Trump's First 100 Days The education of Donald Trump The White House remains on a collision course between the president's fixed habits and the demands of his new job.

The 70-year-old leader of the free world sat behind his desk in the Oval Office last Friday afternoon, doing what he’s done for years: selling himself. His 100th day in office was approaching, and Trump was eager to reshape the hardening narrative of a White House veering off course.

So he took it upon himself to explain that his presidency was actually on track, inviting a pair of POLITICO reporters into the Oval Office for an impromptu meeting. He sat at the Resolute desk, with his daughter Ivanka across from him. One aide said the chat was off-the-record, but Trump insisted, over objections from nervous-looking staffers, that he be quoted.


He addressed the idea that his senior aides weren’t getting along. He called out their names and, one by one, they walked in, each surprised to see reporters in the room—chief of staff Reince Priebus, then chief strategist Steve Bannon, and eventually senior adviser Jared Kushner. “The team gets along really, really well,” he said.

He turned to his relationships with world leaders. “I have a terrific relationship with Xi,” he said, referring to the Chinese president, who Trump recently invited for a weekend visit at his Mar-a-Lago resort.

Finally, he rattled off the biggest hits of his first three months and promised more to come.

It was classic Trump: Confident, hyperbolic and insistent on asserting control.

But interviews with nearly two dozen aides, allies, and others close to the president paint a different picture – one of a White House on a collision course between Trump’s fixed habits and his growing realization that this job is harder than he imagined when he won the election on Nov. 8.

So far, Trump has led a White House gripped by paranoia and insecurity, paralyzed by internal jockeying for power. Mistrust between aides runs so deep that many now employ their own personal P.R. advisers — in part to ensure their own narratives get out. Trump himself has been deeply engaged with media figures, even huddling in the Oval Office with Matt Drudge.

Trump remains reliant as ever on his children and longtime friends for counsel. White House staff have learned to cater to the president’s image obsession by presenting decisions in terms of how they’ll play in the press. Among his first reads in the morning is still the New York Post. When Trump feels like playing golf, he does — at courses he owns. When Trump feels like eating out, he does — at hotels with his name on the outside.

As president, Trump has repeatedly reminded his audiences, both public and private, about his longshot electoral victory. That unexpected win gave him and his closest advisers the false sense that governing would be as easy to master as running a successful campaign turned out to be. It was a rookie mistake. From the indignity of judges halting multiple executive orders on immigration-related matters—most recently this week—to his responses to repeated episodes of North Korean belligerence, it’s all been more complicated than Trump had been prepared to believe.

“I think he’s much more aware how complicated the world is,” said former House Speaker Newt Gingrich, who serves as an informal administration adviser. “This will all be more uphill than he thought it would be because I think he had the old-fashioned American idea that you run for office, you win, then people behave as though you won.”

Trump has had some successes. He nominated and saw confirmed a new Supreme Court justice, rolled back Obama-era regulations, and oversaw dramatic military actions in Syria and Afghanistan. He has signed rafts of executive actions, unilateral decisions familiar to the former Trump Organization president.

Yet he approaches the 100-day mark with record-low approval ratings and no major legislative accomplishment to his credit. Nothing hit Trump harder, according to senior White House officials, than the congressional defeat of his first major legislative package—the bill to repeal Obamacare. As he sat in the Oval Office last week, Trump seemed to concede that even having risen to fame through real estate and entertainment, the presidency represented something very different.

“Making business decisions and buying buildings don’t involve heart,” he said. “This involves heart. These are heavy decisions.”



***

More than 200 of Trump’s campaign promises are scribbled in marker on a whiteboard in Steve Bannon’s West Wing office, which he calls his “war room.” Other pledges are printed and taped beneath a poster that says: “Make America Great Again.”

“Deport 2 million criminal illegal immigrants,” reads one pledge. Others call for all of President Obama’s executive orders to be reversed and for the U.S. to exit the North American Free Trade Agreement, or NAFTA. A few have large check marks next to them. Another sign notes 11 have been delayed. It’s a visual encapsulation of how Bannon sees the presidency about keeping promises.

In Kushner’s office, just steps away, there’s no “Make America Great Again” memorabilia. Instead, the whiteboard lists deadlines for bipartisan projects in his newly-founded Office of American Innovation on infrastructure and veterans’ affairs. Kushner often talks about the presidency like it’s a business, describing it privately as “entrepreneurial” and in “beta mode.” He often doesn’t mind when Trump flip-flops, if it’s in the service of striking a deal.

