Before reading this summary, please read the overview for context.
Chazen v. Marske (2019)
Non-lawyers might want to skip this one. It’s technical and complicated.
Todd Chazen had a lot of felony convictions. He had been convicted for assault, manufacture of a controlled substance, escape from custody, and burglary. He had been convicted for the last of those twice.  In 2011, a Minnesota jury added another to the list, this one for being a felon in possession of a firearm. This would ordinarily result in a maximum sentence of ten years but, if his previous convictions rendered him an armed career criminal, then the sentence had to be at least fifteen years.  The parties argued about which of Mr. Chazen’s previous convictions qualified under the Armed Career Criminal Act, with Chazen asserting it was only two (which was too few) and the prosecution arguing that he had three (which was enough for a sentencing enhancement ). The district court did not decide, saying only that the Act applied because “at least four” of his convictions did (although “there [were] a number of possibilities” as to what those were). The district court therefore sentenced Chazen to 21 years in prison. 
Chazen diligently, but unsuccessfully, sought relief in the federal courts. [3-4] A couple of years later, the Supreme Court of the United States decided Johnson v. United States. In Johnson, the Supreme Court struck down as vague the residual clause of the Armed Career Criminal Act, which permitted sentence enhancements on the basis of a past offence that “otherwise involves conduct that presents a serious potential risk of physical injury to another.” [2,4] Chazen’s sentence stemmed in part from his past conviction for escape, which had been defined as a “violent felony” under this clause. [2,4] Chazen sought permission from the 8th Circuit to challenge his conviction. The government opposed this petition, arguing that even without the escape conviction Chazen had been convicted for three other violent felonies, and the 8th Circuit denied Chazen’s application. [4-5]
A year after that, the Supreme Court decided Mathis v. United States, which restricted the state law crimes that could be considered violent felonies under the ACCA. Citing precedent from both the 7th and 8th Circuit, the district court for the Western District of Wisconsin (the site of Chazen’s confinement) held that Chazen’s burglary convictions no longer qualified as violent felonies and transferred the case back to the District of Minnesota for re-sentencing. The prosecution appealed this decision. [6-7]
The substantial question before the Court of Appeals was whether Chazen’s convictions for second-degree burglary under Minnesota law qualified as violent felonies. In short, Judge Scudder wrote for the Court of Appeals that they did not, because under United States v. Van Cannon second-degree Minnesota burglary was broader than generic burglary in that it did not require proving the suspect intended to commit any crime. [9-17]
The procedural question was equally complex. Chazen could only challenge his sentence in the district of his incarceration if the opportunity to do so in the district of conviction was “inadequate or ineffective,” which meant he did not have “a reasonable opportunity . . . to obtain a reliable judicial determination of the fundamental legality of his conviction and sentence.”  The 7th Circuit had held that this required: a challenge based on a decision construing a statute rather than the Constitution; that the decision had not been available during the previous challenge; that the decision applied retroactively; and that the resulting error could be considered a miscarriage of justice.  The Court of Appeals admitted that it had been inconsistent in interpreting these requirements. [18-19] In this case, Judge Scudder wrote that Chazen met these conditions, because under controlling precedent in the 8th Circuit (including Minnesota) at the time of his conviction burglary qualified as a violent felony. The decision in Mathis let Chazen challenge his sentence in a way that would previously have been futile. Therefore, Mathis had not previously been available, permitting Chazen to raise his new challenge after his conviction. [20-22]
Judge Barrett joined the opinion, which she said was supported by 7th Circuit precedent.  Judge Barrett wrote separately, however, to raise several issues. First, she saw the 7th Circuit’s case law on retroactive challenges based on new rules of statutory construction (introduced in In re Davenport) as having become more generous than the constitutional challenges expressly permitted by Congress. [23-24] For example, the new rule could come from a court of appeals rather than from the Supreme Court.  Judge Barrett also argued that the law governing such a challenge should come from the circuit of conviction, not the circuit of confinement, and stressed that the Court of Appeals had not decided that issue (although she thought it should have). [25-28] Finally, she wrote, the Court of Appeals should clarify what constitutes a “new rule” that would enable such challenges, which it had not found necessary in Chazen. [28-29]
United States v. Cherry (2019)
Bernard Cherry was looking for something in the darkness (at first he said it was a lost key) when he saw a police officer approaching. Mr. Cherry immediately threw down his gun, a .40 calibre Smith & Wesson. [2,5] The police officer, Isaiah Sherrod, thought Cherry seemed intoxicated so he agreed to help Cherry look for the key. While doing so, he noticed the gun and (for unspecified reasons) immediately put Cherry in hand-cuffs. He arrested Cherry after Cherry tried to escape. 
Cherry was charged with being a felon in possession of a firearm. He told the police that he had disarmed someone who pointed a gun at him, driven off his assailant, and remained behind to find the mobile phone that he’d lost in the encounter. He admitted to picking up the gun briefly.  At trial, Cherry requested that the court instruct the jury that he was not guilty if he obtained the firearm innocently, held it with no illicit purpose, and possessed it only momentarily. The government argued that, under United States v. Jackson, innocent possession (if it was even a valid defence) would have required Cherry to immediately relinquish the gun to law enforcement. [3-4] Judge David Herndon agreed with the prosecution, the jury convicted Cherry, and the court ordered Cherry to forfeit the firearm.
