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Erik Prince’s Private Wars

The Blackwater founder wants to bring back his company's glory days — and he's campaigning for Donald Trump's help to do it. But he's haunted by past failures and is facing questions about a mercenary fiasco in Libya
Photo illustration based on photograph by Melissa Golden/Redux

I n the spring of 2019, Khalifa Haftar went to a cafe in Cairo to plot a coup. At the meeting, the Libyan general was shown an $80 million plan to overthrow Libya’s U.N.-recognized government. In a PowerPoint presentation viewed by Rolling Stone, Haftar, a warlord with a power base in the eastern Libyan city of Benghazi, saw plans for an operation that would use two Cobra H1 attack helicopters, mounted with 20mm rotary machine guns and crewed by foreign mercenaries, to swoop down and kill or capture 11 of Haftar’s political enemies. The plan would inject the soldiers of fortune into a nearly decade-old civil war that — fueled by internal instability and foreign meddling in the oil-rich North African nation — has killed thousands of Libyans and displaced many times more. The general gave the operation the green light.

By June 18th, 2019, the operation, named “Project Opus,” was in the final stages of planning, as the mercenaries and their backers attempted to assemble the equipment Haftar had been promised. But they hit a snag when the Kingdom of Jordan refused to sell military helicopters to the group. The mercenaries’ cover story was that they were headed to Libya to support energy-development projects, but Jordanian military officials had grown suspicious because of the equipment being stockpiled.

Professional mercenaries pride themselves on discretion, but this group’s tradecraft was laughable. A former Australian Air Force pilot sent to Jordan to inspect the helicopters identified himself as “Gene Rynack.” The code name was a nod to “Gene Ryack,” the fictional arms-dealer-turned-heroin-smuggler in Air America, a film about private CIA aviation contractors during the Vietnam War. (Think of a spy with the cover name “James Bonde.”) Rynack — whose real name is Christiaan “Serge” Durrant — suggested to Jordanian officials that he had clearances from “everywhere,” effectively attempting to bluff them into believing he had the approval of the U.S. Central Intelligence Agency. Suspicious Jordanian officials dug deeper and found that the operation was a private one that no country had officially sanctioned, and the sale never went through.

Lacking the Jordanian choppers, the mercenaries and their backers scrambled to find replacements, which included trying to buy equipment from private sources. “Opus are now executing their contingency plan1 for non-government support,” a member of Project Opus wrote in a June 18th, 2019, communiqué seen by Rolling Stone. “This places considerable legal risk on Opus and is beyond the scope of the agreed contract.”

The scramble for new aircraft proved at least partially unsuccessful, and when the mercenaries arrived in Libya, they failed to deliver the military equipment their contract called for. Haftar was furious. The mercenaries — a team of a dozen South Africans, five Brits, two Australians, and one American — feared for their lives and fled the country, hopping into inflatable speedboats for a desperate, 18-hour, 350-mile journey across the Mediterranean to Malta. Police detained them on arrival.

The failed Project Opus has since become the subject of a United Nations investigation, which includes a detailed and damning portrait in a 61-page report issued in June. This account of the failed operation in Libya is based on that report, which Rolling Stone obtained.

Still, much remains unknown about the mission. Who was putting up the funds to back Haftar’s attempted overthrow? Who was organizing the mission outside of Libya? And who, approached by a group of mercenaries claiming they were supporting “energy development” projects in a war-torn country, was willing to sell deadly weapons into a nation already consumed by violence?

U.N. investigators are struggling to make sense of who was attempting to get Haftar the personnel and equipment for his planned strike. A complex shell of at least 10 companies in four countries “increased the opacity of the procurement operations and attempted to disguise the identity of the overall planners,” the U.N. panel wrote. But when the mercenaries scrambled to find private sellers for the aircraft Jordan wouldn’t provide, they left a trail of clues about how the operation came together. And a lot of those clues point in the direction of Erik Prince.

