Trump promises New York Times will be "happy" with his immigration bill
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The NYT didn't bring up any immigration-related topics, and Trump only briefly mentioned it. However, what he said was very, very bad:
I feel very strongly about health care. I feel very strongly about an immigration bill that I think even the people in this room can be happy. You know, you’ve been talking about immigration bills for 50 years and nothing’s ever happened. I feel very strongly about an immigration bill that’s fair and just and a lot of other things. There are a lot of things I feel strongly about.
As detailed on the New York Times, NYT editorial, and Andrew Rosenthal pages - and others like DREAM Act, PIIPP, and crops rotting in the fields - any immigration bill that would make the New York Times happy would be very bad for the USA. The NYT wants citizenship for almost all the illegal aliens in the USA, they want guest workers, they want as little border security as possible. All those run counter to what Trump supporters think he's promised them.
Even though Trump has made it clear to those who know about this issue that he supports mass legalization, that doesn't appear to have sunk in to his base. No matter how weak he is on this issue, his base will keep thinking that their shoes are wet because it's raining. They aren't willing and able to do the patriotic thing: demand the best from Trump rather than acting as his fan club.
That said, could Trump just be trying to dupe the NYT? If so, what possible reason could there be for that? It's not like promising them something is going to make them go easy on him. They aren't going to change their coverage of his immigration proposals just because of what he said: they're committed to their loose borders vision and happy talk isn't going to make them change their mind.
What Trump should have done was support a realistic plan that would solve the problem, such as attrition. That's something that would make the NYT very unhappy, as they've made clear. They'd have objections to the plan, which Trump could then answer and use to show their position wrong.
If Trump had engaged the NYT in debate about immigration and worked to discredit their position, he would have done a great public service. Instead, he just showed yet again how fake he is.