Argument analysis

Justices voice skepticism about retroactive sentencing reductions for low-level crack-cocaine offenders

On Tuesday, the Supreme Court heard its last case of the term. The case, Terry v. United States, about sentencing reductions for certain offenses involving crack cocaine, comes just a few months before the petitioner, Tarahrick Terry, is scheduled to be released after serving 13 years in prison. But the court’s eventual decision will likely affect hundreds of similarly situated defendants languishing behind bars. It will resolve a circuit split, determine the scope of a decades-long push to enact sentencing reform, and perhaps speak to the history of racial discrimination and mass incarceration framed by the case. Terry also captures a feature too natural to the lawyer’s mind: a simple reading of congressional intent versus swirling and sophisticated legal reasoning pulling mightily against each other. On a tangential note, the case may also be remembered (God willing) as the last telephonic Supreme Court argument of this taxing COVID-19 period.

The case began in 2008, when Terry, then in his early 20s, was arrested in Florida for carrying just under 4 grams of crack cocaine. He was charged under 21 U.S.C. § 841(a)(1), which outlaws possessing with intent to distribute crack cocaine, and he was sentenced under 21 U.S.C. § 841(b)(1)(C), which sets forth penalties for so-called Tier 3 offenses that typically involve smaller amounts of drugs than Tiers 1 or 2. Terry’s sentence was a result of the 1986 Anti-Drug Abuse Act, which created a 100:1 disparity in the punishment of crack cocaine compared to powdered cocaine.

Decades later, that disparity is widely viewed as ineffective, unjust and a symbol of our national punitiveness in addressing “Black” drug problems. In 2010, Congress addressed the by-then iconic disparity, enacting the Fair Sentencing Act, which reduced the disparity to 18:1 and eliminated the mandatory five-year sentence for crack.

Because so many were previously sentenced under the discriminatory 100:1 ratio, a bipartisan Congress passed the First Step Act in 2018, making sentencing reforms retroactive and past offenders eligible for resentencing. The First Step Act applies retroactively to people sentenced for a “covered offense,” which is defined as “a violation of a Federal criminal statute, the statutory penalties for which were modified by section 2 or 3 of the Fair Sentencing Act of 2010 … that was committed before August 3, 2010.” 

Specifically, the law increased the amount of crack punished as Tier 1 offenses from 50 grams and above to 280 grams and above (defined in subparagraph (A) of 21 U.S.C. § 841(b)(1)). In turn, the range of Tier 2 offenses was changed from between 5 and 50 grams to between 28 and 280 grams (defined in subparagraph (B) of the statute). Though one would think that Tier 3 offenses, previously between 0 and 5 grams, would now be those between 0 and 28 grams (defined in subparagraph (C), the provision under which Terry was sentenced), Congress did not actually change the text of the Tier 3 provision. Under the Trump administration, federal prosecutors took the position that penalties for Tier 3 offenses were not “modified” by the Fair Sentencing Act and thus not eligible for retroactive resentencing under the First Step Act.

This interpretation left those convicted for carrying large amounts of crack eligible for resentencing but excluded those sentenced for carrying the smallest amounts. On March 15, however, the Biden Justice Department reversed the federal government’s position and informed the court that it now believed the First Step Act did cover lower-level offenders. This forced the court to reschedule the argument and appoint outside counsel, Adam Mortara, to serve as amicus in arguing to uphold the judgment of the U.S. Court of Appeals for the 11th Circuit, which ruled that Terry was not eligible for retroactive relief.

The tenor of Tuesday’s argument left the impression that most justices were skeptical of Terry’s (and the government’s) position. Assistant Federal Public Defender Andrew Adler began by arguing that the text, history and common sense all compelled the conclusion that when Congress changed the amount of crack that qualified for Tiers 1 and 2, it necessarily “modified” the statutory penalties for Tier 3. He further anticipated Mortara’s argument that changing the sentencing range of the amount of crack prescribed for each tier was distinct from changing the statutory penalties for each violation. (Recall that the First Step Act uses the phrase “statutory penalties” when defining which offenses are eligible for retroactive resentencing.) Adler argued that even were such niceties linguistically plausible, Congress and the U.S. Sentencing Commission had fallen into the habit of using the phrase “statutory penalties” interchangeably with the sentencing ranges. He emphasized the most obvious point: Why would Congress enact bipartisan reform to permit resentencing of punishments perceived to be disproportionately high, only to create a new anomaly by excluding low-level offenders?

Chief Justice John Roberts began the grilling with a question that revealed a submerged worry about the scope of the requested relief. While the legislation and the case attracted attention because of the disparity between crack and powdered cocaine, Roberts asked if any relief granted would extend beyond those boundaries to people convicted of other drug offenses, because the pivotal subparagraph (C) in Section 841(b)(1) is a catch-all provision that applies to many drugs beyond crack. Adler was adamant that the language and structure of the First Step Act contemplated only crack offenses. This line of questioning was repeated throughout the argument as Adler tried to reassure the justices of the limited reach of relief.

By contrast, Justice Clarence Thomas, noted for his newfound verbosity in the court’s remote hearings, appeared to lean into the decontextualized reading suggested by Mortara (his former clerk). “Before 2010, the statutory penalty was 0 to 20 years” for Terry’s offense, Thomas said. “After 2010, the statutory penalty is still 0 to 20 years. As far as I can see, then, the statutory penalty for petitioner here was not modified.” Put that way, Thomas’s inquiry pushed aside the question posed by the alteration of the surrounding tiers and thus answers itself.

