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Why "second to none" is being considered as "the best" instead of "the worst" (almost non existent)? To my understanding - "none" is "nonexistent", while "second to none" should be... well... almost nonexistent.

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My confusion mostly stems from the fact that OP uses a "three-dimensional" metaphor to quantify his confusion. We usually use the one/two-dimensional metaphoric extent of my confusion. Maybe that's OP's way of emphasising his confusion - it's got more dimensions than most of ours! :) – FumbleFingers Sep 9 '11 at 21:56
"second to none" vs "next to nothing"? – Vaibhav Garg Sep 13 '11 at 11:00
"Second to none" always confused me because of the word "second" in it. Why isn't the phrase simply put "first to none"? There must be some history to the reason the word "second" is in there. – user50179 Aug 21 '13 at 7:23
up vote 14 down vote accepted

To be second to none means that nobody is ahead of you. None is nonexistent, which means that someone nonexistent is ahead of you--nothing better exists so you are the best.

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or the worst, depending on whether you think it's desirable to have more confusion than anyone else! – FumbleFingers Sep 9 '11 at 21:57
Second to none = worse than nothing? – mmyers Sep 9 '11 at 22:35
@mmyers "His ability to screw things up is second to none" doesn't mean "he is the best in fixing things." – kiamlaluno Sep 10 '11 at 9:14
@kiamlaluno but it's very plausible assumption. – Eimantas Sep 10 '11 at 16:04

This dates back to the Coldstream Guards

The regiment is ranked second in the order of precedence, behind the Grenadier Guards. This is because the Grenadier Guards have served the Crown for a longer period of time. However, the Coldstream Guards is an older regiment, and because of this, has the motto Nulli Secundus (Second to None). The regiment has been referred to as the "Second Regiment of Foot Guards" in Parliamentary state papers,1 but this term has long fallen into disuse and was never used by the regiment, hence their motto. When parading with the other four regiments, is always on the extreme left of the line, with the Grenadier Guards on the extreme right. This ensures that the regiment is indeed "Second to None".

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Think of the meaning of the following sentence (modeled off your title):

The size of John's house is second to Jane's house.

While John's house is (presumably) quite large, Jane's is larger.

The size of John's house is second to none

says that there is nothing to which it is second (so it is first).

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Your first example is non-standard. Standard phrasing would be, for example, The size of John's house is less than [that of] Jane's [house]. – FumbleFingers Sep 9 '11 at 21:59
A more natural usage of the expression is like, "John's house is second only to Jane's in terms of size" though the context is still slightly awkward. – tenfour Sep 9 '11 at 23:37

Second to none could be used to mean the best, the worst, the fastest, etc.

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My ability of baking a cake is second to none. Without knowing me would you say I'm the best or the worst cake baker? – Eimantas Sep 9 '11 at 18:26
As you are describing a good quality, I would take it as you are the best cake baker. – kiamlaluno Sep 9 '11 at 18:42
@Eimantas: Without knowing you, I'd say you are a non-native speaker of English, since we would normally speak of ability to bake a cake (or better, skill in baking cakes). But kiamlaluno is essentially correct - ability is generally considered a good quality, so more of it is better. If your ability in some activity is second to none, you've got more of it than anyone else. Send me a sample of your cake-making and I'll check to see if my theory is true! :) – FumbleFingers Sep 9 '11 at 22:09
Sequences are generally understood to be best=first, worst=last. Using them in the opposite way gives the phrase an ironic turn, e.g. "His ability to screw things up was second to none" – zetetic Sep 10 '11 at 3:30

The reasoning that "second to none" could mean "almost the worst" is a fallacy due to the logical form interpretation of the word "none" in this context. In this context the word "none" actually negates the whole expression, so "X is second to none" means "X is not second to any" or more verbosely, "there does not exist any Y with the property that X is second to Y".

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