This article first appeared at ProPublica. ProPublica is a Pulitzer Prize-winning investigative newsroom. Sign up for The Big Story newsletter to receive stories like this one in your inbox.

In late June 2019, right after the U.S. Supreme Court released its final opinion of the term, Justice Clarence Thomas boarded a large private jet headed to Indonesia. He and his wife were going on vacation: nine days of island-hopping in a volcanic archipelago on a superyacht staffed by a coterie of attendants and a private chef.

If Thomas had chartered the plane and the 162-foot yacht himself, the total cost of the trip could have exceeded $500,000. Fortunately for him, that wasn’t necessary: He was on vacation with real estate magnate and Republican megadonor Harlan Crow, who owned the jet — and the yacht, too.

For more than two decades, Thomas has accepted luxury trips virtually every year from the Dallas businessman without disclosing them, documents and interviews show. A public servant who has a salary of $285,000, he has vacationed on Crow’s superyacht around the globe. He flies on Crow’s Bombardier Global 5000 jet. He has gone with Crow to the Bohemian Grove, the exclusive California all-male retreat, and to Crow’s sprawling ranch in East Texas. And Thomas typically spends about a week every summer at Crow’s private resort in the Adirondacks.

The extent and frequency of Crow’s apparent gifts to Thomas have no known precedent in the modern history of the U.S. Supreme Court.

These trips appeared nowhere on Thomas’ financial disclosures. His failure to report the flights appears to violate a law passed after Watergate that requires justices, judges, members of Congress and federal officials to disclose most gifts, two ethics law experts said. He also should have disclosed his trips on the yacht, these experts said.

Thomas did not respond to a detailed list of questions.

In a statement, Crow acknowledged that he’d extended “hospitality” to the Thomases “over the years,” but said that Thomas never asked for any of it and it was “no different from the hospitality we have extended to our many other dear friends.”

Through his largesse, Crow has gained a unique form of access, spending days in private with one of the most powerful people in the country. By accepting the trips, Thomas has broken long-standing norms for judges’ conduct, ethics experts and four current or retired federal judges said.

“It’s incomprehensible to me that someone would do this,” said Nancy Gertner, a retired federal judge appointed by President Bill Clinton. When she was on the bench, Gertner said, she was so cautious about appearances that she wouldn’t mention her title when making dinner reservations: “It was a question of not wanting to use the office for anything other than what it was intended.”

Virginia Canter, a former government ethics lawyer who served in administrations of both parties, said Thomas “seems to have completely disregarded his higher ethical obligations.”

“When a justice’s lifestyle is being subsidized by the rich and famous, it absolutely corrodes public trust,” said Canter, now at the watchdog group CREW. “Quite frankly, it makes my heart sink.”

ProPublica uncovered the details of Thomas’ travel by drawing from flight records, internal documents distributed to Crow’s employees and interviews with dozens of people ranging from his superyacht’s staff to members of the secretive Bohemian Club to an Indonesian scuba diving instructor.

Federal judges sit in a unique position of public trust. They have lifetime tenure, a privilege intended to insulate them from the pressures and potential corruption of politics. A code of conduct for federal judges below the Supreme Court requires them to avoid even the “appearance of impropriety.” Members of the high court, Chief Justice John Roberts has written, “consult” that code for guidance. The Supreme Court is left almost entirely to police itself.

There are few restrictions on what gifts justices can accept. That’s in contrast to the other branches of government. Members of Congress are generally prohibited from taking gifts worth $50 or more and would need pre-approval from an ethics committee to take many of the trips Thomas has accepted from Crow.

Thomas’ approach to ethics has already attracted public attention. Last year, Thomas didn’t recuse himself from cases that touched on the involvement of his wife, Ginni, in efforts to overturn the 2020 presidential election. While his decision generated outcry, it could not be appealed.

Crow met Thomas after he became a justice. The pair have become genuine friends, according to people who know both men. Over the years, some details of Crow’s relationship with the Thomases have emerged. In 2011, The New York Times reported on Crow’s generosity toward the justice. That same year, Politico revealed that Crow had given half a million dollars to a Tea Party group founded by Ginni Thomas, which also paid her a $120,000 salary. But the full scale of Crow’s benefactions has never been revealed.

