Reinstatements Cannot Cure an Invalid Removal Order: Commentary on United States v. Ramirez Rodriguez (2d Cir. 2025)

I. Introduction

The Second Circuit’s decision in United States v. Ramirez Rodriguez, Nos. 24‑2059(L), 24‑2093(Con.) (2d Cir. Dec. 16, 2025), is a significant addition to the law governing illegal reentry prosecutions under 8 U.S.C. § 1326 and the collateral attack of prior removal orders under § 1326(d). The case squarely addresses whether:

A defendant can be prosecuted for illegal reentry when the only removal order ever entered against him is legally invalid; and
The government may rely on later “reinstatements” of that invalid order, or on later criminal convictions, to defeat a showing of prejudice under § 1326(d)(3).

The Second Circuit answers both questions in the negative. It holds that:

Prejudice under § 1326(d)(3) must be assessed at the time of entry of the original removal order; courts may not use later developments (“ex post data”) to cure the original defect.
Reinstatements of an invalid removal order are not new, independent removal orders and cannot provide a valid predicate for an illegal reentry prosecution.
Where the original removal order was entered on the basis of a conviction that did not in fact render the noncitizen removable, the prejudice requirement is satisfied: absent the error, the person would not have been removed.

In doing so, the Second Circuit aligns itself with the Ninth Circuit’s approach in United States v. Arias‑Ordonez, 597 F.3d 972 (9th Cir. 2010), and casts doubt on attempts—such as in the Fifth Circuit’s United States v. Huerta‑Rodriguez, 64 F.4th 270 (5th Cir. 2023)—to treat later illegal reentry convictions as aggravated felonies for all purposes, regardless of the validity of the underlying removal order.

This commentary examines the background of the case, the court’s reasoning, the key precedents, and the likely impact of this opinion on illegal reentry prosecutions and immigration law more broadly.

II. Case Background

A. The Parties

Appellee: United States of America
Defendant–Appellant: Lepido Ramirez Rodriguez, a citizen of the Dominican Republic and a lawful permanent resident (LPR) of the United States since 1990.

B. Factual Narrative

1999 State Drug Conviction and 2000 Removal Order
In 1999, Ramirez Rodriguez was convicted in New York state court of criminal sale of a controlled substance in the second degree, specifically cocaine, in violation of N.Y. Penal Law § 220.41. He was unrepresented at his removal hearing before an Immigration Judge (IJ) in February 2000.

At that hearing:
- He admitted his noncitizenship and his 1999 cocaine conviction.
- The IJ informed him that he was removable because his conviction was both:
  - an “aggravated felony,” and
  - a “controlled substance offense,”
  and bluntly told him, “you can't stay in this country because of your selling of cocaine conviction.”
- When he expressed a desire to remain because of his children, the IJ reiterated that he could not stay.
- He was given the option to appeal to the Board of Immigration Appeals (BIA) or make the decision final; he responded that he did not want to do anything and “just want[ed] to leave this country.”
He was ordered removed to the Dominican Republic and was deported in April 2001.
First Illegal Reentry and 2010 Reinstatement
After the government denied an application for permission to reapply for admission, he reentered the United States without authorization around November 2008. He was later identified via fingerprints submitted for a job application, arrested, and charged with illegal reentry under 8 U.S.C. § 1326.

He pleaded guilty in 2009, received an 18‑month sentence, and upon completion of that sentence in 2010, an immigration officer “reinstated” the 2000 removal order pursuant to 8 U.S.C. § 1231(a)(5). He was then removed again under that prior order.
Second Illegal Reentry and 2016 Reinstatement
He returned again and was arrested in 2013 on a state money‑laundering charge (which was not pursued). He was nonetheless charged with:
- illegal reentry following removal for an aggravated felony; and
- a violation of supervised release stemming from the 2009 conviction.
He pleaded guilty, received 45 months for the new illegal reentry conviction plus 1 month for the supervised release violation. After serving this sentence, in 2016, the government did not initiate new removal proceedings; instead, it again reinstated the 2000 removal order and removed him under that order.
Third Illegal Reentry and the Present Prosecution
He returned once more. In August 2022, he was arrested in the Bronx with over a kilogram of cocaine, charged with various offenses, and ultimately pleaded guilty to third-degree criminal possession of a controlled substance, receiving a two-year sentence in state court.

