Harry Sandick, Partner

The Second Circuit (Walker, Carney, and Koeltl) issued a decision vacating a 10-year sentence of imprisonment for conspiracy to distribute and possess with intent to distribute marihuana.  The Court held that, contrary to the district court’s finding, a prior conviction for the attempted sale of a controlled substance in the fifth degree, in violation of N.Y. Penal Law (NYPL) § 220.31, was not a conviction for a “felony drug offense,” as defined by 21 U.S.C. § 802(44).  The case, United States of America v. Jeremy L. Thompson, 18-2545-cr, clarifies that courts must use the “categorical approach” when identifying predicate felony drug offenses, and that the Second Circuit will not expand § 802(44)’s reach beyond its enumerated classes of drugs.  Although this case arises in the context of the government’s use of a prior felony information, the Court has employed the same type of categorical analysis we see in cases brought under the Armed Career Criminal Act.

In United States v. Zapatero, the Second Circuit (Hall, Sullivan, Bianco) issued a published opinion concerning a narrow sentencing issue, ruling that a district court may not rely on a Sentencing Guidelines § 5G1.3(b) adjustment made at a defendant’s original sentencing to subsequently reduce the defendant’s sentence, pursuant to 18 U.S.C. § 3582(c)(2), to one that falls below the defendant’s amended Guidelines range.  The decision is based on strict interpretation of the Guidelines, which only permit reductions under Section 3582(c)(2) in fairly narrow circumstances.

In United States v. Alexander, the Second Circuit (Sack, Wesley, Livingston) issued a summary order that, among other things, vacated the district court’s restitution order as to two defendants, Marc and Rachael Alexander.  The order is notable primarily because it shows the Circuit’s willingness to scrutinize restitution orders.

In United States v. Parnell, 19-649-cr (May 19, 2020), the Second Circuit (Hall, Lohier, Park) affirmed a judgment ordering the defendant-appellant to pay restitution for the total amount of losses resulting from her crime of wire fraud, including losses that occurred outside the limitations period.

In United States v. Richardson, the Second Circuit (Walker, Chin, Menashi) concluded that the defendant’s sentence was both procedurally and substantively reasonable and, therefore, affirmed.  Richardson pleaded guilty to distribution and possession with intent to distribute a controlled substance, under 21 U.S.C. § 841(a)(1), and was sentenced, as a career offender under U.S.S.G. § 4B1.1, to a prison term of 210 months.

In United States v. Rosemond, 18-3561-cr (May 1, 2020) (Sack, Chin, Bianco), the Second Circuit held principally that Defendant-Appellant James R. Rosemond’s Sixth Amendment “Right to Autonomy” was not violated when his defense attorney, over his objection, conceded an element of the charged murder-for-hire offense—that he had hired individuals to shoot the victim—and instead argued that the government had failed to prove Rosemond’s intent to kill the victim.  The court also rejected Rosemond’s ineffective assistance of counsel claim under Strickland and an evidentiary challenge.  The case is a notable decision for the criminal defense bar, as it lays out the circumstances in which the Circuit believes that a defense lawyer must follow his client’s wishes in planning his defense strategy.

On March 5, 2020, the Second Circuit (Katzmann, Kearse, Bianco) issued a brief per curiam opinion in United States v. Alcius, et al., affirming the defendant’s 20-year sentence on sex trafficking related charges.  Defendant-Appellant Almonte challenged the sufficiency of the evidence supporting her conviction and also appealed the procedural and substantive reasonableness of her sentence.  The court affirmed both the conviction and sentence. 

In United States v. Pilcher, the Second Circuit (Leval, Cabranes, Sack) (per curiam) considered whether a habeas petitioner could proceed anonymously—in this instance holding that he could not (as the case’s caption makes clear).

In United States v. Pugh, No. 17-1889 (2d Cir. Dec. 10, 2019, as amended) (Calabresi, Droney, Underhill, by designation), the Second Circuit affirmed a defendant’s convictions for attempting to provide material support to a foreign terrorist organization and obstruction of justice but vacated the resulting sentence on procedural reasonableness grounds.

On December 3, 2019, the Second Circuit (Kearse, Pooler, Livingston) issued a decision in United States v. Calderon, et al., reversing an $18 million restitution order and otherwise affirming the defendants convictions and sentences.  In reversing the restitution order, the Court determined that the defendants’ fraud had not proximately caused the financial losses suffered by the U.S. Department of Agriculture (“USDA”) and certain banks.