Erik Prince declined repeated requests to comment for this story, including questions about whether he was involved in any way with Project Opus. Prince’s attorney, Matthew Schwartz, of Boies Schiller Flexner LLP, engaged in extensive off-the-record discussions with Rolling Stone over the course of three weeks. He ultimately declined to provide on-the-record responses to Rolling Stone’s inquiries.

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Members of the self-styled Libyan National Army, loyal to strongman Khalifa Haftar, practice firing a Kalashnikov assault rifle as they rest following clashes with militants in Benghazi’s central Akhribish district in November 2017. Abdullah Doma/AFP/Getty Images

Before he was a cheerleader for American military adventurism, before he spent years trying to ingratiate himself in President Trump’s circle while pushing the White House to let him privatize the war in Afghanistan, before his decade as a globe-trotting war profiteer with close ties to ethically questionable regimes, and before he became a symbol of the failures of the war in Iraq when employees of his company, Blackwater, killed more than a dozen unarmed civilians at a Baghdad traffic circle, Erik Prince was the only son of a wealthy Michigan family with an array of opportunities in front of him.

Prince’s father, Edgar, had made a fortune selling General Motors the lighted mirror on cars’ sun visors. Erik Prince, Edgar’s youngest child, flitted between career tracks in his early years. He enrolled in the U.S. Naval Academy after high school, but he quit in a fit of pique after three semesters when he was written up for tardiness, according to Master of War, a biography of Prince by Suzanne Simons. In his senior year at Hillsdale College, he scored a coveted White House internship during the first Bush administration. But he left six months later, upset, among other reasons, that “homosexual groups” had been invited in, according to an article printed at the time in The Grand Rapids Press. He later became an intern at the office of former California Republican Rep. Dana Rohrabacher, who sent him on fact-finding missions around the globe, according to Erik Prince’s own 2013 book, Civilian Warriors.

A revealing passage in Prince’s book suggests his father harbored concerns about his only son’s early lack of focus. Edgar Prince inserted a clause in his will stipulating that Erik, the youngest of his four children, wouldn’t receive any inheritance until he turned 30.

The younger Prince’s life hit a major pivot, however, in 1992, when he left politics to be commissioned as a naval officer and join the elite Navy SEALs. His father, won over by his son’s perseverance, dropped the clause out of the will.

After his father’s death in 1995 at age 63 from a heart attack, Prince resigned his military commission and used his share of the family fortune to build Blackwater USA, which began life as a cross between a shooting range and training facility for special-operations personnel near North Carolina’s Great Dismal Swamp. After 9/11, the company grew rapidly as it filled the government’s need to protect its personnel in Iraq and Afghanistan. Blackwater would go on to bill the U.S. government for more than $1 billion over its lifetime.

Early on, Blackwater earned high marks by providing highly trained ex-Special Ops personnel to protect Department of State and CIA officers in Iraq and Afghanistan. “They were lifesavers,” said Doug Wise, a former CIA officer who served in Afghanistan in the early days of the U.S.-led war there. Prince’s men won plaudits for going above and beyond the call to rescue diplomats and civilians in distress.

After the invasion of Iraq, however, Blackwater grew far faster than Prince’s ability to manage it. The firm became, in Prince’s words, “something resembling its own branch of the military” — though others faulted the company for what they saw as a cavalier, cowboy attitude. There weren’t enough retired special-forces veterans to meet the U.S. government’s staffing needs, and Blackwater began to hire less experienced, far less skilled personnel to meet demand. “They just ran out of people of the quality they needed,” a former senior U.S. military commander in Iraq tells Rolling Stone.

Prince’s rising stock in post-9/11 America was also driven by his work with the CIA. According to Prince, he became an official asset, putting himself and his company’s resources at the spy agency’s disposal. Rolling Stone obtained an unpublished chapter of Prince’s book, which the CIA has blocked from release because it delves into Prince’s classified work. In the chapter, Prince describes how, in addition to training CIA operatives and maintaining the agency’s drone fleet, he helped set up a program to train a terrorist hit squad at the behest of the spy agency. Prince writes that over three years beginning in 2004, he spent a “few million” recruiting and organizing a team of about a dozen foreign mercenaries. The CIA gave him a codename: “Hans.”

