Scott Turow, attorney, author

Buckley v. Valeo (1976) struck down limits on campaign expenditures, which Congress had set in the wake of Watergate. The Court reasoned that campaign spending is not expressive conduct that can be regulated (like burning a draft card), but free speech protected by the First Amendment. Buckley created a permanent advantage for rich candidates, who could now spend all they wanted on their campaigns. Far more important, by treating expenditures as free speech, it set us on course to the justly lamented Citizens United decision of 2010.

Harold Hongju Koh, professor, Yale Law School

The Supreme Court turns away thousands of cases every year, but letting these decisions stand means they could continue to generate bad precedent. In 1950’s United States v. Munsingwear (a k a “the underwear case”), the Court articulated its power to strike lower-court decisions if they have become moot by the time they reach the justices’ desks—a means of supervising and cleaning up our legal system.

Elizabeth Wurtzel, J.D., memoirist

The 1989 case Michael H. v. Gerald D. tells us what would happen if Justice Antonin Scalia wrote a Harlequin romance. We have a California model, her New York City husband, her boyfriend next door, her boyfriend down the road—and the daughter they all love. Scalia led the majority in siding with California law, which generally presumes a woman’s husband to be the father of her children, regardless of anyone else’s claims—because having a stable family matters more than biology.

Theodore B. Olson, former solicitor general

I’d go with a case the Supreme Court didn’t take. In 1793, Secretary of State Thomas Jefferson asked the Court for an advisory opinion on whether the French minister could commission privateers in the U.S., despite President Washington’s Proclamation of Neutrality. Chief Justice John Jay declined to issue one, on separation-of-powers grounds. This established the still-followed precedent for the judiciary to render decisions only on actual cases.

Kathleen M. Sullivan, former dean, Stanford Law School

Everyone has heard of Brown v. Board of Education, which held that segregation violates the Fourteenth Amendment. But that applies only to the states. It was Bolling v. Sharpe (1954), about segregation in D.C. schools, that found discrimination by the federal government to be a violation of the Bill of Rights. Any federal discrimination suit—for example, this year’s case about the Defense of Marriage Act—descends from Bolling.

Andrew Cohen, Atlantic contributing editor

Decided in 1984, Strickland v. Washington created a procedural rule that makes it virtually impossible for a criminal defendant to successfully argue that he or she has been denied the “effective assistance” of counsel—and thus the Sixth Amendment right to a fair trial. The ruling is directly responsible for thousands of Americans’ incarceration after trials in which their lawyers drank, or were using drugs, or were sleeping, or were otherwise clearly incompetent.