Trump's Massive Shakedown

 Our most recent book is The Comeback: The 2024 Elections and American Politics. The first year of the second Trump administration has been full of ominous developments. Scandals persist. Trump is abusing his power to enlarge his political empire.

Josh Dawsey, Dana Mattioli, Annie Linskey and  Emily Glazer at WSJ:

Almost every night in the White House, President Trump calls his fundraiser, Meredith O’Rourke, for an update.

Trump asks O’Rourke which companies and donors have cut checks and which haven’t, and for how much. He often asks her to make much larger financial requests than she was planning—for some donors the ask is $5 million, for others it is $50 million. And the president gives her names to call, often including people who have recently met with him, according to people with knowledge of the calls.

“This is very important to the president. He’s asked me to call you and ask you for this donation,” O’Rourke has relayed on phone calls with companies, persistently following up with them. In some calls, she has referred to Trump as the boss, saying “the boss wants this money.” In turn, Trump has called her the “princess of darkness” because she is such a “killer” with donors, according to people who have heard his comments.

SoftBank donated $50 million toward Trump’s presidential library. Apple cut a check for around $25 million toward his White House ballroom project, while Microsoft gave around $10 million and Amazon chipped in around $5 million, according to people familiar with the contributions. Meta Platforms recently gave $10 million to a Trump-aligned political committee, people familiar said, on top of a multimillion donation to the ballroom and a prior $22 million payment to the planned presidential library.

Trump stands out for taking personal control of the fundraising, and no sitting American president has ever raised these amounts for his pet projects. At the same time, companies have paid new attention to the White House as Trump has gotten involved in regulatory decisions that once were made by independent agencies, dramatically shifting the balance of power across Washington.

Trump has been demanding large checks from companies for a range of political and legacy projects—telling executives and lobbyists that their companies should give $25 million or $50 million. He has sometimes offered donors special access.

No laws prohibit presidents from raising unlimited sums of money for nonprofits, like the ones used for the ballroom and his presidential library, his super PAC or political issue committees. For most of these types of transactions, public disclosure of donors isn’t required and reporting on spending is infrequent.

All told, the second-term president has raised more than $800 million since returning to office, according to an updated Wall Street Journal analysis.

More Ways to Buy Favor with Trump

Our new book is The Comeback: The 2024 Elections and American Politics. The first year of the second Trump administration has been full of ominous developments. Scandals persist.

Karen Yourish, Kenneth P. Vogel, and Charlie Smart at NYT:

Since President Trump was elected a second time, he and his allies have raised nearly $2 billion for his favored political causes and passion projects. That total, which was confirmed by four people involved in the fund-raising, likely eclipses the amount raised to support his 2024 campaign.

The astounding haul hints at a level of transactionalism for which it is difficult to find obvious comparisons in modern American history. The identities of the donors behind much of the cash are not legally required to be, and have not been, publicly disclosed. In some cases, Mr. Trump’s team has offered donors anonymity.

To shed light on what has been a largely opaque fund-raising apparatus, The New York Times conducted a comprehensive investigation. It relied on previously unreported documents and public campaign finance filings, as well as interviews with dozens of people who are familiar with the solicitations or are involved in the fund-raising. It traced a large portion of the funds raised — more than half a billion dollars’ worth — back to 346 donors who each gave at least $250,000. It also found that more than half of them have benefited, or are involved in an industry that has benefited, from the actions or statements of Mr. Trump, the White House or federal agencies.

It is not possible to prove that any of the donations directly led to favorable treatment from the Trump administration. And the contributions do not personally enrich Mr. Trump, unlike some of his family’s cryptocurrency ventures.

But many of the deep-pocketed individuals and corporations who have given large sums have a lot riding on the administration’s actions, raising questions about conflicts of interest.

