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Second Circuit Holds Constitutional Challenge to Prosecution Was Untimely

In United States v. O’Brien, the Second Circuit (Kearse, Livingston, Carney) affirmed the conviction of Michael O’Brien for importing and possessing with intent to distribute methylone and anabolic steroids.  The Court held that (1) the District Court properly denied O’Brien’s suppression motion based on the fact that he was experiencing drug withdrawal symptoms at the time of his arrest, (2) the evidence at trial was sufficient to sustain O’Brien’s conviction, and (3) O’Brien failed to timely raise his defense that methylone was designated as a controlled substance through an unconstitutional delegation of Congressional legislative authority to the Attorney General and the DEA.


In September 2013, agents of the U.S. Customs and Border Patrol seized three packages at John F. Kennedy Airport.  Each package was addressed to a different recipient at a mailbox store and contained one kilogram of methylone—an analog of the drug MDMA, commonly referred to as ecstasy or molly.  One of the packages was addressed to Kimberly Rudd, who was arrested by Homeland Security agents when she retrieved it from a mailbox store.  Rudd’s cellphone contacts pointed agents to an individual referred to as “Big,” who turned out to be O’Brien.

On October 10, 2013, Homeland Security agents Vincent Marino and Edward Alahverdian arrested O’Brien at his apartment in Queens, New York.  What transpired during the arrest was a matter of dispute in the District Court when O’Brien later sought to suppress evidence obtained from two of his apartments and statements he had made to agents during the course of his arrest. 

According to agents Marino and Alahverdian, when they arrived at the apartment, they gave O’Brien Miranda warnings, and O’Brien consented to the search of his apartment.  While searching the apartment, the agents found, among other things, vials labeled “Genzyme” (a type of steroid), money counting machines, 18 cell phones, 12 laptop computers, applications for mailbox rentals at mailbox stores, and a ledger listing types of steroids, phone numbers, and pick-up location.  During the search, O’Brien told the agents that he was addicted to GHB—a psychoactive drug also known as hydroxybutyric acid—and that he would get sick if not permitted to take some GHB.  The agents refused to allow O’Brien to take any GHB, a controlled substance, but agent Marino did allow O’Brien to take a valium, a prescription anti-anxiety medication.  Alahverdian described O’Brien as “very alert,” “very talkative,” and “not slurring his words in any way” during the course of the search and subsequent questioning.  When agents brought O’Brien to the precinct, he signed a consent form permitting agents to search another of his apartments located in Queens.  That search turned up approximately 11 kilograms of methylone, as well as a laptop O’Brien used to place methylone orders from China.  O’Brien was then presented before a New York county court pursuant to a bench warrant related to previous charges on which he had become a fugitive.  He calmly and coherently described GHB to the judge and that he was addicted to it, and was subsequently sent to a hospital for medical evaluation, which was described as “unremarkable” by the hospital’s medical records.

O’Brien’s account of his arrest is quite different.  He did not remember receiving a Miranda warning, giving consent for the search of his apartment, or signing the form consenting to the search of his second apartment.  He recalled telling agent Marino that he was addicted to GHB and that he would die if not taken to a hospital within four hours.  On three occasions during the search of his apartment, he told agents that he needed medical attention.  He said that his recollection was “fuzzy,” however, due to withdrawal symptoms from GHB.  He stated that during his initial appearance in court, he experienced a “massive seizure” while speaking to the judge.  He claimed that he was in and out of consciousness at the hospital for the next several days.

The District Court denied O’Brien’s suppression motion.  It credited the testimony of agents Marino and Alahverdian and held that the government had met its burden of showing that O’Brien had been given a Miranda warning and voluntarily consented to the search of his two apartments.  The District Court credited the agents’ account that O’Brien has been lucid, calm, and aware of his situation when he consented to the searches and spoke voluntarily to the agents.  The District Court further found that O’Brien’s testimony about the extent of his withdrawal symptoms from GHB lacked credibility. 

At trial, O’Brien was found guilty on all counts.  Over a year later, O’Brien moved, pro se, for acquittal on the ground that methylone was designated a controlled substance pursuant to an unconstitutional delegation of Congress’s legislative power to the Attorney General and the DEA.  The District Court denied the motion.

The Court’s Decision

On appeal, O’Brien principally raised three arguments.  First, that the District Court erred in denying his motion to suppress his post-arrest statements and the evidence seized from his two apartments.  Second, that the evidence at trial was insufficient to show that he knew methylone was a controlled substance.  And third, that the designation of methylone as a controlled substance was an unconstitutional delegation of legislative power to the Attorney General and DEA.  The Court rejected these arguments and affirmed O’Brien’s conviction.