The federal government charged him, for the third time, with aggravated illegal reentry under § 1326. This is the case that produced the Second Circuit’s 2025 opinion.

C. The Motion to Dismiss and District Court Ruling

In this third illegal reentry case, Ramirez Rodriguez moved to dismiss the indictment under 8 U.S.C. § 1326(d), collaterally attacking the validity of the 2000 removal order.

The motion relied on the Second Circuit’s intervening decision in United States v. Minter, 80 F.4th 406 (2d Cir. 2023), which held that New York’s second‑degree criminal sale of a controlled substance under N.Y. Penal Law § 220.41 is not a removable offense for immigration purposes. That meant:

The 2000 IJ’s conclusion that the conviction was an aggravated felony and a removable controlled substance offense was legally incorrect.
The 2000 removal order was invalid because it was predicated on a non‑removable offense.

At the district court:

The government conceded that, in light of Minter, the 2000 order was based on legal error and that this constituted a “fundamental procedural error” under § 1326(d)(3).
But the district court denied the motion to dismiss, holding that Ramirez Rodriguez could not show the required prejudice from that error because, by the time of the 2010 and 2016 reinstatements, he had two illegal reentry convictions that (in the district court’s view) qualified as aggravated felonies, rendering him removable and ineligible for relief regardless of the earlier error.
The court therefore held he failed the third prong of § 1326(d), and expressly did not reach the first two prongs (administrative exhaustion and deprivation of judicial review). See United States v. Rodriguez, 722 F. Supp. 3d 264 (S.D.N.Y. 2024).

He then entered a conditional guilty plea preserving his right to appeal the denial of his motion to dismiss, and the government’s right to raise additional grounds for affirmance. He was sentenced to 30 months’ imprisonment and 3 years of supervised release, and he appealed.

III. Summary of the Second Circuit’s Opinion

Writing for a unanimous panel (Judges Newman, Parker, and Merriam), Judge Parker held:

The 2000 removal order was invalid and fundamentally unfair.
The IJ removed Ramirez Rodriguez on the basis of a conviction that did not, as a matter of law, render him removable. This was a fundamental procedural error, and because he could not have been lawfully removed absent that error, he suffered prejudice.
Prejudice under § 1326(d)(3) must be assessed as of the time of the entry of the original removal order.
The statute focuses on the “entry” of the deportation order, imposing a temporal limitation: courts must “reconstruct events as they existed at the time of the disputed deportation proceeding” and may not consider “ex post data.” (United States v. Scott, 394 F.3d 111, 118–19 (2d Cir. 2005).)
Reinstatements of an invalid order are not new removal orders and cannot provide a valid predicate for illegal reentry charges.
Under 8 U.S.C. § 1231(a)(5), reinstatement merely “reinstates” the prior order from its original date; it does not create a new order of removal or a new determination of removability. Reinstatements “bear[] the same taint as the original deportation” (Arias‑Ordonez) and cannot launder an invalid order into a valid one.
The district court erred by focusing on the 2010 and 2016 reinstatements and on later illegal reentry convictions.
The only relevant question under § 1326(d)(3) is whether the entry of the 2000 removal order prejudiced him. Because he would not have been removed but for the IJ’s error, prejudice is established.
Alternative grounds under § 1326(d)(1) and (2) are left to the district court.
Although the government argued on appeal that he failed to exhaust administrative remedies and was not deprived of judicial review, the panel declined to reach these issues because they were not addressed below and might require factual development.
Disposition.
- In Case No. 24‑2093 (the appeal from the current conviction), the court vacated the district court’s judgment and remanded for further proceedings consistent with its opinion.
- In Case No. 24‑2059, the court dismissed for lack of appellate jurisdiction (the opinion does not elaborate, and that aspect is not central to the new legal rule).