Using Government Against the Left

 Our forthcoming book is The Comeback: The 2024 Elections and American Politics. The second Trump administration is off to an ominous start

Kenneth P. Vogel and Shane Goldmacher at NYT:

Executive actions intended to cripple top Democratic law firms. Investigations of Democratic fund-raising and organizing platforms. Ominous suggestions that nonprofits aligned with Democrats or critical of President Trump should have their tax exemptions revoked.

Mr. Trump and his allies are aggressively attacking the players and machinery that power the left, taking a series of highly partisan official actions that, if successful, will threaten to hobble Democrats’ ability to compete in elections for years to come.

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Undermining the left would amount to follow-through on Mr. Trump’s campaign promises to seek “retribution” against his perceived enemies.

The sentiment has been echoed and expanded upon by some of Mr. Trump’s closest advisers.

The billionaire Elon Musk, the top Trump donor leading the administration’s cost-cutting initiative, has appeared to encourage investigations of institutions that form the financial backbone of the left. They include ActBlue, the donation platform that helps fund virtually the entire Democratic Party and that congressional Republicans are already probing, and Arabella Advisors, a consulting firm that manages difficult-to-trace “dark money” groups that collectively have spent billions of dollars helping Democrats and their cause

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Congressional officials say the Trump administration has signaled that it intends to throw its weight behind investigations of ActBlue in the House. And Senator Ted Cruz of Texas has suggested that ActBlue might have criminal exposure. He has also demanded documents from and threatened to subpoena another key company providing digital infrastructure for the left, Bonterra, which runs a crucial Democratic voter database system and supplies much of the party’s organizing software.

Some of the president’s allies have welcomed the moves as payback for Democratic congressional investigations of Mr. Trump and Republican political networks.

Intimidated Donors

Our forthcoming book is The Comeback: The 2024 Elections and American Politics. The second Trump administration is off to an ominous start. 

 Lisa Lerer, Reid J. Epstein and Theodore Schleifer at NYT:

The demoralization and fear gripping blue America in the early weeks of President Trump’s administration have left liberal groups and their allies struggling for cash, hurting their ability to effectively combat the right-wing transformation of the federal government.

The small-dollar online spigot that powered opposition to the first Trump administration has slowed to a trickle as shaken liberal voters withhold their donations.

Charitable foundations that have long supported causes like voting rights, L.G.B.T.Q. equality and immigrants’ rights are pulling back, devoting time to prepare for expected investigations from the Republican-led Congress.

And some of the country’s biggest liberal donors have paused giving, frustrated with what they see as Democrats’ lack of vision and worried about retaliation from a vengeful president. Some Democrats say a few of their reliable donors are now openly supporting Mr. Trump, or at least looking to curry favor with him.

Fund-raising slowdowns are common after a presidential defeat and before marquee midterm races fully begin. But interviews with more than 50 donors, strategists and leaders of activist organizations show that many Democrats believe this year is different.

While Mr. Trump has not taken action against any liberal groups or lawmakers, Democrats worry his frequent threats of retribution during the campaign have led to a chilling effect on the charitable foundations and nonprofit advocacy groups that have long been pillars of the country’s civil society.

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Some donors are hiring additional legal counsel to address worries about tax audits, congressional investigations and lawsuits. Others are moving assets overseas, or at least their foundations to Democratic-controlled states.

Donors increasingly want to stay anonymous, which could slow the flow of cash to Democratic super PACs because they must eventually disclose their donors.

Donors have reason to be afraid.

Alan Rappeport, Andrew Duehren and Maggie Haberman at NYT:

The Internal Revenue Service is preparing to give a team member working with Elon Musk’s so-called Department of Government Efficiency access to sensitive taxpayer data, people familiar with the matter said.

The systems at the I.R.S. contain the private financial data tied to millions of Americans, including their tax returns, Social Security numbers, addresses, banking details and employment information.

“Waste, fraud and abuse have been deeply entrenched in our broken system for far too long,” Harrison Fields, a White House spokesman, said. “It takes direct access to the system to identify and fix it.”

