United States v. Castillo-Martinez

Decision Date27 October 2021
Docket Number19-1971
PartiesUNITED STATES OF AMERICA, Appellee, v. JESUS LEONARDO CASTILLO-MARTINEZ, Defendant, Appellant.
CourtUnited States Courts of Appeals. United States Court of Appeals (1st Circuit)

UNITED STATES OF AMERICA, Appellee,
v.

JESUS LEONARDO CASTILLO-MARTINEZ, Defendant, Appellant.

No. 19-1971

United States Court of Appeals, First Circuit

October 27, 2021


APPEAL FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF MASSACHUSETTS [Hon. Nathaniel M. Gorton, U.S. District Judge]

Zainabu Rumala, Assistant Federal Public Defender, for appellant.

Karen Eisenstadt, Assistant United States Attorney, with whom Alexia R. De Vincentis, Assistant United States Attorney, and Andrew E. Lelling, United States Attorney, were on brief, for appellee.

Before Howard, Chief Judge, Lynch and Barron, Circuit Judges.

1

LYNCH, CIRCUIT JUDGE.

This case concerns the interpretation of a statutory bar in 8 U.S.C. § 1326(d) precluding certain collateral attacks in criminal proceedings. Appellant Jesus Leonardo Castillo-Martinez falls within the ambit of those limitations for the reasons stated below. We affirm the district court's denial of his motion to dismiss the criminal proceedings against him.

Castillo-Martinez was removed to the Dominican Republic in April 2013 after he was convicted in Massachusetts state court of illegally distributing marijuana and in New Hampshire state court of trafficking OxyContin. He illegally returned to the United States and was arrested on August 20, 2016, on a Florida fugitive warrant for a new controlled substances offense committed in Florida. He was removed again on November 1, 2016.

On June 23, 2018, after illegally reentering the United States again, he was arrested in Massachusetts once more on state heroin trafficking charges. He was then federally indicted for unlawfully reentering the United States in violation of 8 U.S.C. § 1326(a), which provides that "any alien who (1) has been . . . deported, or removed or has departed the United States while an order of exclusion, deportation, or removal is outstanding and thereafter (2) enters, attempts to enter, or is at any time found in, the United States . . . shall be fined under Title 18, or imprisoned not more than 2 years, or both."

2

Castillo-Martinez moved to dismiss the indictment under 8 U.S.C. § 1326(d), making two arguments that the element of unlawful reentry was not satisfied because his original removal order was not valid. First, he argued that his original removal order in 2012 was defective because the Notice to Appear ("NTA") he received did not include the time and place of his hearing. Second, he argued that his removal order in 2012 was based on the classification of his marijuana conviction as an aggravated felony, a classification to which he said his immigration counsel provided ineffective assistance by not objecting. He then argued that the classification was improper under the Supreme Court's later decision in Moncrieffe v. Holder, 569 U.S. 184 (2013), issued after his removal order. As a result, he argued, the original removal order must be declared invalid, and the criminal charges for illegal reentry must be dismissed. The district court denied Castillo-Martinez's motion. United States v. Castillo-Martinez, 378 F.Supp.3d 46, 55 (D. Mass. 2019).

We affirm.

I.

Castillo-Martinez was born in the Dominican Republic in 1973 and was admitted to the United States as a lawful permanent resident in 1981. In 1996, he was convicted of violating Mass. Gen. Laws ch. 94C, § 32C by "knowingly or intentionally manufactur[ing], distribut[ing], dispens[ing] or cultivat[ing]"

3

marijuana, a Class D substance under Massachusetts law. For this crime, he received a suspended sentence and probation. See id. §§ 31, 32C. He remained in the United States.

In February 2011, Castillo-Martinez was indicted by a New Hampshire grand jury for conspiring to sell 15, 000 tablets of OxyContin for approximately $272, 000 in violation of N.H. Rev. Stat. Ann. § 318-B:2(I). While he was awaiting trial, U.S. Immigration and Customs Enforcement ("ICE") lodged a detainer against him. He was later convicted of the conspiracy charge in June 2012 and received a suspended sentence and probation.[1]

Shortly after Castillo-Martinez's OxyContin conviction, the Department of Homeland Security ("DHS") served him with an NTA alleging that he was removable from the United States pursuant to 8 U.S.C. § 1227(a)(2)(A)(iii) because he had been convicted of an aggravated felony. The NTA was based on Castillo-Martinez's 1996 marijuana conviction and did not state his OxyContin conviction as its basis. The NTA did not state a specific date or time for Castillo-Martinez's hearing and noted that they were "to be set."

