From Osseo classrooms to northern Minnesota wetlands, five cases reveal the breadth of Chief Justice John Roberts’ judicial reach.
The last two decades have been turbulent ones for the judicial system, including the U.S. Supreme Court at its pinnacle.
During this period, Chief Justice John Roberts has presided over a tribunal that has lost considerable public support, faced ethical challenges, overruled long-standing legal doctrine, and both extended and restricted civil and constitutional rights, among other matters.
The Court has adjudicated a number of cases during that time from Minnesota. The Chief Justice has authored opinions in five notable ones, four for the Court and one in dissent, involving disputes in Hennepin and Ramsey counties and elsewhere in the state.
As the Court begins its 2026–27 term on the traditional first Monday in October, this year Oct. 5, it’s an opportune occasion to review that quintet during the Chief’s two decades on the bench.
Roberts arrived after a short stint on the federal appellate court in Washington, D.C., following a career with the Department of Justice and in private practice. During that career, he argued 39 Supreme Court cases, winning 25 of them, about 64%. Earlier, he served as a law clerk to Justice William Rehnquist, who later became Chief Justice.
Disability Decision
The most recent of these Minnesota rulings occurred at the end of the Court’s 2024–25 term in A.J.T. v. Osseo Area Schools, Independent School District No. 279. Roberts wrote the unanimous decision in a school disability discrimination case arising in the Osseo school district here in Hennepin County.
The issue before the High Court was the standard required for a student to pursue claims under the Americans with Disabilities Act (ADA) and the Rehabilitation Act of 1973 concerning her educational services. Related proceedings had already addressed her rights under the Individuals with Disabilities Education Act (IDEA).
The suit was brought on behalf of a girl who suffered from seizures due to epilepsy. Her parents sought instruction later in the day because her seizures were more severe in the morning. They requested evening instruction to provide a school day extending from noon until around 6 p.m.
The school district declined, prompting the parents to file a complaint with the Minnesota Department of Education. An administrative law judge determined that the district had violated the IDEA and ordered compensatory education and evening instruction. That determination was subsequently affirmed.
The family also pursued claims under Title II of the ADA and Section 504 of the Rehabilitation Act, seeking a permanent injunction, reimbursement for certain costs, and compensatory damages. But U.S. District Judge Michael Davis granted summary judgment to Osseo Area Schools, and the Eighth Circuit affirmed. Both courts applied a standard requiring “bad faith or gross misjudgment,” which they found lacking.
The High Court, in the decision written by Chief Justice Roberts, rejected that heightened showing.
Referring to the issue as a narrow one, the Chief Justice observed that children with disabilities and their parents face “daunting challenges on a daily basis.” Those challenges, he concluded, should not include having to satisfy a more stringent standard than other people bringing federal disability discrimination claims.
The educational disparity was considerable. Between 2015 and 2018, the girl received 4.25 hours of daily instruction, compared with 6.5 hours for her peers, or about 65% of their instructional time.
The Court held that disability discrimination claims concerning educational services must be judged by the same standards applied in other settings. Roberts described the distinctions lower courts generally draw between remedies:
- Injunctive relief: A plaintiff may establish a statutory violation and obtain an injunction without proving discriminatory intent.
- Compensatory damages: Courts generally require intentional discrimination, which most federal appellate courts, including the Eighth Circuit, regard as satisfied by proof of deliberate indifference.
The Court did not settle every question about those underlying standards or determine that the family had proved its claims. It rejected the special, more demanding standard imposed on schoolchildren.
The Eighth Circuit’s judgment was vacated, and the case was remanded for further proceedings. A pair of concurring opinions were issued, one by Justice Clarence Thomas, joined by Justice Brett Kavanaugh, and another by Justice Sonia Sotomayor, joined by Justice Ketanji Brown Jackson.
Disability advocates had been concerned that the Court might adopt a heightened standard that would make it harder for individuals with disabilities to successfully assert their claims. The ruling instead puts students on an even plane with other disability discrimination claimants.
