The inside story of how Trump tried - and failed - to make a deal on health care

And over the next 18 days, until the bill collapsed in the House on Friday afternoon in a humiliating defeat - the sharpest rebuke yet of Trump's young presidency and his negotiating skills - the question continued to nag at the president.

Even as he thrust himself and the trappings of his office into selling the health-care bill, Trump peppered his aides again and again with the same concern, usually after watching cable news reports chronicling the setbacks, according to two of his advisers: "Is this really a good bill?"

In the end, the answer was no - in part because the president himself seemed to doubt it.

"We were a little bit shy - very little, but it was still a little bit shy, so we pulled it," Trump said Friday afternoon in an interview with The Washington Post.

For Trump, it was never supposed to be this hard. As a real estate mogul on the rise, he wrote "The Art of the Deal," and as a political candidate, he boasted that nobody could make deals as beautifully as he could. Replacing Obamacare, a Republican boogeyman since the day it was enacted seven years ago, was Trump's first chance to prove that he had the magic touch that he claimed eluded Washington.

But Trump's effort was plagued from the beginning. The bill itself would have violated a number of Trump's campaign promises, driving up premiums for millions of citizens and throwing millions more off health insurance - including many of the working-class voters who gravitated to his call to "make America great again." Trump was unsure about the American Health Care Act, though he ultimately dug in for the win, as he put it.

There were other problems, too. Trump never made a real effort to reach out to Democrats, and was unable to pressure enough of his fellow Republicans. He did not speak fluently about bill's details and focused his pitch in purely transactional terms. And he failed to appreciate the importance of replacing Obamacare to the Republican base; for the president, it was an obstacle to move past to get to taxes, trade and the rest of his agenda.

Trump's advisers thought he could nudge the bill over the finish line by sheer force of personality. "He is the closer," White House press secretary Sean Spicer boasted on Wednesday.

But by Friday, it was clear that the closer could not close.

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Trump tried to orchestrate his own win.

He cajoled and charmed uncertain members, offering flattery and attention to some and to admonishment and the vague threat of political retribution to others. He invited members to the White House for bowling sessions, gave others rides on Air Force One (complete with lasagna) and grinned for pictures in the Oval Office, where he reminded lawmakers of his margins of victory in their districts.

But legislating, it turned out, was different from cutting deals to splash his name across skyscrapers. And less than 100 days into his administration, the president found himself a red-faced Don Quixote, railing against the intractable forces on Capitol Hill, where Republicans are wearied by years of infighting.

This account of Trump's work on the health-care bill - based on interviews with roughly three dozen White House aides and advisers, members of Congress, and other key figures in the debate - revealed a president in a constant state of negotiation. He remarked to friends and aides that it did not feel much different from his real estate transactions.

"It's the same thing," he said Wednesday in the Oval Office. "Really, it is."

Yet the man accustomed to acting unilaterally as a Manhattan developer faced a series of new and uncomfortable challenges. As president, he was selling the rare product on which he refused to emblazon his name - devoting himself to an issue for which he has little real passion or knowledge and operating as a dealmaker in an unfamiliar town full of conflicting loyalties.

Reflecting Friday on the failure, Trump said he thought he had cultivated a good relationship with the House Freedom Caucus - the band of hard-line conservatives who proudly oppose Ryan and other House leaders.

"I couldn't get them," Trump said in the Post interview. "They just wouldn't do it. . . . I think they made a mistake, but that's OK."

Alluding to the long-running dramas on Capitol Hill, Trump added, "There are years of problems, great hatred and distrust, and, you know, I came into the middle of it."

But that didn't stop the president from trying. Just two days before the bill was withdrawn by House leadership, Trump sat inside the Oval Office at dusk as his aides offered yet another blunt warning in a week full of them: The measure was likely to fail. Too many Republicans were opposed.

Still in a suit jacket and striped red tie Wednesday evening, the president dialed Rep. Joe Barton, a wavering Republican from Texas, and placed the call on speakerphone. He put his finger to his lips to shush the clutch of advisers that always surrounds him. The president listened as the congressman ticked through his concerns, sipping from a glass of Diet Coke and jotting down notes with a thick, black Sharpie.

Never one to get caught up in policy details, Trump concentrated his pitch on the big picture: winning. Trump said he wanted a win for Barton, for Texas, for their party, for the country - and, of course, for himself.

When Barton told Trump that he could probably support the bill, with a few changes, the president smiled and winked at Vice President Mike Pence, who stood hovering over the Resolute desk, and Health and Human Services Secretary Tom Price, who leaned forward to listen. As Trump wrapped up the call - "Talk soon," he told Barton - Pence and Price silently punched their fists in the air. Barton was not an absolute yes but, for the moment, it was good enough.

Then the president was on to the next call.

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The White House had striven to ensure that its first real legislative push would be an organized, disciplined one. But as the bill began to falter, the chaos and turbulence that has become a hallmark of Trump's presidency emerged yet again.

On Thursday, Trump appeared embarrassingly out-of-the-loop; as the congressional whip efforts faltered, Trump was busy at the White House, greeting commercial truckers and climbing into the cab of a eighteen-wheeler to honk the horn.

"It's going to be a very close vote," the president said, referring to what everyone else seemed to know had been delayed.

Trump fashioned himself as the master dealmaker. His senior aides described him as "an extremely good listener" and said his negotiating skills were the product of "total natural talent," saying he could turn up the heat or the charm as needed.

