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Why Trump can’t make a deal

Trump was supposed to be great at making deals. What happened?

Trump deal Photo by Ronen Tivony/NurPhoto via Getty Images

In The Art of the Deal, Donald Trump writes, “You can’t con people, at least not for long. You can create excitement, you can do wonderful promotion and get all kinds of press, and you can throw in a little hyperbole. But if you don’t deliver the goods, people will catch on.”

Trump is having trouble delivering the goods. At this point in his presidency, Barack Obama had far more nominees both named and confirmed, and he had passed the stimulus bill, the Lilly Ledbetter Fair Pay Act, and a massive expansion of the Children’s Health Insurance Program. As of today, Trump hasn’t signed any major legislation, and none seems close to his desk — in fact, Republicans and Democrats both tell me they’re beginning to doubt that Obamacare gets replaced or a major tax reform bill gets passed at all.

The reason the future looks bleak for Trump’s top priorities is that he seems to be doing everything he can to alienate the partners he needs — particularly Democrats, whose cooperation he needs in the Senate. His playbook has been more Breitbart than Art of the Deal.

This has been, to me at least, a surprise. Trump is a New York real estate developer. He’s been negotiating with Democratic politicians to get things done his entire adult life. His first donation to Chuck Schumer, leader of the Senate Democrats, came all the way back in 1996. He knows these people, and he knows how to work with them.

Trump could have fashioned himself a non-ideological negotiator — a CEO president who wanted to run the government like a business. He could have split the Democratic Party by prioritizing an infrastructure bill. He could have invited Nancy Pelosi and Chuck Schumer to the Oval Office three times each week — creating photo opportunities for him and a tough political bind for them.

Instead, Trump has poisoned his relationship with top Democrats. Calling Schumer “Fake Tears Chuck Schumer” might be satisfying for Trump, but it doesn’t endear him to Schumer’s many friends and allies in the caucus, much less to Schumer himself. Similarly, attacking civil rights icon and Atlanta Rep. John Lewis as “all talk, talk, talk — no action or results” infuriates the House Democrats who revere him.

Trump’s more consequential decision, however, has been to prioritize the policies that most outrage the liberal base, like his travel ban targeting Muslims from seven countries and refugees. According to SurveyMonkey, 88 percent of Democrats disapprove of the job Trump is doing as president — and 77 percent “strongly disapprove.” These sorts of numbers make it impossible for even the Democrats who wanted to work with Trump to do so.

There is no doubt Trump understands these dynamics. “You have to convince the other guy it’s in his interest to make the deal,” he said in The Art of the Deal. So what happened?

After asking members of Congress, political consultants, and activists on both sides of the aisle, I found three competing explanations for the path of Trump’s presidency so far.

Theory No. 1 for Trump’s absence of dealmaking: eye for an eye

Trump has often been asked why he doesn’t show a bit more generosity toward his opponents, or calm under fire. His answer — as when he attacked the Muslim parents of a fallen soldier — is familiar to any parent: They started it.

“I’m very good to people who are very good to me,” Trump writes in The Art of the Deal. “But when people treat me badly or unfairly or try to take advantage of me, my general attitude, all my life, has been to fight back very hard. The risk is that you’ll make a bad situation worse, and I certainly don’t recommend this approach to everyone.”

This is the core of Trumpism. Say nice things about him, he’ll say nice things about you. Say mean things about him, and he’ll go nuclear on you.

trump schumer
That is not Trump’s happy face.
Photo by Alex Wong/Getty Images

Trump can’t respond to Democratic attacks by inviting Schumer to golf because that’s simply not who Trump is. He doesn’t do deals with people who mistreat him. He crushes those who mistreat him. He did it in real estate and he did it in the election, and he doesn’t realize, or can’t adapt to, the fact that governing doesn’t work like that. To succeed at governing within the American political system, you have to work with people who mistreat you.

“This is where he and Bill Clinton are really different,” says Ron Klain, who served as chief of staff to both Vice President Al Gore and Vice President Joe Biden. “Bill Clinton could have people calling for his impeachment by day and he’d cut a budget deal with them by night. With Trump, it’s so personal to him. When Chuck Schumer attacks him, Trump can’t then go and do an infrastructure deal. He doesn’t compartmentalize, and it’s why he’s been unable to be an Art of the Deal president.”

This theory converges with the idea, which I heard often, that it’s all Steve Bannon’s fault. While it’s true that Trump’s chief strategist has been pushing Trump to front-load his most divisive ideas and pick fights with Democrats and the media, it’s also true that plenty of people around Trump are recommending a different path. The reason Trump listens to Bannon rather than Reince Priebus or Mike Pence is that Bannon’s advice matches Trump’s personality, while Priebus and Pence’s advice matches Paul Ryan’s personality.

But as Trump presciently warned, the risk of this strategy is it can make a bad situation worse. And it is.

