Who Is Leonard Leo’s Mysterious Dark Money King?

A few months before the midterms, with pollsters spewing red wave predictions

A few months before the midterms, with pollsters spewing red wave predictions and post-Roe conservatives planning to force raped children to give birth, a bit of political news added to progressives’ gloom. A Chicago billionaire had gifted anti-abortion Supreme Court fixer Leonard Leo the largest known tranche of dark money in U.S. history: $1.6 billion. The sum is staggering; it will finance at least a generation of extreme right-wing political proselytizing. And almost no one—except for the conservative cabal that bagged the whale—had heard of him.

The gift from nonagenarian electronics magnate Barre Seid (pronounced Barry Side) is effective altruism in reverse: a fire hose of cash aimed at destroying American liberal culture through lawsuits and support for politicians challenging gay rights, unions, environmental protection, voting rights, and public education. The money will last a good long while. Philanthropic recipients usually follow a 5 percent rule: They try not to spend more than 5 percent of the endowment per year. Seid's pile is so large that it could return an average $136 million a year, or north of $230 million on a good year, to influence U.S. law and policy. Without ever having to touch the nut. For a sense of how enormous that is, consider this. The Heritage Foundation and its affiliates spent about $86 million in 2021. Heritage is a huge, and hugely influential, conservative think tank. Leo could create two Heritage Foundations and one more sizable organization on the side—all, again, without having to dip into the principal at all.

Leo, a New Jersey Roman Catholic and grandson of an Italian immigrant who worked for Brooks Brothers, hobnobs around the upper echelons of American power in natty suits with vests and a pocket watch on a gold chain. This foppish dandy is the Penguin in the pantheon of Washington, D.C., DC Comics villains. Leo is a proud "Knight of the Sovereign Order of Malta," and his long career has been motivated by fanatical opposition to women's rights to reproductive choice. Since Seid handed the money over in 2021, part of the pile has been funneled into black boxes like Donors Trust, a mega-donor money-washing machine. Having succeeded at subjecting American women to forced pregnancy, Leo, 57, is directing the money toward other goals: stopping "woke" culture, ending federal regulations on climate change, and limiting voting rights. Ultimately, Seid's money will be used to shore up society's winners—the American oligarchy, inherited trusts, CEOs, self-made billionaires, corporations—against the demands of the weak. It will be used to make the United States a tougher and, for many, a nastier country, where big money always wins, under the eye of Rambo Jesus.

All that from a man nobody knows.

Steven Baer is, like Leonard Leo, a career anti-choice fanatic, but with a political style from the Roger Stone School of Ratfuckery. The Illinois fringe conservative built himself a minor national reputation by shaming enemies like Donald Trump and Kevin McCarthy with salacious dirt. Even the conservative National Review finds Baer hard to stomach, calling him "the world's most successful email harasser." After decades in Illinois conservative politics, Baer now resides in Florida part-time, and spends his time sipping tequilas and IPAs, and texting streams of Atlantic Coast sunrises, cats, bloody aborted fetuses, and the sins (he uses that word) of Donald Trump and Kevin McCarthy to email addresses and phone numbers of right-wing donors, politicians, and journalists.

Baer had his fetal rights epiphany as a student at Brown in the early 1980s, when he "saw photographs of piles of corpses at Auschwitz juxtaposed to photographs of piles of dead babies," he told me, suggesting that legal abortion was equivalent to the Holocaust and abortion clinics the feminist version of Hitler's gas chambers. He then spent much of his career raising hell and money from a wacky corner of fringe right-wing politics. He famously mass-emailed a rumor about Kevin McCarthy and an extramarital affair in 2015, and before that Baer became known as a kind of right-wing merry prankster, with stunts like holding a press conference in Illinois with fake lawmakers dressed as pigs. He was known in the local press as "a major irritant," forever pulling political pranks and "high jinks," but always good for a quippy quote and some political gossip.

And now, he is the mystery donor's self-appointed Boswell.

When The New York Times broke news of the bequest in August, Baer was the only source among Seid's friends and acquaintances who talked to journalists. And he's still at it. He told me that he wants to talk about the old man because he's afraid that Seid, whom he describes as a father figure, will die without ever getting his proper due as one of the great right-wing financiers of the age.