But the negotiations over the bill's substance took place mostly at the other end of Pennsylvania Avenue. Trump had amicable meetings with members of all stripes, but found himself caught in the middle of factional House GOP dramas that have been simmering for years. As one member of the House Freedom Caucus described it: "We're competing with Ryan. We like Trump."

As the talks stalled later that night, Trump's exasperation with the hemming and hawing of members escalated and he delivered an ultimatum: Go ahead with the vote no matter what on Friday, he said, all but daring fellow Republicans to vote against his first significant bill.

The president was finished negotiating, and his thinking was straight from "The Art of the Deal": If the White House continued to postpone the vote, the holdouts would gain leverage and learn the dangerous lesson that they could challenge Trump and win. Lawmakers wanting to oppose the president would have to do so publicly, in a vote, and face the consequences.

Yet in the end, Trump acquiesced to the preferences of House leaders, who did not want their members voting on a controversial measure if the outcome were in doubt. Realizing the health-care plan did not have the support to pass, Trump and Ryan decided Friday afternoon to pull the bill - news Trump announced in a phone call with The Post, before Ryan even had time to personally brief GOP members.

"Just another day," Trump said in the call. "Just another day in paradise, okay?"

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As the odds for success fluttered, Trump increasingly came to relish the fight, seeing the sprint for passage as a test of whether he could translate abilities from the boardroom to the Oval Office.

Among the lawmakers he courted most intensely was Rep. Mark Meadows, R-N.C., the chairman of the House Freedom Caucus. Trump brought him to the Oval Office, called him regularly and directed White House chief strategist Stephen K. Bannon to call or text him daily. Last weekend, Meadows even journeyed to Mar-a-Lago, Trump's private Florida club, to huddle with Bannon and other aides about the bill.

Meadows said his mantra in negotiating with Trump had been, "If this was about personalities, we'd already be at 'yes.' He's charming and anyone who spends time with him knows that. But this is about policy and we're not going to make it about anything else."

For Meadows, a sticking point was essential health-benefit requirements under the current law for insurance companies, such as maternity and newborn care, and substance-abuse treatment, which he wanted removed and replaced with narrower rules.

Meadows and other Freedom Caucus members met with Trump and Pence at the White House on Thursday, but they left without a deal, even after Trump had worked with them for weeks - leaving Trump's advisers exasperated with the ornery bloc.

It was not only the Freedom Caucus creating problems for Trump. A group of more moderate Republicans, known as the Tuesday group, stood opposed to the bill, despite the president's pleadings.

One such member, Rep. Leonard Lance, R-N.J., attended meetings at the White House and praised Trump's style, saying the president clearly "knows Jersey." But, he added, the bill would harm his constituents who rely on Medicaid and there was nothing Trump could say to persuade him otherwise.

"He's got this wit about him that I enjoy," Lance said, "but I'm a 'no' vote."

On March 8, Trump met with a small group of conservative activists with hopes that their groups would get behind the bill. Someone with direct knowledge of the meeting described it as "a 'Saturday Night Live' skit," with the president boasting about how "great" the bill was and his aides seconding his assessment "like a Greek chorus."

After the meeting, Trump posed for pictures with the activist leaders - from groups such as Tea Party Patriots, Americans for Prosperity and Club for Growth - in the Oval Office. He urged them to address the press corps on the way out with a statement of support for the bill. They spoke to reporters in the West Wing driveway, but were tempered and far more reserved than the president had hoped.

Along the way, the Trump administration kept finding signs of hesitation and doubt. In the Eisenhower Executive Office Building on Wednesday, Rep. Ted Yoho, R-Fla., a member of the Freedom Caucus, irritated top Trump deputies, including Pence, when he walked out of a meeting with the vice president, making a thumbs-down gesture as he departed.

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While Trump turned on his charisma, Pence quietly worked behind the scenes. The vice president has been devoting at least one night a week - usually Wednesday - for get-to-know-you sessions with both lawmakers and their staffs at his residence.

This past Monday night, Pence hosted about a dozen leadership chiefs of staff. As a fire crackled at the Naval Observatory, the group dined on chicken with asparagus and a poached-pear dessert, and the vice president shared complimentary stories about what it was like to work with Trump.

Trump, meanwhile, was candid about the political ramifications of not supporting the bill, which he likened to an act of betrayal, and pointedly reminded lawmakers of his popularity among the Republican base.

Trump used one of his favorite trophies, the Oval Office, as a bargaining tool. He had so many lawmakers in and out in the days leading up to the vote that the stately room felt like a train station.

Trump also sought leverage by surprising members with cold calls. Rep. David Brat, R-Va., was at home near Richmond one day last week, moving boxes into his car, when his cellphone rang.

"Someone came on with this very formal voice and said, 'Please hold for the president of the United States,' " Brat recalled. But when Trump got on the line, the president could not have been less formal, Brat said. "He goes, 'C'mon, Brat, what's going on with this thing?' "

"I said, 'I want you to be a success, but the price has to come down,' " Brat said. "But he puts on the hard sell. He's selling. The salesman in sell mode. On that, he's the best. Humor, heart, personality."

Trump ended the call with a plea: "Dave, c'mon, we're going to get it right." But Brat was unmoved. "I get it," he said he told the president, "but I couldn't get behind it."

Trump was more effective with his call to Barton, who later described him as "a political Rodney Dangerfield." The Texan had been skeptical from the start, but two days after talking to Trump, Barton was ready to join what he thought would be a majority in voting for the bill.

"The choice is 'yes' or 'no,' " he said. "I'm not going to vote 'no' and keep Obamacare. That'd be a stupid damn vote."