I've been pretty critical of Trump's strategy lately but I think the debate was him at his recent best. Funny moments, high energy, successfully avoided a lot of landmines. Seems like people wanted him to be washed out and "reserved" or something but he actually went off script. I personally prefer this version of Trump. He wasn't overly nasty or anything but didn't make it boring either. You could tell his words were his own and not written by a focus group.
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What does it mean to "win" this sort of debate, really?
Normally, "to debate" is to dispute accuracy of basic facts, to provide counter-arguments to a proposal, and so forth. But that takes time, and 2 minutes with a 1 minute rebuttal is not a proper forum for that sort of thing. None of that really happened, but then given the time constraints it could not have happened.
Rather, this type of debate is primarily to generate short clips for insertion into "analysis" videos, by both sides. And there was sufficient fodder for that. Both of them got in good "zingers" in that would play well to their own audiences.
It's also a bit of "image management" for a low-information, low-engagement, audience who probably didn't watch the whole thing. For that, I think Harris came off a bit better: she looked more aggressive and had a more of a rhetorical style that looked like she was making points ("We need X, and we need Y, and we need Z.") If you came in randomly and watched 5 minutes of it, Harris probably came off slightly better than Trump, who was pretty much on the defensive for most of it.
That could be one reason why Trump kept coming back to the migrant crisis over and over--you never know which 5 minutes those people are going to be watching, and it is a pretty important problem and key to many other problems. That is is key to many other problems--crime obviously, but also the economy--is another good reason to keep returning to it.