In 1986, Baer was a twentysomething conservative with a job soliciting money for a fringe offshoot of the Illinois GOP called the United Republican Fund. The organization wasn't doing so well. Baer studied the Lotus spreadsheet and noticed one consistent donor who repeatedly gave $999. The guy had, as Baer saw it, "a funny name, looked Arabic." But the precision of the number and regularity of the gifts suggested a money tree that might be shaken a little harder.

He decided to track down the donor he had taken to calling Mr. 999. He found Barre Seid at the helm of a company called Trippe Manufacturing, in a rented building in the city's downtown, "a rat warren" packed with carrels—a phone operation. The company was just then transitioning from one that produced police and ambulance lights to one that sold digital-age electronic gadgetry. The president explained that he had chosen the $999 number to keep himself anonymous. "He didn't know if it was solicitors or [Federal Election Commission] types or government," Baer recalled. "He had just intuited that nine-nine-nine keeps you off more radars than a thousand. He did it out of a kind of a shyness or a desire not to be in the targets."

Baer quickly recognized in Seid a cultivatable mark. He began spending long evenings talking politics with the old man, who liked to work late after his employees went home. He bought Seid a copy of Chris Matthews's book Hardball to help the older man understand that politics, as generations of Chicago politicians would say, ain't beanbag. Seid, a secular Jew, didn't seem to care much about the abortion issue, but Baer saw his potential. He describes their relationship as a kind of father-son situation (Baer's father was born exactly one day before Seid, who is childless). Mr. 999 was happy to contribute to Baer's United Republican Fund and its events, but he remained adamant about avoiding attention. Nevertheless, by 1990, Baer had persuaded Seid to poke his head above the anonymous parapet. Seid made local news with a $500,000 loan to Baer for a failed gubernatorial run. After that baptism by media, Seid was ready to meet other conservative donors.

Baer likes to say of his father figure that "he's shy," and indeed Seid, who turned 91 in April, has gone to great lengths to protect his "anonymity paranoia," as Seid calls it. Baer noticed that he kept his donations just under the reporting limit. He's been implicated in covert endeavors like trying to transform a broke liberal arts college into a capitalist incubator and rename a public law school after one of the Supreme Court's staunchest right-wingers. Seid even used an alias, Elbert Howell, on official papers as CEO of his own company.

But the shadowy Mr. Howell has lived too many years into the internet age to erase his story entirely. His father and grandparents arrived in New York from Russia before the turn of the last century. Father Reuben heaved himself out of the garment trade, became a prominent Chicago optometrist, and had two sons. Young Barre was very smart. He built a TV remote control as a child. He entered the University of Chicago at age 14 as part of an advanced program for teens and got degrees in English and economics from the universities of Colorado and Pennsylvania.

After a short stint in the Army, Seid went to work. He was good at a lot of things. He had a natural aptitude for engineering and a head for numbers. In 1959, he joined a company that made rotating lights for police cars and ambulances and later became a de facto chief engineer, even though he was not trained in engineering. Within a decade, Seid bought Trippe Manufacturing and became president of Tripp Lite—the company that he expanded into the global electronics concern that Leonard Leo sold for $1.6 billion.

Neither Seid nor Leo would talk to me. Baer would—in fact, he wouldn't stop talking, albeit with brazen exchange demands that involved, at one point, a request that I phone up Herschel Walker and ask him about abortion (I didn't).

To try to cut through the veil, I decided to do my own tour of Barre Seid's Chicago, hoping to coax out former colleagues and friends and relatives. I started with a drive-by of a factory he owns, not far from the shores of Lake Michigan in Michigan City, Indiana. Seid made his fortune in electronics, but his business interests have included industrial chemicals and related manufacturing. While at Tripp Lite, Seid was also president of a chemical company, Yates Manufacturing, in Chicago.

In 1975, he bought a company called Fiber Bond, then located in a heavily polluted industrial swath of Chicago. The company had been in the fiber and fabrics division of Union Carbide, producing padding and fibers, which at the time contained asbestos, for the car industry. Fiber Bond's original Chicago site is fouled with lead paint and asbestos. Seid moved the Fiber Bond factory to Michigan City, and from a blue-and-white plant on an expanse of prairie weeds, it still makes high-tech, nonwoven materials and "paint/finishing filtration" products for HVACs and industry.