IV. Detailed Analysis

A. Statutory and Doctrinal Framework

1. Illegal Reentry and § 1326(d)

Under 8 U.S.C. § 1326(a), a noncitizen who has been removed (or deported) and then reenters or is found in the United States without permission commits the felony of illegal reentry. Section 1326(b) increases penalties where the prior removal followed certain criminal convictions (including aggravated felonies).

In United States v. Mendoza‑Lopez, 481 U.S. 828 (1987), the Supreme Court held that due process requires that a defendant charged with illegal reentry must have some meaningful opportunity to challenge the validity of the underlying deportation order, particularly where defects in the deportation proceedings foreclosed judicial review.

Congress codified a framework for such collateral attacks in § 1326(d). A defendant can invalidate the predicate removal order if he shows:

He exhausted any administrative remedies available to seek relief against the order; (§ 1326(d)(1))
The deportation proceedings improperly deprived him of the opportunity for judicial review; (§ 1326(d)(2))
The entry of the order was “fundamentally unfair.” (§ 1326(d)(3))

The Second Circuit, following Fernandez‑Antonia, interprets “fundamentally unfair” to require:

a fundamental procedural error; and
prejudice resulting from that error.

This structure parallels the Strickland prejudice standard in ineffective assistance of counsel cases: the defendant must show a reasonable probability that, but for the error, the outcome would have been different.

2. Reinstatement of Removal Orders: 8 U.S.C. § 1231(a)(5)

Section 1231(a)(5) allows the government to remove again, more quickly, a noncitizen who illegally reenters after removal. It provides:

If the Attorney General finds that an alien has reentered the United States illegally after having been removed or having departed voluntarily, under an order of removal, the prior order of removal is reinstated from its original date and is not subject to being reopened or reviewed, the alien is not eligible and may not apply for any relief under this chapter, and the alien shall be removed under the prior order at any time after the reentry. (emphasis added)

Key features:

No new determination of removability.
No new order of removal; the prior order is simply “reinstated from its original date.”
Extremely limited procedural protections: no access to the BIA, and no collateral attack on the underlying order in the reinstatement process itself.

In Garcia‑Villeda v. Mukasey, 531 F.3d 141 (2d Cir. 2008), the Second Circuit upheld this streamlined scheme, emphasizing that reinstatement “does not alter the petitioner’s legal condition” because it merely enforces the prior order.

Ramirez Rodriguez tests the limits of that premise: what happens if the prior order is legally invalid? Can the reinstatement process convert that invalid order into a valid predicate for criminal prosecution?

3. The Role of Minter and the Underlying New York Conviction

In United States v. Minter, 80 F.4th 406 (2d Cir. 2023), the Second Circuit held that New York’s second‑degree criminal sale of a controlled substance, N.Y. Penal Law § 220.41, is not categorically a “controlled substance” offense for immigration purposes, nor an aggravated felony (typically, a “drug trafficking crime” as defined in 18 U.S.C. § 924(c) or its equivalent).

That decision had a decisive effect on Ramirez Rodriguez: it meant that the 2000 IJ and the immigration authorities had removed him based on an incorrect legal assumption about his removability. If the conviction does not fall within the federal removal grounds, the removal order was issued without statutory authority.

B. Precedents Cited and How They Shape the Decision

1. United States v. Fernandez‑Antonia, 278 F.3d 150 (2d Cir. 2002)

Fernandez‑Antonia established the two‑part test for “fundamental unfairness” under § 1326(d)(3): a defendant must show:

a fundamental procedural error; and
prejudice—i.e., that he likely would not have been removed if the proceeding had been conducted properly.

In that case, the error concerned failure to advise of the right to appeal or of eligibility for discretionary relief, and the question became whether the defendant could have realistically obtained relief had he been properly informed. If not, there was no prejudice.

In Ramirez Rodriguez, the court uses this framework but applies it to a more basic error: the IJ ordered removal for a crime that, as it turns out, was not a removable offense at all. Under Fernandez‑Antonia’s logic, prejudice is almost self‑evident—if the conviction did not authorize removal, a proper proceeding could not have resulted in removal.