Prince says the off-the-books program had support at the West Wing of the White House and with then-Vice President Dick Cheney. “The program was so secret, I was told that Cheney instructed the agency not to even brief Congress about it,” Prince wrote in the unpublished chapter. According to Vanity Fair, the operatives tracked an Al Qaeda financier in Germany and went to Dubai hunting a Pakistani scientist who spilled nuclear secrets, but they never got the go-ahead to pull the trigger. The CIA reimbursed him for about $1 million, Prince says in his unpublished chapter.

This was the apex of Blackwater, but it soon fell apart — with deadly consequences. On September 16th, 2007, Blackwater personnel shot and killed 14 unarmed civilians in Nisour Square, a traffic circle in Baghdad, and wounded 18 more. The next day, the Iraqi government announced that it would revoke Blackwater’s license to operate and demanded to prosecute the Blackwater guards. The New York Times reported that Blackwater continued to operate in Iraq after Blackwater’s president authorized bribes of about $1 million to Iraqi officials, a charge Prince later dismissed as “false.” But the uproar over the Nisour Square massacre pushed the Bush administration and Congress to investigate the company.

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Erik Prince, then the chairman and CEO of the Prince Group and Blackwater USA, holds up a picture showing the effect of a car bomb as he testifies to the House Oversight and Government Reform Committee hearing on Capitol Hill in October 2007. The committee was hearing testimony from officials regarding private-security contracting in Iraq and Afghanistan. Mark Wilson/Getty Images

The United States promised to handle the case, which has dragged on for years. Last year, one of the guards convicted in the massacre, Nicholas Slatten, was sentenced to life in prison, and three others were resentenced to lengthy terms behind bars. Lawyers representing victims and their families in the Nisour Square massacre obtained a confidential settlement with Blackwater.

While the Nisour Square case was slowly working its way through the legal system, Prince’s off-the-books CIA work met a swift, unceremonious end at the hands of the incoming Obama administration. New CIA director Leon Panetta shut down Prince’s anti-terrorist hit squad. The company, Panetta found, was “free-wheeling” and doing stuff on their own. “It had gotten to the point where they really felt that because of what they were doing, they were somehow entitled to do it their way. That’s kind of what really concerned me,” Panetta tells Rolling Stone.

After Panetta briefed members of Congress on Prince’s activities, Prince’s role in the CIA program leaked to the media. Prince felt badly burned, and he took his frustrations out by telling Vanity Fair about his CIA work, which burned his bridges at the spy agency. “The last thing [the CIA] wants, Panetta tells Rolling Stone, “is a yahoo who’s trying to play up what he’s doing as a lone-wolf approach to doing justice for the country.”

It’s hard to overstate the anger and bitterness that Prince feels over his treatment by the CIA and Congress. Most Americans were introduced to Prince when he took the witness seat before the Democrat-led congressional committee investigating Blackwater. In an early version of Prince’s book obtained by Rolling Stone, he is unsparing in his description of the committee chairman, former Rep. Henry Waxman (a “little bald man” with a “high, oily forehead” and “porcine nose” who “spoke through yellowed buck teeth”).

For Prince, the final indignity came when he lost Blackwater, selling off the company in 2010 after the firm settled a host of federal investigations by agreeing to pay a $42 million fine to the U.S. government.

After burning intelligence-community bridges and facing a host of Blackwater-related lawsuits, Prince spent the next few years in a sort of self-imposed exile. He set about rebuilding his business by offering security services to some of the most repressive regimes in the world, and increasingly, Prince found himself in ethically and legally dubious territory.