From Michigan City, I tooled back to Chicago via the hectic expressway that rims Lake Michigan and passes Gary, Indiana. That city is best known as the birthplace of the Jackson 5. It is also home to the Ninth Avenue Dump, one of the Superfund sites that Fiber Bond and other companies used. Three decades of environmental remediation and lawsuits have still not cleaned the 17-acre site of a witches’ brew of poisons including cyanide, chlorinated ethane, PCBs, volatile organic compounds, and ketones, dumped by a large group of polluters. The Environmental Protection Agency's most recent report states that concerns about area groundwater are still being addressed.

I could find no evidence that Seid ever contributed to the cleanup. In a building application in Chicago, Seid acknowledged that Fiber Bond was notified in 1986 and again in 1989 that it was deemed potentially responsible for dumping at Superfund sites in Michigan City and Gary, but he rejected responsibility. He wrote in the application that "Fiberbond, during the time it has been an ‘affiliated entity’ of Applicant, did not dispose of waste at such landfills." He added that the company had not been ordered to pay "damages, costs, or expenses."

Seid expanded Tripp Lite's products from ambulance, fire truck, and police car lights to electronics in the mid-1980s and started selling surge protectors, power strips, and other digital-age electronic hardware. These products proved to be the old man's ticket to donor Valhalla, ensuring the uninterrupted power supply every man, woman, child, office, hospital, and video gamer needs. "As the computer boom took off, people would get really pissed when there was a power blip, and they’d lose all their Lotus 1-2-3 data," Baer recalled of Tripp Lite's surge protector. "Barre was just an incredibly brilliant Jewish entrepreneur." (Baer is a Christian.)

Seid was perfectly positioned as Bill Gates and Steve Jobs were inventing their products on the West Coast. But he was the opposite of a disruptor. He was not looking to make something to change the world. If a product could be made for less and still work, that was more than good enough for him. His fortuitous timing and penny-wise approach made him very rich. Seid's annual income exploded in the mid-2000s, hitting $157 million in 2018, of which $136 million was from Tripp Lite, according to tax records obtained by ProPublica.

After a visit to Tripp Lite headquarters, I drove north on the first long night of November, the night before the 2022 midterms, to Seid's house. By billionaire standards, the man lives very humbly, in a modern brick two-story, valued at around $2 million, on a street in the upper–middle-class neighborhood of Lincoln Park. It is a family-friendly enclave of wine bars, restaurants, stately homes with porches, sidewalks shaded by large maples, and residential apartment buildings. Seid's five-bed, four-bath, 3,848–square-foot with a three-car garage and roof deck is no fortress, but it's not inviting either—nestled behind ivy-covered walls. The few windows, very high and very small, look like factory exhaust portals.

The arc of Seid's personal life lies entirely in Chicago. It includes two wives and a playboy period spent buying and racing Porsches. In 1968, he married Adrienne Gruber, the child of a Ukrainian immigrant who was apparently hit so hard by the Depression that he sent his son (but not his daughter) to live with foster parents in central Illinois. Adrienne Gruber Seid was a student at the School of the Art Institute of Chicago, or SAIC. In June 1970, two years after their wedding, she died. Seid later founded a small fellowship in her name at SAIC. Next came the decade-long playboy phase. Then, in the early 1980s, with Tripp Lite's surge protectors about to make him superrich, he settled down and married an aspiring Greek American opera singer 25 years younger.

Around the time of his second marriage, he pulled a Charles Foster Kane and founded the Chamber Opera Chicago, a small company that for the next decades showcased Chicago-born mezzo-soprano Barbara Landis Seid in teeny-tiny operas performed at various venues, including a theater not far from their home. A reviewer of the Chamber Opera's production of Il Trovatore in 2003 wrote, "Mezzo soprano Barbara Landis Seid, an attractive young woman, seems to delight in playing deranged ladies, which makes her just right for Azucena."

The couple tried, but never had children. No pets. They favor a spartan lifestyle. They order in, eat at home, and watch old movies, Baer said. Seid fancies himself an aesthete, and, like David Koch in New York, he has donated to his city's cultural institutions. "I’m a successful adult male who gets pleasure out of seeing nice things happen," Seid once told a journalist about founding the opera. "I’m not a musician but I have a talent for running things." He has donated millions to the arts in Chicago, including the University of Chicago, area orchestras, and the School of the Art Institute, where he's an honorary member of the governing committee.