Cherry argued that the district court had erred in refusing to give his requested jury instruction. Judge Barrett held that the district court had been correct. First, the 7th Circuit had not recognised that innocent possession was a defence (absent such circumstances as necessity or duress). Second, on encountering a police officer, Cherry had not attempted (and certainly not immediately attempted) to turn over the pistol. Therefore, 7th Circuit precedent supported Judge Herndon’s decision. [3-4]
Cherry also argued that the court had erred in failing to submit to the jury whether the gun should be forfeited. The government admitted that the court had made a mistake but said that it had not harmed Cherry. Judge Barrett held that the error had not affected Cherry’s substantial rights because, as in United States v. Ryan, no reasonable jury could have failed to find a nexus between the firearm and Cherry’s conviction for possessing that firearm. [5-6] Judge Barrett also observed the inconsistency of claiming that one did not own a gun and that one shouldn’t have to give up one’s gun. [Note 1 on page 5]
The conviction stood, as did the order to forfeit the gun.
Conroy v. Thompson (2019)
Bill Conroy is illiterate and has “emotional issues.”  In June 2004, he tried to convince an under-cover police officer to murder the mother of his children, then (while in custody) to convince another officer to kill her and two others. [Thompson Brief at 1-2] When Mr. Conroy was indicted for soliciting and attempting murder, an Illinois state court heard argument on whether Mr. Conroy was competent to stand trial and decided that he was.  At least one of the prosecution expert witnesses at this hearing, Dr. Neu, did not consider Conroy’s antisocial personality disorder because it did not arise from a mental disease or defect. [Conroy Brief at 6-10, 17-22] After the hearing, Conroy pleaded guilty and was sentenced to 30 years of imprisonment. Later that year, he was diagnosed with depressive and schizoaffective disorders. His mental condition subsequently improved.  Conroy argued that this apparent improvement was the result of brief checks rather than proper examination. [Conroy Brief at 26]
Over the ensuing years, Conroy sought relief from the Illinois courts. Conroy’s brief explains that he did so by seeking (and often purchasing) assistance from other prisoners. [Conroy Brief at 9] In 2016, almost a decade after he pleaded guilty, Conroy applied for habeas corpus in federal court. He argued that he had not received effective assistance of counsel, because his counsel had failed to argue that Dr. Neu had applied the wrong standard for competence. [Conroy Brief at 14, 17-22] At first, although the opinion is vague as to precisely when, Conroy stated that he was not aware of any deadlines.  With the help of a court-appointed public defender, Conroy amended his petition to argue that any deadlines he’d missed should be equitably tolled (i.e. suspended or delayed), because his mental limitations prevented him from understanding the need for them. 
Judge David Herndon dismissed the case. He held that the petition was untimely and that Conroy was not entitled to equitable tolling, because Conroy’s mental limitations did not constitute “an extraordinary circumstance” and because Conroy could not show that he had pursued his claim with diligence.  Judge Herndon also did not grant Conroy a certificate of appealability. Conroy requested such a certificate from the court of appeals, which granted it on the merits (relating to whether he actually had been competent to stand trial) and on whether Conroy was entitled to equitable tolling.  The court only needed to address the latter.
After disposing of an additional procedural challenge, the court held that Conroy was not entitled to equitable tolling. Barrett cited 7th Circuit authority that mental issues could provide “extraordinary circumstances” to justify equitable tolling but only if the petitioner could show that the issues prevented him from understanding or pursuing his claims. Barrett held that Conroy’s evidence of this did not suffice: he had been found competent to stand trial in 2006, which was presumptively correct; his mental condition had subsequently improved; and he had engaged in the legal process before. [5-6] Judge Barrett found that “most damning of all” was that Conroy had originally explained that he had missed the deadline simply because he hadn’t known about it.  Therefore, the district court had been correct to dismiss the petition as untimely.
United States v. Geary (2020)
Sheila Geary’s husband sexually abused their youngest daughter. She did not but she did encourage him to take pornographic pictures of her, which she kept these photos on a memory stick, and view them with her husband. She also found other child pornography for him. [1,3] Ms. Geary was afraid of her husband, who abused her as well as all their children, and she said she kept the photos in case she needed proof. [2,4-5] Nevertheless, when she finally called the police, it was to protect herself rather than her daughter.  When her eldest daughter learned that her father was abusing her sister, Ms. Geary decided to turn over the photos to the polices. 
After Geary pleaded guilty to possessing child pornography, Judge Joseph Van Bokkelen sentenced her to 57 months in prison and to pay $55,600 in restitution to their daughter.  Geary challenged the sentence as excessive but, according to Judge Barrett, such a sentence was within the guidelines for parents who permit their children to engage in sexual behaviour so that others can photograph it. Judge Barrett held that the district court had carefully weighed the testimony in imposing its sentence, rejecting that which it disbelieved, and that even excluding the testimony of Geary’s vengeful husband there was enough evidence to support the enhancement. [3-4] Judge Barrett also held that failing to prevent the abuse counted as permitting it, even if Geary herself did not take part, and observed that the court had considered extenuating circumstances in imposing a comparatively short sentence. [4-5]
Geary also challenged the restitution amount, on the grounds that the court had not properly explained its calculation of the amount. Judge Barrett explained that the basis for the calculation had been determined in the sentencing of Geary’s husband and co-defendant. Citing United States v. Harris, Judge Barrett held that the district court could rely on this evidence so long as Geary had an opportunity to rebut it, and she had when she was informed that the restitution amount would be used in her sentencing. [5-6] Therefore, both the sentence and the award stand.