Long an influential figure in pro-business conservative politics, Crow has spent millions on ideological efforts to shape the law and the judiciary. Crow and his firm have not had a case before the Supreme Court since Thomas joined it, though the court periodically hears major cases that directly impact the real estate industry. The details of his discussions with Thomas over the years remain unknown, and it is unclear if Crow has had any influence on the justice’s views.

In his statement, Crow said that he and his wife have never discussed a pending or lower court case with Thomas. “We have never sought to influence Justice Thomas on any legal or political issue,” he added.

In Thomas’ public appearances over the years, he has presented himself as an everyman with modest tastes.

“I don’t have any problem with going to Europe, but I prefer the United States, and I prefer seeing the regular parts of the United States,” Thomas said in a recent interview for a documentary about his life, which Crow helped finance.

“I prefer the RV parks. I prefer the Walmart parking lots to the beaches and things like that. There’s something normal to me about it,” Thomas said. “I come from regular stock, and I prefer that — I prefer being around that.”

“You Don’t Need to Worry About This — It’s All Covered”

Crow’s private lakeside resort, Camp Topridge, sits in a remote corner of the Adirondacks in upstate New York. Closed off from the public by ornate wooden gates, the 105-acre property, once the summer retreat of the same heiress who built Mar-a-Lago, features an artificial waterfall and a great hall where Crow’s guests are served meals prepared by private chefs. Inside, there’s clear evidence of Crow and Thomas’ relationship: a painting of the two men at the resort, sitting outdoors smoking cigars alongside conservative political operatives. A statue of a Native American man, arms outstretched, stands at the center of the image, which is photographic in its clarity.

The painting captures a scene from around five years ago, said Sharif Tarabay, the artist who was commissioned by Crow to paint it. Thomas has been vacationing at Topridge virtually every summer for more than two decades, according to interviews with more than a dozen visitors and former resort staff, as well as records obtained by ProPublica. He has fished with a guide hired by Crow and danced at concerts put on by musicians Crow brought in. Thomas has slept at perhaps the resort’s most elegant accommodation, an opulent lodge overhanging Upper St. Regis Lake.

The mountainous area draws billionaires from across the globe. Rooms at a nearby hotel built by the Rockefellers start at $2,250 a night. Crow’s invitation-only resort is even more exclusive. Guests stay for free, enjoying Topridge’s more than 25 fireplaces, three boathouses, clay tennis court and batting cage, along with more eccentric features: a lifesize replica of the Harry Potter character Hagrid’s hut, bronze statues of gnomes and a 1950s-style soda fountain where Crow’s staff fixes milkshakes.

Crow’s access to the justice extends to anyone the businessman chooses to invite along. Thomas’ frequent vacations at Topridge have brought him into contact with corporate executives and political activists.

During just one trip in July 2017, Thomas’ fellow guests included executives at Verizon and PricewaterhouseCoopers, major Republican donors and one of the leaders of the American Enterprise Institute, a pro-business conservative think tank, according to records reviewed by ProPublica. The painting of Thomas at Topridge shows him in conversation with Leonard Leo, the Federalist Society leader regarded as an architect of the Supreme Court’s recent turn to the right.

In his statement to ProPublica, Crow said he is “unaware of any of our friends ever lobbying or seeking to influence Justice Thomas on any case, and I would never invite anyone who I believe had any intention of doing that.”

“These are gatherings of friends,” Crow said.

Crow has deep connections in conservative politics. The heir to a real estate fortune, Crow oversees his family’s business empire and recently named Marxism as his greatest fear. He was an early patron of the powerful anti-tax group Club for Growth and has been on the board of AEI for over 25 years. He also sits on the board of the Hoover Institution, another conservative think tank.

A major Republican donor for decades, Crow has given more than $10 million in publicly disclosed political contributions. He’s also given to groups that keep their donors secret — how much of this so-called dark money he’s given and to whom are not fully known. “I don’t disclose what I’m not required to disclose,” Crow once told the Times.

