United States v. Ramirez RodriguezUnited States v. Ramirez Rodriguez
VERNON S. BRODERICK, United States District Judge:
Defendant Lepido Ramirez Rodriguez (“Defendant” or “Ramirez“) is charged with one count of illegal reentry, in violation of
I. Factual Background
A. Defendant‘s Initial Removal Proceedings and 2000 Removal Order
Ramirez was born on August 8, 1958 in the Dominican Republic. (Def. Ex. 15-1.) He became a legal permanent resident of the United States on September 14, 1990. (Def. Ex. 15-2.) Defendant‘s wife and at least five of his children are all United States citizens. (Def. Exs. 3-8). On or about January 21, 1998, Defendant was arrested by the New York City Police Department (“NYPD“) for criminal sale and criminal possession of a controlled substance, (Def. Ex. 15-9), and convicted on July 22, 1999 of second-degree criminal sale of a controlled substance, namely cocaine, in violation of
Following his conviction, Defendant was ordered to appear for a removal proceeding. (Def. Ex. 2.) On December 17, 1999, Defendant appeared before an immigration judge by video from the Riverview Correctional Facility, where he was serving his sentence for his state drug conviction. (Def. Ex. 10; Def. Br. 4.) Defendant was not represented by counsel at the proceeding, and was advised by the immigration judge that although the court did not have a list of available free legal counsel, he had the right to be represented by counsel at his own expense. (Def. Ex. 10 at 01:21-01:41; 3:00-3:35.) After Ramirez informed the immigration judge that he would like an opportunity to try to find counsel to represent him, the immigration judge adjourned
At the hearing on February 11, 2000, Defendant, who had not hired an attorney, again appeared by video from the Riverview Correctional Facility. During that appearance, he admitted that he was a citizen of the Dominican Republic and was not a citizen of the United States, (id. at 08:20-09:10), and that he had been convicted of selling cocaine on July 22, 1999, a conviction for which he was currently serving a prison term and which he did not appeal, (id. at 09:10-09:45). After informing Defendant that his drug conviction was final, the immigration judge then made several factual findings: (1) that Ramirez could be removed from the United States based on his drug conviction; and (2) that he could also be deported because his conviction was an aggravated felony. (Id. 9:45-10:27.) After making the findings, the immigration judge ordered Ramirez removed to the Dominican Republic. (Id. 10:33-11:32.) The immigration judge also advised Ramirez of his right to appeal any final decision to the Board of Immigration Appeals, and asked Defendant whether he wanted to appeal the decision. (Id. at 07:25-07:50.) Ramirez declined to appeal. (Id.)
Following the hearing, the immigration judge issued an order of removal on February 11, 2000. (Def. Ex. 13, “2000 Removal Order“.) On the 2000 Removal Order, which stated “respondent has made no application for relief from removal,” the immigration judge crossed out “has made no application” and instead added a handwritten notation that Ramirez was “not eligible for relief from removal.” (Id.) After completing his state sentence for the drug conviction, Ramirez was released to immigration custody and was deported to the Dominican Republic on April 30, 2001. (Def. Ex. 12; Doc. 1, “Compl.,” ¶ 3(b).) The March 12, 2001 warrant of removal stated that Defendant was to be removed pursuant to the 2000 Removal Order and the provisions of the Immigration and Nationality Act (“INA“) which make non-citizens who have been convicted of an aggravated felony, (see
B. Defendant‘s 2009 and 2013 Illegal Reentry Convictions and 2010 and 2016 Removal Orders
