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Way too many factors to decide this right now. Of course, he can win. Incumbents are hard to beat, but a lot could happen between now and then. Trump is taking a gamble. He is leading directly to his base and basically telling everyone who didn't vote for him to fuck themselves. He will need all of those people to turn out for him again in 2020. If they don't he is in trouble.
We can debate the accuracy of polls or what they mean all day. The truth is in the elections. We will know a lot in a few weeks. If Trump manages to hold onto the House and Senate, it will prove his reach is bigger than his opponents realize. If there is a blue wave, it will show that Democrats are motivated and unless things go really well for him over the next two years he could be in serious trouble in 2020.
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