 

The Leo Network

Our most recent book is titled Divided We Stand: The 2020 Elections and American Politics.  Among other things, it discusses campaign finance.

The iron law of emulation is at work. Conservative groups have made extensive use of dark money.  Liberal groups copied their example, and conservatives are copying them back.

 Heidi Przybyla at Politico:

Leonard Leo, who helped to choose judicial nominees for former President Donald Trump, obtained a historic $1.6 billion gift for his conservative legal network via an introduction through the Federalist Society, whose tax status forbids political activism.

Leo first met Barre Seid, the now 91-year-old manufacturing magnate turned donor, through an introduction arranged by Eugene Meyer, the longtime director of the Federalist Society. At the time, Leo was the society’s executive vice president, and he is currently its co-chair. Meyer envisioned Seid as a contributor to the society, according to a person familiar with the introduction. Instead, Leo cultivated Seid as a funder of his own dark money network. The result was a $1.6 billion gift announced last year — which is believed to be the largest political donation ever.


The unusual arrangement in which Leo met his top donor through the prestigious Federalist Society — which describes itself as a nonpartisan educational organization — suggests closer ties between the society and Leo’s activist network than previously known. Leo has used the dark money network to donate millions of dollars to the society and to pay at least $1.54 million to one Federalist Society employee and $775,000 to an entity run by another, according to federal disclosure forms.

Interviews with people familiar with the internal workings of the Federalist Society, including two board members, paint a picture of a symbiotic relationship in which Leo uses his connection to the vast network of scholars in the society to earn credibility with donors, who then contribute to dark money operations that engage in the kind of partisanship the society officially eschews.

Leo’s political activism and his use of donor money to enhance his own wealth have prompted increasing tensions between him and his fellow co-chair, Northwestern University Law Professor Steven Calabresi, and Meyer, who has been executive director or president for more than 30 years, according to three people familiar with the society. But they said Leo’s ties to the conservative donor base fans fears that a rift would leave the society struggling for funds, while members also worry that any breach in the facade of the conservative legal movement would only empower the liberals that all sides disdain.

Liberal Dark Money and Election Funding

Our recent book is titled Divided We Stand: The 2020 Elections and American Politics.  Among other things, it discusses campaign finance.

The iron law of emulation is at work. Conservative groups have made extensive use of dark money.  lLiberal groups copied their example, and conservatives are copying them back.

Steve Miller at RealClearInvestigations:

Democrats and their progressive allies are vastly expanding their unprecedented efforts, begun in 2020, to use private money to influence and run public elections.

Supported by groups with more than $1 billion at their disposal, according to public records, these partisan groups are working with state and local boards to influence functions that have long been the domain of government or political parties.

Registering and turning out voters - once handled primarily by political parties – and design of election office websites and mail-in ballots are being handed over to those same nonprofits, which are staffed by progressive activists that include former Democratic Party advocates, organized labor adherents and community organizers.

Republicans have opposed such efforts, passing legislation in 24 states since 2020 curbing the private financing of elections. But the GOP does not have a comparable, boots-on-the-ground effort to influence election boards and workers, and the private-funding bans haven’t proved absolute in some states.

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 Many of the progressive groups seeking to influence elections are connected to Arabella Advisors, a Washington-based, for-profit consulting company founded and led by Eric Kessler, a White House appointee during the Clinton administration.

Arabella’s projects, which include the New Venture Fund, the Hopewell Fund, the Sixteen Thirty Fund and Secure Democracy USA, had combined revenues of $1.3 billion between 2020 and 2021, tax filings show. Nonprofits supported by Arabella in 2020 gave out $529 million to “defend democracy.”

That coincided with the rise of private-public election partnerships as Facebook founder Mark Zuckerberg and his wife, Priscilla Chan, donated an estimated $350 million to the progressive Center for Tech and Civil Life (CTCL) to support local efforts in the pandemic-challenged 2020 election.