On November 13, 2019, the Second Circuit (Hall, Lynch, Gardephe) issued a decision in United States v. Balde, vacating the defendant’s guilty plea for unlawful possession of a firearm by an alien who is in the United States illegally or unlawfully, in violation of 18 U.S.C. §§ 922(g)(5)(A) and 924(a)(2).  The panel initially upheld Balde’s conviction on appeal, but eight days after the Court’s original decision, the United States Supreme Court decided Rehaif v. United States, 139 S. Ct. 2191 (2019), holding that a conviction under the relevant statutes required the government to prove that the defendant knew that he or she was in the country illegally at the time he or she possessed the firearm.  Prior to Rehaif, every Circuit to consider the question held that the defendant’s knowledge of this fact was not an element.  The Second Circuit then granted Balde’s petition for rehearing and concluded that the district court had committed plain error in failing to ensure that Balde was apprised of this knowledge requirement before pleading guilty (even though the district court had no reason at the time to think it was an element of the crime) and because the record did not contain facts sufficient to support a conclusion that Balde was aware that he was in the country illegally. 

On November 4, 2019, the Second Circuit (Kearse, Wesley, Chin) issued a decision in United States v. Murphy, vacating a defendant’s guilty plea for traveling interstate for the purpose of engaging in illicit sexual conduct with a minor, in violation of 18 U.S.C § 2243(b).  The panel sided with several sister circuits in concluding that § 2243(b) is not a strict liability crime, and requires that the defendant travel interstate with the requisite intent, regardless of the actual age of the victim.  The Court concluded that the district court had committed plain error in failing to ensure both that the defendant was adequately informed of this essential element of the crime to which he was pleading guilty, or that there was an adequate factual basis for the plea.  Notwithstanding the awful nature of the crime committed here, it is important for courts to make sure that a defendant is advised of the elements of the offense, as required by Rule 11, and that he admits to those elements.

In United States v. Arrington, 17-4092-cr (October 18, 2019) (Lynch, Lohier, Judge Brian M. Cogan of the United States District Court for the Eastern District of New York, sitting by designation), the Second Circuit vacated Defendant-Appellant Roderick Arrington’s convictions for murder in aid of racketeering and related convictions, and remanded for a new trial, holding that he was not provided with adequate information prior to waiving his attorney’s actual conflict of interest. While defendants should have their counsel of choice, and have the right to waive most conflicts of interest, the defendant needs to have sufficient information and independent advice to make a knowing and intelligent waiver of the right to conflict-free counsel. The Court of Appeals has long policed the boundaries of this issue and Arrington will give courts and counsel further guidance about how to approach these notoriously tricky Sixth Amendment questions.

On September 3, 2019, a divided panel issued a decision in United States v. Wallace (Winter, Pooler, Abrams, by designation) affirming the district court’s denial of Wallace’s suppression motion as well as Wallace’s 15-year mandatory minimum sentence under the Armed Career Criminal Act (“ACCA”).  Judge Pooler wrote an 18-page dissent explaining why she believed Wallace’s suppression motion should have been granted.  The primary issue addressed in the competing opinions was whether the prolonging of a traffic stop was supported by reasonable suspicion.

In United States v. Barrett, No. 14-2541 (2d Cir. Aug. 30, 2019) (Winter, Raggi, Droney), the Second Circuit vacated a defendant’s conviction for using a firearm in connection with a “crime of violence” under 18 U.S.C. § 924(c) in the wake of the Supreme Court’s recent decision striking down the residual clause of that statute in United States v. Davis, 139 S. Ct. 2319 (2019).  To understand the Second Circuit’s decision, a brief discussion of Section 924(c) and Davis is warranted.  Section 924(c) raises some of the same questions presented by litigation under the Armed Career Criminal Act (“ACCA”), which has been the subject of repeated litigation in the Supreme Court and the Circuit Courts of Appeal in recent years.

In United States v. DiTomasso, Defendant was convicted of producing child pornography and transporting and distributing child pornography in the Southern District of New York.  The Second Circuit (Kearse, Jacobs, and Sack) held that searches of Defendant’s emails and chats on internet service providers AOL and Omegle, used for a search warrant leading to evidence against Defendant, did not violate Defendant’s Fourth Amendment rights, and that Defendant failed to preserve on appeal his argument that an entity which reports illegal user activity to authorities was a government entity or actor, subjecting that entity’s search to the Fourth Amendment.  In addition, the Circuit held that Defendant’s trial counsel was not ineffective where counsel made a strategy decision not to call Defendant’s uncle (“Marcus”)—who allegedly admitted to Defendant’s crimes—as a witness.

In United States v. Sierra, the Second Circuit (Newman, Jacobs, Droney) wrote a short published decision that rejected the argument raised by several defendants that it violated the “cruel and unusual” provision of the Eighth Amendment to impose a mandatory life sentence in this case involving convictions for murder in aid of racketeering. 