In 2010, Prince, four of his children, and the family dog moved full-time to Abu Dhabi. It was “a bit of an oasis, literally in the desert, of peace and tranquility,” he called it in his testimony before Congress in 2017. Abu Dhabi was thousands of miles away from the “jackals,” as he put in an interview with Men’s Journal, who wanted his money. Documents seen by Rolling Stone show Prince reported an estate of more than $50 million at the time. Prince set about building what The New York Times described as a secret, 800-man mercenary army able to put down threats to the ruler of the United Arab Emirates, Sheikh Mohammed bin Zayad al-Nahyan, commonly known as MBZ.

The relationship eventually soured, however, and Prince believes the Obama administration made that happen. A former associate tells Rolling Stone that Prince once told him that he became persona non grata with the Emiratis after then-Secretary of State Hillary Clinton called MBZ’s mother to tell her that her son would be wise to cut ties. “I think the Obama administration went out of their way to tarnish my ability to do business in the Middle East,” he told Congress a few years later. (Nick Merrill, a spokesman for Secretary Clinton, denied that she had played a role in disrupting his business. “It’s not true, but not a surprise given Erik Prince’s track record of being equal parts conspiracy theorist and full of shit,” Merrill tells Rolling Stone.)

Prince looked further afield and found a new vein of overseas wealth to tap in China. In 2012, Prince traveled to China to offer investors there an opportunity to bankroll African mining and energy projects. Chinese investors didn’t bite, but he came away with another deal: an offer to serve as chairman of Frontier Services Group, a Hong Kong-based company that’s backed in part by CITIC Group, a Chinese state conglomerate. The role, experts told The Washington Post, “puts [Prince] in the unsettling position of advancing the strategic agenda of the United States’ largest rival.”

The initial focus of the company was providing security and logistics in Africa, but Gregg Smith, the former chief executive of Frontier Services Group, tells Rolling Stone that he resigned after learning at a March 2016 board meeting that Frontier Services Group had become, in effect, an arm of the Chinese state run by Americans. The new focus of FSG was to be providing security for China’s Belt-and-Road initiative, a colossal project that aims to increase China’s global influence by building infrastructure projects across the developing world.

“Going forward, we were told, Frontier Services Group is Erik Prince, it’s CITIC, and it’ll be providing security for Belt-and-Road,” Smith says. In addition, Smith tells Rolling Stone he was disturbed when, he says, the CIA told him that a key company official was affiliated with Chinese intelligence.

As well as furthering China’s aims abroad, a Frontier Services Group press release suggests that it may be helping the Chinese Communist Party’s domestic repression. In 2018, Frontier Services Group announced it was building “training facilities” and related “security equipment” in Xinjiang province, home to 11 million Uighurs, a predominantly Muslim ethnic minority that has been brutally repressed by the Chinese state. Nearly 1 million Uighurs and other mostly Muslim minority groups are held in extrajudicial detention in camps in Xinjiang, according to a group of experts cited by the United Nations. The U.S. government has sanctioned companies implicated in human rights abuses in Xinjiang. Prince has said that his own company’s press release was wrong; FSG was not building a training facility in Xinjiang, rather it was providing “construction services.” Prince also has said that the work being done by FSG is meant to protect Chinese enterprises in Africa and Asia, not to support China’s domestic police or military.

Frontier Services Group did not return messages left seeking comment.

The ties between FSG and China were of enough interest to the FBI that the bureau recently spoke with Smith about American FSG personnel in China other than Prince. The conversation also touched on other matters, including what Smith calls Prince’s self-dealing at the company — a major factor in Smith’s decision to quit, he tells Rolling Stone. While Prince spent much of the Obama administration abroad, he never gave up on regaining the influential (and lucrative) place he once had in the military-industrial complex. And he saw his chance for a homecoming with the rise of Donald Trump.

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This photo taken on June 4th, 2019, shows the Chinese flag behind razor wire at a housing compound in Yangisar, south of Kashgar, in China’s western Xinjiang region, a region whose Uighur minority is straitjacketed by surveillance and mass detentions. Greg Baker/AFP/Getty Images

“Did Julian Assange chicken out?” Erik Prince asked.