The gap in worldview and temperament between the two has produced the most combustible, and consequential, conflict in the West Wing. In the first days following Trump’s inauguration, it was Bannon who pushed to speed through a blitz of executive orders, including the ill-fated travel ban. And it’s been Kushner, a 36-year-old real estate scion, who’s leaned the other way, encouraging his capricious father-in-law to espouse less divisive positions.

“It’s an ideas and ideology battle every day,” one senior administration official said.

Perhaps the defining and unanswered question of the Trump presidency is what he truly believes in. Is he the inflexible immigration hardliner who described undocumented Mexican immigrants as “rapists” in his June 2015 kickoff speech or the president who recently said those brought here illegally as children should “rest easy” because he doesn’t plan to deport them? Will he try to make deals with Democrats? Or will he devote himself to Bannon’s nationalist agenda? And, other than winning, what does Trump really want?

No single day was more telling about the ambiguity of Trumpism than April 12. It was that day that Trump not-so-quietly reversed himself on at least four of his campaign promises. He canceled a federal hiring freeze imposed in his first week. He flipped on labeling China a currency manipulator. He endorsed the Export-Import bank that he had called to eliminate. He declared NATO relevant, after trashing it repeatedly on the campaign trail.

“I said it was obsolete,” Trump said. “It is no longer obsolete.”

Trump’s critics and supporters alike are equally flummoxed about what this president stands for.

White House communications director Mike Dubke told staff in a recent meeting “there is no Trump doctrine” when it comes to foreign policy. The president was moved to send missiles into Syria in part based on gruesome images of dead Syrian children he saw on TV. But he’s maintained the same hardline that those suffering children should not be accepted into America as refugees. Trump has overseen the use of the largest bomb short of a nuclear weapon in Afghanistan and talks tough about obliterating the Islamic State. Yet in a recent chat in his West Wing office, Priebus backed away from the idea of greater troop engagement, saying the administration doesn’t want to engage in “long-term ground wars in the Middle East.”

“He is not a movement conservative. He is definitely not an establishment Republican,” said Ken Blackwell, who headed domestic policy during Trump’s transition. “He’s transactional and makes calls based on his gut. Those of us who are accustomed to an ideological framework — it takes getting used to.”

But Trump’s ideologically noncommittal approach has bumped up against the constraints of a hyperpartisan Washington where the letters on congressional vote cards — D or R — are paramount.

Some are whispering that Trump should work with Democrats on infrastructure. Others say he must forge ahead only with Republicans on health care. Maybe he should work with both on taxes. Trump, it seems, is just looking for success.

“I am flexible,” as Trump said recently in a Rose Garden appearance. “And I’m proud of that flexibility.”



***

When Donald Trump gets angry, he fumes. “You can’t make them happy,” he said. “These people want more and more.”

He was complaining to friends that he had negotiated for weeks with Freedom Caucus members and he couldn’t believe the group was still against the health care legislation. Trump and his advisers were buzzing about making an enemies list and wanted to force a vote. But it was Trump, a man who hates to show weakness, who had to blink. As support flagged, the bill was shelved.

“I kind of pooh-poohed the experience stuff when I first got here,” one White House official said of these early months. “But this shit is hard.”

Nowhere has Trump’s learning curve been steeper than Capitol Hill. According to people close to the president, Trump believed that in selecting Priebus as chief of staff he was getting a deeply connected Washington wise man, someone who could guide his agenda through Capitol Hill.

Between Priebus and Vice President Mike Pence, who once served in House leadership, Trump thought he had the experts he needed and wouldn’t have to worry about Congress that much. But Priebus is a political insider, not a congressional one. And Pence, who was governor of Indiana before joining Trump’s ticket, has been absent from the Hill during the rise of the House Freedom Caucus, the ideological hardliners who delivered Trump the most stinging defeat of his young presidency.

House Republicans’ rejection of his plan to repeal-and-replace Obamacare served as a wake-up call — and a clarifying moment when he realized he couldn’t leave Congress to others, even Speaker Paul Ryan.

Trump had campaigned in generalities — “repeal-and-replace with something terrific,” he’d promised — and after the election Trump and his team decided to let Ryan take the lead on health care. Trump just wanted to sign a bill. He didn’t necessarily care what it said.