Crow has long supported efforts to move the judiciary to the right. He has donated to the Federalist Society and given millions of dollars to groups dedicated to tort reform and conservative jurisprudence. AEI and the Hoover Institution publish scholarship advancing conservative legal theories, and fellows at the think tanks occasionally file amicus briefs with the Supreme Court.

On the court since 1991, Thomas is a deeply conservative jurist known for his “originalism,” an approach that seeks to adhere to close readings of the text of the Constitution. While he has been resolute in this general approach, his views on specific matters have sometimes evolved. Recently, Thomas harshly criticized one of his own earlier opinions as he embraced a legal theory, newly popular on the right, that would limit government regulation. Small evolutions in a justice’s thinking or even select words used in an opinion can affect entire bodies of law, and shifts in Thomas’ views can be especially consequential. He’s taken unorthodox legal positions that have been adopted by the court’s majority years down the line.

Soon after Crow met Thomas three decades ago, he began lavishing the justice with gifts, including a $19,000 bible that belonged to Frederick Douglass, which Thomas disclosed. Recently, Crow gave Thomas a portrait of the justice and his wife, according to Tarabay, who painted it. Crow’s foundation also gave $105,000 to Yale Law School, Thomas’ alma mater, for the “Justice Thomas Portrait Fund,” tax filings show.

Crow said that he and his wife have funded a number of projects that celebrate Thomas. “We believe it is important to make sure as many people as possible learn about him, remember him and understand the ideals for which he stands,” he said.

To trace Thomas’ trips around the world on Crow’s superyacht, ProPublica spoke to more than 15 former yacht workers and tour guides and obtained records documenting the ship’s travels.

On the Indonesia trip in the summer of 2019, Thomas flew to the country on Crow’s jet, according to another passenger on the plane. Clarence and Ginni Thomas were traveling with Crow and his wife, Kathy. Crow’s yacht, the Michaela Rose, decked out with motorboats and a giant inflatable rubber duck, met the travelers at a fishing town on the island of Flores.

Touring the Lesser Sunda Islands, the group made stops at Komodo National Park, home of the eponymous reptiles; at the volcanic lakes of Mount Kelimutu; and at Pantai Meko, a spit of pristine beach accessible only by boat. Another guest was Mark Paoletta, a friend of the Thomases then serving as the general counsel of the Office of Management and Budget in the administration of President Donald Trump.

Paoletta was bound by executive branch ethics rules at the time and told ProPublica that he discussed the trip with an ethics lawyer at his agency before accepting the Crows’ invitation. “Based on that counsel’s advice, I reimbursed Harlan for the costs,” Paoletta said in an email. He did not respond to a question about how much he paid Crow.

(Paoletta has long been a pugnacious defender of Thomas and recently testified before Congress against strengthening judicial ethics rules. “There is nothing wrong with ethics or recusals at the Supreme Court,” he said, adding, “To support any reform legislation right now would be to validate these vicious political attacks on the Supreme Court,” referring to criticism of Thomas and his wife.)

The Indonesia vacation wasn’t Thomas’ first time on the Michaela Rose. He went on a river day trip around Savannah, Georgia, and an extended cruise in New Zealand roughly a decade ago.

As a token of his appreciation, he gave one yacht worker a copy of his memoir. Thomas signed the book: “Thank you so much for all your hard work on our New Zealand adventure.”

Crow’s policy was that guests didn’t pay, former Michaela Rose staff said. “You don’t need to worry about this — it’s all covered,” one recalled the guests being told.

There’s evidence Thomas has taken even more trips on the superyacht. Crow often gave his guests custom polo shirts commemorating their vacations, according to staff. ProPublica found photographs of Thomas wearing at least two of those shirts. In one, he wears a blue polo shirt embroidered with the Michaela Rose’s logo and the words “March 2007” and “Greek Islands.”

Thomas didn’t report any of the trips ProPublica identified on his annual financial disclosures. Ethics experts said the law clearly requires disclosure for private jet flights and Thomas appears to have violated it.

