The Supreme Court case Golden, Acting District Attorney of Kings County v. Zwickler (1968) revolved around the issue of mootness in a constitutional challenge to a New York statute that criminalized anonymous election leaflets. The respondent, Zwickler, had previously been convicted under this law for distributing anonymous pamphlets criticizing a Congressman during his re-election campaign. After serving his sentence and paying his fine, he brought suit against the petitioner, Golden (the acting district attorney), seeking declaratory relief and an injunction preventing future prosecutions under this statute. However, by the time the case reached the Supreme Court on appeal from lower courts' decisions favoring Zwickler's claim that such laws violated First Amendment rights to free speech - there was no longer any live controversy as said Congressman had retired from politics permanently. In its decision authored by Justice Brennan Jr., SCOTUS ruled 7-2 in favor of Golden stating that federal courts should not decide abstract or hypothetical questions; they must avoid giving advisory opinions unless there is an actual ongoing dispute between parties with adverse legal interests. Hence it held that since there was no reasonable expectation or demonstrated probability that Zwickler would be subjected again to prosecution under same law due to changed circumstances – hence rendering it moot.

In the dissenting opinion for Golden v. Zwickler, Justice Harlan argued that the majority's decision was based on an overly narrow interpretation of federal jurisdiction and mootness doctrine. He contended that there was a reasonable expectation or demonstrated probability that the same controversy could recur involving the same complaining party, thus making it not moot. Furthermore, he disagreed with their view about "chilling effect" on First Amendment rights as being speculative; instead he believed such chilling effects were real and substantial enough to warrant judicial intervention even in absence of immediate threat of prosecution. Lastly, Justice Harlan criticized his colleagues' reluctance to exercise federal jurisdiction over state officials when constitutional issues are at stake - a stance which according to him undermined national supremacy in matters pertaining to individual liberties under Constitution.