But the Freedom Caucus did. They felt left out of the process—and they hated Ryan’s bill. They complained to the White House almost every day and made threats. They seized on the bill’s anemic public approval.

So Trump personally got involved, just as he had long negotiated with business partners, offering a mix of wooing and threats. He even dispatched his budget director, Mick Mulvaney, a former House GOP hardliner himself, to threaten a particularly outspoken critic, Rep. Mark Sanford.

It backfired. Freedom Caucus members weren’t afraid to say no. In an embarrassing setback, Trump called to pull the bill.

President Donald Trump’s critics and supporters alike are equally flummoxed about what this president stands for. | Getty

White House officials played down the loss in recent conversations -- even as Trump has put immense pressure on Pence and Priebus to resuscitate the bill. “The narrative that somehow or another a signature piece of legislation must be out of the House and Senate in 100 days is a ridiculous standard,” Priebus said.

Trump seemed, at first, not to even understand the scope of his health care failure. He called reporters and spoke about moving on. Top-level aides bragged about his good mood. “No bullshit, I think he’s actually pretty comfortable with the outcome,” a senior White House official crowed.

After the health care fight, Marc Short, the president’s legislative director, had a meeting with his team on “lessons learned,” people familiar with the meeting say. Several administration officials said Trump has told them not to leave the Congressional details to Ryan and others – and that he eventually grasped how damaging the health care defeat could be to the rest of his agenda.

“I don’t think they realized what a big issue this was for the grassroots,” said Jenny Beth Martin, head of Tea Party Patriots, who had met with Trump.

Trump’s team now has another chance to pass the law. They spent several weeks wooing conservatives – and secured the backing Wednesday of the Freedom Caucus, which blocked the first bill from passing. They brought members and outside groups – including those funded by the conservative billionaire donors Charles and David Koch – to the White House.

They successfully convinced the conservatives who don’t like Ryan to get on board. But now, moderates concerned about making health benefits worse for their constituents are balking. White House officials are hoping to have a vote Friday or Saturday, just in time for Trump’s 100-day mark.

The defeat represented an early inflection point for a president who is openly more transactional than ideological. More than anything, it reinforced the president’s conviction that he could only trust the tight circle of people closest to him.

Now, Trump is forging ahead alone on taxes, rolling out a dramatic package of tax cuts on Wednesday without input from Hill leaders. “We aren’t listening to anyone else on taxes,” said one senior administration official, referring to Ryan. “It’s our plan.”



***

As Trump is beginning to better understand the challenges—and the limits—of the presidency, his aides are understanding better how to manage perhaps the most improvisational and free-wheeling president in history. “If you’re an adviser to him, your job is to help him at the margins,” said one Trump confidante. “To talk him out of doing crazy things.”

Interviews with White House officials, friends of Trump, veterans of his campaign and lawmakers paint a picture of a White House that has been slow to adapt to the demands of the most powerful office on earth.

“Everyone is concerned that things are not running that well,” said one senior official. “There should be more structure in place so we know who is working on what and who is responsible for what, instead of everyone freelancing on everything.”

But they’re learning. One key development: White House aides have figured out that it’s best not to present Trump with too many competing options when it comes to matters of policy or strategy. Instead, the way to win Trump over, they say, is to present him a single preferred course of action and then walk him through what the outcome could be – and especially how it will play in the press.

“You don’t walk in with a traditional presentation, like a binder or a PowerPoint. He doesn’t care. He doesn’t consume information that way,” said one senior administration official. “You go in and tell him the pros and cons, and what the media coverage is going to be like.”

Downplaying the downside risk of a decision can win out in the short term. But the risk is a presidential dressing-down—delivered in a yell. “You don’t want to be the person who sold him on something that turned out to be a bad idea,” the person said.

Advisers have tried to curtail Trump’s idle hours, hoping to prevent him from watching cable news or calling old friends and then tweeting about it. That only works during the workday, though—Trump’s evenings and weekends have remained largely his own.

“It’s not like the White House doesn’t have a plan to fill his time productively but at the end of the day he’s in charge of his schedule,” said one person close to the White House. “He does not like being managed.”

He also doesn’t like managing—or, rather, doesn’t mind stoking competition among his staffers. While his predecessor was known as “no-drama Obama,” Trump has presided over a series of melodramas involving his top aides, including Priebus, Bannon, counselor Kellyanne Conway and economic adviser Gary Cohn.

