8.) Wager With Fauxcahontas

Trump ripped potential 2020 opponent Sen. Warren (D-Mass.), and even got in a joke on the #MeToo movement, saying that when he tossed the Ancestry.com kit at her, he would try not bruise her arm. He even bet her $1 million that she wouldn’t test as a Native American! This moment has to be one of the least politically correct moments in presidential history, which is why we saved it for last. 

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