", the only time an adjective came after "and" was in "small and lean, not large and mean", which is unambiguous since it contrasts two pairs of words joined by "and". –  Peter Shor Nov 18 '11 at 21:55

5 Answers 5

up vote 4 down vote accepted

I would understand this sentence to read "not knowing and not willful." There is no concrete rule stating that it must be understood this way, but if someone meant "not knowing but also willful," he would certainly word the phrase differently to prevent the inherent ambiguity. A sentence meaning the latter would more likely be worded: "His failure to register was not knowing but was indeed willful."

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Checking this context, it should read more like this:

His failure to register was not "knowing and willful".

...which means that it was either not knowing, not willful, or both not knowing and not willful.

EDIT: This does not constitute legal opinion, by the way, just ordinary interpretation of the negation of a phrase with two conditions joined by "and". There were several places I found the phrase, and they all hinge on interpretation of legal phrase "knowing and willful", so if the OP can post the original context, it may be helpful.

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The former. Think about it like this:

His failure to register was not "knowing and willful"

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I think ususually when someone says "not X and Y" they mean "not X and also not Y". If you want to express the idea that it is not X but it is Y, the simplest thing to do is switch the order, to say, "Y and not X", like, "Fred is tall and not bald." Then it's clear that tall = true and bald = false. If you want to express the two ideas in a particular order for emphasis or whatever, you should add a couple of words to eliminate the ambiguity, like, "Fed is not bald and he is tall." When the ideas contrast, you can change the "and" to a "but" or similar contrasting conjunction. For example, "Mary was not napping but completely alert."

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Very helpful. Thank you. –  Jon Nov 18 '11 at 22:42

Funnily enough, it doesn't mean either one: "knowing and willful" is a single set phrase, so "not {knowing and willful}" means "{not knowing} and/or {not willful}". That is, something could be "knowing", but still be "not {knowing and willful}", provided it's not willful; and vice versa.

This may seem odd, but if we put it in a more "rule-based" context, it becomes intuitive. Consider something like the following:

To vote in the U.S., you have to be a U.S. citizen and at least eighteen years old. If you're not a U.S. citizen and at least eighteen years old, then you can't vote in the U.S.

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Not the best example: I'm over eighteen but not American, so I can't vote. If all I had to work on was your quotation, I might pretend to be under eighteen, thinking that might bypass the rule. –  TimLymington Nov 19 '11 at 11:11
    
@TimLymington: That's true of any example. The construction is ambiguous. I'm just explaining what it happens to mean here, and giving an example where that interpretation is more intuitive. Obviously this example can be interpreted in a different way, but I still think it's helpful. –  ruakh Nov 19 '11 at 14:05

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