A conservative group will soon ask a federal court to determine whether it can take unlimited political contributions in a potential test case that campaign finance watchers claim may clear the way for a second generation of 527 groups to operate freely.

Speechnow.org, a group headed by executives at the Club for Growth and Center for Competitive Politics, will file court papers within days challenging the Federal Election Commission’s advice that it should file as a political committee and adhere to yearly $5,000 individual contribution limits.

David Keating, the conservative Club for Growth’s executive director, is Speech now.org’s president. Former Republican FEC Commissioner Brad Smith and the Institute for Justice’s Steve Simpson will represent the group in the case.

So far, Fred Young, a Wisconsin donor, has promised the group $110,000. In a recent FEC filing, the group suggested it may run ads against Rep. Dan Burton (R-Ind.), who faces a challenge from the right in the May 6 primary, and Sen. Mary Landrieu (D-La.), who is running neck-and-neck against State Treasurer John Kennedy (R).

But any final determination from the court or involvement by the group in Congressional races may be many months off — and perhaps by design.

According to Rick Hasen, an election law expert at Loyola Law School in Los Angeles, Keating, Smith and other prominent conservative activists involved with the group are merely testing the John Roberts-led Supreme Court on an obscure part of campaign-finance law involving 11th hour outside ad buys — “independent expenditures” that flood battlegrounds in the weeks and days before primary and general elections.

In two recent cases, Randall v. Sorrell and Wisconsin Right to Life v. Federal Election Commission, Hasen said, the high court has been skeptical of wide portions of election law now on the books. Hasen described the court’s guidance on independent expenditures as murky and said it’s largely confined to a 30- year-old decision and a “cryptic footnote” from Senate Minority Leader Mitch McConnell’s (R-Ky.) challenge of the 2002 Bipartisan Campaign Reform Act.

“It’s a very savvy political strategy,” Hasen said. “It’s another test case to try and push the new Supreme Court justices into the deregulation camp.”

“The current Supreme Court could well view the issue differently,” he added.

If Speechnow.org ultimately wins in court, the group agreed that other activists, conservative and liberal alike, could copy its carefully crafted bylaws, raise unlimited cash from individuals and begin running ads in favor of or opposing candidates, expenditures that would be disclosed to the FEC.

In addition to not incorporating — the group is a membership-based association — Speechnow.org also has promised it will not take corporate or labor union money.

Keating told Roll Call in an interview that the group could become a template for other outside political activists.

“No one understands messaging around an election,” Keating said. “It’s way too complicated. … [The case] makes clear and simple rules, without limits, about how much money people can raise and how they can spend it.”

Former FEC Commissioner Smith agreed that political groups are subjected to a dizzying array of broadcast advertisement regulations in so-called blackout periods that precede elections.

He called a potential victory in the case “a wonderful clearing away of an underbrush that the vast majority of Americans don’t think should be there.”

But Paul Ryan of the Campaign Legal Center said the public should be a little more skeptical about the case, arguing that Speechnow.org is little more than a 2004-cycle 527 hiding under a populist veil of constitutional rights. Ryan agreed with Hasen that the group simply is pushing the court to provide clear guidance on independent expenditures.

“Speechnow.org is proposing to engage in virtually the same activity— if not even more explicit — election influencing activity than all the 527 groups that the Federal Election Commission has entered into conciliation agreements with, finding that they broke federal law by not abiding by contribution limits in 2004,” Ryan said. “The average citizen doesn’t have more than $5,000 per year to give to these groups. This issue is often pitched as: Reformers or speech haters are trying to squelch grass-roots political activity.”

In late 2006, the FEC began handing stiff fines to 527s active in the 2004 election cycle: GOP-leaning Swift Boat Veterans for Truth, its Democratic counterpart, America Coming Together, along with handful of other liberal and conservative groups.

Swift Boat Veterans for Truth ultimately was fined almost $300,000 and America Coming Together was hit with a $775,000 fine for violating campaign finance law.

America Coming Together president John Podesta, a chief of staff in the Clinton White House, labor leader Anna Burger and philanthropist Rob McKay in late 2007 formed the liberal Fund for America, another 527, version 2.0. The group is expected to spend more than $100 million this cycle.