The title of the talk was “The War in Syria Is Not Over,” but it was more like Nir Rosen’s valedictory address. For roughly 20 minutes, the gonzo war-journalist-turned-mysterious-diplomatic-operator—who counts top advisers to both former U.S. President Barack Obama and Syrian dictator Bashar Assad among his acquaintances and admirers—laid out his narrative of Syria’s civil war, the most lethal and defining conflict of the 21st century. In the speaker’s view, no one but he had gotten it right.

The U.S., Europe, and others that continued to sanction and isolate the Assad regime would be culpable for the “new social collapse” likely to follow Assad’s reconquest of much of his devastated country, Rosen told his audience at a Valdai Discussion Club event in Moscow in late February of 2019. “The same countries who claimed to care about the Syrian people and speak on their behalf supported insurgents, tried to overthrow the government and now are trying to starve Syrians,” the published version of the speech reads. “That the Syrian government behaved abhorrently does not justify the international intervention that followed and in fact the intervention helped cause these crimes.” The West’s motives for these ongoing “crimes” in the Levant were so obscure that they could only be described in theoretical terms. “Capitalism doesn’t work the same way everywhere,” he explained. “[T]he value of the Middle East is the accumulation of capital through war.”

In the text, one can forget Rosen is discussing a government that had murdered tens of thousands of people in a network of secret torture camps, bombed bread lines and hospitals, and gassed entire towns. In fact the Syrian dictator and his backers deserved thanks for defending the global order against the jihadist hordes at a steep cost in manpower and prestige. “The world owes Russia and Iran a debt of gratitude for preventing the collapse of the Syrian state,” Rosen said, to an audience that included senior Iranian and Russian foreign policy officials, as well as Robert Malley, the National Security Council’s Middle East director for most of Barack Obama’s second presidential term.

The fact of Rosen speaking on-record was more surprising than any of his actual statements. The Moscow speech represented some of Rosen’s only attributed public statements since 2012—a long public silence that would once have been unthinkable. In the 2000s, Rosen emerged as one of the edgiest American journalists working in the Middle East, embedding with Iraqi insurgents, Hezbollah, and the Taliban and publishing richly detailed, sometimes-admiring accounts of their operations.

Rosen’s work often reflected an ideological belief that the exercise of Western power in the Middle East was inherently wrong, a view partly shaped during a trip to Israel early in the decade. According to an April 2002 essay for CounterPunch, which is still preserved online, Rosen had spent at least some of his childhood in Israel; in the early 2000s, much of his extended family still lived there.  In the essay, a then 25-year-old Rosen recounts a visit to the Jewish state the year before and candidly grapples with his heritage in light of his revulsion at the moral and political state of the country. “As my El Al plane landed in Tel Aviv, the intercom played an Israeli folk song of my childhood, ‘It’s so good that you’ve come home,’” he wrote. “Despite my cynicism, the child in me wanted to cry. I stifled the nascent tears, which I rejected as a vestigial remnant of the nationalist propaganda they had inculcated me with in the summer camps of my coastal village.”

Rosen was visiting during the height of a Palestinian terror campaign against Israeli civilian targets. In a time when pizza shops, discotheques, and Seders were under routine attack, Rosen found that his “whole conception of good guy and bad guy, of victim and victimizer, was backwards.” What he saw, he wrote, was the bigotry and complicity of his closest family members in their country’s subjugation of another people. “To my dismay, my parents, and all moderate Israelis have been radicalized. Now I find an unbridgeable rift widening between myself and my family, over which we communicate only by screaming.”

By the end of the 2000s, Rosen had published two hotly discussed books about American policy in the Middle East and contributed major feature stories to places like The New Yorker and The New York Times Magazine. Starting in 2012, however, Rosen left journalism and began working for the Center for Humanitarian Dialogue, a conflict resolution organization based in Geneva whose work building contacts between rival combatants in war zones is discrete bordering on secretive. Rosen’s role was to foster ground-level peacebuilding in Syria, but he also shuttled between Damascus, Beirut, Geneva, Washington, the UN’s Syria missions, and various European cities. His work had little in common with the daily activities of nearly any of the journalists, think tankers, or NGO employees who have moved through Syria over seven years of war.

Despite his fraught and easily Google-able origins, Rosen achieved a level of access in Damascus that was practically unmatched among American citizens. While the Assad regime is famously paranoid—even Joshua Landis, an academic authority on Syria at the University of Oklahoma and himself a supporter of greater Western engagement with Assad, claims to be unwelcome in the country—none of the dozens of experts, activists, regime opponents, regime supporters, and bipartisan U.S. government staffers consulted for this article disputed that Rosen enjoyed uniquely close contact at high levels of the regime.

To some, Rosen’s proximity to a regime run by the most notorious mass killer on the planet is ipso facto proof of malign intent, since only grave moral or material trade-offs could have won the trust of Assad’s coterie of paranoid and anti-Semitic murderers and thugs. To others, Rosen is a heroic figure, someone who risked his reputation and physical safety to try to end the world’s deadliest conflict.

Steven Simon, one of Malley’s recent predecessors as senior Middle East director on the National Security Council and someone who says he has been friendly with Rosen since the early 2000s, describes Rosen as “unencumbered by the Washington mindset or the preconceptions that tend to regulate policy analysis and even to some extent intelligence analysis … he’s on the ground, he speaks the language, he travels widely, he is weirdly immune to concerns for his personal safety … It’s not hard for him to think outside of the box because he is outside of the box.”