The 2016 election was a month away, and Prince was emailing and texting with Roger Stone, Trump’s longtime political adviser, to find out what was going on with Wikileaks. Prince wanted to know if Julian Assange, Wikileaks’ founder, was still planning to release a trove of emails that would damage Hillary Clinton’s presidential campaign.

“The payload is still coming,” Stone told Prince.

Later that day, Prince texted Stone again. “Did you hear anything more from London?” Assange was then holed up in the Ecuadorian Embassy in the British capital.

“Yes,” Stone replied. “Want to talk on a secure line?”

Assange had not chickened out. A few days later — hours after Trump was caught on tape bragging about serially sexually assaulting women — Wikileaks began releasing the hacked emails of Clinton campaign manager John Podesta.

The back-and-forth between Prince and Stone was made public by prosecutors at Stone’s 2019 trial over lying to Congress, but Rolling Stone has learned that the two were also engaged in another anti-Clinton, pro-Trump effort. Prince was helping Stone with a project that aimed at dampening black voter turnout during the 2016 election. In an email sent in late October 2016 and obtained by Rolling Stone, Prince encouraged his contacts to donate to the voter outreach and suppression project, which he openly acknowledged was “targeted at the black community to help them think twice about supporting Hillary and her deadbeat husband.”

The effort involved Danney Williams, who claims to be the illegitimate son of former President Bill Clinton and an African American prostitute. Prince was soliciting contributions for the Committee for American Sovereignty Education Fund, a 501(c)(4) organization that was helping Williams tell his story in videos and interviews on “urban radio” in cities with large African American populations, including Detroit, Philadelphia, and Milwaukee. Prince attached a plan for what was called “Project Clintonson,” which made its goals abundantly clear: “We do not need to make major gains among African American voters, we merely need to dampen turn out and make it difficult for black Democratic elected officials in Hillary’s pocket [to] turn out black voters at Obama-like levels.”

On October 3rd, 2016, Stone emailed Prince a link to a story in the conservative blog Gateway Pundit about Williams with the subject line, “It has begun.”

“Funds sent,” Prince replied. “More to come.”

Prince’s relationship and giddy correspondence with Stone, who would later be convicted of lying to Congress about his dealings with Wikileaks, came amid Prince’s efforts to climb the ladder into Trumpworld. For Prince, facing irrelevance in Washington power politics after his Blackwater debacle and acrimonious relationship with the Obama-Clinton Democratic party, Trump was a way back into the upper echelon.

A recently released memorandum summarizing Prince’s April 2018 interview with Special Counsel Robert Mueller’s office, obtained under a Freedom of Information Act lawsuit filed by Buzzfeed and CNN, reveals that initially Prince had not supported Trump, but as the campaign heated up, he found he agreed with Trump’s positions. Prince knew a host of Trump campaign officials and went on hunting trips with the president’s sons, according to a memo of the FBI’s interview with Steve Bannon, the Trump campaign’s CEO.

Early on, Bannon was a key point of contact. Prince would forward his ideas to Bannon, including one memo in which Prince told Bannon the Trump campaign should focus on developing America’s capabilities in what Prince called the “dark arts,” which included “political and surrogate warfare, covert action, sabotage, information war, propaganda, etc.”

The political “dark arts” were very much on Prince’s mind during the 2016 campaign. Prince arranged a meeting in Trump Tower with Donald Trump Jr. and the head of Psy Group, an Israeli company that specializes in social media manipulation, according to the Mueller Report. The report also noted that Prince helped pay for an effort to validate a purported tranche of Hillary Clinton emails, which turned out to be bogus. He also remained in frequent contact with Stone, another practitioner of the political dark arts, throughout the campaign. In April and May of 2016, around the time Trump declared himself the “presumptive nominee” of the Republican Party, Prince and Stone spoke by phone 67 times, according to the final volume of the Senate Intelligence Committee’s report on Trump and Russia.

Prince has denied that he had any formal or informal role in the campaign. He told Mueller’s office he met Trump briefly on three occasions during the campaign. The FBI memo of the conversation noted, however, that Prince had Trump’s phone numbers in his cellphone. Prince also spent election night at Trump Tower, watching the voting returns. After the election, Prince kept his Trump ties.