Ramirez returned to the United States several times after he was first removed on April 30, 2001. On or about March 12, 2006, Ramirez applied for permission to reapply for admission into the United States. (Gov‘t. Ex. 1.2) Despite the Department of Homeland Security‘s denial of his application, issued on or about October 16, 2008, (see id.), Defendant nonetheless returned to the United States. On or about July 24, 2009, Ramirez was arrested by immigration authorities, and was later charged in this district with illegal reentry after having been removed subsequent to an aggravated felony conviction. (See United States v. Ramirez, No. 09-CR-751 (RWS); Compl. ¶ 3(d).) Defendant pled guilty to this charge on October 14, 2009, and was sentenced to 18 months’ imprisonment. (See Compl. ¶ 3(e).) The INA provides that if a non-citizen reenters the United States “illegally after having been removed . . . 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 non-citizen is “not eligible and may not apply for any relief,” and the non-citizen “shall be
Following his second deportation, Ramirez again illegally entered the United States. On June 4, 2013, Defendant was arrested by the Drug Enforcement Administration and the NYPD. Although Defendant was initially charged with money laundering in connection with this arrest, he ultimately was not prosecuted for this charge. (Compl. ¶ 3(f).) Defendant was, however, again charged with illegal reentry, along with having violated the conditions of his supervision in connection with the 2009 illegal reentry case. Defendant pled guilty on or about August 7, 2013, and was sentenced to 45 months’ imprisonment to be followed by one month of imprisonment, to be served consecutively, on the violation. (Id.) Defendant was deported to the Dominican Republic pursuant to a September 14, 2016 warrant of removal which was, again, based on a reinstatement of the 2000 Removal Order. (See Gov‘t. Ex. 5.) As with the first illegal reentry charge, Defendant neither moved to dismiss or appeal this charge, and did not otherwise collaterally attack the underlying 2000 Removal Order.
After illegally returning to the United States a third time, Defendant was arrested by the NYPD on or about October 27, 2022, and charged with first-degree criminal possession of a controlled substance, in violation of
II. Procedural History
Defendant filed a motion to dismiss the single-count indictment, as well as his accompanying memorandum of law and exhibits, on November 8, 2023. (Docs. 14-15.) The Government filed its opposition and exhibits on December 4, 2023. (Doc. 20.) Defendant then filed his reply on December 8, 2023. (Doc. 21, “Def. Reply“.) Oral argument was held on February 1, 2024. (Doc. 25, “Oral Arg. Tr.“.)
III. Applicable Law
A defendant may move to dismiss an indictment for failure to state an offense. See
As set forth in the Second Circuit‘s decisions in United States v. Copeland, 376 F.3d 61 (2d Cir. 2004), United States v. Sosa, 387 F.3d 131 (2d Cir. 2004), and United States v. Calderon, 391 F.3d 370 (2d Cir. 2004), a defendant must be excused from proving the first two requirements of Section 1326(d) in circumstances which implicate constitutional due process considerations. In Copeland, the court held that there is no “realistic opportunity for judicial review” in circumstances where a defendant is misinformed by an immigration judge because the “waiver of the right to appeal is not knowing,” and where “the interval between entry of the final deportation order and the physical deportation is too brief to afford a realistic possibility of filing a habeas petition.” 376 F.3d at 68 & n.6. In Sosa, the court similarly held that Section 1326(d)(1)‘s exhaustion requirement “must be excused where an [non-citizen]‘s failure to exhaust results from an invalid waiver of the right to an administrative appeal.” 387 F.3d at 136. In Calderon, the Second Circuit further held that “a failure to exhaust administrative remedies bars collateral review of a deportation proceeding under Section 1326(d)(1) . . . only where an [non-citizen]‘s waiver of administrative review was knowing and intelligent.” 391 F.3d at 374-75 (internal quotation marks and citation omitted). In so holding, the court reasoned that a failure to permit excusal under such circumstances “would offend the principles enunciated in United States v. Mendoza-Lopez, 481 U.S. 828 (1987).” Id.