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“He has always been a guy who loves the idea of being a royal surrounded by a court,” said Michael D’Antonio, one of Trump’s biographers.

Many of those aides spent the opening weeks of the presidency pushing their own agendas – and sparring with one another. Priebus brought into the White House his chief of staff, chief operating officer and chief strategist from the RNC; Bannon has his own P.R. person and two writers from Breitbart; Kushner brought allies from the business world, and recently recruited his own publicity adviser; Conway has her own chief of staff; now Ivanka Trump has a chief of staff, too.

For now, all sides seem to have forged a delicate détente. Kushner and Bannon met earlier this month at Trump’s Mar-a-Lago estate and agreed to work out their differences. Trump aides now downplay talk of a shakeup involving Bannon – talk that, until just a few days ago, had reached a fever pitch. There have been a few changes here and there – Katie Walsh is out as deputy chief of staff, and KT McFarland has been moved off the national security team – but don’t expect any big personnel changes anytime soon, they say.

Yet there is little question that the months of infighting have taken a toll on Trump’s aides. Many are unaccustomed to working for a man who can consult with 20 outside associates a day, change his mind in a minute and change his mood even quicker.

Of late, some Republican National Committee members have become deeply concerned about Priebus, who was party chairman before joining Trump’s team. Priebus, who is distrusted by some rival White House factions and lacks the control previous chiefs of staff have had, has privately complained about the profound frustrations of the job.

Priebus, who is married and has two young children, has vented about the long hours he’s had to spend away from his family. In March, he missed an RNC donor retreat in Florida because, he told friends at the time, he needed to be at home to celebrate one of his children’s birthdays.

Trump the businessman and presidential candidate loved pitting top aides against one another. The internal competition ensured that the best ideas would rise to the top, he believed. Plus, he liked telling people, it made his employees work even harder to impress him.



***

White House Press Secretary Sean Spicer has developed a ritual of sorts: Just before going onstage for his televised briefings, he usually walks down the hall to the Oval Office to ask Trump what he wants to hear on TV that day. Cable news only occasionally carried press briefings from Obama’s secretaries in the later years of his presidency, but Spicer’s almost-daily outings have become a regular, wall-to-wall fixture.

His sessions with Trump were described by people familiar with them as part pep talk and part talking-point seminar. In the early days, Trump criticized Spicer fiercely, prompting him to upgrade his delivery at the podium as well as his wardrobe of suits. Now, people close to the president say, Trump brags about Spicer’s ratings.

Yet Trump continues to see himself as the best guardian of his own image. In New York, he infamously made calls to reporters pretending to be a spokesman. He personally called into the New York tabloid gossip pages as a source for years, and he even dialed cable news control rooms to suggest coverage after he became the presumptive Republican nominee in 2016.

That hasn’t changed in the White House, where Trump continues to crave attention and approval from news media figures. Trump huddled in the Oval Office with Matt Drudge, the reclusive operator of the influential Drudge Report, to talk about his administration and the site. Drudge and Kushner have also begun to communicate frequently, said people familiar with the conversations. Drudge, whose visits to the White House haven’t previously been reported, didn’t respond to a request for comment.

Several senior administration aides said Trump loves nothing more than talking to reporters – no matter what he says about the “failing” New York Times or CNN – and he often seems personally stung by negative coverage, cursing and yelling at the TV. Kushner, too, sometimes calls TV personalities and executives, in particular MSNBC host Joe Scarborough, according to people close to the Trump son-in-law. (It didn’t go unnoticed in the West Wing that, at the height of the Kushner-Bannon war, the Drudge Report and Scarborough’s Morning Joe had an anti-Bannon flair to their coverage.)

If the goal of most administrations has been to set the media agenda for the day, it’s often the reverse in Trump’s White House, where what the president hears on the cable morning gabfests on Fox News, MSNBC and CNN can redirect his attention, schedule and agenda. The three TVs in the chief-of-staff's office sometimes dictate the 8 a.m. meeting – and are always turned on to cable news, West Wing officials say.

Behind the scenes, Trump – who beneath his confident veneer can be deeply sensitive to criticism – has been jolted when lawmakers took to TV to jab the president. If anyone had anything to say to the president, White House aides vented, they should do it with him personally – not from the camera. “If you go on TV and blast him, it’s over,” one senior administration official said.

