Would Singapore have been in better condition if Churchill had never been Chancellor or returned as First Lord?
Short answerProbably somewhat better without his Chancellorship because another minister might have cut less deeply, while his later First Lord term had little effect on Singapore's preparation.
NotesChurchill used his naval reputation to justify an unusually hard line on Navy spending while at the Treasury. His later return as First Lord matters less to Singapore than that earlier budget role. Extra resources might have supported pillboxes on the island and a defensive line farther north, though they would not have removed the wider strategic weaknesses.