In Palomar-Santiago, the Supreme Court recently rejected Ninth Circuit precedent as set forth in United States v. Ochoa, 861 F.3d 1010 (9th Cir. 2017), which—like the Second Circuit cases cited above—excused defendants from complying with § 1326(d)‘s requirement that they exhaust their administrative and judicial remedies if the underlying removal order is based on a conviction that did not render the defendant removable. 141 S. Ct. at 1620-21; see Ochoa, 861 F.3d at 1015. The Supreme Court unanimously found that “[t]he Ninth Circuit‘s interpretation is incompatible with the text of § 1326(d)” because the statute plainly states that “defendants charged with unlawful reentry ‘may not’ challenge their underlying removal orders ‘unless’ they ‘demonstrat[e]‘” that the three requirements are met.” Id. at 1620.3
Defendant argues his state drug conviction is not a removable offense and, therefore, that the 2000 Removal Order, which the instant illegal reentry charge is based on, is invalid. (Def. Br. 3.) Although the Government concedes that Defendant was not charged with a removeable offense during the 2000 removal proceedings, it argues that Defendant‘s collateral attack fails because he was not prejudiced by any fundamental procedural error. Specifically, the Government argues that because the Defendant was subsequently convicted twice of illegal reentry, convictions which qualify as aggravated felonies and render him statutorily ineligible for any immigration relief, he cannot establish the only prejudice he claims—that he would not have been deported. (Gov‘t. Opp. 2.) The Government further argues that the Defendant‘s failure to exhaust his administrative remedies and seek judicial review—requirements when mounting a collateral challenge under Section 1326(d)—cannot be excused based on the Supreme Court‘s recent decision in Palomar-Santiago. (Id. at 3 (citing Palomar-Santiago, 141 S. Ct. at 1620-21).)
A. The 2000 Removal Order Involved a Fundamental Procedural Error
Because any assessment of Defendant‘s failure to exhaust his administrative remedies and to seek judicial relief is necessarily informed by whether the 2000 Removal Order was fundamentally unfair, I begin my analysis with the third prong of Section 1326(d). In order to demonstrate fundamental unfairness, a defendant “must show both a fundamental procedural error and prejudice resulting from that error.” United States v. Fernandez-Antonia, 278 F.3d 150, 159 (2d Cir. 2002); United States v. Lopez, 445 F.3d 90, 100 (2d Cir. 2006). “The [non-citizen] bears the burden of showing that entry of the removal order was fundamentally unfair.” United States v. Daley, 702 F.3d 96, 100 (2d Cir. 2012). Defendant argues that the 2000 Removal Order was fundamentally unfair because
Pursuant to the INA, a non-citizen must be deported if he falls under certain enumerated classes that are not eligible for voluntary departure. See
In United States v. Minter, the Second Circuit recently held that because New York state law criminalizes conduct that the federal Controlled Substances Act does not, that “New York‘s definition of cocaine is categorically broader than its federal counterpart.” 80 F. 4th 406, 411 (2d Cir. 2023). Under Minter, because New York‘s definition of “narcotic drugs” sweeps more broadly than its federal analog, such convictions cannot constitute a “controlled substance offense” under the categorical approach. Id. Defendant asserts that Minter is “merely a clarification of what the law has always been since 1986” rather than a change in the law. (Oral Arg. Tr. 13-14.) Defendant argues, therefore, that his conviction was not—now or at the time—a controlled substance offense, and that the immigration judge committed a procedural error when she deemed Defendant removable based on her determination otherwise. (Def. Br. 10.) The Government concedes, apparently in
B. The Defendant Cannot Establish Prejudice
The prejudice prong of the two-pronged test of fundamental unfairness requires Defendant to establish that “absent the procedural errors, he would not have been removed.” Fernandez-Antonia, 278 F.3d at 159; see also United States v. Copeland, 376 F.3d 61, 73 (2d Cir. 2004) (“Prejudice is shown where defects in the deportation proceedings may well have resulted in a deportation that would not otherwise have occurred.“) (internal quotation marks and citation omitted). Defendant argues that he suffered prejudice because but-for the immigration judge‘s erroneous determination that Defendant had committed an aggravated felony and a controlled substance offense, he would have been permitted to remain in the United States as a lawful permeant resident. (Def. Br. 10.) The Government asserts that Defendant cannot establish prejudice because even if he would have been permitted to remain in the United States but-for the immigration judge‘s fundamental procedural error, he subsequently became removable and statutorily ineligible for any immigration relief after pleading guilty to illegal reentry in 2009 and 2013, convictions that were themselves aggravated felonies under the INA predating the reinstatements of the removal order. (Gov‘t. Opp. 12.)
