The Supreme Court case, Stanley v. City of Sanford, Florida. The central question is whether a former employee, who alleges disability discrimination regarding post-employment benefits, can sue under the Americans with Disabilities Act (ADA) even if the alleged discrimination occurred before the employee's retirement. The arguments presented by both sides explore various interpretations of the ADA, focusing on the "qualified individual" requirement and the timing of the discriminatory acts. The Solicitor General also participates, offering an alternative legal argument. The justices' questions probe the implications of different rulings, examining potential impacts on future cases and exploring related legal concepts like reasonable accommodation.

The Supreme Court case, Hewitt v. United States. The case centers on whether the Act applies to resentencings following vacated sentences, a point of contention regarding the interpretation of the phrase "a sentence for the offense has not been imposed." The justices debated the statutory language's ambiguity, considering the present-perfect tense and broader legal context, including the principle of vacatur. Arguments focused on whether the statute intended to address only initial sentencings or also include resentencings, with implications for fairness and finality of judgments. The Court grappled with potential anomalies and inconsistencies arising from different interpretations of the law.

The Supreme Court case, TikTok, Inc., et al. v. Merrick B. Garland, and a consolidated case. The arguments center on the constitutionality of a law mandating TikTok's divestiture from its Chinese parent company, ByteDance, due to national security concerns. The petitioners argue the law violates TikTok's First Amendment rights, while the respondent, the Attorney General, contends the law addresses compelling national security interests related to data security and covert content manipulation. The justices' questions explore various aspects of First Amendment jurisprudence, the feasibility of divestiture, and the government's justifications. The core issue debated is whether the law's restriction on TikTok's operations constitutes an impermissible infringement on free speech.