Perhaps most noteworthy were the questions from an increasingly frustrated Justice Stephen Breyer, whose queries painted him as a swing vote. Breyer recognized that the vast disparity between crack and powered cocaine was “ridiculous,” yet he struggled against a statutory wrinkle to apply the resentencing in this case. In short, Breyer argued that regardless of whether the First Step Act “modified” the Tier 3 offenses under which Terry was charged, Terry was sentenced pursuant to separate but related statutory enhancements as a “career criminal” and thus not obviously entitled to relief. Early in the oral argument, Breyer professed he would like to see the case differently, inviting Adler to convince him.

Adler responded by pointing out that even under the career-criminal penalties, judges often looked to see where in the range an offense fell, often granting lighter sentences for drug offenses in the lower portion of a range. Thus, the shifting of the ranges under the Fair Sentencing Act could have a material effect on the sentence imposed on a defendant like Terry. He later reiterated this point in fending off similar questions from Justice Elena Kagan and pointed out that the retroactive provisions had already been applied in similar cases in the restructured higher-tiered offenses.

Breyer posed the same question to Deputy Solicitor General Eric Feigin, who argued on behalf of the federal government, and more forcefully to Mortara. In that last exchange, Breyer declared that if he was correct that being sentenced under the career-criminal penalties barred Terry from the contemplated relief, surely the government knew that; why then would the government argue as it did? Mortara’s reply – “Your Honor, I am here to explain many things. The behavior of the United States government in this case is not one of them.” – was seen as the wittiest of the morning, though counsel on the other side surely felt it as more stinging than amusing.

Even Justice Sonia Sotomayor, presumably the friendliest ear on the bench for Terry, balked at moments. Sotomayor started by focusing again on the most obvious argument for Terry: the anomaly of permitting high-level kingpins the opportunity for resentencing while denying a petty dealer the same. At times her arguments seemed aimed at building a case with her colleagues for fixing this seemingly obvious mistake. Even with this noted, Sotomayor chided Adler for claiming his reading of the statute was unambiguous, suggesting the opposition’s reading was simpler and more direct. Whether elegant rhetoric ensuring her colleagues did not feel their own doubts ignored or a genuine expression of unease, only the decision will tell. 

Feigin, for his part, was immediately pressed on the government’s 11th hour reversal by Roberts, who asked if there were specific standards determining when to switch positions in these kind of cases. Feigin could only reply that the switch was given much consideration, while listing a number of factors that led the government to adopt its new position. He was later asked by Justice Amy Coney Barrett if the Trump administration’s contrary legal position was implausible; he declined to go so far, describing it as “ultimately unsound.” Feigin’s arguments also stood out for being among the rare moments when the racially disproportionate nature of the crack/powder cocaine disparity was explicitly addressed.

Given that from a bird’s eye view, this case is one of simple congressional oversight and obvious legislative math, the task facing Mortara, arguing to uphold the 11th Circuit’s decision, seemed formidable before Tuesday. Mortara premised his case on a doggedly textual interpretation of the statute. Whatever the Fair Sentencing and First Step Acts did to the statutory range of offenses for which one could be convicted, they did not modify the penalties for those offense, he said. Thus, Terry is not entitled to resentencing because the penalty for his specific statutory offense – 21 U.S.C. § 814(b)(1)(C) – was not changed. Mortara analogized the case to changing the elements of a murder statute. That might mean more or less people were guilty of murder but it did not necessarily entail that the penalties for murder had been changed.

One dissonant note came late in the morning, when Justice Brett Kavanaugh embarked on an extended exchange with Mortara. Rather than a sharp set of questions, Kavanaugh ruminated on, among other things, the history that led to the sentencing regime Congress sought to fix. He recalled the 1986 death of college-basketball star Len Bias from a cocaine overdose that shocked the nation and brought cocaine use squarely into the spotlight. Recalling that Bias was only a year older than him and that he looked up to him, Kavanaugh (himself an avid basketball player and coach) mused that Bias’ death had motivated congressional action to impose harsher penalties on cocaine use, noting only casually that Bias died after using powdered cocaine. It was, to this observer, a cringe-worthy moment of naivete; to draw a clear path from the traumatizing death of Bias to harsher punishment of crack cocaine is to ignore a sea of racial politics. Len Bias’s death did not lead Congress to hammer down on Wall Street bankers doing coke.

Despite his perhaps formally coherent position that changing the tier ranges for crack-cocaine violations did not change the punishments, Mortara still faced the challenge of explaining why Congress would establish such a “curious” system – one that privileged kingpins while leaving the little guy in prison. Particularly challenging was the amicus brief filed by the four bipartisan senators who were largely responsible for drafting the First Step Act and now argue that it should apply retroactively to people like Terry. When asked about the senators’ brief, Mortara coolly held his position, arguing that the understanding of those four senators was no substitute for the intention of all of Congress; only the bill itself represented that. At most points, he reinforced the position that the text represented what Congress did rather than permit the court to substitute what it imagined Congress wanted to do.

But perhaps his most adept work was in proposing an at least sensible, not to say convincing, rationale. By using the contrasting case of Dorsey v. United States, he hinted that Congress may have provided relief for those at the highest end of the crack-cocaine disparity because their sentences would be the most disproportionate. On this reading, Congress provided relief where it wished, the Sentencing Commission considered and altered lower-level offenders where it wished, and the peculiarity of Terry not being granted resentencing as a small-time repeat offender makes perfect sense.

Whether the court finds that ultimately persuasive, we now wait to see. More importantly, perhaps hundreds of inmates who look like Terry are watching closely.