In January of 2017, Prince flew to the Seychelles, an island archipelago off the coast of East Africa, to meet with a Russian government official who was looking to make contacts with the incoming administration. The Russian official was Kirill Dmitriev, a former Goldman Sachs banker who headed Russia’s $10 billion sovereign wealth fund, which was subject to U.S. sanctions. Dmitriev reported directly to Russian President Vladimir Putin, whom he referred to as his “boss.” Prince told Mueller’s office that he and Dmitriev spent most of their time discussing oil prices.

Prince told Congress under oath that he and Dmitriev met once in the Seychelles. He later conceded they met twice. (According to the Mueller Report, the second meeting came at Prince’s request, so he could tell Russia, via Dmitriev, that he didn’t want Russia meddling in Libya; the North African nation was “off the table.”) Also contrary to what he told the House, Prince told Robert Mueller’s investigators that he had reported back to Bannon about his meeting with Dmitriev, texting him from the Seychelles and briefing him upon his return home. The FBI found those text messages had disappeared from both men’s phones, and neither man, when asked by the bureau, could explain why, according to FBI summaries of the interviews. (Bannon told the FBI that Prince never told him he met with a Russian government official.)

In 2019, the House intelligence committee referred Prince to the Department of Justice for possible prosecution on perjury charges stemming from his deceptive account of the Seychelles meeting. “The evidence strongly suggests that he willingly misled our committee,” said Rep. Adam Schiff, chairman of the House intelligence committee. The Wall Street Journal reported in February that prosecutors were nearing a decision on whether to charge Prince. (“There is nothing new here,” Prince’s attorney, Matthew Schwartz, told the Journal, adding that Prince had “cooperated completely” in Mueller’s investigation. “Erik Prince’s House testimony has been public for more than a year.”) The investigation appears to have stalled in the Justice Department under Attorney General William Barr.

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Smoke fumes rise above buildings in Tripoli, the Libyan capital, during reported shelling by strongman Khalifa Haftar’s forces this May. Mahmud Turkia/AFP/Getty Images

After Trump’s 2016 election, Prince set about trying to rebuild his military contracting empire. “Prince’s main policy desire was to have a president that would be open to private contractors conducting stability operations,” reads the FBI memo of Prince’s conversation with Mueller’s investigators. But whatever influence Prince amassed courting Bannon and the Trump family, it hasn’t been enough to realize his dream of rebuilding his business — at least not yet.

After Trump took office, Prince drafted a proposal to have roughly 6,000 private contractors replace U.S. troops in Afghanistan. A carefully crafted pitch and selective leaks to reporters were designed to catch the eye of an easily distracted president. Prince likened the privatization of the war in Afghanistan to Trump’s 1980s remake of Wollman Skating Rink in New York’s Central Park, as shown in a photo of Prince’s presentation published by The Atlantic.

Defense Secretary James Mattis shot down the proposal, telling reporters “When Americans put their nation’s credibility on the line, privatizing it is probably not a wise idea.”

But Mattis is now long gone, and Prince hasn’t given up. Every few months, he appears on Tucker Carlson’s Fox News show, making the same pitch to the network’s most important viewer. “For less than 6,000 contractors remaining, you can keep the Afghan government upright,” Prince told Carlson in July, when he appeared on the same show with his sister, Education Secretary Betsy DeVos.

Prince still hasn’t gotten the military contract he had been lobbying for, but his other adventures in Trumpworld have recently come back to bite him. Prince was a member of the advisory board of a charity Bannon was promoting to raise private funds to build a wall along the U.S.-Mexico border. Bannon was indicted in August on charges he defrauded donors to the “We Build a Wall” campaign. Prince said on Fox News Radio that he never attended any board meetings and had no part in fundraising or oversight. “If I saw something unsavory, I would have done something about it,” he said.