Residents Ruling
The taxation of stipends paid to medical residents was addressed by the Chief Justice in his 2011 decision for the Court in Mayo Foundation for Medical Education and Research v. United States. The case concerned Mayo and the University of Minnesota seeking refunds of FICA taxes for Social Security and Medicare paid on compensation to medical residents.
A pair of Minnesota jurists reached differing results in the lower courts. U.S. District Judge Richard Kyle ruled in favor of Mayo and the University, but the Eighth Circuit, in a decision written by Chief Judge James Loken of Minnesota, reversed.
The case reached the Supreme Court, where Chief Justice Roberts, writing for a unanimous Court with Justice Elena Kagan not participating, affirmed the Eighth Circuit’s decision.
The ruling upheld the Treasury Department’s full-time employee rule. Under that regulation, an employee normally scheduled to work 40 hours or more per week does not qualify for the student exemption from FICA taxes, even when the work has an educational component.
The Court evaluated the regulation under the then-prevailing doctrine established in Chevron U.S.A. Inc. v. Natural Resources Defense Council, Inc.. That doctrine called for judicial deference to an agency’s reasonable interpretation of an ambiguous statute it administers.
Congress had not directly resolved whether medical residents qualified for the student exemption. The Court therefore considered whether Treasury’s full-time employee rule was a reasonable interpretation of the statute.
Roberts acknowledged that the residents were “engaged in a valuable educational pursuit” and were “students of their craft.” Nonetheless, Treasury could reasonably treat them as full-time employees for FICA purposes.
Judge Loken’s decision was therefore correct. The residents’ compensation was subject to FICA taxes, and the refund requests were rejected.
Interestingly, the Chevron doctrine, which formed the basis for Chief Justice Roberts’ reasoning, was overturned in 2024 in Loper Bright Enterprises v. Raimondo, another decision written by Roberts.
That decision ended the requirement that courts defer to reasonable agency interpretations merely because a statute is ambiguous. It did not, however, automatically overturn earlier decisions upholding agency actions under Chevron. The Court expressly preserved those decisions’ entitlement to statutory stare decisis.
Apparel Action
Chief Justice Roberts led the Court into and out of a political thicket in 2018 in Minnesota Voters Alliance v. Mansky.
The issue concerned a Minnesota election law, Minn. Stat. § 211B.11, subdivision 1, barring political badges, buttons, or other political insignia inside polling places on Election Day.
Minnesota Voters Alliance and other groups and individuals, organizing under the name Election Integrity Watch, challenged the law on First Amendment grounds. The challengers included a former Ramsey County election judge and a Hennepin County voter.
The case had a twisted lower-court history. U.S. District Judge Joan Ericksen initially dismissed the action for failure to state a claim. The Eighth Circuit affirmed in part, reversed in part, and remanded.
In her second look at the case, Judge Ericksen entered summary judgment against the challengers on the remaining claims, which the Court of Appeals affirmed.
Those rulings were wiped out when the High Court took the case and deemed the political apparel ban unconstitutional. The Chief Justice, writing for a 7–2 majority, pointed out that the state could pursue the permissible objective of creating a calm, peaceful setting for voters at polling places. But its restrictions needed a reasonable boundary.
As Roberts explained, the state had to articulate:
“some sensible basis for distinguishing what may come in from what must stay out.”
The statute’s “unmoored” use of the term “political,” coupled with the state’s “haphazard interpretations,” failed that test.
The Chief’s decision recognized the state’s interest in protecting the voting environment while accommodating political expression. But Minnesota’s prohibition was not capable of reasoned application, rendering it constitutionally infirm.
The decision drew a dissent by Justice Sotomayor, joined by Justice Stephen Breyer. She argued that the Court should first give the Minnesota Supreme Court an opportunity to interpret the statute by certifying the state-law question to it. The majority declined to do so.
Following the decision, the statute was amended to address the deficiencies. The current law ties its restrictions to candidates and questions appearing on the ballot and political parties represented there. It covers specified names, likenesses, logos, slogans, and ballot-question identifiers, rather than political expression generally.
