United States v. Ramirez RodriguezUnited States v. Ramirez Rodriguez
Before: NEWMAN, PARKER, AND MERRIAM, Circuit Judges.
In 1999, Defendant-Appellant Lepido Ramirez Rodriguez, who was a legal permanent resident of the United States, was convicted of criminal sale of a controlled substance in the second degree, in violation of New York law. At a hearing in February 2000, an Immigration Judge (“IJ“) determined that Ramirez Rodriguez‘s conviction was an aggravated felony and a controlled substance offense that rendered him removable and ordered him deported. Following his deportation, Ramirez Rodriguez twice re-entered the United States without authorization. Both times, he was convicted of illegal reentry and the 2000 removal order was reinstated.
But the 2000 removal order was invalid. As this Court made clear in United States v. Minter, 80 F.4th 406 (2d Cir. 2023), criminal sale of a controlled substance in the second degree under New York law is not a removable offense. Accordingly, when Ramirez Rodriguez was charged with illegal reentry for a third time in the case before us, he moved to dismiss the indictment pursuant to
The district court, relying on the two subsequent illegal rеentry convictions, concluded that Ramirez Rodriguez was not prejudiced by the error and denied the motion. He then pleaded guilty but preserved his right to appeal the denial of his motion to dismiss. The district court entered a final judgment from which Ramirez Rodriguez appeals.
We agree with Ramirez Rodriguez that the district court incorrectly relied on the two later reinstatements of the removal order. The only remоval order ever entered against Ramirez Rodriguez was based on a crime that did not render him removable. Because the subsequent reinstatements of the invalid 2000 removal order are not new removal orders, they do not supply a valid basis for the illegal reentry conviction that is the subject of this appeal, nor is it appropriate to look at the circumstances at the time they were entered to assess prejudice. Accordingly, in Case No. 24-2093, we VACATE the judgment of the district court and REMAND for further proceedings consistent with this opinion. Case No. 24-2059 is DISMISSED for lack of appellate jurisdiction.
FOR APPELLANT: SIOBAHN C. ATKINS, Assistant Federal Public Defender, (Edward S. Zas, Assistant Federal Public Defender, on the brief), New York, NY.
FOR APPELLEE: JERRY FANG, Assistant United States Attorney (Michael D. Maimin, Assistant United States Attorney, on the brief), for Matthew Podolsky, Acting United States Attorney for the Southern District of New York, New York, NY.
BARRINGTON D. PARKER, Circuit Judge:
In 1999, Defendant-Appellant Lepido Ramirez Rodriguez, who was a legal permanent resident, was convicted of criminal sale of a controlled substance in the second degree, in violation of New York law. At a hearing in February 2000, an Immigration Judge (“IJ“) determined that Ramirez Rodriguez‘s conviction was an aggravated felony and a controlled substance offense that rendered him removable and ordered him deported. Following his deрortation, Ramirez Rodriguez twice re-entered the United States without authorization. Both times, he was arrested and convicted of illegal reentry, and both times, the 2000 removal order was reinstated.
But the 2000 removal order was invalid. In United States v. Minter, 80 F.4th 406 (2d Cir. 2023), we held that criminal sale of
The district court, relying on the subsequent illegal reentry convictions, concluded that Ramirez Rodriguez had not established that he was prejudiced by the error, as we have held is required by
We agree with Ramirez Rodriguez that the district court incorrectly relied on the two later reinstatements of the removal order. The only removal order entered against him was based on a crime that did not render him removable. Because the subsequent reinstatements of the invalid 2000 removal order are not new removal orders, they do not supply a valid basis for the illegal reentry conviction that is the subject of this appeal, nor is it appropriate to look at the circumstances at the time they were entered to assess prejudice. Accordingly, in Case No. 24-2093, we VACATE the judgment of the district court and REMAND for further proceedings consistent with this opinion. Case No. 24-2059 is DISMISSED for lack of appellate jurisdiction.
BACKGROUND
I. Ramirez Rodriguez‘s Initial Conviction and Removal Order
Ramirez Rodriguez, a citizen and national of the Dominican Republic, became a legal permanent resident of the United States in 1990. In 1999, he was convicted in New York state court of second-degree criminal sale of a controlled substance, cocaine, in violation of
Following his conviction, Ramirez Rodriguez was ordered to appear for removal proceedings in December 1999. He did not have counsel. The IJ initially adjourned the hearing to afford him the opportunity to obtain counsel, but he was unsuccessful in doing so.
