The last of the 33 Christian ministers who took part in “Pulpit Freedom Sunday” almost two weeks ago mailed their sermons to the Internal Revenue Service this week, the Alliance Defense Fund, which is bankrolling the ministers’ legal bills, told Money Matters on Wednesday.

The group said it is now preparing to fight federal tax authorities in court. [IMGCAP(1)]

“It’s going to take them about two months at the earliest before we hear anything,” Alliance Defense Fund spokesman Erik Stanley said. “We expect one of two things: Either nothing will happen and they won’t come after these pastors because they’ll understand that this is an exercise of constitutional freedoms. Or they’ll attempt to apply the law against these pastors in a way that prohibits them from preaching their sermons on Sundays. My suspicion is that they will” come after the ministers.

Citing a federal law barring the agency from discussing possible enforcement matters, the Internal Revenue Service declined to discuss the 33 ministers — there may have been more — who took part in the protest. The agency, however, did provide an earlier statement by the head of the IRS’s nonprofit unit, who said that “education has been and remains the first goal of the IRS’s program on political activity by tax-exempt organizations.”

But the agency also pointed to previous letters it has written that appear to paint a relatively bright line for nonprofit groups looking to get into the business of politics, a move that could threaten their tax-exempt status by showing a “preference for or against a certain candidate or party.”

“Under federal law tax-exempt charitable organizations are prohibited from endorsing any candidates, making donations to their campaigns, engaging in fund-raising, distributing statements, or becoming involved in any other activities that may be beneficial or detrimental to any candidate,” the IRS wrote in an April, 18, 2008, letter to political committees. “Even activities that encourage people to vote for or against a particular candidate on the basis of nonpartisan criteria violate the political campaign prohibition of section 501(c)(3).”

Still, news accounts of the Sept. 28 protests suggest that many ministers used the IRS warnings as a template for what to say, rather than what not to. According to an Associated Press account, Minnesota-based evangelical Pastor Luke Emrich appeared to walk right up to the IRS’ imaginary line, take a few steps back and run — jumping as far as he could over it.

“I’m telling you straight up, I would choose life,” Emrich told to his flock, according to the AP. “I would cast a vote for John McCain and Sarah Palin.”

“But friends, it’s your choice to make, it’s not my choice,” he added. “I won’t be in the voting booth with you.”

Raking It In. Rep. Kenny Hulshof (R-Mo.), who is locked in a tight gubernatorial race with Missouri Attorney General Jay Nixon (D), is taking full advantage of the Show Me State’s new campaign finance abyss, hauling in more than $1.75 million in previously restricted big-dollar gifts in the past month alone.

According to disclosure statements analyzed by Money Matters, since Sept. 2, Hulshof has received at least 25 checks and in-kind gifts from party and political action committees totaling roughly $1 million, including a single $400,000 check from the RGA Missouri 2008 PAC.

Hulshof’s campaign also received at least 15 checks from individuals totaling about $500,000, including four $100,000 individual contributions directly from executives at Missouri-based TAMKO Building Products Inc. Enterprise Rent-a-Car’s Jack and Andrew Taylor also personally gave Hulshof’s campaign $35,000, while the St. Louis-based company’s PAC also gave the lawmaker $10,000.

Other Missouri-based companies also wrote big checks to Hulshof’s campaign directly out of their corporate coffers, contributions that federal candidates and committees are not allowed to accept. According to Hulshof’s campaign finance records, drug distributor Express Scripts Inc. gave the lawmaker $15,000, the law firm Thompson Coburn gave the lawmaker $20,000 and electronics maker Emerson Electric Co. gave him $30,000.

Herzog Contracting Corp., a division of regional engineering giant Herzog Companies Inc., also wrote Hulshof’s campaign a check for $25,000, while packaging manufacturer Smurfit Stone gave him $10,000.

In May, the Missouri Legislature approved a late-session measure lifting all campaign finance restrictions for gubernatorial and legislative races. Before retiring Gov. Matt Blunt (R) signed the law, political contributions in the state were limited to $1,275.

A call to Hulshof’s campaign manager was not returned by press time.

IEs Off the Charts. In a vivid illustration of how the Democratic Congressional Campaign Committee’s stark financial advantage over the National Republican Congressional Committee is coming into play late in the cycle, the DCCC reported independent expenditures in 40 separate House races on Tuesday alone. The NRCC on the same day reported one.

The DCCC’s expenditures included media buys of at least $100,000 in nine districts. The NRCC’s lone expenditure was $39,000 on the open-seat race in Ohio’s 15th district.

All told, the DCCC had spent at least $22.8 million on IEs through Tuesday; the NRCC had spent $403,000.

Between now and Election Day, Roll Call will update the two committees’ expenditures every weekday on its Web site. Look for Roll Call’s IE tracker at RollCall.com/ietracker.

Josh Kurtz contributed to this report.

Send items of interest on money in politics to mtm@rollcall.com.