He's confronting a critical moment -- which would daunt the most experienced, popular and statesmanlike President -- with little to no political juice to achieve his aims.
His fiery rhetoric appears to be exacerbating a North Korean nuclear showdown. Though that's one crisis not of his own making, it will require him to show intricate diplomatic skills to prevent a devastating war with Asia.
The President must meanwhile pilot emergency relief for Hurricane Harvey victims through Congress, while avoiding a series of fiscal cliffs and can't-miss funding deadlines and demonstrating that an administration that lacks signature achievements after seven months in office can fulfill the basics of governance.
"It's going to be a busy September," said White House press secretary Sarah Huckabee Sanders last week, in an uncharacteristically understated moment in the administration.
Lack of political standing
The political labyrinth that Trump must navigate is made even more complicated by his own compromised political standing.
His credibility and moral authority have been tarnished by a summer marked by his hesitation in singling out white supremacists after violence in Charlottesville, Virginia. Trump's threats to shut down the government if Congress does not finance a border wall that he promised Mexico would pay for angered many of his fellow Republicans. He has feuded publicly with Senate Majority leader Mitch McConnell
and earned rebukes from House Speaker Paul Ryan
. Some top Republicans such as Sen. Bob Corker have questioned the President's stability
. Arizona Sen. John McCain is meanwhile calling on colleagues to act as a counter to Trump's power.
"Congress must govern with a president who has no experience of public office, is often poorly informed and can be impulsive in his speech and conduct," McCain wrote in a stinging Washington Post op-ed
Trump has responded to adversity by embracing his staunchly loyal political base.
He pardoned former Arizona sheriff Joe Arpaio, despite his conviction for contempt in a case linked to racial profiling. On Tuesday, Trump is expected to end a program protecting undocumented immigrants brought to the US as children. He has barred transgender troops from serving openly in the military. He's threatening to kill NAFTA and tear up a trade deal with South Korea.
While such moves and threats honor campaign promises, they have deepened the estrangement between Trump and senior Republican leaders in a way that could make it more difficult for him to pass key agenda items, including tax reform. That remains the President's main hope for a major legislative triumph in his first year, following the GOP's failure to repeal or replace Obamacare.
Trump is making clear he believes that Republicans on Capitol Hill are not showing sufficient loyalty to his agenda and respect for his election victory.
"I don't want to be disappointed by Congress, do you understand me? Do you understand?" Trump said at a tax reform event in West Virginia last week.
Turmoil at the White House
With his relations with fellow Republicans compromised, the President has also been beset by turmoil in his own political inner circle.
New White House chief of staff John Kelly has spent the summer trying to impose a traditional West Wing structure on Trump's chaotic operation. He has shown the door to the outspoken members of the President's inner circle, like populist guru Steve Bannon and pugilistic aide Sebastian Gorka. But administration officials have told CNN that Trump is already chafing at controls Kelly has imposed on who he can see and what information reaches his desk.
The test of Kelly's strategy will unfold in the coming months.
If the former Marine Corps general shows Trump the new disciplined approach can deliver, he may convince the freewheeling President to stick with the program. If not, his tenure may play out in months rather than years.
While Trump adjusts to the Kelly era, other senior officials have followed senior congressional leaders and even US foes like North Korean leader Kim Jong Un in showing that they are not cowed by the President.
Trump is still stewing over criticisms from his top economic adviser Gary Cohn about his response to Charlottesville, according to multiple sources. And there is speculation about how long Secretary of State Rex Tillerson will last.
Then there is the Russia cloud.
Intense media coverage of Harvey last week overshadowed several key developments in special counsel Robert Mueller's investigation.
The Wall Street Journal first reported that Trump's lawyers filed memos with Mueller arguing that the President was simply exercising constitutional powers in firing former FBI chief James Comey while he was investigating whether Trump campaign aides colluded with Russia in election meddling. There were also revelations that Mueller had a copy of a draft letter that Trump wrote to Comey -- but never sent -- that could offer insight into Trump's motives.
Much is unknown about Mueller's probe. But it is becoming increasingly clear that the special counsel is mounting a serious investigation into whether Trump obstructed justice, an effort that could have grave implications for his presidency.
The White House must put aside such distractions, however.
The President's first task is to quickly enact nearly $8 billion in hurricane aid for Harvey victims. He will huddle with Republican leaders and top Cabinet officials at the White House on Tuesday to chart a course on this and other issues.
Treasury Secretary Steven Mnuchin said on "Fox News Sunday" that Harvey aid should be folded into a bill raising the government's borrowing ceiling. Such a maneuver could defuse a showdown with House conservatives over the debt limit.
Republican Rep. Blake Farenthold of Texas last week described how fiscal conservatives would have little choice but to go along.
"I'm not going to like it, but I think they can probably throw a debt ceiling in it and I'd vote for it," he said on CNN's "New Day."
But such a move may only put off an imbroglio for a few weeks. Recovery efforts will soon require a much larger rescue package: Texas Gov. Greg Abbott has said as much as $125 billion might be necessary. Conservatives may renew demands for spending cuts to compensate for such a price tag. And Republicans already lukewarm on funding a border wall may find the prospect even less appetizing after such a huge outlay.
Still, there are also signs the White House may also be looking to put off a showdown over wall funding for a few months. Some Hill Republicans believe Trump will not insist that a likely short-term funding bill to keep the government open until December contain cash for the wall. But experience shows that at any time, a presidential tweet could undermine legislative compromises.
And putting off the wall fight could simply set up a new government shutdown showdown before the Christmas and New Year recess, given that Trump is still telling supporters at packed rallies the wall will be built.
Given the complexity of the coming months, it's difficult to see what success for Trump would look like. The most he can hope for might be escaping the year without a damaging government shutdown, with some kind of tax cut or reform legislation passed, and with his most prominent achievement, the installation of new Supreme Court Justice Neil Gorsuch, to celebrate.
The White House, hungry for wins, is promising much more, including a new attempt to repeal Obamacare and a push for Trump's long-delayed infrastructure bill, insisting the crush of business is no reason for inaction.
"We like to say here, we can walk and chew gum at the same time," Sanders, the White House press secretary, said.