“I’ll get Congress,” Trump replied. “I’ve been getting politicians to pass whatever I wanted all my life. Nobody has more experience — you know, it’s sort of interesting, nobody has more experience dealing with politicians. I’ve been dealing with them all my life.”

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How? As a developer.

“Whether it’s big New York City zoning deals — which, by the way, are probably tougher than most of the things I’ll be dealing with foreign countries,” he continued. “I mean, I built a city on the West Side of Manhattan. You talk about getting zoning. Getting zoned for Trump Tower: 68 stories on 57th and 5th. Let me tell you, I’ve been dealing with politicians all my life. They’re fine. They’re wonderful. They’re all talk, they’re no action. They’re selling this country down the tubes, and they’re easy to deal with. Believe me.”

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In 1980, the New York Times explained how Trump finessed the zoning board for the development of Trump Tower. After quoting a business partner of Trump’s, who said that Trump “knows how to get things done in New York,” the paper explained: “In part, that is a matter of politics.” The only donor who gave more money than Trump to the campaign of the incumbent governor, it reported, was the governor’s brother. While a deputy mayor also said that Trump “could be very convincing” when selling a project, a city council member told the Times that “Trump runs with the same clique that continues to manipulate things behind the scenes in this city,” including links to a Democratic Party machine in Brooklyn connected through his father.

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The Times also reported that the final negotiated height of Trump Tower was 56 stories, not 68.

Why re-litigate 40-year-old news articles and four-year-old news conferences? Because it’s worth remembering that Trump at no time was prepared to manage the process of passing legislation through the House and the Senate. The current government shutdown, approaching three weeks in length, stemmed from dual failures on Trump’s part: Most recently in an inability to cajole members of Congress to see his side on funding for a wall on the border with Mexico and, earlier, a failure to passing a funding mechanism for that wall during the two years when Republicans controlled the House and the Senate.

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Trump will note (and has noted) that the existence of the filibuster makes passing legislation trickier than bare majorities might make it seem. And that’s fair — but it also means that Trump at no point was able to use those zoning-board skills to persuade even eight Democrats to join his view of an issue. At one point, a deal seemed to be in the works with the Democratic minority, trading wall money for the protection of immigrants covered under the Deferred Action for Childhood Arrivals program.

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Trump rejected that deal, and here we are.

At times over his first two years in office, Trump was unable to even navigate issues popular with the Republican base and that didn’t require a 60-vote margin. He deferred to congressional leaders on the outlines of an overhaul to the Affordable Care Act, later disparaging a House-passed bill before it got to the Senate. When a reform effort came to the Senate under reconciliation rules that required only 50 votes, Trump could not persuade those “easy-to-deal-with” politicians to pass it, despite his party’s majority.

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That Trump’s team didn’t advance the overhaul legislation is the least surprising part of this. At the same news conference in Iowa, he proudly proclaimed that he was reticent to put together position papers — both because voters don’t really care about them (fair enough) and because they would tie his hands in negotiations. Part of it, too, was obviously that the specifics of drafting legislation never appealed to him. So he has continually left the details up to his colleagues on the Hill, then has had to advocate for things that he himself didn’t develop. Pun intended.

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There are a lot of reasons that the current fight with Congress is unwinnable for the president. He chose to make a stand on his most politically divisive proposal precisely because it is so divisive and, therefore, so important to the most vocal part of his base. But it also gives his opponents even less incentive to side with him than they might otherwise have. He has been ineffective at making his case, in part because the case he’s making is the same one he has made over the entire course of his political career. He is left flailing, with no obvious way out but to fold.

That, too, is part of the Trump business legacy. Over his multiple decades in the real estate industry, he has walked away from bad or failing projects, such as his casinos in Atlantic City.

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Or that “city” Trump built on the West Side of Manhattan.

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It was not the evidence of his savvy that Trump presented in Iowa. Intending the development to feature the tallest building in the world, he had hoped to lure NBC to it. That never materialized, thanks in part to tax concessions that NBC received to stay in Rockefeller Center — concessions that Trump had sought to aid his development project.

The Times noted at the time that Trump had “suffered only defeats” in advancing the project, writing that “Trump does not so much avoid failure as know how to land on his feet and change course so deftly that no one catches on.”