With respect to his motion to suppress, O’Brien contended that it should have been granted because he was under the effects of GHB withdrawal at the time of his arrest and was unable to voluntarily consent to the search of his apartments or to voluntarily waive his Miranda rights.  The Court held that the District Court was entitled to credit the testimony of agents Marino and Alahverdian that Miranda warnings were administered and that O’Brien was in a proper state of mind to knowingly and voluntarily make statements to the agents and consent to the search of his properties.  It also noted that O’Brien’s testimony during the suppression hearing was contradicted by a recording of a telephone conversation O’Brien had while in jail with his ex-fiancé, in which he admitted that he told agents they could search his apartment.

O’Brien next contended that the evidence at trial was insufficient to show that he knew methylone was a controlled substance.  The Court noted that the jury had been properly instructed that to convict, they must find that O’Brien knew the substances he had imported and possessed were controlled substances, but need not find that he knew precisely what the substance was.  The jury’s verdict was supported by evidence that O’Brien knew he was dealing with illegal drugs, including that he used Bitcoin rather than dollars to help evade detection, and that he hired other people to pick up the deliveries rather than addressing them to himself.  On this record, the jury was entitled to find that O’Brien knowingly dealt in methylone and anabolic steroids, drugs he knew were controlled substances.

Finally, O’Brien argued that the designation of methylone as a controlled substance was unconstitutional because it was an improper delegation of legislative authority from Congress to the Attorney General, and then from the Attorney General to the DEA.  As discussed in more detail below, the Court first noted that O’Brien abandoned this argument by not raising it in a pretrial motion, as required by Federal Rule of Criminal Procedure 12(b)(3).  The Court further held that, even if  O’Brien had timely raised the argument, it was foreclosed by the Supreme Court’s decision in Touby v. United States, 500 U.S. 160, 162 (1991), which rejected the same argument concerning another drug.


In this otherwise straightforward case, the Court addressed the types of defenses that must be raised in a pretrial motion under Federal Rule of Criminal Procedure 12(b)(3).  That rule provides that two categories of defenses—“a defect in instituting the prosecution” and “a defect in the indictment or information”—must be raised by pretrial motion “if the basis for the motion is then reasonably available and the motion can be determined without a trial on the merits.”  Fed. R. Crim. P. 12(b)(3).  The rule also provides examples of defenses that fall within its scope, including “failure to state an offense,” and “an error on the grand jury proceeding.”  These types of motions are far less common in criminal cases than they are in civil cases, where motions to dismiss for failure to state a claim are frequently made under Federal Rule of Civil Procedure 12(b)(6).  In two cases interpreting this rule, the Supreme Court held that the rule applies to post-trial challenges to grand jury defects even though the challenge rested on constitutional grounds.  See Davis v. United States, 411 U.S. 233, 241 (1973); Shotwell Mfg. Co. v. United States, 371 U.S. 341, 362 (1963).  In those cases, the constitutional defense was that the grand juries had not been convened pursuant to selection methods designed to draw from a cross-section of the community

The Court here held that the reasoning of Davis and Shotwell apply to O’Brien’s post-trial argument concerning improper delegation of legislative authority.   It reasoned that Davis and Shotwell involved a “defect in the institution of the prosecution” because the indictments were “issued by an entity that was not constitutionally authorized to accuse any person of any crime.”  Similarly, O’Brien’s challenge to Congress’s delegation of legislative authority “posits that the targeted conduct has been designated a crime by an entity not constitutionally authorized to say that any person may be prosecuted for that conduct.”  As in Davis and Shotwell, “[i]f a defendant wishes to assert such a flaw, he must make his motion prior to trial if the basis for his assertion is then reasonably available.”  Because the designation of methylone occurred long before O’Brien’s arrest, he could have raised his delegation argument in a pre-trial motion.  Finally, the Court held that O’Brien had not shown “good cause” to excuse his waiver of the delegation defense.

This case shows that Rule 12(b)(3) has teeth.  Defendants must timely assert most generalized constitutional challenges to their prosecution before trial.  If they fail to do so, they will only be able to raise the defense in a post-trial motion if they can show good cause for the delay.  It makes sense to require defendants to raise these issues before committing the parties’ and the court’s time and resources to a trial—especially since the government might be able to reframe its charges if an infirmity existed.  The cost of inaction, however, is steep—absent good cause, the legal defense is waived entirely.  Only a motion to dismiss for lack of jurisdiction may be made at any time in the proceedings.  See Fed. R. Crim. P. 12(b)(2).

-By George B. Fleming and Harry Sandick