2. United States v. Copeland, 376 F.3d 61 (2d Cir. 2004)

Copeland elaborated on the prejudice standard, explicitly analogizing it to the Strickland standard in ineffective assistance of counsel cases:

“[T]he appropriate test for prejudice is the one used to decide ineffective assistance of counsel claims, namely, prejudice is shown where ‘there is a reasonable probability that, but for counsel's unprofessional errors, the result of the proceeding would have been different.’”

Ramirez Rodriguez invokes this analogy to underscore that the prejudice inquiry focuses on the likely outcome of the specific proceeding infected by error. Here, the infected proceeding is the 2000 removal hearing, not the later reinstatements. If he could not have been lawfully removed at that hearing when the law is properly applied, the prejudice requirement is met.

3. United States v. Scott, 394 F.3d 111 (2d Cir. 2005)

Scott is central to the temporal dimension of the analysis. There, the court interpreted § 1326(d)(3)’s language—“the entry of the deportation order was fundamentally unfair”—to have a temporal focus on the entry of the order. The court held:

Courts must “reconstruct events as they existed at the time of the disputed deportation proceeding.”
They may not consider “ex post data,” such as later criminal convictions, to conclude that the defendant would have been deported anyway.

Thus, the question is whether the 1996 order in Scott itself prejudiced the defendant, “regardless of [his] potential deportability for some later crimes.”

In Ramirez Rodriguez, the panel applies Scott directly:

The “disputed deportation proceeding” is the 2000 removal hearing.
The fact that he later incurred illegal reentry convictions (or other crimes) is irrelevant to whether the 2000 order was fundamentally unfair at the time it was entered.
The district court erred by shifting the focus to the 2010 and 2016 reinstatements and treating them as the relevant proceedings for prejudice analysis.

4. Garcia‑Villeda v. Mukasey, 531 F.3d 141 (2d Cir. 2008)

Garcia‑Villeda upheld the reinstatement process under § 1231(a)(5), emphasizing that due process is not offended because reinstatement “does not alter [the] petitioner’s legal condition” but simply enforces a valid prior removal order.

Ramirez Rodriguez invokes this principle but to a different end:

If reinstatement does not alter legal status and merely enforces the prior order, its validity can rise no higher than that of the underlying order.
Allowing reinstatement to serve as an independent, valid predicate for criminal prosecution—even where the underlying order was invalid—would contradict Garcia‑Villeda’s premise and effectively expand reinstatement into a new removal determination without adequate procedural safeguards.

5. United States v. Arias‑Ordonez, 597 F.3d 972 (9th Cir. 2010)

The panel explicitly aligns with the Ninth Circuit’s reasoning in Arias‑Ordonez. The Ninth Circuit had held:

If the original removal order was not legally sound, then “none of the reinstatements is legally any stronger than the original order.”
“[Y]ou can't take a reinstatement and launder the original deportation because the reinstatement bears the same taint as the original deportation.”

The Second Circuit adopts this “taint” concept:

The only removal order ever entered against Ramirez Rodriguez is the 2000 order.
Reinstatements do not create new orders and thus cannot cure, or be insulated from, the original legal defect.
An illegal reentry prosecution cannot stand on a reinstatement of a removal order that itself was unlawful.

6. United States v. Huerta‑Rodriguez, 64 F.4th 270 (5th Cir. 2023)

The district court relied heavily on Huerta‑Rodriguez, in which the Fifth Circuit held that an illegal reentry conviction can itself be an “aggravated felony” under 8 U.S.C. § 1101(a)(43)(O), for sentencing enhancement purposes, without revisiting whether the predicate removal was based on a valid aggravated felony. The Second Circuit notes:

It is “skeptical” of extending that logic to a § 1326(d) motion to dismiss based on an invalid underlying removal order, especially where the supposed predicate “aggravated felony” was not actually an aggravated felony under current law.
It emphasizes that the Fifth Circuit itself restricted Huerta‑Rodriguez to a narrow sentencing context, not to the validity of the underlying deportation order in a collateral attack.

