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I have no sig to speak of, so let's make it $100? I'll bet he stays until 2020, and is not impeached and does not resign. If he leaves office voluntarily, by impeachment, or by any due process of law, though not through harm, Force Majeure, or civil collapse, before Jan 20th 2021, you win. If he remains in office through the morning of Jan 20th 2021 I win.
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