It's a good bet that the School of the Art Institute's administrators and other culture beneficiaries do not support, say, the seating of homophobes and right-wing extremist justices on the nation's highest court, who will reinstate back-alley abortions, discrimination against gays, and limiting voter rights to favor a fascist minority. But school officials I reached out to declined to talk about him. Former and current Chamber Opera creative directors, musicians, and set directors also ran for the hills. A Bulgarian sculptor whose work is planted in the Tripp Lite HQ parking lot was the only one who talked. In the aughts, Seid bought a large work—a delicately wrought iron model of a ship—by Boyan Marinov, and invited him to his office to close the deal. Marinov remembers a small man with a large telescope near his desk. "It was like meeting Bruce Wayne," he said.

After Baer came along, Seid was dabbling in the political influence game, but mostly on local candidates who supported issues like school choice. He made four- and five-figure donations in local races in Illinois and Wisconsin and Iowa where candidates were pushing his pet issues. Baer introduced Seid to the Koch network. "Around 2005, 2004, 2005, I’m pushing Barre to swing for the fences regarding applying his money to affect American politics and culture," Baer said. "I spoke at two of Koch's big famous donor gatherings in Palm Springs and Aspen." Seid, of course, didn't attend these events, but through Baer he started "fraternizing" with Charles Koch, who had just set up the Cato Institute as a nonprofit think tank. In the early 1990s, Seid forked over what Baer reckons to be many tens of millions for a Cato spin-off, U.S. Term Limits. The project was an early test of the power of Koch dark money, and an incubator for rising right-wing politicos like Mike Pompeo. "Barre had this low profile and a kind of a fearlessness," Baer said. "When he intuited yeah, this is really good and it's compelling, he would then drop unbelievable amounts of money, by my standards. I remember one year it was $20 million. All of it 501(c)(4) invisible."

During those years, Baer encouraged Seid to deepen his support for Israel, introducing him to a project that connected Israeli right-wingers with American evangelicals, so-called Christian Zionism. Seid then became a generous donor to Israeli causes. In 2011, he traveled to Israel with his wife to accept an honorary degree from Bar-Ilan University for "supporting those organizations which will fortify Israel's position in the world." A photo from the award ceremony is one of the few publicly available pictures of Seid.

Besides the cultural recipients of Seid's largesse, political beneficiaries have largely maintained omertà. To mangle an idiom: Why expose a gift horse with your mouth? The Chicago-based climate-denial Heartland Institute, for example, received many of Seid's millions. Its leaders refused to acknowledge him publicly, even after he was outed, continuing to refer to him as "anonymous." "He is entitled to his privacy," said Joseph Morris, the chairman of Heartland's board of directors, when I called his office.

The only chatterer has been Steve Baer, a man who, before retiring, dabbled in reverse mortgages for senior citizens. As I reported on this story, Baer veered between helpful and avenging-angel righteous, hell-bent on converting a feminist into an "abortion abolitionist." He put me on a text string that he boasted included Ohio Representative Jim Jordan and Leonard Leo. Few recipients replied to his memes and effusions, with the exception of one or two delicate flowers from the anti-choice movement, presumably female, horrified at Baer's repeated use of the word "pussy," who begged to be removed. He ignored them.

As crude as he is, Baer has clearly been useful to both Seid and Leo. Baer was a key link in the chain between the reticent Midwestern billionaire and the powerful D.C. fixer whom The Washington Post has anointed as a man "on a mission to turn back the clock," and whom Clarence Thomas has called "the number three most powerful person in the world."

About 20 years ago, as Seid was turning 70 and rolling in the dough, he started thinking about his legacy, Baer recalled. His younger brother Richard is a liberal with six kids—Seid refers to one of the children as "nepot" and tried to help get that one into law school. Gifting already comfortably well-off relatives didn't appeal to him. Nor did buying a "Seid" wing for a hospital or a university. Baer recalled: "He's 70. He's making maybe 30 million a year on S-corp profits. He joked about the Edifice complex. He would give what he wanted to give, but he was never motivated by the plaque or the name."