The Second Circuit (Walker, Cabranes, Sack) issued a per curiam decision in United States v. Bleau, 18-cr-1574 affirming a sentence based on a conviction for receiving and possessing child pornography, but remanding for further consideration of whether to impose a particular special condition of supervised release. 

The Second Circuit (Pooler, Jacobs, Wesley) issued an opinion holding that a criminal forfeiture order in an insider trading case is not limited to the amount of funds acquired through illegal activity but may extend to the appreciation of those funds.  In the case United States v. Afriyie, 17-cr-2444 and 17-cr-4045, the Court upheld a conviction for securities fraud and wire fraud, and upheld an almost $2.8 million forfeiture order, but vacated and remanded a restitution order in light of the Supreme Court’s recent decision in Lagos v. United States, 138 S. Ct. 1684 (2018).

In United States v. Pauling, the Second Circuit (Katzmann, Kearse, and Chin) affirmed the District Court’s post-trial order granting Pauling’s motion under Federal Rule of Criminal Procedure 29 to set aside his conviction for Conspiracy to Distribute or Possess with Intent to Distribute 100 Grams or More of Heroin.  The Court concluded that the District Court had correctly found that the evidence at trial was insufficient to establish the quantity element of the offense (100 grams or more), and therefore entered judgment of conviction instead to a lesser included offense that did not have a quantity requirement (and did not carry a mandatory minimum sentence).

On April 24, 2019, the Second Circuit issued a per curiam decision in United States v. Hausa (Kearse, Jacobs, and Hall) affirming the conviction of Ibrahim Hausa—a member of Al Qaeda known as Spin Ghul (the “White Rose”)—on charges related to his participation in attacks on United States and coalition forces in Afghanistan, which resulted in the deaths of two U.S. soldiers.

In United States v. Walker, 17-1896-cr (Jacobs, Calabresi, and Rakoff, by designation) (April 4, 2019), the Second Circuit held that the Government breached its plea agreement with the defendant by advocating for a term of imprisonment that was substantially higher than the Government’s initial sentencing estimate in the plea agreement.  In support of the increased sentence, the Government pointed only to information known to the Government at the time of the plea.  The decision addresses so-called “Pimentel estimates” used in the Eastern District of New York, in which the Government provides the defendant with pre-sentencing notice of its calculation of the applicable Sentencing Guidelines range in a plea agreement, while cautioning that this estimate may change in the future.  The panel held that, at least on these facts, the defendant was entitled to rely on the Government’s Pimentel estimate despite the cautionary language and, accordingly, the Government unlawfully changed its position based on information known from the outset.  As a result, the case will be remanded for resentencing to a new district judge.

In United States v. Lyle, 15-058-cr (April 1, 2019) (Raggi, Chin, Lohier), the Second Circuit, following a remand from the United States Supreme Court, once again held that the search of a rental car that James Lyle was driving (1) without a valid driver’s license, (2) without the permission of the rental car company, but (3) with the permission of the authorized driver, was lawful.  We covered the panel’s original opinion in United States v. Lyle, 856 F.3d 191 (2d Cir. 2017) in a June 1, 2017 post.  That post lays out the rather interesting facts and procedural history of this methamphetamine distribution and conspiracy case, and discusses each of the issues originally raised on appeal by Lyles and his co-defendant, Michael Van Praagh, including the panel’s original treatment of the rental car search issue.  Subsequent to that blog post, the United States Supreme Court granted Lyle’s petition for a writ of certiorari challenging the search of the rental car and remanded to the Second Circuit for further consideration in light of its unanimous decision in Byrd v. United States, 584 U.S. ---, 138 S. Ct. 1518 (2018).  Byrd included grand rhetoric about the Fourth Amendment, with Justice Kennedy writing that “[f]ew protections are as essential to individual liberty as the right to be free from unreasonable searches and seizures.”  138 S. Ct. at 1526.  On remand, however, the Circuit once again upheld the search of the rental car. 

In an appeal arising in the aftermath of Raj Rajaratnam’s criminal conviction for insider trading, the Second Circuit (Lynch, Raggi, Droney) issued an opinion upholding an almost $93 million Securities and Exchange Commission (“SEC”) civil penalty that was imposed based on the same conduct that served as the basis for Rajaratnam’s conviction.  The case, Securities and Exchange Commission v. Raj Rajaratnam, No. 11-5124-cv, demonstrates that an individual convicted of insider trading may be required to pay a sizable fine under Section 21A of the Securities Exchange Act, despite having already paid a significant criminal penalty.  Despite some provocative comments by the district court about the defendant, the Circuit held that the imposition of the maximum possible fine under the statute was supported by law.