Army Appeal
Another regulatory ruling in a Minnesota case written by Chief Justice Roberts was United States Army Corps of Engineers v. Hawkes Co., Inc., decided in 2016.
A peat-mining company and affiliated property owners sought judicial review of the Corps’ determination that wetlands on a 530-acre tract in Marshall County in northwestern Minnesota were subject to the Clean Water Act.
The dispute arose during the permitting process. The Corps issued an approved jurisdictional determination concluding that the property contained federally regulated waters. The owners challenged that determination before undertaking activities that could expose them to enforcement proceedings and substantial penalties.
The issue before the Court was whether the determination was subject to judicial review under the Administrative Procedure Act. U.S. District Judge Ann Montgomery dismissed the case, concluding that the determination was not reviewable final agency action. The Eighth Circuit reversed.
Writing for a Court unanimous in the result, Chief Justice Roberts affirmed the Eighth Circuit’s ruling. He held that the Corps’ approved jurisdictional determination constituted final agency action subject to judicial review.
Taking a pragmatic approach, Roberts reasoned that the owners had no adequate alternative route to court. They did not have to discharge material without a permit and risk an enforcement proceeding to obtain a ruling on whether the Act applied to their property.
Nor were they required to complete a lengthy and expensive permitting process before challenging the Corps’ jurisdictional determination. The ruling allowed them to seek judicial review before facing fines or other enforcement consequences; no fines had already been imposed in the dispute before the Court.
Justices Anthony Kennedy and Elena Kagan wrote separate concurrences. Justice Ruth Bader Ginsburg concurred in part and in the judgment.
Retroactivity Reversed
Chief Justice Roberts also opined about retroactivity in a criminal case from Hennepin County that went through the Minnesota state court system, Danforth v. Minnesota, decided in 2008. This time, he was in the minority.
A man convicted in Hennepin County District Court of first-degree criminal sexual conduct sought post-conviction relief on the ground that a videotaped interview with the victim had been admitted into evidence in violation of the rule subsequently announced in Crawford v. Washington.
That decision restricted the admission of testimonial statements from witnesses who did not appear at trial, generally requiring that the witness be unavailable and that the defendant have had a prior opportunity for cross-examination.
The issue was whether Crawford could be applied retroactively to Danforth’s conviction. The Hennepin County District Court denied relief, and both the Minnesota Court of Appeals and the Minnesota Supreme Court affirmed.
But the U.S. Supreme Court reversed and remanded. In a decision written by Justice John Paul Stevens, the Court held that state courts could give new rules of federal criminal procedure broader retroactive effect in state post-conviction proceedings than federal courts would give them under Teague v. Lane.
The Teague rule generally limits the application of new constitutional rules of criminal procedure to convictions already final when those rules are announced. The majority held that this restriction on federal habeas relief did not prevent states from providing broader relief in their own courts.
But Chief Justice Roberts disagreed in a dissent joined by Justice Anthony Kennedy, viewing the retroactivity of the Court’s constitutional decisions as a question of federal law.
He regarded the majority’s approach as startling because it could lead to different results for similarly situated defendants in different states. In his view, allowing states to depart from the federal retroactivity determination undermined the uniformity required by the Supremacy Clause and represented a radical departure from federal judicial authority.
Because Danforth’s conviction was final before Crawford was announced, the Chief felt that the new rule should not apply retroactively on post-conviction review under Teague, rather than leaving states free to adopt a broader approach.
Despite the Chief’s dissent, the case returned to the Minnesota court system. In its 2009 decision on remand, the Minnesota Supreme Court exercised the discretion the High Court had recognized, chose to retain the Teague framework as a matter of state law, and again denied relief, leaving the sex abuser’s conviction intact.
While Chief Justice Roberts has participated in many other Minnesota-based cases from both the federal and state court systems, this quintet is notable for his authorship of opinions for the Court or in dissent.
These cases also reflect the wide range of issues that have come before the High Court from Minnesota during the Roberts era, a range likely to continue as the Chief Justice remains at the helm of that august, but tattered, tribunal.
