There was a lot a chatter about 4-down in The Stickler Weekly 219, Who’s transport is behind time on a road? (6). Is it grammatical, is the clue sound? I’ve used a ploy here that I use occasionally when I want to convey something that the right language isn’t totally capable of. I’ve talked about this sort of thing before. Essentially I take advantage of the fact that people don’t generally pay close attention to language these days, relying much more on the sound or how something reads to make sense of what’s written. I’m happy for a clue to be technically ungrammatical (while still appearing to be right) as long as the integrity of the wordplay is maintained.
4-down works from a deception point of view purely due to the “?” at the end. Without this, “Who’s” would have struck people as being possessive more readily, thereby taking away some of the deception from the clue. By making the clue a question, I have hopefully created an environment where “Who’s” is mistaken for “Whose” in the mind, even for just a short time until the clue can be properly broken down. In everyday prose, I would say the clue was ungrammatical, as the “?” indicates that the clue is a question (and it isn’t), but in cryptic clue terms, where a question mark can have multiple meanings, I believe a possessive “Who’s” can live happily with the “?” without affecting the integrity of the clue.