Dark Money, Aliases, and the Iron Law of Emulation

Our new book is titled Divided We Stand: The 2020 Elections and American Politics.  Among other things, it discusses campaign finance.

The iron law of emulation is at work. Conservative groups have made extensive use of dark money.  lLiberal groups copied their example, and conservatives are copying them back.

Anna Massoglia at Open Secrets:

A “dark money” group at the center of a secretive network that helped former President Donald Trump remake the federal judiciary brought in at least $50 million in revenue after it rebranded at the start of 2020 and created an alias focused on elections, an OpenSecrets’ review of tax records found.

The Judicial Education Project legally changed its name to the 85 Fund at the start of 2020. As part of the redesign, the 85 Fund took on “fictitious names” — or legal aliases — allowing it to operate under multiple different identities. The 85 Fund is part of a shape-shifting network of secretly-funded conservative nonprofits that includes the Concord Fund, which is better known as the Judicial Crisis Network.

One of the most prominent identities adopted by the 85 Fund is the Honest Elections Project, which pushed for voting restrictions ahead of the 2020 election. As a 501(c)(3) nonprofit, the 85 Fund is not allowed to spend on political activity in support of candidates but spending on voter engagement and other election issues is generally not considered to be political activity so long as it is done in a nonpartisan way.

The network is closely linked to Leonard Leo, a powerful leader in the conservative legal movement who helped shape Trump’s unprecedented effort to stack the federal judiciary with conservative judges. Leo told Axios the nonprofits were rebranded to funnel tens of millions of dollars into conservative causes around the country in a move “inspired” by the growth of an opaque liberal dark money network. Sixteen Thirty Fund, the 501(c)(4) at the center of this liberal dark money network, has sponsored projects that rivalled the conservative network’s spending on judicial nominations and Supreme Court confirmation processes.

The 85 Fund’s tax returns have not been made public as of the date of publication, but the haul of at least $50 million in 2020 marks a new record for the group’s annual revenue, raising nearly as much in 2020 as it did in the entire decade prior. In 2019, the 85 Fund raised about $13 million and in 2018 it raised less than $8 million.

Trump Warchest

Our new book is titled Divided We Stand: The 2020 Elections and American Politics.  Among other things, it discusses campaign finance.

 In 2020, Trump scammed contributors by tricking them into multiple donations that they never intend

Shane Goldmacher and Rachel Shorey report that Trump committees have nearly $102 million in cash on hand -- more than each of the party committees.

The next strongest online fund-raiser among Republican politicians was Senator Tim Scott of South Carolina, who delivered the G.O.P. response to President Biden’s first address to Congress in the spring. Mr. Scott raised $7.8 million online.

Mr. Trump’s advisers inaccurately announced on Saturday that “his affiliated political committees raised nearly $82 million” in the first six months of 2021.

That figure counted at least $23 million in transfers to his new political action committees that had actually been raised last year in other Trump-affiliated accounts, according to an analysis of federal filings.

Jason Miller, a spokesman for Mr. Trump, defended the operation’s accounting. “If we didn’t announce this entire amount, you’d be asking why we’re ignoring all of this period’s receipts,” he said of the transfers.

All told, WinRed’s filings showed that Mr. Trump had collected more than $56 million online into various accounts in the first six months of the year.

The biggest share, $34.3 million, came into a shared account with the Republican National Committee, which is known as the Trump Make America Great Again Committee; Mr. Trump’s political action committee is set to receive 75 percent of what went into the shared account, and the party received 25 percent.

In addition, Mr. Trump raised more than $21 million online directly into two new Save America political action committees that he controls.

Peter Stone at The Guardian:

Just days after his defeat last November, Trump launched a new political action committee, dubbed Save America, that together with his campaign and the Republican National Committee quickly raked in tens of millions of dollars through text and email appeals for a Trump “election defense fund”, ostensibly to fight the results with baseless lawsuits alleging fraud.

