Justices weigh available defenses to criminal re-entry for certain immigrants

The court heard argument on Tuesday in United States v. Palomar-Santiago, a case involving certain noncitizens’ ability to defend themselves from federal charges for re-entering the country after they were deported. The charge of criminal re-entry requires the prior existence of a removal order entered by a federal immigration agency. In Refugio Palomar-Santiago’s case, that prior removal order did exist. However, the Supreme Court’s 2004 decision in Leocal v. Ashcroft, decided after the entry of his removal order, revealed that the administrative agency’s decision to deport him was not justified by law. Nonetheless, federal prosecutors brought a re-entry charge against him based on that same order. The question is whether Palomar-Santiago can defend against the re-entry prosecution based on the invalidity of the original removal order, or whether his defense must fail because he cannot meet additional requirements set forth by statute — namely, that he “exhausted” his options for pursuing an administrative appeal of the removal order, and that the original proceedings deprived him of judicial review.

The government’s case, presented by Assistant to the Solicitor General Erica Ross, emphasized the text of the statutory provision governing a noncitizen’s ability to challenge the validity of a prior removal order during a re-entry prosecution. That statute, 8 U.S.C. § 1326(d), was enacted by Congress after the court’s 1987 decision in United States v. Mendoza-Lopez, and according to Ross provides only a “narrow escape hatch” for such challenges. The government’s overall theory is that Congress reasonably intended for the additional requirements (administrative exhaustion and deprivation of judicial review) to apply even in cases like Palomar-Santiago’s, where the prior removal order was found to lack a legal basis. Ross emphasized that Congress sought to prevent people from “taking the law into their own hands” by re-entering the country and challenging the prior order only upon indictment for re-entry.

Arguing for Palomar-Santiago, Bradley Garcia asserted that Section 1326(d) — which describes how to “challenge the validity of the deportation order” — contains an implicit assumption that the removal order is, in fact, valid. Accordingly, Congress did not intend for re-entry prosecutions based on removal orders already deemed invalid to proceed at all, and so all of the statutory requirements need not apply. Under this reasoning, re-entry prosecutions based on an invalid removal order simply “cannot proceed.” Throughout his argument, Garcia emphasized the substantive invalidity of the prior order. But even assuming that noncitizens must satisfy Section 1326(d)’s requirements, he argued that Palomar-Santiago has already met them because the required administrative remedies were not practically available to him.

Several justices probed the significance and meaning of the prior removal order being deemed invalid. Chief Justice John Roberts solicited the government’s views on Palomar-Santiago’s characterization of the removal order as void ab initio (i.e., void from the beginning), and Justice Clarence Thomas asked whether the government conceded that the underlying removal order could be characterized as “substantively wrong.” The government agreed that, under Leocal, Palomar-Santiago could not be deported for the same driving-under-the-influence conviction that served as the basis of his prior removal order. However, Ross resisted characterizing the removal order as either a “legal nullity” or equivalent to the immigration agency lacking jurisdiction to enter the order at all. Instead, Ross insisted that whatever defects existed in the prior order did not absolve Palomar-Santiago of the need to satisfy the strict requirements of Section 1326(d). Justice Stephen Breyer drew a comparison to the criminal context, asking whether anomalous results follow given that someone who is convicted of an offense that the courts later determine the government had no power to criminalize can seek a remedy via habeas review, but that in this case, a person was “put in jail.” In response, Ross distinguished Palomar-Santiago’s case from ones in which actual innocence is asserted, and contended that “an error-free removal order is not an element” necessary to prosecute someone for criminal re-entry.

Addressing Garcia on similar questions related to the validity of the prior order, Roberts expressed skepticism over the argument that once a change or clarification in the law occurs, the right to a legal remedy is automatic — a position the chief justice suggested was akin to, “we now know this was wrong, so we have to go back and … unscramble the egg.” Similarly, Justice Samuel Alito observed to Garcia that, despite Garcia’s claims about the invalidity of the order, his client’s defense still seemed subject to Section 1326(d)’s requirements, which describes a “challenge [to] the validity of the deportation order.” Breyer asked whether characterizing Palomar-Santiago’s prior order as unlawful would be true only if “he really wasn’t driving under the influence 35 years ago.” Garcia emphasized the undisputed nature of the removal order’s invalidity and the problem of imposing additional punishment based on an order that the government “knows is invalid.”