Although the panel does not definitively reject the Fifth Circuit’s approach (and notes that it need not reach the issue to resolve the case), its skepticism signals that, in the Second Circuit, courts should be wary of bootstrapping later illegal reentry convictions into “aggravated felonies” when the foundational order is invalid.

C. The Court’s Legal Reasoning

1. Fundamental Procedural Error

The government conceded, and the court accepted, that the 2000 IJ committed a fundamental error: he removed Ramirez Rodriguez on the basis of a conviction that, under Minter, does not satisfy the statutory criteria for removability as either:

an aggravated felony; or
a controlled substance offense.

Put simply, the government had no legal authority to remove him on that basis. Even though Minter was decided decades later, courts apply the then‑correct interpretation of the statute to determine whether the earlier proceedings were lawful. Under that interpretation, the 2000 order was ultra vires.

2. Prejudice: Why It Was “Straightforward” Here

The central analytic move is the court’s treatment of prejudice. The court observes:

Prejudice is satisfied where “defects in the deportation proceedings may well have resulted in a deportation that would not otherwise have occurred.”
Here, absent the legal error about his removability, Ramirez Rodriguez could not have been ordered removed in 2000.

Thus:

No complex analysis of possible discretionary relief (e.g., § 212(c) relief) is needed.
The result is binary: with correct law, there was no ground for removal; therefore he would not have been removed; therefore he suffered prejudice.

This is tantamount to the strongest possible showing of prejudice: the error was not just procedural in a technical sense, but dispositive of the government’s authority to remove him.

3. Rejecting the District Court’s “Later Convictions” Approach

The district court reasoned that even if the 2000 removal was flawed, later illegal reentry convictions in 2009 and 2013:

constituted aggravated felonies; and
therefore, by the time of the 2010 and 2016 reinstatements, he was clearly removable and ineligible for relief, so he was not prejudiced by the earlier error.

The Second Circuit rejected this reasoning on two grounds:

Temporal Focus under § 1326(d)(3) and Scott
Section 1326(d)(3) asks whether the “entry of the deportation order” was fundamentally unfair, which, under Scott, means:
- Courts must focus on the circumstances as they existed at the time the order was entered—in this case, 2000—not on later developments such as subsequent convictions.
- The possibility that he later became removable is irrelevant to whether the 2000 removal order itself was valid and prejudicial.
Reinstatements Are Not New Removal Orders
By reframing the “disputed deportation proceedings” as the 2010 and 2016 reinstatements, the district court effectively treated reinstatements as new removal orders. The Second Circuit corrects this:
- Reinstatement under § 1231(a)(5) does not create a new order of removal.
- The noncitizen is removed “under the prior order,” which is “reinstated from its original date.”
- Because no new order is entered, the only order that can serve as a predicate for an illegal reentry prosecution is the original 2000 order—and that order is invalid.
- Accordingly, it is improper to shift the prejudice analysis to the time of reinstatement.

Having corrected the temporal and conceptual focus, the panel concludes that the prejudice analysis is, in fact, “straightforward”: he was removed under an order that could not have been lawfully entered, and thus he was prejudiced.

4. Reinstatements Cannot “Launder” an Invalid Order

Central to the opinion is the court’s insistence that reinstatements cannot cure or insulate an invalid order:

Reinstatement is a summary enforcement mechanism, not a new adjudication of removability.
Under Garcia‑Villeda, reinstatement was upheld on the theory that it does not change the person’s legal condition; it assumes a valid prior order.
If an illegal reentry prosecution could rest solely on reinstatements of an invalid order, reinstatement would, in effect, become a new removal process—but without adequate procedural rights to challenge the foundational error.
Adopting the Ninth Circuit’s formulation, the Second Circuit holds that “none of the reinstatements is legally any stronger than the original order,” and that they “bear the same taint” if the original order was invalid.

The practical consequence: prosecutors in the Second Circuit may not sidestep a flawed original order by invoking later reinstatements as independent predicates for a § 1326 prosecution.