1. Defendant‘s Subsequent Illegal Reentry Convictions Constitute Aggravated Felonies
As a threshold matter, the Government‘s prejudice argument depends on my finding that the Defendant‘s 2009 and 2013 convictions constitute aggravated felonies. The aggravated felony definition under the INA includes “an offense described in section 1325(a) or 1326 of this title committed by [a non-citizen] who was previously deported on the basis of a conviction for an offense described in another subparagraph of this paragraph.”
The Second Circuit has not yet addressed whether an illegal reentry conviction that is predicated on an offense that is, itself, no longer an aggravated felony may nonetheless still qualify as an aggravated felony. The Government urges me to adopt the reasoning of the Fifth Circuit, the only federal court of appeals to have considered this exact question, in United States v. Huerta-Rodriguez, 64 F.4th 270, 276 (5th Cir. 2023), which held that an intervening illegal reentry conviction is itself an aggravated felony even if the predicate offense on which the conviction is based no longer constitutes an aggravated felony. (See Gov‘t. Opp. 14 (citing United States v. Huerta-Rodriguez, 64 F.4th 270, 276 (5th Cir. 2023)).)
Although I am not bound by Huerta-Rodriguez, I nonetheless find the court‘s reasoning instructive and persuasive. In Huerta-Rodriguez, the defendant was convicted of first-degree burglary and was deported to Mexico after being released on parole. Id. at 273. Thereafter, the defendant was then convicted three times of illegal reentry. After his first illegal reentry conviction, the Supreme Court issued an opinion making clear that defendant‘s burglary no longer qualified as an aggravated felony. Id. at 274 (citing Mathis v. United States, 579 U.S. 500, 604 (2016)). Subsequently, the defendant was convicted for the second time of illegal reentry, and the Presentence Investigation Report (“PSR“) identified both the burglary and the defendant‘s first illegal reentry conviction as aggravated felonies. Id. at 275. Defendant objected to the PSR, arguing that an aggravated-felony enhancement should not apply because, after Mathis, his burglary conviction no longer qualified as an aggravated felony. Id. The district court disagreed, and sentenced the defendant to a two-year prison term after which he was deported to Mexico for a third time in August 2018. Id.
After defendant reentered the country, he was convicted for a third time of illegal reentry, and again objected to the PSR‘s characterization of his burglary and two prior illegal reentry convictions as aggravated felonies. Although the Government conceded that the defendant‘s burglary offense no longer qualified as an aggravated felony under Mathis, it argued that
On appeal, the defendant challenged the district court‘s characterization of both his burglary and prior illegal reentry convictions, arguing that because his burglary offense no longer constituted an aggravated felony, neither did his illegal reentry convictions. Id. at 277. The Fifth Circuit disagreed, holding that even though the predicate burglary offense no longer qualified as an aggravated felony, the defendant‘s intervening illegal reentry conviction was still, itself, an aggravated felony that supported the enhanced penalties under
Although the parties disagree concerning whether the Fifth Circuit intended to limit its holding to the sentencing context, as Defendant argues, or more broadly to cases involving a non-aggravated felony predicate offense and an intervening aggravated felony conviction, as the Government suggests, I need not resolve that dispute, as I find the Fifth Circuit‘s statutory analysis applicable and persuasive irrespective of the holding‘s scope. Although Defendant identifies several purported errors in the Fifth Circuit‘s reasoning, I do not find these arguments compelling. First, Defendant argues that the Fifth Circuit‘s holding conflicts with Second Circuit caselaw establishing that courts must analyze a
Here, as in Huerta-Rodriguez, Defendant was convicted of a state drug offense that is no longer considered an aggravated felony, but which served as the predicate offense for his 2009 and 2013 illegal reentry convictions. After Defendant was removed from the United States in 2001, he reentered the United States three times with the understanding that his previous drug conviction was an aggravated felony. Indeed, Defendant pled guilty in 2009 and 2013 to illegal reentry after removal for an aggravated felony. Thus, adopting the reasoning of the Fifth Circuit, I find that regardless of the status of Defendant‘s state drug conviction, his 2009 and 2013 illegal reentry convictions constitute aggravated felonies.