Seid had very particular political interests, simultaneously regressive and grand. In 2007 and 2008, a tiny, nearly broke Chicago-area college that focused on the Great Books received an anonymous infusion of $825,000. The money saved Shimer College but it came at a price. First, the college's board of trustees was expanded, with 13 new members, who all turned out to be right-wing activists. Most had financial ties to Seid, either as employees, colleagues, or recipients of his political donations. They included John C. Marienau, at the time president of Fiber Bond, and an array of beneficiaries of Seid's political money, including Joseph Bast, the president and chief executive of the Heartland Institute; television producer Bob Chitester, who founded the right-wing Palmer R. Chitester Fund; and Dennis Katz, a rabbi of the Congregation Shaare Tikvah B’nai Zion in Chicago.

Shimer's new president, Thomas Lindsay, who served in the Bush administration as deputy chairman of the National Endowment for the Humanities, installed the new trustees. Soon, the tiny school (enrollment around 100) was offering a new class called the Morality of Capitalism, created and taught by Marsha Familaro Enright, a member of the adjunct faculty. Enright was also talking about creating a college, to be called the College of the United States, which was going to offer a "curriculum that demonstrates the virtues of Western culture, capitalism, and markets."

Before the school could be turned into anything resembling the College of the United States, a former student ferreted out the source of the funds: the Barbara and Barre Seid Foundation. The school's students and faculty rebelled, and the takeover failed. But the goal of selling capitalism as a moral virtue never died. Prior to his death in 2011, Seid's CEO Marienau arranged for an annual posthumous symposium in his name at his alma mater in Nebraska. The John C. Marienau Symposium on the Morality of Capitalism appears to still be functioning. Just before the Covid shutdown in March 2020, the symposium sponsored a two-day event in Omaha promoting the benefits of market-based rural health care. The theme of the symposium was "Schumpeter's Creative Destruction: How Market Forces and Technology Will Reshape Rural Health Care."

Elbert Howell moved on to bigger institutions. Between 1998 and 2006, Seid pumped more than $3 million to the Mercatus Center, a free-market think tank at George Mason University.

Seid soon bankrolled a much more successful right-wing school takeover at GMU's law school. In 2016, the George Mason School of Law announced it was changing its name to the Antonin Scalia Law School. At the time, The Washington Post reported that a $20 million grant from an anonymous donor had made the name change a condition of the gift. A former student discovered the likely source, gaining access to a trove of emails through the Freedom of Information Act. The group UnKoch My Campus eventually issued a report, based on a public-records request, implicating Seid as the anonymous donor behind the name change.

Besides that revelation, the 800 pages of FOIA’ed emails showcase the fawning obsequiousness of GMU's law school dean and others. They flatter Seid's intellect. They trash climate change, the welfare state, and the "ugly apparatus of modern government" with him, hurl loathing at the American Bar Association for its judicial accreditation process, and sneer at the university accreditation system. The men never miss a chance to turn an interaction with the whale into an opportunity for personal puffery, book promotion, and general unctuousness.

In August 2019, Seid shot Francis H. "Frank" Buckley, a conservative GMU law professor, a link to an article about how lawyers had moved dangerously to the left. "This change in an important class of citizens contributes greatly to the restless state of our republic," wrote the author, John O. McGinnis. "Lawyers as a group also pose the greatest obstacle to a revival of a sound jurisprudence, like an originalism that appropriately respects precedent." Buckley shot back: "Yeah. And I’m teaching them! My hope is that the Scalia brand tends to inoculate them."

The emails also suggest Seid was pushing certain people on to GMU faculty, such as Douglas Ginsburg, a former chief judge of the U.S. Court of Appeals for the District of Columbia Circuit. In addition, according to UnKoch My Campus volunteer advocate Allison Pienta, Seid may have had a say in appointing Brett Kavanaugh as an adjunct. He was appointed three months after GMU notified a donor—believed to be Seid—regarding potential faculty hires. Any hint of a Seid-Kavanaugh connection is catnip for researchers and conspiracy theorists who have tried and failed to learn who paid Kavanaugh's credit card debt (estimated to be between $60,000 and $200,000) before he was nominated to the Supreme Court. There has never been an on-the-record answer to this question. The FBI briefed the Senate Judiciary Committee on Kavanaugh behind closed doors. Among the attendees was Rhode Island Democratic Senator Sheldon Whitehouse, a Judiciary Committee member and opponent of dark money.

