There was a moment late last season when Des was a free agent and Chiefy was really, really struggling. The Nix could have sacked Chiefy and tried to get Des then. But I suspect that even as a free agent he was already too big for us at that point and it was never on the cards. The big Des what if is really the All Whites job, where Des was keen but NZF disregarded him and went all in for Herdman.
Edit: and also of course when it was a straight shootout between Des and Hay for the job and Hay got it
Edit: and also of course when it was a straight shootout between Des and Hay for the job and Hay got it