Castillo-Martinez, acting through counsel, conceded removability as alleged in the NTA under the law of the First Circuit, which held that his marijuana conviction was an aggravated

4

felony. Castillo-Martinez made the counseled choice to apply for deferral of removal under the Convention Against Torture ("CAT"). He submitted affidavits in support of his CAT petition and testified at an immigration hearing. On November 1, 2012, an immigration judge ("IJ") denied him CAT relief and ordered that he be removed to the Dominican Republic.[2] Castillo-Martinez unsuccessfully appealed this decision to the Board of Immigration Appeals ("BIA") on March 13, 2013, and was removed to the Dominican Republic on April 16, 2013. He did not challenge the BIA's decision by seeking a petition for review.

Castillo-Martinez returned to the United States at some point before April 28, 2016, when he was arrested in Florida on another controlled substance charge. He fled Florida, and was arrested on August 20, 2016, in Massachusetts pursuant to a "Fugitive from Justice" warrant from Florida and was taken into administrative custody by ICE. His removal order was reinstated, and, on November 1, 2016, he was removed to the Dominican Republic.

5

Castillo-Martinez returned to the United States again. On June 23, 2018, he was arrested in Massachusetts and charged with trafficking heroin. On August 2, 2018, he was federally indicted for unlawfully reentering the United States in violation of 8 U.S.C. § 1326(a).

In February 2019, Castillo-Martinez moved to dismiss the unlawful reentry charge. He made two arguments that the unlawful reentry element of 8 U.S.C. § 1326(a) was not met because there was no valid prior removal order. His first argument was that there was no valid prior removal order because under the Supreme Court's decision in Pereira v. Sessions, 138 S.Ct. 2105 (2018), the fact that the NTA did not include a specific date or time deprived the immigration court of jurisdiction and prevented it from ordering his removal. His second argument was that there was no valid prior removal order based on the Supreme Court's divided decision in Moncrieffe, issued shortly after his removal. He argued that under Moncrieffe, his marijuana conviction could not serve as the basis for his 2012 removal order because that conviction was not an aggravated felony, and further that his counsel's failure to object on this basis amounted to ineffective assistance.

The government responded to Castillo-Martinez's two arguments. As to the second argument, the government relied on the statutory limitations on collateral attacks set forth in 8 U.S.C. § 1326(d)

6

and specifically argued that he did not fall within any of the narrow exceptions that would have permitted a collateral attack. Subsection 1326(d) states that in a criminal proceeding under 8 U.S.C. § 1326(a), "an alien may not challenge the validity of [a] deportation order . . . unless" the alien makes three showings: (1) "the alien exhausted any administrative remedies that may have been available to seek relief against the order"; (2) "the deportation proceedings at which the order was issued improperly deprived the alien of the opportunity for judicial review"; and (3) "the entry of the order was fundamentally unfair." 8 U.S.C. § 1326(d). The government argued that Castillo-Martinez failed to exhaust his administrative remedies, that he was not denied the opportunity for judicial review, and that the removal proceedings were not fundamentally unfair.

The district court denied the motion. As to Castillo-Martinez's first argument, relying on case law from other courts of appeals, it held that the IJ had jurisdiction to issue a removal order "[b]ecause Castillo-Martinez was served with an NTA containing all of the required information and was presumably served a separate Notice of Hearing informing him of the time and place of his removal hearing (given that he actually appeared at that hearing)." Castillo-Martinez, 378 F.Supp.3d at 53; see also Santos-Santos v. Barr, 917 F.3d 486, 490 (6th Cir. 2019); Karingithi v. Whitaker, 913 F.3d 1158, 1162 (9th Cir. 2019).

7

As to his second argument, the district court held that Castillo-Martinez had not made the required showings necessary under 8 U.S.C. § 1326(d) to collaterally attack the validity of his original removal order. Castillo-Martinez, 378 F.Supp.3d at 54. First, because Castillo-Martinez "concede[d] that he failed to exhaust his administrative remedies and was not denied an opportunity for judicial review," the court held that he had not satisfied the first two § 1326(d) requirements. See id.; 8 U.S.C. § 1326(d)(1)-(2). Next, the court held that even if Castillo-Martinez could be excused from meeting some of § 1326(d)'s requirements if he could show his counsel had been ineffective, he still could not prevail because he had not shown that his counsel's performance was deficient or that he was prejudiced by either his counsel's actions or the deportation order. Castillo-Martinez, 378 F.Supp.3d at 54-55; see also 8 U.S.C. § 1326(d)(3) (requiring a showing that "the entry of the [deportation] order was fundamentally unfair" to collaterally attack it in a criminal proceeding).

Castillo-Martinez pleaded guilty to the unlawful reentry charge. He was sentenced to time served and a three-year...

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