Justices are generally required to publicly report all gifts worth more than $415, defined as “anything of value” that isn’t fully reimbursed. There are exceptions: If someone hosts a justice at their own property, free food and lodging don’t have to be disclosed. That would exempt dinner at a friend’s house. The exemption never applied to transportation, such as private jet flights, experts said, a fact that was made explicit in recently updated filing instructions for the judiciary.

Two ethics law experts told ProPublica that Thomas’ yacht cruises, a form of transportation, also required disclosure.

“If Justice Thomas received free travel on private planes and yachts, failure to report the gifts is a violation of the disclosure law,” said Kedric Payne, senior director for ethics at the nonprofit government watchdog Campaign Legal Center. (Thomas himself once reported receiving a private jet trip from Crow, on his disclosure for 1997.)

The experts said Thomas’ stays at Topridge may have required disclosure too, in part because Crow owns it not personally but through a company. Until recently, the judiciary’s ethics guidance didn’t explicitly address the ownership issue. The recent update to the filing instructions clarifies that disclosure is required for such stays.

How many times Thomas failed to disclose trips remains unclear. Flight records from the Federal Aviation Administration and FlightAware suggest he makes regular use of Crow’s plane. The jet often follows a pattern: from its home base in Dallas to Washington Dulles airport for a brief stop, then on to a destination Thomas is visiting and back again.

ProPublica identified five such trips in addition to the Indonesia vacation.

On July 7 last year, Crow’s jet made a 40-minute stop at Dulles and then flew to a small airport near Topridge, returning to Dulles six days later. Thomas was at the resort that week for his regular summer visit, according to a person who was there. Twice in recent years, the jet has followed the pattern when Thomas appeared at Crow’s properties in Dallas — once for the Jan. 4, 2018, swearing-in of Fifth Circuit Judge James Ho at Crow’s private library and again for a conservative think tank conference Crow hosted last May.

Thomas has even used the plane for a three-hour trip. On Feb. 11, 2016, the plane flew from Dallas to Dulles to New Haven, Connecticut, before flying back later that afternoon. ProPublica confirmed that Thomas was on the jet through Supreme Court security records obtained by the nonprofit Fix the Court, private jet data, a New Haven plane spotter and another person at the airport. There are no reports of Thomas making a public appearance that day, and the purpose of the trip remains unclear.

Jet charter companies told ProPublica that renting an equivalent plane for the New Haven trip could cost around $70,000.

On the weekend of Oct. 16, 2021, Crow’s jet repeated the pattern. That weekend, Thomas and Crow traveled to a Catholic cemetery in a bucolic suburb of New York City. They were there for the unveiling of a bronze statue of the justice’s beloved eighth grade teacher, a nun, according to Catholic Cemetery magazine.

As Thomas spoke from a lectern, the monument towered over him, standing 7 feet tall and weighing 1,800 pounds, its granite base inscribed with words his teacher once told him. Thomas told the nuns assembled before him, “This extraordinary statue is dedicated to you sisters.”

He also thanked the donors who paid for the statue: Harlan and Kathy Crow.

This story first appeared at ProPublica. ProPublica is a Pulitzer Prize-winning investigative newsroom. Sign up for The Big Story newsletter to receive stories like this one in your inbox.

Flying to Ireland to inhale the seaside air as you drive a golf ball into the scenic distance. Crossing the country to reach your enormous yacht, which is ready for your Hudson River pleasure cruise. Hosting a governor’s wife on your very own aircraft. These are only a few of the joys that the richest Americans have experienced in recent years through their private jets. And what made them all the sweeter is that they came with a tax write-off.

Over the past two years, ProPublica has documented the many ways that the ultrawealthy avoid taxes. The biggest or most daringmaneuvers scale in the billions of dollars, and while the tax deductibility of private jets isn’t the most important feature of U.S. tax law, the fact that billionaires’ luxury rides come with millions in tax savings says a lot about how the system really works.

There are dozens of examples of wealthy Americans taking these sorts of deductions, which are premised on the notion that the planes are used mainly for business, in the massive trove of tax records that have formed the basis for ProPublica’s “Secret IRS Files” series. The ultrawealthy, however, can easily blur business and pleasure. And when they purport to make their planes available for leasing, to fulfill one definition of using the planes for business, they tend to be more adept at generating tax deductions than revenue.

