A part of me really wants to like it but I just don't. Maybe for the same reason I really like Percival "Percy" but would never use it. It just doesn't seem to fit my family at all no matter how much I like it.
I think it's a good name for a cat or dog. Winston from "new girl" comes to mind also. I don't like the way it sounds, I think it sounds nerdy. Sorry if that's too harsh.. I get that it's a legitimate historical name, I'm just not a fan.
I like it. It follows the trend of giving boys last names as first names (ala Jackson, Miller, Fisher, etc) but it's not super popular itself and is legitimately the first name of a pretty BA famous person (Winston Churchill).
I am not big on my WW2 Allied Powers history, so all I know about Churchill is the standard cigar smoking politician who fought Hitler narrative - it might be worth it to research the man more closely though before you give your son the same name.
Re: What do you think?
Especially the nn Win