Of anyone I know

The anyone/everyone difficulty is interesting. If John is the tallest of the group of everyone I know, his height exceeds that of all other members of that group. That being so, his height exceeds that of any one of the group; he is taller than any one of the group.

This argument leads to the notion that he is the tallest of everyone, and taller than anyone. These alternatives read well but when applied to intelligence the proper use of comparatives fails us. To say He is the more intelligent of anyone ..., although logically justified, is ungrammatical, inelegant or pedantic. GJC makes a good suggestion about this inelegance - it would read better as "He is more intelligent than anyone ...". The Heritage Dictionary folk seem to have overlooked the most/more, tallest/taller issue in their discussions.

If I make a one by one mental comparison of all those I know, my mind ranges (or at least tries to range) over each of them so as to select the most intelligent (or whatever quality is in question). It is rather like the physical comparison of looking at a city skyline and selecting the highest building, but no such physical line up of intelligent people is possible so it has to be attempted mentally.

The heart of the issue is whether “anyone I know” refers to an individual or to a group.

“Everyone I know” is clearly a group of people, so there is no logical issue with picking an individual from that group.

On the other hand, “anyone I know” refers - superficially, at least - to a single individual. Parallels include “anything in the store” (a single unspecified item) or “anywhere but here” (a single unspecified location). This explains the dictionary’s reference to “everyone” being a more logical choice in the given context.

The follow-up comment about a “one-by-one” comparison builds on this. To retain the ‘single individual’ character of “anyone”, the phrase “of anyone I know” isn’t expanded to a group. Instead of collecting all the “anyone”s to do a comparison, the idea is that you are invited to pick an individual for the comparison. Which individual? Well, just go through them all one by one and pick the ‘best’. It uses the same singular/plural distinction between “you can have anything in the shop” and “you can have everything in the shop”.

The broader question is whether the superficial singularity of “anyone” has drifted idiomatically to a plural notion. Popular usage suggests that it has, but the dictionary’s editors evidently feel that the plural underpinnings of “anyone” is shaky. I’d be inclined to agree, but it’s anyone’s guess as to when or whether this singular will subsume the plural.