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In order to be granted relief under Federal Rule of Criminal Procedure Rule 52(b) (“Rule 52(b)”), plain-error review requires that a defendant establish prejudice by proving that the error affected a substantial right. See Brief for Petitioner, Saul Molina-Martinez at 17–19. In this case, the Supreme Court has an opportunity to determine whether an appellate court, applying plain-error review, should presume a rebuttable presumption of prejudice if there is a miscalculation of a defendant’s sentencing range under the United States Sentencing Guidelines (“Sentencing Guidelines”). See id. at i. Molina-Martinez, the petitioner, argues that an erroneous sentencing calculation under the Sentencing Guidelines should result in a rebuttable presumption that the error affected a defendant’s substantial rights. See id. at 15. The United States, the respondent, counters that because the misapplication of the Sentencing Guidelines is a non-structural error, Molina-Martinez retains the burden of showing prejudice. See Brief for Respondent, United States at 15, 24–28. The Court’s decision will potentially impact appellate courts’ application of plain-error review under Rule 52(b) and affect the procedural strategy and substantive rights of criminal trial litigants. See Brief for Petitioner at 45, 48; Brief for Respondent at 45–50.

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In this case, the Supreme Court will consider whether the United States must prove elements of a crime not contained in the relevant criminal statute but included in an erroneous jury instruction if the government failed to object to that instruction at trial.  The Court will also consider whether an appellate court may review a statute-of-limitations defense not raised at trial. See Brief for Petitioner, Michael Musacchio at i; Brief for Respondent, United States at i. Michael Musacchio was convicted of conspiracy to access a computer system without authorization. According to the relevant statute, the United States had to demonstrate “Mussachio had agreed to make unauthorized access or exceed authorized access” of a computer system. See United States v. Musacchio, 590 Fed. Appx. 360, 362 (5th Cir. 2014). However, the trial court’s jury instructions stated that the jury must find that Musacchio “intentionally access[ed] a protected computer without authorization and exceed[ed] authorized access.” (emphasis added) See id. at 361. Neither Musacchio nor the United States objected to the instruction. On appeal, Musacchio challenged the sufficiency of the government’s evidence. Musacchio contends that the law-of-the-case doctrine requires the United States to prove the elements of the crime as described in the jury instructions, even when the jury instructions were erroneous and imposed a heightened burden on the government. See Brief for Petitioner, Michael Musacchio, at 19–22. Musacchio also argues that a statue-of-limitations defense not raised at trial is reviewable on appeal. See id. at 37–39; 53. The United States contends that the law-of-the-case doctrine is inapplicable, because the jury instructions were patently erroneous, and the proper statutory elements were stated in the indictment. See Brief for Respondent, United States at 13. The United States further argues that Musacchio waived his statute-of-limitations defense by failing to raise it at trial. See id. at 40–41. The Court’s decision in this case may affect the government’s prosecutorial power, the fairness of trials, and the availability of statute of limitations defenses. See Brief for Petitioner at 19-20; Brief for Respondent at 13, 48-51.

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The Supreme Court will determine whether it is “appropriate equitable relief” under the Employee Retirement Income Security Act of 1974 (ERISA) to require a person to reimburse his benefits plan for medical expenses even though his settlement proceeds are dissipated. See Brief for Petitioner, Robert Montanile at i. ERISA governs the administration of private pension funds. ERISA section 502(a)(3) provides that “[a] civil action may be brought . . . by . . . [a] fiduciary . . . to obtain . . . appropriate equitable relief.” See 29 U.S.C. § 1132(a)(3). Robert Montanile received a $500,000 settlement in connection with injuries he sustained when he was in an accident with a drunk driver. Pursuant to an agreement, the Board of Trustees (the “Board”) of Montanile’s insurance plan sought to recover $120,044.02 from the settlement proceeds to reimburse the plan for covering Montanile’s medical expenses. When the parties were unable to settle, the Board sued Montanile under section 502(a)(3). But Montanile argues that reimbursement is not an appropriate equitable remedy here, because his settlement fund has been dissipated and an equitable lien by agreement can only be enforced against identifiable property and not Montanile’s general assets. See Brief for Petitioner at 29-32. The Board maintains that reimbursement is appropriate equitable relief, because the insurance plan has a reimbursement provision requiring Montanile to repay medical expenses. See Brief for Respondent, Board of Trustees of the National Elevator Industry Health Benefit Plan at 19. The Board contends that dissipation of the settlement fund does not nullify the insurance plan’s reimbursement provision. See id. The Court’s decision in this case could change benefit plans’ method of reimbursement and may cause beneficiaries to incur additional costs. See Brief of Amicus Curiae National Coordinating Committee for Multiemployer Plans, in Support of Respondent at 9-10, 12-15.

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This case presents the Supreme Court with an opportunity to determine whether Miller v. Alabama’s prohibition of mandatory sentencing schemes requiring juveniles to be sentenced to life in prison without parole applies retroactively to offenders seeking collateral review. See  Brief for Petitioner, Henry Montgomery at i. Montgomery argues that Miller applies retroactively, because it announces a new substantive rule altering the range of available sentencing options, and it establishes a substantive right to individualized sentencing for juveniles facing life without parole. See id. at 16–19. However, Louisiana argues that Miller does not apply retroactively because it proscribes a procedural rather than a substantive rule. See Brief for Respondent, Louisiana at 16. The Court’s decision will impact the treatment of juveniles in sentencing proceedings.