Maybe so, but Prince’s legal and ethical issues have multiplied since Trump took office. He made a not-so-secret trip to Venezuela where he reportedly met with a top aide to President Nicolas Maduro, who is the subject of U.S. sanctions. Citing two unnamed senior U.S. officials, the Associated Press reported that Prince was referred to the U.S. Treasury Department for possible sanctions violations. Both Prince and the Trump administration have denied that he was acting on behalf of the U.S. government; Bloomberg LP reported that according to people familiar with the matter, he was scouting gold investments. (Prince’s lawyer, Matthew Schwartz, told Bloomberg his client went to Caracas “as a private citizen” and “received clear legal guidance which he scrupulously followed. While there, he did not discuss any business nor did he receive anything of value.”)

And there may be more trouble on the horizon with the U.N. investigation into Libya.

Mercenary operations are designed to leave no trace. Opaque corporate shells have frustrated investigators trying to understand who was behind the mercenary operation in Libya.

Given the challenges of investigating the murky world of private military contracting, it’s surprising we know as much as we do about the Libya plot, thanks in part to the Keystone Kops nature of the operation.

Prince’s name doesn’t appear in the U.N. report, and his spokesman told The New York Times in March that Prince had “nothing whatsoever to do with any alleged private military operation in Libya.” However, the latest U.N. report names Prince’s company, Frontier Services Group.

When the failed deal with the Kingdom of Jordan left the mercenaries searching for replacement aircraft in June 2019, one of the planes that showed up was a Soviet-era Antonov 26B. It was hastily acquired from an aviation subsidiary of Frontier Services Group, according to the U.N. report. Prince has been a key part of the Hong Kong-based logistics firm since 2014.

According to U.N. investigators, the money for the plane changed hands right as the plane arrived in Jordan, dispensing with the lengthy due diligence and inspections typical for aircraft sales. “This is indicative of a need to deploy an asset very quickly,” the U.N. report states. “The panel finds it almost certain that the asset was already under the control of an individual or entity related to the operation.”

Gregg Smith, the former CEO of Frontier Services Group, tells Rolling Stone that the aircraft is one both he and Prince know well: It was one of Prince’s favorites. “Why would you need to do due diligence on a plane that you know so well?” Smith said. “That’s the only way it could have transferred in a day.”

While the plane seems to be the clearest link to Prince’s world, a host of figures linked to the Blackwater founder also took part in the operation. Three companies and 21 individuals from six different countries involved in the operation are now represented by Vince Gordon, a lawyer in Abu Dhabi who has previously performed legal work for Prince’s businesses. The U.N. report says it’s “beyond the possibility of coincidence” that 21 people and three companies involved in the operation all have the same lawyer. The concerted defense “establishes” that those responsible for the mercenary operation are now coordinating a response to the U.N. inquiry.

One of the people Gordon is representing is Christiaan “Serge” Durrant, the man who the U.N. report says was calling himself “Gene Rynack,” a longtime associate and former employee of Prince’s who still considers him a friend. The U.N. report concludes that Durrant was “at least complicit in the planning and execution of a military operation in support of an armed group in Libya.” (“Mr. Durrant is not aware of any role Mr. Prince has played in connection with the matters purportedly reported on in the U.N. report,” Gordon tells Rolling Stone. He also denied that Durrant is involved in a contract with General Haftar. ) 

Another link to Prince’s world is a Maltese arms dealer named James Fenech, another of Prince’s former business associates, who, according to an earlier U.N. report, leased some of the boats that were used in the operation.

The New York Times quoted an unnamed spokesman for Prince as saying that Prince had “nothing whatsoever to do with any alleged private military operation in Libya.” And it’s possible that all these ties are a coincidence. But it strains credulity to believe that Prince had nothing to do with or no knowledge of an operation that involves his company’s plane, at least two of his former business associates, and a former lawyer for his businesses — all allegedly involved in a planned operation in a country in which he has repeatedly shown intense interest.