5. Skepticism About Treating Subsequent Illegal Reentry Convictions as Aggravated Felonies

In a notable aside, the panel expresses skepticism about the district court’s additional premise: that Ramirez Rodriguez’s later illegal reentry convictions were aggravated felonies under 8 U.S.C. § 1101(a)(43)(O).

Section 1101(a)(43)(O) defines as an aggravated felony:

“an offense described in [8 U.S.C. § 1326] committed by an alien who was previously deported on the basis of a conviction for an offense described in another subparagraph of this paragraph.”

The problem here is that:

He was “previously deported” in 2001 on the basis of a conviction (the 1999 New York drug conviction) that was not actually an aggravated felony.
If the prior deportation did not rest on a qualifying aggravated felony, it is far from clear that the later illegal reentry convictions can themselves be classified as aggravated felonies under § 1101(a)(43)(O).

The panel does not resolve this question definitively (and notes that it need not to decide the case), but flags its doubts. It also emphasizes that the Fifth Circuit’s Huerta‑Rodriguez decision was expressly limited to a narrow sentencing context and did not address the kind of collateral attack presented here.

6. Alternative Grounds Under § 1326(d)(1) and (2)

On appeal, the government argued that even if prejudice was shown, the court could affirm on the alternative grounds that:

Ramirez Rodriguez failed to exhaust administrative remedies (by declining to appeal to the BIA), and
He was not improperly deprived of the opportunity for judicial review.

The panel declines to address these issues, adhering to the general rule that appellate courts do not decide questions not passed upon by the district court, especially where they may require factual development. It remands for the district court to address:

Whether, in light of the IJ’s statements and the circumstances, administrative remedies were meaningfully available to him at the 2000 hearing; and
Whether he was effectively deprived of a realistic opportunity for judicial review.

This preserves the possibility that, despite proving fundamental unfairness, the government might yet argue that he cannot satisfy § 1326(d)(1)–(2). But the key doctrinal holding on prejudice and reinstatements stands regardless of how those gatekeeping issues are resolved on remand.

V. Impact and Implications

A. For Illegal Reentry Prosecutions in the Second Circuit

The decision has several immediate consequences for § 1326 prosecutions:

Invalid Underlying Orders Cannot Be Salvaged by Reinstatements.
If a defendant demonstrates that the underlying removal order was based on an offense that is not, in fact, a ground of removability, that order cannot serve as a predicate for § 1326, and its later reinstatements are equally unusable.
Prejudice Must Be Assessed at the Time of the Original Order.
Prosecutors cannot argue that later criminal conduct—which might make a person removable today—retroactively cures the prejudice from an invalid earlier removal order. This forecloses a common “would have been removed anyway” argument based on post‑removal conduct.
Expanded Scope for Collateral Attacks Based on Legal Changes.
Decisions like Minter, which clarify that particular state offenses are not removable, open the door to collateral attacks on long‑final orders used as predicates in § 1326 cases. Ramirez Rodriguez confirms that such clarification can support a finding of fundamental unfairness even decades later.

B. For Immigration Law and Reinstatement Practice

On the immigration‑only side:

The opinion reinforces that reinstatement is procedurally summary precisely because it presupposes a valid prior order. Where the prior order is infirm, reinstatement has no independent legal force and cannot be treated as a new adjudication of removability.
Noncitizens with reinstated orders in the Second Circuit may now invoke this reasoning to argue, in appropriate forums, that if the original order was unlawful, subsequent enforcement actions built upon it are likewise suspect—particularly when criminal charges or other serious consequences are at stake.

C. Inter‑Circuit Dynamics and Potential Tension

The Second Circuit’s explicit alignment with the Ninth Circuit and its skepticism toward the Fifth Circuit’s approach foreshadows potential inter‑circuit divergence:

The Second and Ninth Circuits reject the idea that reinstatements or later illegal reentry convictions can insulate an invalid original order from collateral attack in a § 1326 prosecution.
The Fifth Circuit, while formally limiting its holding in Huerta‑Rodriguez to sentencing, appears more willing to accept prior illegal reentry convictions as aggravated felonies even where the foundational order is questionable.