Theory No. 2 for Trump’s absence of dealmaking: all part of the plan

Some Republicans see strategy in Trump’s sequencing. Trump is starting with the most polarizing parts of his agenda — a conservative Supreme Court pick, the travel ban, Obamacare repeal, and tax cuts. If he succeeds in passing all four, he will have made good on his promises to the right, and will have time and capital with which to pursue goals that appeal to Democrats and alienate conservatives, like a pricey infrastructure bill.

There’s some evidence the Trump administration buys this theory, too. The White House has convinced itself, or been convinced, that delaying an infrastructure bill into 2018 is a brilliant strategy. “Republican strategists say that Democrats, who'll be reluctant to give Trump a win, will be in a jam as midterm elections close in,” report Mike Allen and Jonathan Swan.

As my colleague Matthew Yglesias dryly notes, “it’s a little unclear who is spinning whom here. But either way, this is nonsense.” If Trump spends a year enraging Democrats, he’s not going to be able to spend his second year merrily splitting the party. The less popular Trump becomes, and the more blood Democrats smell in the 2018 elections, the easier it will be for them to oppose everything he does — and the harder it will be for him to hold Republicans together. It’s incumbent parties, not minority parties, that grow more fractious before midterm elections.

The other problem with this theory is that replacing Obamacare and reforming the tax code will be much, much harder without Democratic support. A full-on health reform bill, for instance, will need 60 votes in the Senate, and a tax bill might need Democratic support to cover Republican defections, as well.

Meanwhile, to go back to theory 1, if Trump spends his first year or more on the priorities Democrats hate most, then by the time he tries to turn to dealmaking, Democrats will have said so many unkind things about him, and he will have said so many unkind things about them, that sheer personal enmity will make cooperation impossible.

Theory No. 3 for Trump’s absence of dealmaking: there is no plan

Perhaps all this makes the mistake of attributing to malice what is really best understood as incompetence.

When Sen. Obama was elected to the presidency, he brought a slew of congressional veterans in with him. Joe Biden, his vice president, was one of the Senate’s longest-serving members; Rahm Emanuel, his chief of staff, was a member of the House Democratic leadership; Phil Schiliro, his top legislative aide, was chief of staff to Rep. Henry Waxman; Pete Rouse, his consigliere, had been chief of staff to Senate Majority Leader Tom Daschle; Peter Orszag, his budget director, had led the Congressional Budget Office; the list could go on. This was an administration thick with congressional talent and consumed by congressional strategizing.

Rahm Emanuel is probably telling Obama a fun fact about congressional procedure.
Photo by Ralf-Finn Hestoft/Corbis via Getty Images

But it’s worth noting that even with all that experience, and even with the administration focused on the mechanics of passing bills through Congress, this was still the hardest part of Obama’s job — and today, you’ll find plenty on the Hill who thought Obama underinvested in both congressional relationships and process.

Unlike Obama, Trump has no personal experience in Congress, few close advisers with experience in Congress, and little evident knowledge of or interest in how Congress works. He’s lagging far behind past presidents both on nominating candidates to key positions and on getting them confirmed. On the Hill, there is widespread confusion on what Trump wants done, how he wants Congress to do it, and whether he wants to be involved.

It’s possible Trump simply does not understand what Congress needs from him. It’s possible he doesn’t realize, and isn’t being told, how imperiled his agenda truly is. But before a deal can be made, a tremendous amount of work must be done to get a bill conceived, drafted, and near to passage. Perhaps Trump could be a dealmaker if there were deals on offer, but his administration is so adrift on all the preliminary steps that his talents are being wasted.

The space for dealmaking is shrinking

There is a reason presidents tend to begin with their hardest congressional lifts: The longer a presidency continues, the harder it becomes to get big things done. Crises erupt. Political capital dissipates. Elections looms. Investigations distract.

Soon, Trump will have to work with congressional Republicans to pass the spending bills that keep the government open, and soon after that, he’ll have to figure out how to raise the debt ceiling — a bill the House Freedom Caucus isn’t likely to let pass quietly. All of this will be hard, and it will distract from his agenda, consume his time, and sap his popularity.

Nor will it be easy for Trump to reverse course in his personal relationships with Democrats. If he had made overtures to Schumer and Pelosi upon taking office, it would have been hard for them to resist. Now that he has repeatedly mocked them and their most admired colleagues, few will fault them for treating his outreach skeptically, and Trump himself is not likely to be able to overlook their criticisms long enough to build a relationship.

trump cameras Don Emmert/AFP/Getty Images

All of which suggests that Trump’s presidency is more adrift than many realize. How you start often decides how you end. The best theories of how an outsider like Trump would lead a successful presidency tended to revolve around him revealing himself a skilled manager and non-ideological dealmaker, and running an administration that effectively triangulated between Democrats and Republicans. But the window for that strategy to work is closing, and may already be shut.

Plan B, it seems, is for Trump to pick enough fights with the media and Democrats that people excuse his failures as the result of their obstruction. Perhaps that will work politically. But it’s not likely to help him get anything done. And as Trump himself wrote, you can only con people for so long. If you don’t deliver the goods, voters will catch on.