These cases are presented in the order that is easiest to read. As always, before reading this summary, please read the overview for context.
United States v. Sparkman (3 September, 2020)
Tony Sparkman was a gangster who robbed drug dealers. His gang committed robberies, kidnappings, and even murders.  Mr. Sparkman was convicted of many crimes and, in 2012, he was sentenced to 42 years’ imprisonment. At the time, this was the minimum sentence a judge could impose on one so convicted. [2-3] In United States v. Caradena, the Court of Appeals for the 7th Circuit vacated the sentence of Sparkman and many of his comrades. Judge Joan Gottschall then re-sentenced Sparkman to 40 years.
The First Step Act became law after Sparkman filed his notice of appeal but before he filed his first brief.  The First Step Act reduced the sentences for a variety of crimes. Section 403(b) of the Act applied to previously committed offences “if a sentence for the offense ha[d] not been imposed” when the Act was enacted. 
On 31 May, 2019, long before the Court of Appeals for the 7th Circuit decided on Sparkman’s appeal, a separate panel of the Court of Appeals addressed retroactive application of the First Step Act. In United States v. Pierson, Judge Hamilton wrote for the Court of Appeals that a sentence was imposed under the First Step Act when a district court issued its sentence, not when a court of appeals affirmed it. Therefore, a defendant who had been sentenced prior to the First Step Act could not claim its protection, even if the resulting sentence was on appeal when the Act was passed. [Pierson at 22-24] In October of 2019, another panel of the 7th Circuit cited Pierson as grounds for reaching the same conclusion. [United States v. Jackson at 9-10] On 9 March, 2020, the Supreme Court of the United States vacated the decision in Pierson for reasons unrelated to its analysis of the First Step Act. (Mr. Pierson has since filed an equally unrelated petition for certiorari).
Sparkman argued that, because his second sentence was on appeal when the First Step Act was passed, a sentence had not yet been imposed. Therefore, he was entitled to a reduced sentence under the Act. Judge Barrett wrote that the Court of Appeals had rejected this argument in Pierson. Sparkman argued that Pierson had covered a different section of the First Step Act but that section was the same, word-for-word, on the subject of retroactive application. Judge Barrett held that identical phrases in the same statute should be interpreted to have the same meaning. Therefore, the First Step Act did not apply to Sparkman’s sentence. [5-7]
Sparkman also issued a challenge to his conviction. He argued that an error identified in his last appeal was structural and, therefore, that the Court of Appeals had been wrong in finding that it did not affect his substantial rights. Judge Barrett held that the law of the case doctrine prevented parties from changing their positions on subsequent appeals unless they had new evidence or the law had changed. Judge Barrett rejected Sparkman’s argument that an intervening Supreme Court decision, United States v. Davis, counted because it did not mention structural error. [4-5] Judge Barrett also observed, citing Hedgpeth v. Pulido, that his argument would have failed anyway. 
United States v. Uriarte (15 September, 2020)
Hector Uriarte was a confederate of Sparkman. [2-3, 27] Indeed, Judge Barrett deemed him more involved with their crimes than Sparkman.  Mr. Uriarte’s sentence had been vacated with Sparkman’s. [2-4, 27] Unlike Sparkman, Uriarte had not been re-sentenced when the First Step Act was enacted.  Judge Barrett explained that this was because Uriarte “delayed the court with continuances.”  Uriarte argued that the First Step Act applied retroactively, because he did not have a sentence when it became law. Judge Joan Gottschall (who had also sentenced Sparkman) agreed, sentencing Uriarte to twenty years’ imprisonment rather than the 40 he otherwise would have received. [4-5]
The Court of Appeals for the 7th Circuit sat en banc to consider Uriarte’s case. [Note * on page 1] The question before the Court was whether the retroactivity provisions of the First Step Act applied to someone who had been sentenced but whose sentence had been vacated before enactment. Judge Ripple, who had joined Judge Barrett’s decision in Sparkman, wrote for the Court of Appeals. He emphasised that Uriarte’s sentence had been entirely vacated. [Note 2 on pages 5-7] Judge Ripple began by presuming, as courts do, that Congress knew legal principles and terminology when it enacted the statute. [8-9] Judge Ripple wrote that a vacatur typically “wipe[s] the state clean.” Therefore, absent an indication to the contrary, a convict whose sentence was vacated was effectively a convict for whom “a sentence . . . ha[d] not been imposed” when the Act became law. Judge Ripple found no such indication and also thought that this interpretation was most consistent with the purpose of the statute. [8-10]
Judge Ripple then defended that interpretation against challenged. First, Judge Ripple rejected the argument that the “sentence” in question was the previously vacated sentence, as this would require the Court to ignore the legal background against which Congress legislated. [10-11] Judge Ripple then rejected the argument that drawing the line at the first sentence was better policy, both because good policy was not the court’s business and because the statute did not indicate that concurrently sentenced defendants should be treated differently. [11-12] Finally, the Court refused to find significance in the use of “a sentence” rather than “the sentence.” Given the legal background and the rest of the text, Judge Ripple found that the difference was not significant. Congress had not said “a final sentence” but nor had it said “an initial sentence” and, if Congress wished to be as broad as possible, it could have said “any sentence” (as it referred to “any offence” only a few words prior). [12-14] Judge Ripple also observed that, if there were any doubt, the Rule of Lenity required construing ambiguity in favour of the defendant. [Note 7 on page 14]
Judge Ripple also rejected the argument that Pierson foreclosed this interpretation. Pierson applied to a prisoner whose sentence was on appeal, not one like Uriarte who had no sentence at the time. None of the other cases citing Pierson had addressed the vacatur of a sentence before the Act became law. [15 and note 8 on pages 15-16] Judge Ripple again opined that this conclusion was most consistent with the policy behind the First Step Act. [16-17] For what it’s worth, this opinion was joined by the entire panel that decided Pierson (as well as two-thirds of the panel that decided Jackson but only Ripple himself from Sparkman).
