President Trump Donald John TrumpSteele Dossier sub-source was subject of FBI counterintelligence probe Pelosi slams Trump executive order on pre-existing conditions: It 'isn't worth the paper it's signed on' Trump 'no longer angry' at Romney because of Supreme Court stance MORE looks to be increasingly boxed in on his effort to add a controversial citizenship question to the 2020 census.

Judges have repeatedly ruled against the Trump administration on the question since officials first announced last year that it would be included in the next decennial population survey.

But that hasn’t stopped the president from doubling down on the issue, even as census materials are being printed without the controversial question.

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If Trump issues an executive order or another kind of presidential directive to include the question, as he’s widely expected to, it’s guaranteed to be met with another round of legal challenges. And experts told The Hill that with constitutionally mandated census deadlines approaching, there simply may not be enough time to relitigate the issue.

Add in House Democrats’ vows not to approve extra funds to print forms with the citizenship question, and Trump is looking more boxed in than ever on the census.

Jessica Levinson, a professor at Loyola Law School, said that an order from the president that effectively seeks to overturn the recent Supreme Court ruling against the citizenship question could cause confusion over exactly which directive officials should respond to.

Attorney General William Barr Bill BarrHillicon Valley: Subpoenas for Facebook, Google and Twitter on the cards | Wray rebuffs mail-in voting conspiracies | Reps. raise mass surveillance concerns Bipartisan representatives demand answers on expired surveillance programs YouTube to battle mail-in voting misinformation with info panel on videos MORE indicated earlier this week that he believes the administration can legally include the citizenship question on the census, but he did not elaborate.

A senior official told The Associated Press at the time that Trump may issue a presidential memorandum to the Commerce Department requiring the agency to include the question on the census.

Levinson said that if that pathway is taken, “at that point you truly do have a constitutional crisis.”

“You have the Supreme Court saying one thing, the chief executive saying another, members of the federal government don’t know who to respond to,” Levinson said. “That is where the Constitution starts to pull apart at the seams.”

“We’ve gone through the stress test and that would be a fracture,” she added.

While the Commerce Department is tasked with overseeing the census, conducting a population count every 10 years is Congress’s responsibility under the Constitution. Lawmakers in turn delegated that duty to the Census Bureau through federal law.

Those clashing constitutional authorities could lead to an executive order failing in court.

Louis Rulli, a professor at Penn Law, said that by issuing an executive order, Trump would effectively be taking the matter surrounding the citizenship question out of the scope of federal administrative law, which dictates the procedures through which federal agencies must adopt new policies.

He said that doing so may be considered by a court to be “highly suspect.”

Several judges have struck down the question as a violation of those administrative procedures, although the Supreme Court’s conservative majority found that its addition did not violate that statute.

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“I think that an executive order is probably the most likely next step. But I think it's one that is very difficult, given the posture and history of this case, and the fact that Congress has not given the president authority here in this arena,” Rulli said. “And that really raises the question: Was the president pushing as hard as he is not so much for a legal purpose, but for a political purpose, whether or not even knowing that he may not prevail? Whether he gains politically with his base and with voters who may share his views?”

And that directive could be further hobbled by whatever reasoning for the question’s addition is given by administration officials going forward.

Chief Justice John Roberts wrote in the Supreme Court’s 5-4 ruling on the question in late June that the facts of the case simply didn’t match up with the original reasoning behind the question’s addition, enforcing the Voting Rights Act.

The Justice Department appeared to initially concede the legal fight last week, but that was swiftly reversed after Trump vowed to move forward with trying to add the question to the census.

“I have to say that it is incredibly difficult to come up with new rationale that has any credibility after finding that the exclusive rationale used over the last more than a year is, to use the words of Chief Justice Roberts, contrived and pretextual,” Rulli said.

And Rulli pointed to a recent tweet sent by Trump that stated the citizenship question is needed for “redistricting” as potentially undermining his administration’s legal case.

DOJ lawyers also indicated in a court filing last week that, if a new reasoning for the question is adopted, they will go to the Supreme Court to ask justices for instructions on how “to govern further proceedings in order to simplify and expedite the remaining litigation and provide clarity to the process going forward.”

However, experts noted to The Hill that Roberts’s opinion in the census case directly sent the case back to the district court where it originated — to Judge Jesse Furman’s court in New York — and that the justices may decline to offer further directions that would speed up the process, ensuring that the case would continue to play out in the lower court for an unspecified period of time.