Since taking office, Trump has 16 times tagged Fox and Friends, the network’s morning show, in his tweets, and countless other times weighed in on whatever they were talking about on air. After Democratic Rep. Elijah Cummings went on Morning Joe and asked the president to call him, Trump did. After Republican Rep. Dana Rohrabacher defended Trump in an early Saturday morning Fox News hit, Trump called him moments later, inviting him to an Oval Office meeting. And after news segments, Trump will sometimes call his own advisers to discuss what he saw.

No slight is too small to ignore. West Wing staffers have even fumed about news coverage of the Easter Egg Roll. First, it was that Trump’s White House wouldn’t be smart enough to pull it off. Then, it was that no one would be there. And after the Easter Egg Roll went off without a hitch, “no one wanted to give us any credit,” said one senior administration official.

It is part of a siege mentality that has taken hold, from the president down, with Trump and his associates believing their coverage has stayed just as bad — or gotten worse — since the campaign ended in November. Senior administration officials said they’ve never seen Trump angrier than when the media focused its attention on the crowd size at his inauguration.

The darkest cloud shadowing the West Wing has been continuous questions about the Trump campaign’s connections to Russia.

The FBI director testified he is investigating Trump associates for possible collusion with a hostile foreign power, Trump’s first national security adviser, Michael Flynn, resigned over his interactions with the Russian Ambassador Sergey Kislyak and Attorney General Jeff Sessions ultimately had to recuse himself from his own department’s investigation after he failed to disclose his own conversations with Kislyak.

“If we have a good day, then within 48 hours there’s a Russia story,” said another senior administration official. “That’s just how it works.”

The news about Sessions’ interaction with the Russian ambassador came the day after Trump’s widely praised speech to a joint session of Congress. And it stomped on any momentum the White House had, especially Trump’s trip to an aircraft carrier later that week. At the end of the week, after Sessions recused himself from the probe, Trump exploded at his aides about his frustrations.



***

Yet Trump was grinning in his office last week. He wanted to pose for pictures behind the cleaned-off Resolute desk and in front of his gold curtains. He has posed for hundreds of pictures there – sometimes with a grin, sometimes with a thumbs-up – and has guests stand behind him. He seemed a man of few worries -- even though his aides were back out pushing a high-stakes health care vote, the government was one week from shutting down and North Korea was continuing its provocations.

The fact that 100 days, as a marker, has no legal or actual significance outside the media has not seemed to matter to Trump. While he has publicly derided the deadline as “ridiculous” on Twitter, he has decidedly reshuffled his schedule, priorities and agenda in the last two weeks to notch political points, knowing the deadline would get inordinate media coverage.

He has repeatedly pressed aides to have a health care vote before Saturday. He surprised his own staff by promising a tax reform plan by this week and urged them to round out his list of accomplishments. He has maintained an aggressive calendar, wooing conservative outlets and traditional reporters alike.

He told aides this week needed to be a busy one — just as he told them after his inauguration.

In days 1 through 10, it was executive orders on a federal hiring freeze, abortions abroad, withdrawing from an Asian trade deal and the explosive immigration order barring immigrants from certain Muslim-majority countries. He got into a diplomatic row with Australia, one of America’s closest allies. The immigration order sparked international protests and was stopped in court. Trump later told advisers he regretted how it was handled.

In days 90 through 100, it was a flurry of executive orders. He got into a diplomatic row with Canada, one of America’s closest allies, threatening a trade war. He moved toward unwinding NAFTA. “There is no way we can do everything he wants to do this week,” one senior official said.

“Trump is a guy of action. He likes to move,” said Chris Ruddy, a close friend. “He doesn’t necessarily worry about all the collateral damage or the consequences.”

White House officials say they now have a more deliberative process of decision-making. Issues don’t go to his desk until they’ve had a thorough vetting in at least three meetings. Aides have cautioned him to slow down and have told him everything is not possible in his time frame. Sometimes, administration officials say, he listens and takes the news well. Sometimes, he keeps the demands going.

Trump may be learning and adjusting. But he is still Trump. On Saturday, he’ll celebrate his 100th day in office by boycotting the traditional White House Correspondents’ Dinner in favor of a rally in Harrisburg, Pennsylvania. The rallies, which remind him of the campaign trail, often improve his mood, several people close to him say. “I will be holding a BIG rally in Pennsylvania,” he tweeted by way of announcement. “Look forward to it!”

Ben White contributed to this report.