Whitehouse told me he wouldn't rule out a Seid connection. "It would not surprise me," Whitehouse said. "Kavanaugh was a very enthusiastic and energetic campaigner auditioning for the Supreme Court. He made 50 appearances at the Federalist Society, where Leo was executive vice president for many years. He managed to get himself on the Leo-managed Trump list. Clearly there was a lot going on behind the scenes."

The first public connection between Barre Seid and Leonard Leo is believed to have happened around 2011, when Leo joined the board of an entity Seid had founded, the Chicago Freedom Trust, which was in some ways a predecessor to Marble Freedom Trust, the portal through which Seid's $1.6 billion entered Leonard Leo's right-wing dark money sphere.

Seid could have donated his fortune to any number of right-wing players. But he chose a Catholic fanatic whose main issue has been forcing women to give birth—never an issue Seid was really moved by, according to Baer. Why did he choose Leo? Precisely because of Leo's control over the court system. "The intersection is the Supreme Court," Baer said. "Because the Supreme Court deals in all subject matter, and if you could get a Supreme Court that's originalist along Scalia/Thomas lines, then that's great. And Leonard's famous skill building the Federalist Society and then eventually, most famously, becoming the guy who holds the hors d’oeuvre tray up to Trump that says: Here, pick Amy [Coney Barrett] or pick Neil [Gorsuch]. That, I believe, is what closed the sale for Barre. I think [the deal] was going before, say, Amy, but that proximity to power and the ability to serve up originalist judges, because it really covers all of American life, business, as well as the one thing Leonard cares about." (Leo pulled back from the Federalist Society in 2020 but has remained involved in right-wing judicial activism.)

Seid's bequest to Leonard Leo was a complex tax maneuver long in the planning. The legacy involved cashing in not only his own businesses, but his brother's pigeon repellent company. In 2021, Seid's brother's company, Bird-X, and Tripp Lite formally combined. Seid donated 100 percent of the shares of Tripp Lite to Marble Freedom Trust, just before Tripp Lite was sold to an Irish company for $1.6 billion. The operation was cloaked in secrecy. Eaton, the Irish company that bought Tripp Lite in March 2021, revealed nothing in its purchase announcement. As a private company, Tripp Lite was not required to disclose the donation.

As trustee and chairman of the Marble trust, Leo makes $350,000 a year and has "primary authority" to decide how the money is spent, according to a tax filing reviewed by The New York Times. And in its filing, Leo's Marble trust never named Tripp Lite, "to protect donor confidentiality," according to the Times. The scheme enabled Seid to avoid about $400 million in federal and state tax.

Leo has only made one statement about the bequest—comparing Seid to the Hungarian billionaire George Soros, the mythic bogeyman for the right wing. "It's high time for the conservative movement to be among the ranks of George Soros, Hansjörg Wyss, Arabella Advisors, and other left-wing philanthropists, going toe-to-toe in the fight to defend our Constitution and its ideals," Leo said to The New York Times.

Since the bequest was revealed, researchers and journalists have been trying to identify how the money is being used. Leo appears to be funneling it into a dark money network that buys election influence through what the IRS classifies as "social welfare" and indirectly through the courts. Some of the money already appears to be influencing the 2024 election: According to an April report in The Lever, Leo has directed funds to a super PAC backing Ron DeSantis and to nonprofits affiliated with Mike Pence and Nikki Haley.

The amicus curiae brief is one of the network's favored weapons. ProPublica has identified at least six groups funded by Leo's network that have filed amicus briefs supporting a Colorado web designer, Lorie Smith, who wants to refuse to work for gay people, and whose lawsuit, now at the Supreme Court, would overturn Colorado's anti-discrimination law. Twenty Republican attorneys general have also filed an amicus brief in support of the case through the Republican Attorneys General Association. RAGA has received huge tranches of Leo's largesse for years. In 2022, a Leo-connected group donated $6.5 million to RAGA, according to ProPublica. RAGA money went into PACs targeting Democrats in the midterms. RAGA coordinates Republican attorneys general in pro-corporate, anti-progressive legal action. Those include 19 attorneys general who are pressuring investors like BlackRock to abandon environmental, social, and governance, or ESG, investments aimed at curtailing climate pollution. RAGA money has also been traced to organizations involved in the January 6 insurrection, and the group filed an amicus brief in support of dismissing federal criminal charges against Michael Flynn, the Trump administration's former national security adviser who pleaded guilty to lying to the FBI.