The fledgling Pac had raised a whopping $31.5m by year’s end, but Save America spent nothing on legal expenses in this same period, according to public records. Run by Trump’s 2016 campaign manager Corey Lewandowski, Save America only spent $340,000 on fundraising expenses last year.

In another move, Trump last month announced he was filing class-action lawsuits against Facebook, Google and Twitter, alleging “censorship” due to bans by the platforms after the 6 January Capitol attack that Trump helped stoke. But the move prompted several legal experts to pan the lawsuits as frivolous and a fundraising ploy.

Trump’s new legal stratagem raised red flags, in part because he teamed up with America First Policy Institute (AFPI), a non-profit group led by ex-White House official Brooke Rollins. At a press briefing with Trump, Rollins publicly told supporters they could “join the lawsuit” by signing up on a website, takeonbigtech.org, a claim belied by details on the website which featured a red button with the words “DONATE to AFPI”.

“Donald Trump is a one-man scam Pac,” said Paul S Ryan, vice-president of policy and litigation with Common Cause. “Bait-and-switch is among his favorite fundraising tactics,” Ryan stressed, noting that Trump’s Save America Pac told “supporters he needed money to challenge the result of an election he clearly lost”, and then wound up not spending any on litigation last year.

“Now he’s at it again, with frivolous lawsuits filed [in July] against Facebook, Twitter and Google, accompanied by fundraising appeals,” Ryan added. “This time he’s got the unlimited dark money group America First Policy Institute in on the racket.”

Changed World for the Crossroads Groups

Eric Lichtblau and Maggie Haberman report at The New York Times that the Crossroads groups are facing an environment that has changed considerably since 2010.

The nonprofit arm of Crossroads is facing an Internal Revenue Service review that could eviscerate its fund-raising. Data projects nurtured by Mr. Rove are being supplanted in Republican circles by a more successful initiative funded by the Koch political network, which has leapfrogged the Crossroads organizations in size and reach.

And the group faces intense competition for donors from a new wave of “super PACs” that are being set up by backers of the leading Republican candidates for president, who are unwilling to defer to Mr. Rove’s authority or cede strategic and fund-raising dominance to the organizations he helped start.

In recent weeks, Crossroads has begun carving a niche for itself in attacking Hillary Rodham Clinton, the presumed Democratic front-runner. The group will use polling data and opposition research to paint her as “a typical politician who would say or do anything to get elected,” said Steven Law, president of Crossroads.

If the group’s role seems diminished, Crossroads officials are not complaining publicly. If anything, they are lowering expectations for an organization that raised $300 million in the 2012 cycle.

“Our goal is not to make American Crossroads the big dog of 2016,” Mr. Law said in an interview. “Our goal is to win the White House and hold the Senate and the House.”

Outside Money: The Next Generation

Kenneth P. Vogel writes:

Since federal courts struck down key campaign cash restrictions in 2010, a few dozen super-rich activists have gone on a historic spending spree that has reshaped American politics. The group skews older and male, and a single death in its ranks can fundamentally reorder the political landscape.

“Obviously, I knew that he was older and that he had his health issues, but he was always really vibrant and on the go, never frail,” [CREW's Melanie] Sloan said of [liberal mogul Peter] Lewis. “I always knew that Peter was not making bequests to his groups — that the money was going to be left to his kids. So I wasn’t surprised that he didn’t leave anything for us, but that doesn’t mean it wasn’t a shock.”

Like Lewis, neither Houston homebuilder Bob Perry nor billionaire Dallas investor Harold Simmons left much in the way of a political money succession plan, and their 2013 deaths shook the financial foundation of the right. The pair had combined to donate $132 million in federal contributions, including $44 million to Karl Rove’s American Crossroads super PAC.

“When they lost those two donors last year, it was really debilitating,” a prominent conservative fundraiser said of American Crossroads.

