John Kelly is right: Trump’s war against the establishment is a two-edged sword

President Trump is putting Washington, D.C. to the test. He gave the Beltway establishment the middle finger in 2016 and he’s made it clear that he’ll keep doing so. And while Trump’s against-the-fray mentality has helped him deliver some important wins against the regulatory regime, it’s proven to be its own kind of stumbling block.

The question here is whether a political outsider can successfully navigate and shape the political landscape without the establishment, and in some cases, in spite of it. Trump continues to argue that he can, in spite of the rogue “Deep State” operatives who attempt to undermine his presidency. Because the establishment refuses to help, he’s had to find a way around it.

But it’s for this very reason that Trump is staring down impeachment. Working around the establishment has often meant rooting out or bypassing establishment types within his administration and replacing them with people he can trust — people who tend to also be on the outside of the respected status quo. And in doing so, Trump has blurred the line between what is legal and what is standard practice.

Take, for example, the Ukraine scandal, which gave House Democrats the perfect excuse to launch their long-hoped-for impeachment efforts. Instead of relying on authorized government officials to deal with negotiations between himself and Ukrainian President Volodymyr Zelensky, Trump handed the reins to his personal lawyer, Rudy Giuliani, and a few other trusted allies, such as Gordon Sondland. Trump even booted the then-sitting U.S. ambassador to Ukraine, Marie Yovanovitch, when it became clear she wouldn’t turn a blind eye to Giuliani’s backchanneling.

This setup so disturbed William Taylor, the current U.S. ambassador to Ukraine, that he described Giuliani’s unauthorized efforts as a “highly irregular” channel of policymaking that often undermined U.S. interests in Ukraine.

The problem, of course, is that Trump’s circumvention wasn’t just “highly” irregular. It was also more than likely illegal, and impeachment is the result. Trump could have avoided all of this if he had just trusted Secretary of State Mike Pompeo, Attorney General William Barr, or even Taylor with the situation in Ukraine. But because he’s wary of the establishment, as he sees it, he chose to go a different route.

This political stubbornness had already cost Trump dearly, even before the Ukraine scandal broke. His inability to heed the advice of his advisers has resulted in one departure after another, the most telling of which was former Defense Secretary Jim Mattis, whose presence was seen as a stabilizing security in an often chaotic, turbulent administration.

Former chief of staff John Kelly claims to have seen all of this coming, and says he warned Trump before he left last year that the president should choose advisers who are willing and able to temper the president’s worst impulses.

“I said, whatever you do — and we were still in the process of trying to find someone to take my place — I said whatever you do, don’t hire a ‘yes man,’ someone who won’t tell you the truth — don’t do that. Because if you do, I believe you will be impeached,” Kelly said at the Sea Island Summit, a political conference hosted by the Washington Examiner.

As with any disgruntled former employee, Kelly’s words should be taken with a grain of salt. But they do speak to a pattern in the Trump White House. Political know-hows such as Kelly and Mattis leave, and Trump replaces them with personal favorites, such as Giuliani. Each time this happens, the White House comes to rely less on the institutions that hold the president’s power in check, and more on the whims of a man who’s determined to put those institutions to the test.

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