The attempt does not have to be successful, but it needs to involve some effort and political capital; not just a throwaway comment here and there.
Resolves based on my own judgement of what counts as "a serious attempt". I won't bet.
(The January 6th shenanigans and constant accusations of voter fraud last time were severe enough to count under this criterion.)
Resolves N/A if he dies before the last year of his term, and he has not already done something that would qualify.
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@JoshuaB I don't see a legal path toward remaining in power after the end of a term. Any "shenanigans" "tomfoolery" "antics" or "horsing around" would be violations of the Constitution, unless he gets it changed before then or invalidates it.
@JoshuaB That would count unless he also credibly claims he plans not to seek a third term. Legal approaches qualify. (I believe claims of voter fraud are legal under the 1st amendment?)
Why anyone would think he's more likely to go quietly in future, beats me.
This is an important and well-posed question. Thanks for creating it! And a meta question about Manifold norms: I'd like to point friends and family at this question but they may be like "resolves according to whose own judgment now?" and be reluctant to bet. So, is it rude or uncool if I steal this question, i.e., make my own version of it that's basically identical except it's my judgment or maybe a neutral third party if I can find one?