Trump Faces Deal-Making Challenges as Congress Returns

“Legislatively, September may be the longest month of the year, with several must pass items that face an uphill climb,” said Doug Heye, a longtime Republican strategist. The president’s decision to push the immigrant program to Congress “only makes that harder, on an issue that for years Republicans have struggled to make any headway on. The question is whether this was a strategic decision by the White House.”

His self-proclaimed deal-making skills could also be put to the test in foreign policy as he decides how to respond to North Korea’s nuclear saber-rattling while separately seeking to renegotiate the North American Free Trade Agreement with Mexico and Canada and broker peace between Israelis and Palestinians. And he may alienate America’s traditional European allies if he tries to scuttle Mr. Obama’s nuclear agreement with Iran by declaring Tehran out of compliance over their objections.

.. As he pressures North Korea to curb its nuclear program, he has belittled South Korea for “appeasement” and threatened to tear up its trade deal with the United States. As he lobbies lawmakers to back his legislative priorities, he has castigated Senator Mitch McConnell, the majority leader, and other Republicans crucial to passage.

.. Mr. Trump’s allies argue that he had a better summer than the Washington conventional wisdom would suggest and that he has a path forward. They contend that after the fights of early August, the president took on the mantle of a national leader with a vigorous and visible response to Hurricane Harvey, and that cleaning up the devastation may prove both a rallying point and a strategic leverage.

.. “It may sound counterintuitive, but the president heads into September with a bit of wind at his back,” said Michael Dubke, who served as his White House communications director. “Harvey was handled well, tax reform is back on track, the debt ceiling showdown will be pushed to a later date and while there are no good choices in North Korea, the president’s national security team is second to none.”

.. It’s not a mistake to disagree when you disagree; it is a mistake to suggest that somehow this president, who was elected just as the Constitution prescribed, and has the responsibility to lead the country, that somehow we need to not work with this president.”

.. On Tuesday afternoon, Mr. Trump will host a group that has been dubbed the Big Six to discuss his tax overhaul —

  1. Mr. McConnell;
  2. House Speaker Paul D. Ryan;
  3. Treasury Secretary Steven Mnuchin;
  4. Gary D. Cohn, the president’s national economics adviser;and
  5. Senator Orrin G. Hatch of Utah and
  6. Representative Kevin Brady of Texas, the Republican chairmen of the tax-writing committees.

.. Allies said Mr. Trump’s approach to negotiations, however, is to hold out for the best deal possible until the last moment, so it is too soon to judge.

.. “My style of deal-making is quite simple and straightforward,” he once wrote. “I aim very high, and then I just keep pushing and pushing and pushing to get what I’m after. Sometimes I settle for less than I sought, but in most cases I still end up with what I want.”

.. But those who have studied his career in real estate and business said that it has been marked by as many failed deals as successful ones.

  • He bought an airline that failed.
  • He bought a football team in a league that collapsed.
  • He filed for bankruptcy protection multiple times.

“If you look at his record, there are a lot of deals that didn’t work out,” said Michael D’Antonio, a Trump biographer. “So if you think about the true record of performance, he is very good at promotion and creating the idea that he is a deal maker, but not very good at making actual successful deals.”

.. some Democrats argue that Mr. Trump’s very weakness may yet prove to be a boon. Since legislating entirely with fellow Republicans has yet to yield the results Mr. Trump had hoped, he may have more incentive to work with Democrats on areas where they could find agreement, particularly

  • infrastructure and the
  • tax code.

Democrats would also like to work on legislation stabilizing the Obama health care markets.