His hearing took place on February 11, 2000. Ramirez Rodriguez admitted that he was not a citizen of the United States; that he had been convicted on July 22, 1999, for the sale of cocaine in the second degree; that he was serving a prison term for the convictiоn; and that he had not appealed his conviction. The IJ told Ramirez Rodriguez that he could be removed from the country both because he was convicted of a drug offense and because his conviction was for an aggravated felony. The IJ concluded: “Mr. Ramirez, you can‘t stay in this country because of your selling of cocaine conviction.” App‘x at 52.
The IJ told Ramirez Rodriguez that he would be deрorted and asked where he wanted to go. Ramirez Rodriguez answered that he wanted to stay in the United States because he has children here. The IJ responded: “You will not stay in this country, Mr. Ramirez.” Id. Ramirez Rodriguez then exclaimed, “I‘m leaving, I‘m leaving, I‘m leaving.” Id. The IJ ordered Ramirez Rodriguez deported to the Dominican Republic. He informed Ramirez Rodriguez that he could appeal the decision to the BIA or make it finаl that day; Ramirez Rodriguez said: “No, I don‘t want to do anything, I just want to leave this country and that‘s it.” Id. The IJ stated,
Ramirez Rodriguez was granted conditional parole for deportation. On April 19, 2001, he was transferred to immigration custody and deported eleven days later.
II. Ramirez Rodriguez‘s Subsequent Illegal Reentry Convictions and Removals
In the following two decades, Rаmirez Rodriguez returned to the United States twice, both times without authorization. In November 2008, after the government denied his application for permission to reapply for admission, Ramirez Rodriguez returned to the United States. A few months later, when Ramirez Rodriguez submitted his fingerprints to New York State as part of a job application, he was arrested and charged with illegal reentry. See United States v. Ramirez, No. 09-cr-0751 (RWS), 2009 WL 4722237 (S.D.N.Y. Dec. 4, 2009). He pleaded guilty to the charge, was sentenced to eighteen months’ imprisonment, and served the term. In 2010, once he completed the term, an immigration official “reinstated” the 2000 removal order; Ramirez Rodriguez was again deported to the Dominican Republic on that basis.
Ramirez Rodriguez returned to the United States again. This time, he was arrested in 2013 and charged with a state money-laundering offense. He ultimately was not prosecuted for that crime, but he was charged again with illegal reentry following removal for an aggravated felony, along with a violation of supervised release arising from the 2009 illegal reentry conviction. See United States v. Ramirez, No. 13-cr-0468 (KMW) (S.D.N.Y.). He pleaded guilty again and was sentenced to forty-five months imprisonment on the illegal reentry conviction, to be followed by one month of imprisonment for the violation of supervised release. In 2016, after he served his sentence, the government did not institute new removal proceedings but simply reinstated the 2000 removal order and removed him again on that basis.
III. The Current Charge and Proceedings
Ramirez Rodriguez returned to the United States again. In August 2022, he was arrested in the Bronx with over a kilogram of cocaine and charged with various crimes. He pleaded guilty to criminal possession of a controlled substance in the third degree and was sentenced to two years’ imprisonment. He was also charged, for a third time, with aggravated illegal reentry—the offense underlying this appeal.
This time, however, Ramirez Rodriguez moved to dismiss the Indictment, challenging the validity of the 2000 removal order. See
At oral argument before the District Court, thе government conceded that, in light of Minter, the conviction underlying the 2000 removal order was not an aggravated felony or a controlled substance offense. See App‘x at 159. But the district court nonetheless denied Ramirez Rodriguez‘s motion to dismiss. It concluded that although the government had conceded a fundamental procedural error, Ramirez Rodriguez could not demonstrate prejudice resulting from that error, a showing necessary to meet the third prong of
Ramirez Rodriguez then pleaded guilty to the illegal reentry сount pursuant to an agreement that preserved both his right to appeal the ruling denying his motion to dismiss and the government‘s right to “raise on appeal any argument for affirmance of the district court‘s ruling, including arguments not reached by or raised before the district court.” App‘x at 231. In July 2024, the district court sentenced Ramirez Rodriguez to a thirty-month term of incarceration, to be followed by three years of supervised release. The court entered a final judgment, and Ramirez Rodriguez appealed.
DISCUSSION
I. Standard of Review
Before trial, a defendant “may raise by . . . motion any defense, objection, or request that the court can determine without a trial on the merits,” including a motion alleging “a defect in the indictment.”