Tony Alvarez and Bryan Marsal built a successful consulting firm specializing in restructuring — advising struggling or bankrupt companies on what to sell and whom to lay off. It can be a grim business: Marsal has been known to announce to prone firms that they were now a “community of pain.” But the partners, who are also close friends, own another enterprise, the Hogs Head Golf Club (“Built by Friends, for Friends, for Fun”), on the southwest coast of Ireland. It boasts views of the nearby mountains and bay.

In 2016, before opening their new course, the pair teamed up, via an LLC they named after their golf club, to buy a 2001 Gulfstream IV jet. The next year, President Donald Trump signed his big tax cut into law. It made buying a plane even more attractive: The full price of the plane could be deducted in the first year, a perk called “bonus depreciation.” Before, depreciation was typically only partially front-loaded, with the full balance spread over five years. The law also for the first time made pre-owned planes eligible for this treatment.

As a result, when Alvarez and Marsal sprang for their second plane in 2018, this one a Gulfstream V, the entire cost was deductible. That year, the pair’s two planes netted them a tax deduction of $14 million.

Last August, their Gulfstream V took off from Westchester County Airport in New York state for Ireland. About an hour later, their Gulfstream IV left for the same destination, a small airport in County Kerry near their club. Both planes can comfortably seat over a dozen passengers, but flight records don’t show who was on board. Over the coming month and a half, the two planes crisscrossed the Atlantic several times.

Were these business trips? Possibly, yes. (ProPublica’s records do not indicate whether specific trips were taken as deductions.) If so, operating expenses — including crew, fuel and other costs — from the partners’ trips to oversee the course would be fully deductible. These deductions would come in addition to depreciation.

Michael Kosnitzky, co-chair of the private client and family office group at the law firm Pillsbury Winthrop, said his wealthy clients often own a business, such as an art gallery, in the same area where they own a vacation home. If the main purpose of a flight there is to attend to that business, jet owners must take care to make that as clear as possible. “I advise my clients to go to their secondary business location first” upon landing, he said, as a way to help build the case.

Accounting for how a jet is used can get complicated. If nonbusiness guests, such as family, ride along on a business flight, it’s treated as a fringe benefit, which is taxable. (The benefit is typically attributed to the jet owner, experts said.) But that wrinkle isn’t too bad: The IRS formula used to calculate the benefit drastically undervalues the cost of riding on a private jet and is closer to the price of a first-class commercial ticket.

Last Christmas, flight records show the two Gulfstreams again leaving together, this time to St. Vincent and the Grenadines in the Caribbean. While Alvarez and Marsal’s consulting firm boasts an office in the Cayman Islands, there isn’t one on these particular islands (which are about 1,400 miles from the Caymans), making it appear this was a family trip. Operating costs from “entertainment” flights like these are not deductible under tax law. But indulging in some pleasure doesn’t necessarily imperil the key tax prize of bonus depreciation: As long as, over the course of a year, the jet is used over 50% of the time for business, the owner gets to keep that perk.

A spokesperson for Alvarez and Marsal’s firm did not respond to a request for comment.

Mori Hosseini made his fortune as a Florida homebuilder and has owned a plane since at least 2006. When Trump’s tax bill began to gain momentum in Congress in the fall of 2017, he decided it was time for a new jet.

The $19.5 million he paid for his nine-seat Bombardier Challenger 350 appeared as a deduction on his 2017 taxes, leading to almost $8 million in tax savings right off the bat. But there were more deductions to come. Even the interest on the loan he’d taken out to buy the plane was deductible, and his 2018 taxes show a $600,000 expense.

Soon, Hosseini, a longtime Republican donor and close adviser to Florida Gov. Ron DeSantis, was helping the governor and his family travel in style. In 2019, DeSantis’ wife, Casey, flew on the jet from Tallahassee to Jacksonville to attend a fundraiser held by a defense contractor. It was just one of several times that the DeSantises or the campaign have used the jet over the past few years, according to campaign finance records. Such flights are generally allowed under Florida law as long as they are disclosed as in-kind contributions. Hosseini did not respond to questions from ProPublica.