Other organizations linked to Leo, including the Judicial Crisis Network and the Republican State Leadership Committee's Judicial Fairness Initiative, are pouring money into state judge races. A Grid News investigation found that Leo-connected groups have put "$31 million in campaign funds into at least 42 races for seats on state Supreme Courts or other high-level state judgeships in 15 states since 2010." These obscure, low-interest races are increasingly critical as the Supreme Court tosses decisions about everything from abortion to elections down to the states.

Senator Whitehouse has devoted himself to tracking dark money, especially money aimed at reshaping the law and court-packing. He has given much thought to what motivates a man to leave his entire fortune to a regressive, dark money funnel. "Poor man wanna be rich, rich man wanna be king," Whitehouse said, quoting Bruce Springsteen. "That's the song. If you are a creepy right-wing billionaire and you know the public hates your view of the world, the only way to be king is to work your way around democratic processes, go clandestine, and find a scamp like Leonard Leo who knows how to move levers secretly."

Seid's bequest is believed to be the largest dark money donation in U.S. history. Charitable nonprofits are required to disclose their major donors, but the IRS class of political recipients defined as "social welfare" groups like Leo's Marble trust are not. "Seid's donation seems to be one of the largest, if not the largest, single political donation ever given," said Kathleen Enright, president of the Council on Foundations, a nonprofit association of philanthropic entities. "But to be clear, this is not a charitable contribution by any means. It is a political contribution made to support a political agenda."

How it works is: If Warren Buffett sets up a charitable foundation, a 501(c)(3) organization under IRS rules, it must spend transparently. Political action committees engaging in candidate support also must disclose donors. But when a billionaire throws a fortune at a "social welfare," 501(c)(4) status organization, the IRS doesn't require donor disclosure. Beyond Leo and his coterie, nobody knows how the money is being spent, or whether Seid put any restrictions on it. If Leo's past is precedent, the money will support cherished right-wing goals: expanded gun rights, further erasure of the wall between church and state, rollbacks of civil rights on various fronts, and federal and state judges who will rule favorably on those issues.

Some of the money might wind up in the pockets of Leo and his pals. In March, Politico published an investigation finding that Leo-controlled nonprofits moved $43 million into his for-profit political consultancy, CRC Advisors, which he has been running since around the time of the Seid donation. The investigation dated the start of Leo's "lifestyle upgrade," with real estate and other perks, to 2016, the year he became Trump's judge-picker.

In the wake of the Politico report, Senator Whitehouse and others are calling for an IRS investigation. "Leonard Leo's new lavish lifestyle appears to be his reward for helping anonymous right-wing billionaires capture our Supreme Court," Whitehouse said in a statement to The New Republic. "But questions remain about how he is getting paid and by whom, and who is behind the front groups communicating instructions to the justices through amicus briefs. People need to understand the level of coordination among dozens of supposedly independent groups that are played like piano keys by a manipulative donor elite. It's an operation, not a coincidence."

Whitehouse cited "Republican political battering of a previous IRS Commissioner" for the agency's oversight "ineffectuality." Kathleen Enright concurred. "The charitable sector has always valued and supported fair oversight," she said. "However, the IRS division that regulates these organizations has been hollowed out in recent years, so the mechanisms to ensure the checks and balances that preserve the credibility of nonprofits, and the people and organizations that fund them, is woefully inadequate. Rebuilding that accountability and enforcement capacity is an important first step to rebuilding trust in the sector."

Besides the question of what to spend Seid's pile on, Leo can also decide how long to hold on to the money. He could spend Seid's money all at once, essentially dropping a billion on a candidate or cause on one or a few cycles. Or he could treat it more like an endowment, invest it, and spend the income. That choice is not available to most charitable entities, since they rarely receive such large gifts, Enright said. "An operating nonprofit that received a gift of this size would be wise to put some portion into an endowment for future needs, given that it's unlikely they will receive similar gifts in the future."

