The Second Circuit Court of Appeals has delivered a significant ruling that provides a critical defense pathway for individuals facing criminal charges for illegal reentry following a prior, flawed deportation order. In a decision released in December 2025, the court overturned the conviction of Lepido Ramirez Rodriguez, finding that subsequent reinstatements of an initial, invalid removal order cannot cure the fundamental unfairness of the original proceeding.
The case centers on the complex interplay between immigration removal proceedings and subsequent federal criminal prosecution under 8 U.S.C. § 1326(d), which allows a defendant to collaterally attack the validity of a prior deportation order when charged with illegal reentry.
The Flawed Foundation: A 2000 Removal Order
Ramirez Rodriguez, a legal permanent resident, was convicted in 1999 in New York state court for criminal sale of a controlled substance in the second degree. Based on this conviction, an Immigration Judge (IJ) ordered him deported in February 2000, determining the crime qualified as both an aggravated felony and a controlled substance offense.
The problem, as the Second Circuit previously established in *United States v. Minter* (2023), is that the specific New York statute Ramirez Rodriguez violated does not actually constitute a removable offense under federal immigration law.
Following his deportation in 2001, Ramirez Rodriguez illegally re-entered the U.S. twice—once in 2008 and again sometime before 2013. Both times, he was convicted of illegal reentry, and each time, the government simply “reinstated” the original, invalid 2000 removal order rather than initiating new proceedings.
The Current Charge and the District Court’s Reasoning
When Ramirez Rodriguez was arrested for a third illegal reentry in 2022, he moved to dismiss the indictment under § 1326(d). He argued that the foundation of the charge—the 2000 removal order—was fundamentally unfair because it was based on a non-removable offense.
The government conceded that, in light of the *Minter* decision, the 2000 order was procedurally flawed. However, the U.S. District Court for the Southern District of New York denied the motion to dismiss. The district court reasoned that Ramirez Rodriguez could not show “prejudice” resulting from the initial error, because his two subsequent illegal reentry convictions (in 2009 and 2013) were themselves considered aggravated felonies that made him removable regardless of the initial defect.
Ramirez Rodriguez pleaded guilty while preserving his right to appeal this specific denial.
The Circuit Court Steps In: Focusing on the Original Defect
The Second Circuit panel, consisting of Judges Newman, Parker, and Merriam, disagreed with the district court’s prejudice analysis. Writing for the court, Judge Barrington D. Parker emphasized the strict temporal limitations required when evaluating the fundamental unfairness prong of § 1326(d).
To succeed on a challenge to a prior removal order, a defendant must show a fundamental procedural error and prejudice resulting from that error. The court stressed that prejudice must be analyzed based on the facts as they existed *at the time the original removal order was entered.*
“The case law thus focuses on the outcome of the hearing infected by a fundamental procedural error,” the opinion states. “If a noncitizen can show that, absent that procedural error, he likely would not have been removed, he has shown prejudice.”
Since the 2000 removal order was based on a crime that did not make Ramirez Rodriguez removable, the court concluded that, absent that error, he would not have been deported in the first place. This established prejudice.
Why Reinstatements Don’t “Launder” Invalid Orders
The core of the district court’s error, according to the Second Circuit, was shifting the focus from the 2000 order to the 2010 and 2016 reinstatements. The appellate court firmly rejected this approach.
The opinion clarifies that under 8 U.S.C. § 1231(a)(5), reinstatement is not a new removal proceeding; it simply enforces the *prior* order. If the prior order is invalid, any subsequent reinstatement carries the same defect.
“Where a removal order is invalid, reinstatements of that same removal order carry no independent validity,” the court asserted. Citing the Ninth Circuit’s *Arias-Ordonez* decision, the panel noted, “you can’t take a reinstatement and launder the original deportation because the reinstatement bears the same taint as the original deportation.”
Therefore, the subsequent illegal reentry convictions, while resulting in new criminal penalties, could not be used by the district court to retroactively negate the prejudice Ramirez Rodriguez suffered when he was initially, and unlawfully, deported in 2001.
The court acknowledged the government’s argument that Ramirez Rodriguez might have failed the other two prongs of the § 1326(d) test—administrative exhaustion and opportunity for judicial review—but declined to rule on those issues, as they were not fully addressed by the district court.
The judgment against Ramirez Rodriguez in Case No. 24-2093 was vacated, and the case was remanded back to the district court for further proceedings consistent with the appellate court’s findings, likely requiring dismissal of the third illegal reentry indictment. The related appeal, Case No. 24-2059, was dismissed for lack of jurisdiction.
This ruling reinforces the importance of jurisdictional integrity in immigration proceedings, ensuring that criminal sanctions for reentry are only based on removal orders that were legally sound from the outset.