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The Supreme Court will rule on whether the Fourteenth Amendment requires states to recognize same-sex marriages lawfully performed out-of-state and to grant same-sex marriage licenses. Regarding the first issue, Petitioner James Obergefell argues that the Court’s 2013 ruling in United States v. Windsor invalidates Ohio’s marriage-recognition laws, which Obergefell claims disadvantage and overburden same-sex couples and their families. Obergefell’s arguments regarding this issue are generally representative of those brought forth by the Petitioners in consolidated cases Tanco v. Haslam and Bourge v. Beshear. However, Respondent Richard Hodges—whose position generally aligns with the various Respondents in the consolidated cases Tanco v. Haslam and Bourge v. Beshear—counters that the Windsor Court did not interpret the Fourteenth Amendment to contemplate a “freestanding marriage-recognition right” and argues that a recognition right would undermine the democratic processes that led to the current legislation. On the second issue, Petitioner Deboer—from the consolidated case Deboer v. Snyder—argues that Due Process and the Equal Protection Clauses of the Constitution require that states license same-sex marriage, and compels the Court to rule on this issue. The Respondent in Deboer, Governor Snyder, argues that nothing in the Fourteenth Amendment’s history or plain text meaning requires states to license same-sex marriage, nor does it compel the Court to rule on the issue. The Court’s ruling in these cases may affect the legal rights of children of same-sex couples, the rights of people who identify as gay, and the states’ sovereign right to enact legislation that defines the status of same-sex marriages within their borders.

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The Supreme Court will determine whether the courts of appeals have jurisdiction to review a non-citizen’s request that the Board of Immigration Appeals (“BIA”) equitably toll the 90-day filing deadline on the non-citizen’s motion to reopen the non-citizen’s removal proceeding due to ineffective assistance of counsel. Peterson, arguing by Court appointment in support of the lower court’s judgment, argues that the Fifth Circuit properly characterized Mata’s request to reopen his removal proceeding as an invitation for the BIA to reopen the proceeding sua sponte, and that the Fifth Circuit lacks jurisdiction to review the BIA’s discretionary decision. However, Mata contends that the Fifth Circuit erred in construing his request for equitable tolling as a request for the BIA to reopen the proceeding sua sponte, and that Congress specifically grants courts of appeals the jurisdiction to review final orders of removal and BIA decisions on motions to reopen via statute. Holder agrees with Mata that the Fifth Circuit mischaracterized Mata’s request to reopen and that Congress provided courts of appeals a statutory basis upon which to review final orders of removal and BIA decisions on motions to reopen. Holder further contends that courts should apply a deferential abuse-of-discretion standard in reviewing agency determinations. The Supreme Court’s ruling implicates the due process rights of non-citizens and the fairness and substantive legality of the immigration system.

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In this case, the Supreme Court will decide whether a pretrial detainee’s § 1983 excessive force claim requires a showing that the force used by the state actor was objectively unreasonable and that the use of force was deliberate. Petitioner, Michael Kingsley, argues that an excessive force claim brought by a pretrial detainee requires only a showing that the force used was objectively unreasonable. Respondents, represented by Stan Hendrickson, argue that an excessive force claim brought by a pretrial detainee requires a showing of the state actor’s subjective intent to be reckless or deliberate. The Court’s decision will impact the means by which pretrial detainees bring excessive-force claims and the policies that govern prisons.

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The Supreme Court will consider the following three issues: (1) whether a state violates the Eighth Amendment when the state uses a three-drug protocol for executions, where the first drug does not always relieve the prisoner from pain and or put the prisoner in a deep state of unconsciousness; (2) whether Baze v. Rees is the proper standard for obtaining a stay of execution; and (3) whether a prisoner challenging a state’s lethal injection protocol is required to establish the availability of alternative drugs. See Brief for Petitioner, Richard E. Glossip at i. Glossip contends that midazolam is incapable of reliably rendering prisoners unconscious and creates a substantial risk of harm that violates the Eighth Amendment, that the standard for obtaining a stay of execution should continue to be “a significant possibility of success on the merits” as established in Baze, and that prisoners should not be required to establish the availability of alternative drugs. See id. at 28, 39, 46. Gross counters that using midazolam does not create a substantial risk of harm since it is highly likely to render prisoners unconscious and insensate, that Baze clearly established a heightened stay request standard, and that establishing the availability of alternative drugs is required post-Baze. See Brief for Respondent, Kevin J. Gross at 41, 57–58, 61–62. The Supreme Court’s decision will potentially affect the availability of certain execution methods as well as address the acceptability of lethal injection protocols that potentially result in a lingering and painful death. See Brief of Former State Attorneys General, in Support of Petitioners at 23; Brief for National Catholic Reporter, in Support of Petitioner at 8.

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The Supreme Court will determine whether—to obtain a conviction under the Analogue Act—the government must prove the defendant had knowledge that a substance the defendant was distributing was a controlled substance analogue. McFadden claims that under the Analogue Act, the government must prove a defendant's knowledge of the illegal nature of a substance by showing that the defendant knew the substance was substantially similar to a controlled substance. The United States agrees with McFadden in that Analogue Act violations can be proven by demonstrating the defendant's knowledge of the illegal nature of a substance, but the United States counters that knowledge of illegality can be proven through circumstantial evidence. The Supreme Court’s decision will clarify a long-standing circuit split over the mens rea requirement the government must satisfy to prosecute Analogue Act violations, which will have further implications on the government’s ability to target street-level dealers under the Analogue Act. 

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