Jared Kushner, the president’s son-in-law and senior adviser, is hoping he can break the impasse between Donald Trump and the Democrats on immigration, reportedly spitballing solutions to the problem during a White House whiteboard meeting last week in an effort to, as one attendee told Axios, “replicate” for border security the kind of bipartisan deal he managed to strike on criminal-justice reform. “They would like to try and replicate at some level a bipartisan coalition on immigration issues, something paired with border security as well,” Mark Holden, a Koch Industries executive, told the publication.

It’s an ambitious—and likely unrealistic—undertaking. Last year, Kushner convinced Trump, who ran as a law-and-order candidate, to sign a bill that emphasized reducing recidivism rates, providing exemptions to mandatory minimum sentences, and expanding opportunities for early release in what was seen as a strong step toward improving the broken criminal-justice system. In that instance, however, he was simply nailing down specifics around a bipartisan consensus. As a senior White House official put it to Axios, “He convinced Democrats to support something they already agreed with.”

That’s not so with immigration. Here, Trump’s marquee demand is his long-promised border wall, which he wants close to $6 billion in taxpayer dollars to build. Democrats, who control the House of Representatives, have no desire or reason to give it to him, particularly after Trump caved on his own request last week and reopened the government without a cent for the wall. To get Dems to budge, Kushner will have to offer a concession significant enough for them to consider yielding the upper hand. The problem, of course, lies in convincing his father-in-law to go along with such a concession, especially in the face of inevitable backlash from his base.

Further complicating the issue is Trump’s warning that, if a bipartisan panel doesn’t come up with a workable solution by February 15, he’ll either shut down the government again—something Mitch McConnell and other Republicans on Capitol Hill have suggested they could overrule—or declare a national emergency to fund the wall without Congress. Putting the nuclear option on the table, as Trump apparently did against Kushner’s wishes, may already have doomed a potential compromise. After all, what motivation does Trump’s base have to go along with a middle ground when they’re convinced he can easily avoid compromising altogether?

Given all the obstacles in his path, even conservatives are questioning why Kushner thinks he can succeed where so many others have failed. “Border security and immigration reform are much more complex issues than criminal justice reform,” Tea Party Patriots co-founder Jenny Beth Martin told Axios. Kushner’s mandate, which includes nothing less than the reinvention of the executive branch itself, has always seemed comically broad, in part due to his total lack of relevant experience or expertise. But with two parties at total loggerheads, and apparently no confidence from the president, he seems especially in over his head, despite his insistence that he’s the one who can “land this plane.” “Unless he’s able to convince his father-in-law to abandon his obsession with building a medieval border wall,” Rep. Hakeem Jeffries told The New York Times, “then he’s not going to be successful in finding a bipartisan agreement.”

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