Judge Ripple acknowledged that a defendant whose sentence was vacated after the First Step Act was passed would not fall so neatly into the statutory language. The Court of Appeals did not need to reach that situation and so did not. [Note 3 on page 10] Judge Barrett stressed that the majority had not ruled on this issue. [Note 1 on page 19]
Judge Barrett dissented from the majority opinion. She would have found that “no sentence ha[d] . . . been imposed” only refers to defendants who have never been sentenced, not to defendants who had been sentenced and had that sentence vacated. [20-21] Judge Barrett found Pierson consistent with her understanding of “imposed” as a matter of historical fact rather than legal status. [21-22] She wrote that the 3rd Circuit had interpreted Pierson in the same way. [21-22 and note 2 on page 22] Judge Barrett also found that the indefinite term “a” supported her reading of the statute. After all, “a sentence” had been imposed on Uriarte, even if it was vacated on appeal. [22-23]
Judge Barrett then disagreed with Judge Ripple’s argument that vacating a sentence resulted in a “clean slate.” She argued that the Sentencing Reform Act directs courts to re-sentence a defendant according to the guidelines in place at the time of the previous sentence and that it is otherwise common for courts to apply law (even unfavourable law) that controlled at the time of the first sentence rather than at the time of the re-sentencing. [23-24] Because the statute could be construed through the usual canons, Judge Barrett did not think the rule of lenity applied. [Note 4 on page 24]
In a paean to textualism, Judge Barrett then argued that judges had no idea what Congress intended. She found it more equitable that defendants receive sentences similar to those who were convicted at the same time, not those who were sentenced at the same time. [26-27] She also objected that, under the majority’s holding, whether a vacatur was plenary or partial took on a great deal of importance. [24-25]
United States v. Rutherford (23 June, 2020)
In 2008, Toby Rutherford was sentenced to 300 months in prison for several drug crimes.  In 2015, after the sentencing guidelines were amended, Mr. Rutherford convinced a judge to reduce his sentence to 240 months (20 years, which the opinion describes as the minimum sentence for a single “crack-cocaine conviction”). 
In 2018, Rutherford sought a further reduction of his sentence under the First Step Act. Specifically, he requested the district court reduce his sentence under section 404(b) of the Act, which permitted – but explicitly did not require – the court to reduce his sentence by retroactively applying section 2 and section 3 of the Fair Sentencing Act of 2010. [1-2] Judge James Shadid declined to further reduce Rutherford’s sentence. 
Rutherford received an extension of time to appeal Judge Shadid’s decision. Even so, Rutherford did not file his notice of appeal on the deadline, instead asking the district court to reconsider its decision. Judge Shadid denied Rutherford’s request and Rutherford filed a notice of appeal within the subsequent time limit. The government argued that Rutherford had missed the original deadline, so the Court of Appeals should disregard Rutherford’s appeal. 
Judges Easterbrook and Rovner concluded on behalf of the Court of Appeals for the 7th Circuit that motions to reconsider in criminal cases extend the time to appeal. The Court cited three Supreme Court cases that supported this proposition and a 7th Circuit decision, United States v. Rollins, that analysed and applied those decisions.  The Court held that the authority cited by the government, United States v. Townsend, addressed a rule (Federal Rule of Criminal Procedure 35) that did not apply to motions under the First Step Act. [2-3]
Section 404(c) of the Act also prohibited second motions when a first was denied “after a complete review of the motion on the merits.” The Court held that a motion for reconsideration was not a successive motion but was part of the “complete review” of the first motion, citing Banister v. Davis, in which the Supreme Court had rejected the very same argument while interpreting a similarly structured provision of procedural law. 
Having decided that it had jurisdiction to entertain Rutherford’s appeal, however, the Court quickly held that the district court had been within its discretion to deny Rutherford’s motion. [3-4]
Judge Barrett dissented. She argued that Townsend was the applicable decision, because Rollins and one cited Supreme Court decision applied to conviction rather than sentencing.  Under Townsend, Rutherford could move for reconsideration only if it was authorised by a statute or Rule 35. The First Step Act did not expressly permit Rutherford to seek reconsideration. Therefore, Judge Barrett would have held that Rutherford could have sought reconsideration only under Rule 35, which did not extend the time to appeal. [5-6] Judge Barrett accordingly would have held that the Court could review the denial of Rutherford’s motion for reconsideration but not the denial of his initial motion for re-sentencing.  The former was much narrower and Judge Barrett quickly stated that Rutherford did not meet the standards.  Judge Barrett also emphasised that the decision was not precedential and stated that the Court should correct its “error” in future.