II. Fundamental Unfairness
“[W]here a determination made in an administrative proceeding is to play a critical role in the subsequent imposition of a criminal sanction, there must be some meaningful review of the administrative proceeding.” United States v. Mendoza Lopez, 481 U.S. 828, 837–88 (1987). Accordingly, an individual facing an illegal reentry charge under
There is no dispute that Ramirez Rodriguez carried his burden to show that the 2000 removal order involved a fundamental procedural error. See Gov‘t Br. at 28. Ramirez Rodriguez was ordered removed following his conviction for a crime that was not a removable offense. The district court nonetheless denied his motion to dismiss based solely on its determination that Ramirez Rodriguez failed to meet his burden to demonstrate prejudice resulting from that error. The district court held that “[b]ecause Defendant‘s 2009 and 2013 illegal reentry convictions, which predated the reinstatement of the 2000 removal order, constitute aggravated felonies rendering him ineligible for immigration relief, Defеndant cannot establish he suffered prejudice
“Prejudice is shown where ‘defects in the deportation proceedings may well have resulted in a deportation that would not otherwise have occurred.‘” Copeland, 376 F.3d at 73 (quoting Fernandez-Antonia, 278 F.3d at 159). For example, where the error at issue is that a noncitizen was not informеd of his right to Section 212(c) relief, but the noncitizen cannot show that he likely would have been granted that relief, he fails to show prejudice. See Copeland, 376 F.3d at 73. In the same vein, where the error at issue is that a noncitizen was not informed of his right to appeal an adverse decision, but the noncitizen cannot show that he likely would have prevailed in such an appeal—that is, he cannot show that “he would not have been removed even after a procedurally perfect removal proceeding“—he fails to demonstrate prejudice. Fernandez-Antonia, 278 F.3d at 159–60.
The case law thus focuses on the outcome of the hearing infected by a fundamental procedural error. If a noncitizen can show that, absent that procedural error, he likely would not have been removed, he has shown prejudice. The analysis is akin to the Strickland standard for ineffective assistance of counsel.1
Herе, the prejudice analysis is straightforward. The fundamental procedural error at the 2000 hearing was that Ramirez Rodriguez was deemed removable for a crime that did not, in fact, render him removable. Absent that error, Ramirez Rodriguez could not have been found removable and therefore would not have been removed.
Our case law is clear that even if a defendant has later convictions that render him rеmovable, that does not change the prejudice analysis.2 In United
States v. Scott, we explained that the language of
The district court, recognizing the force of Scott, nonetheless found that it could consider the subsequent illegаl reentry convictions in assessing prejudice by focusing its prejudice analysis on a different point in time: not at the time of entry of the 2000 removal order, but at the time of the 2010 and 2016 reinstatements of the removal order. The district court recast the 2010 and 2016 reinstatements, not the 2000 removal order, as the “disputed deportation proceeding.” Rodriguez, 722 F. Supp. 3d at 275. The district court distinguished Scott: “Critically, Scott involved a single removal order.” Id. at 276.
But this case too involves a single removal order. Reinstatement of removal is governed by
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.
We have said that this lack of procedural protections “does not offend due process” because “reinstatement of the prior deportation order does not alter petitioner‘s legal condition.” Garcia-Villeda, 531 F.3d at 150. But if an illegal reentry charge may be predicated on reinstatement of an invalid removal order, the reinstatement would fundamentally alter the noncitizen‘s legal condition because it would provide an independent basis for a criminal charge. That cannot be the case. Where a removal order is invalid, reinstatements of that same removal order carry no independent validity. If the government cannot support an illegal reentry charge against Ramirez Rodriguez based on the 2000 removal order—and it cannot—it similarly cannot support that charge based on the reinstatements of the same prior invalid removal order. For that reason, looking at the time of the reinstatements rather than the time of the initial removal order in assessing prejudice is improper. In so holding, we join the Ninth Circuit, which has explained that where the original removal “was not legally sound . . . none of the reinstatements is
Our consideration is limited to whether the original removal order—the only removal order—was fundamentally unfair. As set forth above, it was. Ramirez Rodriguez was ordered removed for a crime that did not render him removable. That is the only removal order that has ever been entered against him. There is no dispute that it is invalid and that Ramirez Rodriguez was prejudiced based on the facts as they existed at the time of that removal proceeding.
III. Alternative Grounds
The government argues that even if we believe that Ramirez Rodriguez established prejudice, we should nonetheless affirm the denial of his motion to dismiss on the alternative grounds that Ramirez Rodriguez did not satisfy the gatekeeping requirements of
We decline the government‘s invitation. We typically “do[] not consider an issue not passed upon below.” Booking v. Gen. Star Mgmt. Co., 254 F.3d 414, 418 (2d Cir. 2001). The district court did not address these questions below. They may involve factual inquiry and are best left to the district court to resolve in the first instance.
CONCLUSION
For the foregoing reasons, in Case No. 24-2093, we VACATE the judgment of the district court and REMAND for further proceedings consistent with this opinion. Case No. 24-2059 is DISMISSED for lack of jurisdiction.