If Trump wanted to guarantee a win he would publish a checklist of his election promises and associated due dates for each of them upon his inauguration.
Then he would commit to the American people that he will pay a fine for each promise that is not completed by a given time assuming no unreasonable barrier to their completion exists.
Incentives run the world.
A fine to who? Maybe charities? Hurricane relief?
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Me? I guess charities…or maybe the DNC as an extra motivation.