The Constitution states that the census must be conducted every decade. Authorities must get the forms out to residents by April 2020.

It’s those requirements that turns the census into a ticking time bomb for Trump. And delays over resolving any new legal challenges to the question in court could be enough to stop the question from appearing on the census.

Levinson said Roberts may have said that another rationale for the question would be allowed with the intention of letting officials try to do so for a later version of the census.

As the Justice Department attorneys press on with their efforts, experts said the Trump administration may be hard pressed to have the full confidence of the court.

Justice Department lawyers had repeatedly argued in court filings that they needed a swift ruling on whether the citizenship question in order to meet a June 30 deadline to finalize census materials so they could be printed on time. Those filings did not provide a full reasoning behind that deadline.

But the administration is continuing with that push, well past that deadline, even as a version of the census forms is printed that doesn’t feature a citizenship question.

At the same time, the Department of Justice (DOJ) announced that it was abruptly changing out its entire legal team handling the census cases, fueling speculation that career lawyers at the agency were no longer comfortable arguing on behalf of the administration in court.

Furman, the New York judge overseeing one of the census cases, on Tuesday rejected DOJ’s attempt to pull the lawyers who had worked on the case for more than a year without presenting a reason. He appeared frustrated in the scathing opinion, pointing to government lawyer’s insistence that the case be resolved quickly and questioning how the case would not be delayed by changing the legal representation.

"As this court observed many months ago, this case has been litigated on the premise — based 'in no small part' on Defendants’ own 'insist[ence]' — that the speedy resolution of Plaintiffs’ claims is a matter of great private and public importance," Furman, an Obama appointee, wrote. "If anything, that urgency — and the need for efficient judicial proceedings — has only grown since that time."

But some fear that even without the question’s inclusion on the census, the confusion on the status of the citizenship question may be enough to deter people, including immigrants and Hispanics, from answering the survey.

That potential was amplified when documents pulled from the hard drives of the late GOP strategist Thomas Hofeller indicated that he may have played a role in the orchestration of the citizenship question.

Hofeller conducted a 2015 unpublished study that found asking about citizenship would help Republicans and non-Hispanic whites when it comes to redrawing congressional districts, but hurts Hispanic communities and Democrats.

That evidence, along with other documents alleging Hofeller played a hand in the question’s addition to the census, is now at the heart of further litigation surrounding the question in federal court in Maryland.

Judge George Hazel is currently considering whether there was a discriminatory intent behind the question’s inclusion on the 2020 census, a different legal question than the one considered by the Supreme Court. That sets the stage for Hazel, an Obama appointee, to issue another ruling against the citizenship question on the grounds that it violates equal protection claims enshrined in the Constitution.

Even if Trump’s efforts do hold up in court, whether lawmakers would approve the funding needed to add the question to the census presents yet another hurdle to the administration.

Rep. José Serrano (D-N.Y.), who chairs the House Appropriations subcommittee that oversees funds for the Commerce Department and Census Bureau, vowed on Tuesday to block any federal funding that would go toward the citizenship question.

“I want to make one thing clear: I have no intention of allowing this flagrant waste of money. I once again urge the Trump Administration to give up this fight and allow for a depoliticized and accurate census, as we always have," Serrano said in a statement.

The House has already passed a spending package that features a measure that would block the Census Bureau from including the question on the 2020 census. The White House has indicated that Trump would veto that version of the legislation.

House Democrats will have to reconcile that iteration of the spending bill with the GOP-held Senate and the White House in order to avoid a government shutdown come October, when federal funds will run out.

Regardless, House Democrats appear determined to not allow the citizenship question on the census.

"They want to make sure that certain people are counted. It's really disgraceful. And it's not what our founders had in mind," Speaker Nancy Pelosi Nancy PelosiPelosi slams Trump executive order on pre-existing conditions: It 'isn't worth the paper it's signed on' On The Money: Anxious Democrats push for vote on COVID-19 aid | Pelosi, Mnuchin ready to restart talks | Weekly jobless claims increase | Senate treads close to shutdown deadline Trump signs largely symbolic pre-existing conditions order amid lawsuit MORE (D-Calif.) said of the citizenship question on Tuesday. "What they want to do is put a chilling effect so certain populations will not answer the form."