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Donald Trump is obsessed with winning, and that's why he's losing

  • President Trump famously promised Americans so much winning that they'd be sick of it.
  • Trump has lost on Obamacare repeal, health care reform, a Muslim ban and more.
  • He is so focused on winning every little battle that he has neglected the patient work required to win big wars in Congress.
Fans react after watching the U.S. lose to Belgium in the World Cup during a viewing party in the Kogod Courtyard of the Smithsonian National Portait Gallery July 1, 2014
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President Donald Trump famously promised Americans so much winning that they'd be sick of it. He appears obsessed with this promise, to the point of actively undermining it. He is so focused on winning — or claiming to win — every little battle, that he has neglected the patient work required to win big wars in Congress.

This strategy should unnerve conservatives; almost any other Republican president drawn from last year's primary field would be scoring more wins for their cause right now than Trump has. It should especially worry Trump's advisers. This week, the president appears set to obsess his way into a series of unforced errors that could hurt his agenda in the months and years to come.

Nearly 100 days into his term, Trump has delivered few major victories, either for the country or for his own supporters.

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He lost in his short-lived bid to repeal and replace Obamacare, demanding a rushed vote on a much-derided bill, only to back down at the last moment when it was clear he didn't have the votes. Courts have blocked two of his attempts to ban refugees and travel from several Muslim-majority countries.

Trump backed out of a currency fight with China, which he promised repeatedly while campaigning. He keeps punting on a pledge to detail his tax reform plan, and he hasn't stoked anything close to a massive jobs revival in manufacturing or coal mining.

His wins, such as they are, would be layups for any Republican president working with a full congressional majority. He nominated a Supreme Court justice who was confirmed by a GOP majority in the Senate that was willing to abolish the filibuster for judicial nominations. He canceled or began the work of rolling back several major regulations issued by President Barack Obama. He scorched a Syrian air strip, which appears to have won him a fleeting polling bump, but probably not much more. He has empowered Customs and Border Patrol agents to step up their aggressiveness in the deportation of undocumented immigrants.

Where Trump has soared, compared to any other possible Republican in the White House, is in the deflection of defeats and the claiming of faux-victories. He has taken credit for thousands of job-creation announcements that were often planned long before his election. He says the health care effort wasn't a loss, only an ongoing negotiation. Last week, after Republicans just barely managed to force a run-off in a special election for a GOP-stronghold congressional seat in Georgia, he tweeted this:

Limping to a run-off for the seat formerly held — and repeatedly won handily — by Trump's Health and Human Services secretary is by no means a win for Republicans. It could be, when the special election is held in June, but for now, it's claimable as a victory by Trump, because it's not a proven loss, either. The same is true for health care, China policy, and a host of other issues; until Trump actually loses on any of them, he can say he's winning.

Which brings us to this week, which Trump has built into a minefield of his own making.

How Trump could lose his 100th day

It wouldn't be hard for the president to ring in his 100th day in office with a few small victories, while quietly laying the groundwork for some larger ones by day 300 or so. The last round of government funding approved by Congress is about to run out, and Trump could sign a bill that continues it for a few weeks, to buy time for his fully detailed budget to be released. He'd avoid a government shutdown, and he could use the accompanying fanfare to clearly lay out his must-haves — on military spending increases, for example, or domestic spending cuts — to sign a longer-term spending plan.

He could announce a deadline for his economic team to produce an opening draft of a tax reform negotiation with Congress, one with more specifics attached than even his various campaign tax plans ever had. He could make clear which parts of that plan were most important — for example, middle-class tax cuts, or a low corporate rate — and avoid many of the mistakes he made in his half-engagement in health care, where he never put forth an actual plan for Congress to work with.

Speaking of health care, he could finally craft that plan, his true vision of Trumpcare, and announce its details as a challenge to Republicans in Congress to get in line or face the consequences.

Right now, Trump is no closer to passing those large pieces of legislation than he was when he took office — if anything, the congressional dynamics look more challenging. He rushed health care. He's been publicly passive on tax reform. He has allowed advisers to make competing statements about his priorities on both issues, or to admit, even today, that they're not sure if, say, a big temporary tax cut would be better than a small permanent one. He could be using this moment to take a breath, dive into the weeds, and build a foundation on both those issues.

That's not the week Trump is about to have. Instead, by several accounts in newspapers and from the mouths of his advisers on TV news shows, Trump plans to push Congress to score a bunch of "wins" for him on policy this week.

He wants a health care vote in the House, on a revised plan that still does not appear to be fully translated into legislative text.

He plans to make what he originally billed as a big announcement on tax reform, which his aides have since clarified will simply be a broad outline of principles. If it yields few major specifics, journalists and market participants may intensify questions about whether Trump is prepared to lead a successful tax reform effort.

Most importantly, he is pushing Congress hard to approve some funding for his signature campaign promise (albeit, the one Mexico was supposed to pay for): the construction of a wall across America's Southern border. Democrats are spoiling for that fight; they have threatened to force a shutdown to block that money. Top Republicans in the House and Senate seem eager to avoid the battle; they're pushing to keep the wall funding out of this week's bill and deal with it separately.

Nevertheless, Trump's budget director will not rule out Trump vetoing a funding bill that doesn't include money for the wall.

Trump needs big wins, not little ones

As my former colleague Bob Costa of the Washington Post tweeted on Sunday, Trump is driving this train himself:

This is a strategy that prizes short-term "wins" above all else. It carries several dangers for Trump. It distracts him and his team from the quiet work they need to do behind the scenes to craft bills that can unite a fractured House majority and clear the Senate, either via budget reconciliation or by picking up Democratic votes.

It also gives Democrats chances to score real wins against him, particularly if the government shuts down over wall funding and angry Americans blame Trump for it. (Democrats need those wins — they haven't actually defeated Trump on anything yet.)

There is a theory of momentum in politics — that small wins build to larger wins, which build to happy voters, which build to the even larger wins. That was what Trump promised all campaign.

That theory only works if you are actually winning, not pretending to win. Trump's core supporters continue to believe that he will actually win on big, core issue. So, to a diminishing degree, do financial markets. But as 100 days turn to 200, to 400, to the 2018 midterms, Trump will need concrete wins to keep his folks happy. To get them, he needs to be strategic.

You can feed people pretend wins for four years, but they'll probably get sick of it.

Commentary by Jim Tankersley, policy and politics editor for Vox.

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