Ted Olson, with Gibson Dunn & Crutcher, speaking outside the U.S. Supreme Court in Washington after oral arguments in the consolidated cases Department of Homeland Security v. Regents of the University of California, on Tuesday, November 11, 2019.

Immigration: Dept. of Homeland Security v. Regents of the University of California 

Gibson, Dunn & Crutcher's Ted Olson argued against the Trump administration's move to end the Obama-era program Deferred Action of Childhood Arrivals, or DACA, benefiting some 700,000 individuals who arrived in the U.S. as minors. The case doesn't test the merits of the program but, rather, whether Trump agency officials took lawful steps to unwind the program. Chief Justice John Roberts Jr. and Justice Neil Gorsuch both raised questions at the Nov. 12 argument confronting the Trump administration's justifications. Roberts at one point asked U.S. Solicitor General Noel Francisco, "What if the attorney general said he, in his exercise of prosecutorial discretion, was not going to enforce any of the immigration laws? Would that still be non-reviewable?" Francisco said an exception would apply to that scenario, which he described as a "complete abdication of authority." California Solicitor General Michael Mongan, making his high court debut, argued for Democratic-led states in support of DACA.

Affordable Care Act: Maine Community Health Options v. United States

Kirkland & Ellis' Paul Clement, who led previous challenges to the Affordable Care Act, was back at the court in December—arguing instead in support of the law. Or at least a provision that required, as he claimed, the government to fulfill a promise to cover certain losses to insurers that participated in the health exchange markets. The U.S. Justice Department faced a skeptical U.S. Supreme Court over arguments that the government had no obligation to pay $12 billion in losses incurred by insurance companies. Clement, at the Dec. 10 hearing, called the government's failures to pay out a "massive bait and switch."

LGBT Employment Rights: R.G. and G.R. Harris Funeral Homes v. EEOC, Bostock v. Clayton County and Altitude Express v. Zarda

The justices on Oct. 8 heard a trio of cases that confront the scope of Title VII rights for gay, lesbian and transgender workers. At issue was the language "because of sex" in the law's prohibition of sexual discrimination. The Trump administration argued for a narrow interpretation. Stanford Law School's Pam Karlan pushed the justices to read the statute as it appears. "The textual evidence is very close" on whether the law does bar discrimination because of sexual orientation and gender identity, Justice Neil Gorsuch said during the oral arguments. Where Gorsuch might see some ambiguity in the text, Justice Elena Kagan saw clarity. "Title VII is a statute about individuals," Kagan said. "Is a particular person being treated differently because of her sex? It's as simple as looking at the language of the statute," Kagan said.

Civil Rights: Comcast v. National Association of African American-Owned Media

Two media companies faced off Nov. 13 in a case involving one of the nation's oldest civil rights laws. Originally part of the Civil Rights Act of 1866, 42 U.S.C. Section 1981 prohibits racial discrimination in contracting. Entertainment Studio Networks, represented by Erwin Chemerinsky, dean of the University of California Berkeley School of Law, is owned by African American entrepreneur and entertainer Byron Allen. Allen has alleged Comcast Corp., represented by Gibson, Dunn & Crutcher partner Miguel Estrada, gave "pretextual" reasons for declining to carry Studio Networks channels. "All eyes should be on this critical case," Sherrilyn Ifill, president and director-counsel of the NAACP Legal Defense Fund, said in a statement. "An adverse decision by the Supreme Court could imperil the integrity of section 1981 as a tool for protecting the full economic and legal rights of black people." In the government's amicus brief, backing Comcast, U.S. Solicitor General Noel Francisco said the outcome of the case could have repercussions for other federal anti-discrimination laws.

Second Amendment: New York State Rifle & Pistol Association v. New York City

Argued Dec. 2, one of the central issues of this case is whether there's even a case at all. The Supreme Court last year said it would take up the dispute, involving a New York City law—but that provision, restricting the movement of firearms, was scrapped after the justices said they'd review a lower court ruling upholding the law. Justices Neil Gorsuch and Samuel Alito Jr.  appeared to strive to save the U.S. Supreme Court's first major gun rights case in nearly a decade from disappearing without a ruling on the scope of the Second Amendment. Groups supporting broad firearm rights, critical of how lower courts have applied the Second Amendment, have urged the court to use the case to announce a tough standard or test that governments must meet in order for regulations to be upheld as constitutional. Justice Ruth Bader Ginsburg, questioning Kirkland & Ellis partner Paul Clement, lead counsel for the New York State Rifle & Pistol Association, said the new state law blocks whatever the city attempted to do. "What's left of this case?" she asked. "Petitioners have gotten all that they sought."