Will Donald Trump serve any prison sentence before the end of 2029?
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2030
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Resolves YES if Donald Trump spends any positive amount of time in prison while serving a sentence before the end of 2029. It doesn't count if he is held while awaiting trial or sentencing. House arrest also doesn't count, it must be an official prison. However, it DOES count if he is held in prison awaiting execution or similar.

Resolves NO otherwise

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I assume you mean jail as well as prison, since people don’t get put in prison for holding purposes.