At Vox, Matt Yglesias argues that Trump is not failing:
Yet since his ascension to the White House, conventional wisdom has developed an odd tendency to describe his inability to make major legislative changes as an indication that his presidency is failing. It's certainly true that Paul Ryan’s speakership of the House is failing, arguable that Mitch McConnell’s tenure as majority leader of the Senate is failing, and indisputably true that the Koch brothers’ drive to infuse hardcore libertarian ideological zeal into the GOP is failing.
But Trump isn’t failing. He and his family appear to be making money hand over fist. It's a spectacle the likes of which we've never seen in the United States, and while it may end in disaster for the Trumps someday, for now it shows no real sign of failure.
Despite the fact that I often find Yglesias's stuff needlessly contrarian, I think he is mostly right in his assessment here.
Trump has exactly one policy objective: Trump. There are two legs to this policy: financial gain and personal aggrandizement. The financial gain is currently proceeding quite well—as Yglesias details in his post—and it shows no sign of stopping in the near term.
What will be interesting (in the Chinese curse sense of the word) to watch is the second bit—the personal aggrandizement. Trump always wants to feel like a Big Man, and took to politics as the venue for that pursuit once the world of real estate and finance was finally closed off to him due of his miserable record of continuous failure.
Thus far, politics has worked as an outlet and ameliorative for Trump’s insecurities. He gets to jet back and forth between the White House and his private resort, be feted by the media and favor-seeking foreign diplomats and businesspeople, and run his family and hangers-on through his weird little power games. Throughout, he has managed to maintain a sufficient level of dog-whistling and grievance-stoking to keep the tribalist fires burning with his core supporters—angry, resentful white people. Meanwhile, the Republican party’s seemingly unresolvable internal conflicts have allowed Trump to skate by as that bunch fights among themselves, while Trump’s “I’ll sign anything as long as I can make it look like a win for Trump” policy gives them hope of converting their wildly unpopular and vile policy agenda into law.
Where it gets interesting is if any of that starts to change. If Trump starts to feel like the world of politics is making him look small and pathetic, if his lack of any actual policy agenda or accomplishments starts to erode the loyalty of his base, if the GOP starts to turn against him… what then?
The best-case scenario is that he walks away from it, either literally or figuratively. And to be clear, when I say “best-case” here, I mean it only in a relative sense, because that scenario leaves us with either a) an executive branch that is even more rudderless and unpredictable than it is right now, or b) Mike Pence in charge of things.
That said, I tend to think that the “He’s going to get tired of it and walk away” predictions are wishful thinking. Trump is a con man, and this is his last con. He has nowhere else to go. His real estate empire is hollow, no banks will lend him any more money, and absent the shield of the White House, the vultures will swoop in to pick clean the carcass of his brand. Trump is all in, and if he starts getting desperate, he will begin pulling every lever he can get his hands on. If you think things are scary and disturbing now, that prospect ought to terrify you.
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