Thus, the most influential political money networks on the left and the right have increasingly encouraged their donors’ kids to attend the closed-door confabs that serve as de facto private conventions for the big-money set, complete with strategy presentations from operatives and get-to-know-you sessions with the most in-demand politicians.

Chase Koch, the 37-year-old son of billionaire industrialist Charles Koch, has been spearheading an initiative to involve the children of wealthy contributors in the Koch brothers’ vast political network, partly by holding special events for them at the network’s twice-annual donor seminars.

The Democracy Alliance

The iron law of emulation continues to work. At Politico, Kenneth P. Vogel shines a spotlight on the Democracy Alliance:

The 21 groups at the core of the Democracy Alliance’s portfolio intend to spend $374 million during the midterm election cycle — including nearly $200 million this year — to boost liberal candidates and causes in 2014 and beyond, according to internal documents obtained by POLITICO.

While growing sums of that cash are being spent vilifying the billionaire conservative industrialists Charles and David Koch over their own network’s political spending, the documents reveal the extent to which the Democracy Alliance network mirrors the Kochs’ — and is obsessed with it.

“Conservatives, particularly the Koch Brothers, are playing for keeps with an even more pronounced financial advantages than in recent election cycles,” reads the introduction to a 62-page briefing book provided to donors ahead of April’s annual spring meeting of the DA, as the club is known, at Chicago’s tony Ritz-Carlton hotel.

The briefing book reveals a sort of DA-funded extra-party political machine that includes sophisticated voter databases and plans to mobilize pivotal Democratic voting blocs, air ads boosting Democratic candidates, while also — perhaps ironically — working to reduce the influence of money in politics.

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Liberals and conservatives have been jealously eyeing and trying to copy each others’ extraparty political and intellectual infrastructure since at least the early 1970s, when future Supreme Court Justice Lewis Powell encouraged the business community to build institutions to fight well-financed “Communists, New Leftists and other revolutionaries,” including Ralph Nader. The Powell Memo was cited approvingly by the liberal strategists who started the DA back in 2005, while Karl Rove and operatives associated with the Kochs pointed to the DA and the unions as a model for their side to replicate after Obama’s win in 2008.

Naming Names

The IRS is going after yet another conservative group.  The New York Times reports:

In a famously left-leaning Hollywood, where Democratic fund-raisers fill the social calendar, Friends of Abe stands out as a conservative group that bucks the prevailing political winds.

A collection of perhaps 1,500 right-leaning players in the entertainment industry, Friends of Abe keeps a low profile and fiercely protects its membership list, to avoid what it presumes would result in a sort of 21st-century blacklist, albeit on the other side of the partisan spectrum. 

Now the Internal Revenue Service is reviewing the group’s activities in connection with its application for tax-exempt status. Last week, federal tax authorities presented the group with a 10-point request for detailed information about its meetings with politicians like Paul D. Ryan, Thaddeus McCotter and Herman Cain, among other matters, according to people briefed on the inquiry.

The people spoke on the condition of anonymity because of the organization’s confidentiality strictures, and to avoid complicating discussions with the I.R.S.

Those people said that the application had been under review for roughly two years, and had at one point included a demand — which was not met — for enhanced access to the group’s security-protected website, which would have revealed member names. Tax experts said that an organization’s membership list is information that would not typically be required. The I.R.S. already had access to the site’s basic levels, a request it considers routine for applications for 501(c)(3) nonprofit status

Do people in the entertainment industry have any reason to fear a blacklist?  In San Francisco, KPIX reports:

An actress is facing a backlash in San Francisco’s Latino community, after she voiced support for a conservative candidate for California governor.

Maria Conchita Alonso starred in a campaign ad for Assemblyman Tim Donnelly of San Bernardino County, a Tea Party favorite who is seeking the Republican nomination.