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A fighter loyal to Libya’s internationally recognized Government of National Accord prepares to fire a machine gun as a press photographer take pictures of the scene during clashes against forces loyal to strongman Khalifa Haftar in May 2019, in the Airport Road Area, south of Tripoli. Mahmud Turkia/AFP/Getty Images

Private military contracting is a word-of-mouth business, and Prince has built up a valuable network of mercenaries who can fight private wars around the world on short notice. “Because it’s illicit, it’s all who you know, and it’s all vouching for people,” says Sean McFate, an ex-Army paratrooper and former private military contractor who has written a book on the industry, The New Rules of War. In McFate’s view, back-to-back fiascos in Libya also fit with how some in the mercenary world view Prince. “He’s an attention-seeking Kardashian who’s largely despised,” McFate says. “On top of that, he’s a failure as a mercenary … He doesn’t have any successful operations.”

While the U.N. tries to untangle Project Opus, nearly a dozen people marked for kill or capture in the 2019 Libya mission are lucky the operation was such a boondoggle. The U.N. report notes that two of the men targeted for assassination in Libya, Mahdi al-Harrati, a former mayor of Tripoli, and Husam “Irish Sam” Najjar, had Irish citizenship. (U.N. investigators say they have not yet determined who presented the idea of killing the men to Haftar in the Cairo cafe and whether it was that person or the general who came up with the idea for a kill list.)

After the disastrous misadventure from 2019, a new group of mercenaries and a few veterans from the previous short-lived operation were hired for another attempt on Tripoli. According to the U.N. report, the soldiers of fortune traveled to Dubai, and then were told to head to nearby Abu Dhabi. There, they learned their mission would be a repeat of the first one. U.N. investigators are examining whether Prince had any involvement with the second planned assault on Tripoli and whether he attended a briefing for the mercenaries in Abu Dhabi.

The second planned incursion in Libya, like the earlier one, ran aground. The U.N. report notes that what it calls “Project Opus 2” was similar to the original, with the use of helicopters and light aircraft to support Haftar’s forces in Libya. The mercenaries deployed to Egypt and then arrived in Libya. They had been told that they had a clear path to Tripoli, but the Turks, who back the government in Tripoli, were protecting the city with air defenses that could shred a helicopter as well as surface-to-air missiles. The mercenaries, realizing they had no chance of success, quickly left.

Libya has attracted soldiers of fortune from around the globe, sort of like the Star Wars cantina for mercenaries. Russia’s Wagner Group is said to be operating in the country, along with fighters from Syria and elsewhere. Prince has been fascinated with Libya for years, in part because the United States has a limited footprint there. He told Mueller’s office that he has focused on “peripheral” areas, such as Libya, Yemen, and Somalia, where the Department of Defense does not have a significant presence. Prince also has an eye for resource-rich countries in Africa, and Libya’s large reserves of cheap, sweet crude oil make an enticing prospect.

Whatever the truth is about Prince and Libya, what’s clear is that Prince’s wealth has enabled a chaotic and uneven business career with a track record of collapsed companies, burnt bridges, and accusations of ethical lapses and callous disregard for the lives of non-Americans. He is in many ways an echo of Trump: a relentless self-promoter, brimming with a confidence in his own capabilities and a belief that there is no problem he cannot solve — despite the failures from Nisour Square on.

Prince paints himself as continually undercut by unscrupulous enemies in the Democratic Party, but some of his colleagues say his problems are of his own making. “He is selling the Erik Prince show,” says one former associate who has known him for years. “And he does not know what he’s doing.” An international security investigator laughs at the mention of Prince’s name, saying “You mean the world’s worst mercenary?”

“I respect Erik’s intellect,” says another former associate. “I have less than zero respect for his ethics.”

The criticisms haven’t kept Prince from pushing his next big idea. Prince has hung on to the Blackwater trademark for all these years, and he recently announced that the company is once again providing security services, although Prince was vague about the details.

“Blackwater is back,” Prince said in a Fox News Radio interview in August “and hopefully, much to the consternation of the raging, loony left.”

Andy Kroll contributed to this report.