Palomar-Santiago’s briefing argued that underlying constitutional concerns should shape the court’s reading of the statute, and while such considerations surfaced on Tuesday, they did not dominate the argument. Thomas and Justice Sonia Sotomayor asked Ross for the government’s position regarding those constitutional concerns, which she largely dismissed as irrelevant given the clarity of the statute. Sotomayor expressed her view that constitutional issues were indeed present in the case, given the absence of opportunities for a noncitizen to reverse a removal order deemed invalid. Ross pressed the government’s view that Congress is permitted to criminalize offenses based on administrative orders when a person does not make use of the procedures available to challenge those orders. On this point, Palomar-Santiago’s attorney sought to limit the primary case cited by the government, Yakus v. United States, to its wartime context.

Given that one of Section 1326(d)’s requirements is administrative exhaustion, the justices had questions about whether exhaustion in the form of an appeal to the Board of Immigration Appeals is practically available to noncitizens like Palomar-Santiago. Justice Elena Kagan posed questions for both sides on how potential misrepresentations by the immigration judge would impact the availability of administrative exhaustion, leading to various exchanges over the application of the exceptions to administrative exhaustion and the meaning of availability of a review process. Thomas, Kagan and Justice Amy Coney Barrett asked Garcia whether the complexity of his client’s potential legal claim on appeal — which Garcia contended would require mastery of “legal doctrines that are mystifying and opaque” — should count as a factor in assessing whether administrative exhaustion was available. Garcia contended that the availability of administrative remedies should be an individualized analysis that accounts for legal complexity, among other factors, and also drew attention to the practical barriers faced by noncitizens, as detailed in an amicus brief submitted by the National Immigration Project.

Alito and Sotomayor sought to better understand the options that Palomar-Santiago might have pursued other than a direct administrative appeal to remedy the defect in his removal order. The government emphasized that apart from administrative appeal, he might have filed a motion to reopen, or sought discretionary relief from the attorney general. However, Garcia asserted that Palomar-Santiago’s motion to reopen would have been “barred by [federal] regulation” for a period of time (presumably referring to the “post-departure bar,” a federal regulation which prohibits many noncitizens who physically departed the United States from filing a motion to reopen, although many federal appeals courts began to invalidate the rule beginning in roughly 2010). Sotomayor seemed particularly interested in the additional remedies, and commented on the lack of briefing on the issue.

Finally, some of the justices appeared to search for the broader implications of the case. Breyer suggested that only a “handful” of people might be affected by a decision favoring Palomar-Santiago, a contention with which Garcia agreed. Other justices sought to assess the scope of the parties’ arguments, but both sides generally avoided providing definitive positions. Thomas, for instance, asked Garcia whether the result would be different if Palomar-Santiago had been represented by counsel during his original removal proceeding, and Alito asked Ross whether the government believed the exhaustion requirement would have been satisfied if Palomar-Santiago had filed an administrative motion to reopen, but not an appeal to the Board of Immigration Appeals.

It is unclear how the court is leaning. Justices Neil Gorsuch and Brett Kavanaugh asked no questions of either party. Justices on differing sides of the court’s political aisle both expressed sympathy for Palomar-Santiago and conveyed a measure of skepticism over the implications of the substantive invalidity of the removal order. Although an amicus brief from several immigration law scholars detailed how racial animus motivated the enactment and continuation of the re-entry statute, racial justice concerns did not arise at all. The decision will likely turn on how a majority of the justices view the significance of the validity of the prior removal order, the influence of constitutional norms on the court’s reading of the statute, and the court’s assessment of the extent to which administrative remedies were available to Palomar-Santiago.