From what-if + -ery.
what-iffery (uncountable)
- (informal) Speculation as to what might have happened if things had happened differently.
2000, Yvonne Sherwood, A biblical text and its afterlives, page 209:[…] what if Jonah is a piece of what-iffery, a story, an experiment with words, rather than a carefully honed piece of polemic […]
2007 January 9, Stuart Jeffries, “A prime minister in the dock”, in The Guardian[1]:The film's what-iffery becomes even more compelling when Blair, played, as in A Very Social Secretary, by a twitchingly reptilian Robert Lindsay, decides to stand down shortly before the 2010 general election.
2021, Greg Jenner, Ask A Historian: 50 Surprising Answers to Things You Always Wanted to Know[2], Hachette, →ISBN:My name is Greg Jenner, and I'm pathologically sceptical towards historical what-iffery. Let me clarify—there's nothing wrong with asking, ‘What if this hadn't happened?’
