Jared Kushner, the president’s son-in-law, was confident in his ability as a good-faith negotiator who could find a compromise to end the government shutdown.
His pitch to Democratic lawmakers was simple: He told them he was the person who could “land this plane.”
Buoyed by his success in helping pass a criminal justice bill, Mr. Kushner, a senior White House adviser, agreed to take the lead when the president asked him to find a way to end the monthlong stalemate. He hoped his experience winning over Democrats skeptical of the Trump administration during negotiations for that measure would produce a similarly successful conclusion.
But negotiating a broad immigration deal that would satisfy a president committed to a border wall as well as Democrats who have cast it as immoral proved to be more like Mr. Kushner’s elusive goal of solving Middle East peace than passing a criminal justice overhaul that already had bipartisan support.
For one, Mr. Kushner inaccurately believed that moderate rank-and-file Democrats were open to a compromise and had no issue funding a wall as part of a broader deal.
“If Jared Kushner thinks there is any daylight between House Democratic leadership and rank-and-file members on this issue, then the extent that he lands this plane it will land in the Alamo,” said Representative Hakeem Jeffries, Democrat of New York.
And Democratic leaders like Senator Chuck Schumer, party officials said, did not believe that Mr. Kushner had the power to circumvent Stephen Miller, a senior policy adviser to the president. In meetings, they also noticed, Mr. Kushner appeared to prop up Mr. Miller as an expert on immigration, noting that Mr. Miller’s reputation as a hard-liner was out of sync with his reasonable nature.
On Friday, President Trump did what Mr. Kushner had privately insisted was not an option on the table: He folded.