Congress’s effort to curtail the rights of private organizations to pay for political advertisements near Election Day will come under challenge tomorrow before the U.S. Supreme Court in a case that may set the boundaries for public participation in the 2008 electoral cycle.

The case presents the federal high court with an opportunity to strike down regulations on socalled “issue ads,” which since the late 1990s have come to play a major role in politics. The Roberts court could use the case to reconsider the rationale that the court has previously accepted for limiting the First Amendment rights of groups to make political contributions and expenditures.

Still, the fact that the case is so loaded with potential legal changes is surprising, given that the court upheld the regulations now at issue in a 2003 decision, McConnell v. Federal Election Commission. In that 5–4 decision, the court upheld Congress’s Bipartisan Campaign Reform Act of 2002, commonly known as McCain-Feingold.

Justice O’Connor was the swing vote for the majority in that case, giving rise to speculation that a newly composed court might want to revisit the issue. That speculation was strengthened last year when the court reversed a lower court’s dismissal of the current case, called Wisconsin Right to Life v. Federal Election Commission.

“This is a core First Amendment issue that presumably had been resolved but is now wide open again,” a law professor at New York University, Samuel Issacharoff, said.

At the center of the case is a provision of the law that establishes a blackout on certain “electioneering communications” that refer to candidates for federal office during the two months before Election Day and one month before a primary. The ban covers most so-called “issue ads” that are funded from the general treasury of unions, for-profit corporations, or nonprofit organizations. It does not cover ads paid for by political action committees.

The case scheduled for oral arguments tomorrow involves several such advertisements by a group in Wisconsin that is opposed to legalized abortion. The ads, aired briefly in 2004 before the blackout period, called on residents to contact their senators to oppose an anticipated Senate filibuster against President Bush’s judicial nominees. The advertisements urged voters to contact both of Wisconsin’s senators. Because one of the lawmakers, Senator Feingold, was up for re-election, the ads potentially fell under the restrictions.

For decades, such ads were unregulated so long as they did not contain an explicit endorsement of a particular candidate. Beginning in the late 1990s, such ads proliferated, and Congress decided that these ads allowed an end run around stringent restrictions on campaign donations. In the past, the court has justified campaign finance regulations on the grounds that Congress had an interest in safeguarding against corruption.

But Congress made no effort in the 2002 Act to distinguish between advertisements that were intended to sway the electorate toward a particular candidate or advertisements that were intended to mobilize the electorate around a specific issue.

Such regulations “captured a lot of issue speech,” an associate general counsel of the AFL-CIO, Laurence Gold, whose organization filed a brief in the case, said. “Its cynical and unfair to view everything through an electoral lens. We don’t think that comports with either the First Amendment or reality.”

In the 2003 decision, the court, in effect, upheld the regulations because drawing a line between the two types of speech was difficult to do. Now, on account of the same difficulty, the court could reverse itself and decide that it must strike down the regulation on such issue ads. The National Rifle Association, in a brief arguing against the act, said the 2003 decision drew “the wrong conclusion from this reality, reasoning that, if one cannot distinguish between protected speech and unprotected electioneering communications, then the State may outlaw all of it.”

Alternatively, some legal observers expect the court to attempt to articulate a standard that would exempt some issue ads from the blackout period.

“We’re trying to separate something that in real life is intermingled,” a professor at the University of California, Los Angeles, Daniel Lowenstein, said. “That’s the genuine difficulty of the case. There is so much overlap between campaign communications — which can be regulated — and other types of political speech, which cannot be.”