2. Defendant Was Not Prejudiced
Having found that Defendant‘s two prior illegal convictions constitute aggravated felonies, I now consider what impact, if any, those convictions have on Defendant‘s argument that he was prejudiced by the 2000 Removal Order. The Government argues the 2010 and 2016 reinstatements of the initial removal order—reinstatements which occurred after Defendant had been convicted of two aggravated felonies that would have rendered him statutorily ineligible for any immigration relief—do not themselves give rise to any prejudice. (Gov‘t. Opp. 13.) Defendant argues that regardless of whether he would have been removable based on the subsequent convictions, the only relevant issue before me on a
Defendant cites a number of cases where courts have found prejudice in circumstances where immigration judges issued a removal order based on an erroneous determination that the defendant was removable. (See Def. Br. 10-11 (collecting cases).) In each of these cited cases, however, as is required under the law, see Fernandez-Antonia, 278 F.3d at 159, the immigration judge‘s error resulted in a deportation that would not have otherwise occurred. That is not the case here. None of the cases cited by defendant feature an intervening aggravated felony conviction that occurred prior to the reinstatement of the removal order, let alone two intervening felony convictions that were not otherwise challenged and rendered Defendant deportable.
As the Government notes, Judge Jed S. Rakoff denied a defendant‘s motion to dismiss the indictment in a case which, unlike the cases cited by Defendant, did feature an intervening felony. (See Gov‘t. Opp. 12-13 (citing United States v. Barrera Moreno, 410 F. Supp. 3d 697 (S.D.N.Y. 2019).)
Defendant also asserts that he need not establish that he was prejudiced from the 2010 and 2016 reinstatements of the 2000 Removal Order, and that Barrera Moreno contravenes the Second Circuit‘s decision in United States v. Scott, 394 F.3d 111 (2d Cir. 2005). In so arguing, Defendant suggests that Scott prohibits me from considering whether Defendant suffered any prejudice with respect to subsequent reinstatements of the removal order. (Oral Arg. Tr. 46.) However, that is a misreading of Scott. In Scott the defendant was a lawful permanent resident who was ordered removed after being convicted of two state criminal offenses. Scott, 394 F.3d at 113-14. After he was ordered removed in absentia, he appealed to the Board of Immigration Appeals (“BIA“). Id. at 114. He was then convicted of possession of burglar‘s tools. Id. A few years later, after the BIA dismissed his appeal, defendant was deported. Defendant then reentered the United States, and was arrested for, among other things, grand larceny. Id. He was then charged with illegal reentry after deportation. He moved to dismiss the indictment and collaterally challenged his deportation.
On appeal, the Second Circuit held that the district court had erred in considering “ex post data,” the conviction for possession of burglar‘s tools, in assessing whether the defendant was prejudiced by the fundamental procedural error that had occurred during the defendant‘s removal proceedings. The court‘s directive that
Because Defendant cannot demonstrate that he suffered prejudice as a result of the immigration judge‘s procedural error, he has not demonstrated fundamental unfairness under
V. Conclusion
For the foregoing reasons, Defendant‘s motion is DENIED. The Clerk of the Court is respectfully directed to terminate the open motion at Doc. 14.
SO ORDERED.
Dated: March 7, 2024
New York, New York
Vernon S. Broderick
United States District Judge