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I figured it out.
The plan is to alienate our long term allies in Europe, Mexico, and Canada, and we cozy up to dictators in Russia, Turkey, and North Korea. Evidently in Trump's world view, democracies are for chumps.
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My sources tell me that when his advisors told Trump he was going to a Singapore resort to meet with Kim, he asked if she would be wearing her bikini. Those advisors then explained that it was Kim Jong Un he was going to meet, not Kim Kardashian.