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Alonso is an actress of Cuban and Venezuelan descent. She is perhaps best known for her role in the movie “Moscow on the Hudson” with co-star Robin Williams.

The actress was to perform next month at the Brava Theater Center in San Francisco’s Mission District in a Spanish-language version of “The Vagina Monologues,” scheduled for a run from February 14th through 17th. The show is being produced by none other than Eliana Lopez, wife of San Francisco Sheriff Ross Mirkarimi.

“We really cannot have her in the show, unfortunately,” Lopez told KPIX 5. She said Alonso abruptly resigned from the cast on Friday, given the backlash on the immigration issue.

“Of course she has the right to say whatever she wants. But we’re in the middle of the Mission. Doing what she is doing is against what we believe,” Lopez said.

Heritage v. The Administration on Libya

Following a similar video by American Crossroads, Heritage takes on the administration's changing account of the Libya terror attack:

Where to Give?

At The Wall Street Journal, Rachel Louise Ensign offers advice for people who want to give political money:

You should also be aware that some of these organizations now operate in tandem with super PACs. One of the most powerful conservative pairings of this kind is American Crossroads, a super PAC, and Crossroads GPS, a 501(c)4. The difference between the two: "On the policy side, Crossroads GPS, we are working to stop President Obama's agenda. On the political side, American Crossroads, we're looking to replace him as president," says Nate Hodson, a spokesman for both organizations.

One appeal of 501(c) groups is the promise of donor anonymity. If you give more than $200 through the traditional system or to a super PAC, your name, address and size of donation will be disclosed by the Federal Election Commission and published online. With these politically active 501(c) organizations, that's not the case.

"It's something that's worth a moment's thought," says Mr. Samples of the Cato Institute. "A Google search will frequently turn up these things."

But a word of caution: The promised anonymity may not be guaranteed. A U.S. district-court judge ruled last month that the FEC went beyond its authority when it allowed nonprofits to keep secret the identities of donors who financed certain election ads. This sets the stage for a battle over donor anonymity, says Mr. Mann of the Brookings Institution.

Meanwhile, the Internal Revenue Service—which is responsible for granting 501(c)4 status to organizations—recently asked for extensive details from certain conservative groups applying for that status, including the names of donors.

That suggests some groups may fail to pass muster, leaving their donors' names open to public scrutiny. So donors who expect anonymity should at least be sure that an organization has secured the necessary status before making a contribution

Outside Spending for Gingrich

Jeremy W. Peters reports at The New York Times:

His cash-short campaign unable to buy much advertising of its own, Newt Gingrich’s well-financed allies are coming to his rescue in Iowa, securing large chunks of airtime across the state.

Newsmax, the conservative magazine and Web site, will show a 30-minute special on Mr. Gingrich throughout the weekend in all of Iowa’s major television markets. The program is hosted by Michael Reagan, son of the former president, and makes the case that Mr. Gingrich is the strongest candidate to carry forward Ronald Reagan’s legacy.
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A second major player in conservative circles, Liberty University, the evangelical institution founded by Jerry Falwell, is also giving Mr. Gingrich some help in Iowa, running 30-second commercials in which Mr. Gingrich extols the virtues of a Liberty education.

Neither video explicitly endorses Mr. Gingrich as the Republican nominee, but their pro-Gingrich messages raise a host of election law questions and highlight how loopholes in the law allow politically motivated groups to influence the outcome of elections. Liberty, a nonprofit, tax-exempt organization, is prohibited by law from participating in campaign activities on behalf of any candidate. Newsmax, a corporate entity, is also limited in its political activities but is now much freer to get involved since the 2010 Citizens United Supreme Court case.

Liberty is the second organization in recent weeks to advertise on Mr. Gingrich’s behalf in Iowa. Citizens United, the nonprofit that produces conservative films, has been showing old commercials featuring Mr. Gingrich, the former House speaker, and his wife, Callista, promoting a video on Ronald Reagan.