On his taxes, Hosseini says the LLC that holds his plane is in the business of “aircraft leasing.” It’s a very common move among jet owners. When they are not using the plane, they rent out the plane for charter flights, usually via an independent leasing company. Not only does this defray the costs of ownership, but it has tax benefits, too. It helps them establish that they bought the aircraft for a business purpose, the business of chartering.

In theory, taxpayers aren’t allowed to deduct losses from something that has no hope of being a profitable business. In practice, though, some billionaire-owned operations that look like expensive hobbies, such as racing horses in the Kentucky Derby, rack up business deductions by the tens of millions of dollars.

ProPublica examined the tax records of over 30 wealthy Americans who owned planes, and one thing was very clear: Profits in the airplane chartering business for this set, judging from their taxes, were extremely rare. Hosseini’s records show two years of profit over an eleven-year period.

Or take George Argyros, a California billionaire real estate developer who once owned the Seattle Mariners. A major GOP donor, he also was the U.S. ambassador to Spain from 2001 to 2004. Argyros, 86, has leased out his aircraft through his own chartering company for decades. From 2002 through 2019, his tax records show, his company pulled a profit just twice. Overall, he deducted over $50 million in net losses over the years.

In June 2021, Argyros’ Gulfstream landed at the small airport near Newburgh in New York’s Hudson Valley, having flown cross-country from California. Nearby, his $83 million, 248-foot yacht the Huntress awaited. Over the coming weeks, the ship would be seen cruising up and down the Hudson River, astounding locals who gawked at its six decks, helipad and hot tub.

A representative for Argyros declined to comment.

Yachts are dealt with differently from airplanes in tax law. They are considered entertainment facilities, so you can’t claim deductions on the premise that you used it for business travel.

But that doesn’t mean there’s no tax savings to be had. Mike Fernandez is a capable businessman, having made a fortune starting and investing in health care companies. But the Florida-based investor seems to have abysmal luck with one of his businesses: leasing out his 180-foot yacht, the Lady Michelle, when he’s not using it. On his 2017 and 2018 tax returns, he claimed a total of $11.3 million in expenses connected with the Lady Michelle from depreciation, repairs, wages and other costs. Meanwhile, his revenue over the two years totaled $178,000. Fernandez did not respond to questions from ProPublica.

Should the IRS audit one of these businesses — itself unlikely over the past decade, due to the gutting of the agency’s budget — the IRS faces a high hurdle: proving that not only was the business not profitable, but that the business owner was not really trying to profit. The case of personal jets adds an additional difficulty for an auditor. The ultrawealthy can often argue that, even if chartering did not result in profits, they also used the plane to help conduct their main business.

Robert Bigelow made his fortune in real estate and owns Budget Suites of America, an extended-stay apartment chain. His passions, however, reach to the skies and beyond. For decades, he’s poured resources into investigating UFO sightings and paranormal phenomena. Two years ago, he announced $1 million in grants from his Bigelow Institute for Consciousness Studies for research “into contact and communication with post-mortem or discarnate consciousness.”

His main focus, however, has been space. He founded Bigelow Aerospace, a company focused on building expandable space habitats. The company has had some successes, winning a contract from NASA for a module for use on the International Space Station. But what it has not had is profits. Bigelow put more than $350 million into the company, “my own real black hole,” as he’s put it.

In the two decades prior to 2018, even as Forbes and The Wall Street Journal variously estimated his net worth as $700 million and $900 million, Bigelow posted negative incomes on his taxes most years, as large losses from his aerospace company wiped out his other income. His personal jet, held by Cosmos Air LLC, also played a role. From 2005 to 2018, he deducted a total of $51 million related to use of his plane. ProPublica could not find evidence that Bigelow charters his aircraft, nor did Bigelow respond to ProPublica’s requests for comment.

Of course, the deductions could also be justified on the basis that the aircraft is necessary to tend to Bigelow’s various businesses. The plane is a luxury expense, in other words, essential to help him run up millions more in tax deductions — one black hole orbiting another.