Gara LaMarche is a past president of Democracy Alliance, a group of liberal donors, and no stranger to allocating big money. In his previous position as president of Atlantic Philanthropies, LaMarche spent half a billion dollars a year in the process of doling out a $4 billion fund according to the wishes of billionaire Chuck Feeney, who made his fortune in duty-free shops. Feeney had mandated that the money be spent over a short time on four program areas: population health, aging, disadvantaged youth, and human rights and reconciliation. Atlantic laid a great deal of grassroots groundwork for the passage of Obamacare.

Still, LaMarche is impressed by the Seid donation, which he compared to the endowment of a very significant charitable foundation. The Democracy Alliance has never spent more than $100 million a year, he said. He wouldn't hazard a guess as to what Leo plans to spend it on, but LaMarche suggested several possible spending styles. Leo could spend it fast—say, $400 million over four election cycles. "Shorter time, bigger impact," said LaMarche. "Or he could save it and spend it as an endowment. It's enough money so you could have a very significant program just off the interest of the endowment—hundreds of millions of dollars without touching the nut. My guess is it will be a combination."

Besides legally saving him hundreds of millions in taxes, Seid's structuring the gift as a stock transfer increased the size of the gift by 20 to 25 percent over what it would have been if Seid first sold his shares and then made the donation. "Under current law, that approach just makes sense," Enright said. "However, the broader questions remain of whether this scale of influence on our elections is good for our democratic system, and whether donors to political causes should be able to reap tax benefits by structuring gifts in this way. If you believe unchecked political giving is unhealthy, as we do, that requires changes to the law."

Philip Hackney is associate professor of law at the University of Pittsburgh, specializing in nonprofits and their tax exemptions. Hackney explained that the IRS has been battered from the right, first in 2014, after a manufactured scandal alleging that the Obama IRS targeted conservatives, and further with a Trump-era IRS decision to stop requiring recipients of political dark money to reveal the names of donors. "The system is allowing people to completely avoid wealth tax on future generations and accomplish political goals," Hackney said. "Then the IRS moves in 2019–2020 made it very hard to see these wealth games happening. We are ensconcing dynasties and giving federal money to accomplish that. Why would you allow a billionaire to use this system to get more money from government to accomplish their goals?" Hackney offered an answer to his own question: "There is a part of our institutional structure that believes wealthy people are brilliant and deserve the right to ample political speech."

The Barre Seid bequest should alert all Americans to the extent of the damage Citizens United does to democracy. So far, it has only caused ripples of fear through the political junkie class on the progressive side. But it should freak you out, and here's why.

The Federalist Society, with an annual expenditure of around $20 million, remade the Supreme Court and seeded the federal bench with enough extremists to overturn gun control laws in places like New York and Chicago, chip away at the Affordable Care Act, and overturn the Food and Drug Administration when it comes to approval of an abortion pill. Leo's people spent a mere $6.5 million to gin up an amicus curiae machine that, for example, aims to ensure that discriminating against gay people is federally protected.

With Seid's help, Leo and friends can blow $30 million a year – almost twice the Federalist Society's old budget, a drop from the Seid bucket, pushing the federal bench further to the right. They could blow another $30 million promoting lies about fossil fuels. And on and on and on.

Why stop there? With Seid's help, Leo and friends can blow $30 million a year—almost twice the Federalist Society's old budget, a drop from the Seid bucket, pushing the federal bench further to the right. They could blow another $30 million promoting lies about fossil fuels. And another $30 million helping radical right-wing state legislators ban the teaching of slavery. They could found a whole institution dedicated to the cherished extremist goal of ending the progressive income tax. Spend $100 million on that project—and still not have touched the principal.

All that, and Mr. Leo will have spent just $200 million, a mere 12.5 percent of the Seid bequest, easily covered by the average income it accrues annually. Leonard Leo, Sovereign Knight of Malta, can run such projects, and anything else that strikes his regressive fancy, year after year, remaking American society in as many ways as there are right-wing causes, as long as money exists.

Medieval popes had less power.

Nina Burleigh is working on a memoir about growing up Iraqi American.

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