In the opening weeks of his presidency, Mr. Trump issued an executive order banning citizens from seven majority-Muslim countries from entering the United States. That ban was almost immediately halted in court. A second, rewritten version, however, was upheld by the Supreme Court and was seen as at least a partial victory for the administration.
But Mr. Trump vented, privately and publicly, that the version that passed legal muster was “watered down” and “P.C.,” and made him look “weak.”
How Mr. Trump found himself in his most recent predicament can be traced back to September, when White House aides and conservative lawmakers urged the president to engage in a fight for wall funding. But he was told to postpone the fight until after the election, to avoid forcing vulnerable Republicans in swing districts to take a politically perilous stance on the wall.
When he looked like he might compromise and support a bill that provided far less money for the wall than he asked for, conservatives like Ann Coulter excoriated him, describing him as “gutless,” and he backed down. Soon he was telling Mr. Schumer and Ms. Pelosi during a televised Oval Office meeting last month that he would proudly “own the shutdown,” thrilling conservatives.
Buoyed by the praise, and encouraged by the acting White House chief of staff, Mick Mulvaney, Mr. Trump decided to keep digging in.
But that encouragement for what played well in a viral television moment never led to a coherent strategy for a prolonged stalemate, according to a half-dozen people in the White House or working with the administration on a way to end the shutdown.
Mr. Trump’s allies insist that he is winning the political battle.
“Democrats are boxed in,” said Greg Mueller, a conservative strategist. “Every time the president and G.O.P. go to the Democrats with a fix, they say no, which positions them as obstructionists ignoring the problem, and opening themselves up for major troubles in 2020.”