If other circuits take differing paths, this could eventually produce a conflict warranting Supreme Court attention, especially given the volume of illegal reentry prosecutions nationally.

D. For Defense Counsel and Prosecutors

For defense counsel:

The case underscores the importance of closely examining the original removal order in any § 1326 prosecution, including:
- whether the predicate conviction is, in fact, a removable offense under current law; and
- whether the client was advised of relief and appeal rights.
It encourages more aggressive use of changes in circuit law (like Minter) to mount collateral attacks under § 1326(d).

For prosecutors:

The decision cautions against relying reflexively on reinstated orders or later criminal history to shore up an invalid removal predicate.
It may prompt more careful review of the original removal records before bringing § 1326 charges, especially where the underlying conviction sits in an area of evolving categorical‑approach doctrine.

VI. Key Concepts Simplified

For clarity, the following concepts are central to understanding the opinion:

Aggravated Felony
A term of art in immigration law, defined at 8 U.S.C. § 1101(a)(43), covering numerous offenses (e.g., certain drug trafficking, violent crimes, thefts). Being convicted of an aggravated felony has severe immigration consequences, including near‑automatic removal and loss of most forms of relief.
Controlled Substance Offense (for Immigration Purposes)
A conviction relating to a controlled substance, as defined by federal law, can make a noncitizen removable. However, under the “categorical approach,” a state statute only counts if its elements match (or are narrower than) the federal definition. If the state law is broader (e.g., covers substances not on the federal schedules), the conviction may not be a removable controlled substance offense.
Reinstatement of Removal
When a previously removed noncitizen reenters illegally, the government can “reinstate” the old removal order under § 1231(a)(5) instead of starting new proceedings:
- This is a quick administrative process.
- It does not involve a new hearing before an IJ or the BIA.
- The person is removed again “under the prior order.”
Collateral Attack Under § 1326(d)
In a criminal case for illegal reentry, the defendant can challenge the validity of the prior removal order if he satisfies all three prongs of § 1326(d):
1. He exhausted administrative remedies (e.g., appealed to the BIA), unless those remedies were effectively unavailable.
2. He was improperly deprived of the opportunity for judicial review (e.g., by being misadvised or procedurally blocked).
3. The entry of the order was fundamentally unfair, meaning there was a basic procedural defect and it mattered (prejudice).
Fundamental Unfairness & Prejudice
A removal proceeding is fundamentally unfair if:
- there was a serious procedural error (e.g., incorrect statement of the law, denial of counsel, failure to advise of rights); and
- there is a reasonable probability that, but for the error, the person would not have been removed.
In Ramirez Rodriguez, the error was so fundamental (no statutory authority to remove him) that prejudice followed directly.

VII. Conclusion

United States v. Ramirez Rodriguez clarifies and strengthens the protections available to noncitizens charged with illegal reentry in the Second Circuit. Its central contributions are:

It reaffirms that prejudice under § 1326(d)(3) must be evaluated at the time of entry of the original removal order, not in light of later criminal conduct or reinstatements.
It holds that reinstatements under § 1231(a)(5) are not new removal orders and cannot serve as independent, valid predicates for illegal reentry prosecutions when the underlying order is invalid.
It confirms that a removal order based on a conviction that is not in fact a removable offense is both fundamentally unfair and prejudicial under § 1326(d).
It aligns the Second Circuit with the Ninth Circuit’s view that reinstatements “bear the same taint” as the original order and signals skepticism toward broader, bootstrap approaches in other circuits.

While leaving open for remand the questions of administrative exhaustion and deprivation of judicial review, the court sets a clear doctrinal marker: the government cannot prosecute a person for illegal reentry on the basis of an order that the law did not permit in the first place, nor can it use the procedural device of reinstatement or later criminal history to rehabilitate such an order. In the broader landscape of immigration and criminal law, Ramirez Rodriguez is a robust affirmation that the integrity of the original removal proceeding matters—and that legality cannot be retrofitted after the fact.

Reinstatements Cannot Cure an Invalid Removal Order: A Comprehensive Commentary on United States v. Ramirez Rodriguez