Others are less generous. Rosen is alleged to be good at collecting information and then twisting it to his own ends. “Nir is a big narratives guy. Nir is not about details—or, let’s say, the truth,” says one Rosen associate. A Syrian opposition figure who has also met Rosen similarly describes him as “calm, speaking with a very low voice, never agitated.” The source, who doesn’t like Rosen, nevertheless acknowledged his abilities: “He sits and he fucks your eyeballs with his eyeballs. When you’re talking he’s looking at you—are you lying?, he’s thinking. He has these black eyes, and he just sits with confidence and when you’re telling him a story he’s assessing it at two terrabytes a second.”

The most salient questions to ask about Rosen require no deep inquiry into his mind and soul, however interesting a place they each might be. How did someone of his personal and professional background ingratiate himself with senior security and intelligence officials for one of the most isolated and notoriously brutal governments in the world? Is it a sign of strength that the U.S. foreign policy establishment eventually found a use for someone with Rosen’s talents and worldview—or a sign of decay that a person offering such connections was ever deemed useful? These questions point to a third way of understanding Rosen, one that pegs him as neither a hero nor an Assadist but an egoist drawn toward whoever could magnify his own importance. By this interpretation, a hotline to Damascus gave Rosen what he and maybe every other journalist who is drawn to big international and political stories secretly crave: the chance to influence events, rather than simply record and analyze them. 

Whatever his motives, Rosen’s career in Syria shows how foreign policy works in the 21st century. The shapers of world events often hold no official portfolio, operating through channels that even those inside of government can’t always see or understand. Policy inputs originate far beyond any knowable org chart, and they result from furtive negotiations of access whose true parameters are unknown to all but the required few. At times, policy can resemble a kind of freelance spycraft by which decision-makers on multiple continents find and activate Rosen-like figures who are unencumbered by employment with any publicly accountable organization.

At that rare Moscow appearance, Rosen took some shots at the Assad regime, calling it “feudal” and “incompetent.” When he began criticizing Assad for lacking a post-conflict reconstruction strategy, Bouthaina Shabaan, the Assad regime’s longtime liaison to the Western press, walked out of the speech in dismay. According to attendees, Rosen did not seem perturbed.

“Look, the people Nir interacts with are much higher than Bouthaina,” says Randa Slim, the director of conflict resolution at the Middle East Institute and someone who attended the talk. “She is a political, civilized figure of the regime, and the people Nir interacts with are the ugliest security and intelligence people.”

Some of the most brutal and powerful officials in Damascus apparently saw Nir Rosen as a useful instrument. The question is why—and for what?

***

Rosen’s first entry into global affairs was in 1999, when he traveled to Serbia, technically still part of a rump Yugoslavia, not long after the NATO bombing campaign against Slobodan Milosevic’s government concluded. According to a published essay recounting a misadventurous stay in a Serbian prison in early 2000, Rosen went to the country partly because he was dating a Serbian woman and had grown interested in her rapidly disintegrating homeland.

Rosen was then in his early 20s, a few years out of LaGuardia High School, a public art-focused school in New York City. He had grown up in an apartment on First Avenue in the 80s, which is hardly the fanciest part of the Upper East Side but also an unlikely prelude to an adult life spent roughing it in some of the world’s most dangerous places. Very little else is known about his family and ethnic background. What is known is that until the end of ninth grade, Rosen attended Ramaz, the elite Upper East Side Jewish day school—which, depending on your feelings about the circumscribed world of well-off Manhattan Jews, might seem like an unlikely precursor to his later politics or a perfectly logical prelude to a life of hostility toward the Jewish state. Rosen  had the ability to fit in anywhere. Like his later self, the pre-journalism Rosen was outgoing and fashionable, unafraid to talk to people of different backgrounds or to draw attention to himself.

In late 1999 and early 2000, Rosen worked as a bouncer at Cities nightclub in Washington, D.C.’s Adams Morgan neighborhood while trying to launch a writing career. Then, and now, Rosen was well built—associates say he often shows up to meetings with a duffel bag, as if he is on his way to or from the gym. He never consumes alcohol. “Every time he came back he would start looking more like the Assad militias,” recalls one former U.S. foreign policy official who regularly met with Rosen while in government.

Rosen belongs to a generation of writers who built their careers in post-invasion Iraq. He first went to the country not long after the beginning of the insurgency and apparently without any significant Arabic skills; his early work appeared in outlets like the Asia Times. By mid-decade, he had met future U.S. decision-makers like Simon and Malley and was writing articles for The New Yorker, Time, and The New York Times Magazine. He set himself apart from other wartime freelancers through a thirst for detail and a willingness to embed with just about anyone in Iraq’s vast constellation of armed groups, regardless of their ideological or political alignment or apparent disrespect for basic human rights.

In the course of his reporting, Rosen became a fluent Arabic speaker and impressed senior figures in the U.S. government, who believed his work presented a more accurate picture of the Iraqi insurgency than the American intelligence community’s classified products. “I remember giving one of his articles to Ambassador [Zalmay] Khalilzad who says with some anger, how could someone like this understand these guys better than our intel does?” recalls Robert Ford, the last American ambassador to Syria and the political counselor at the U.S.’ Baghdad Embassy from 2004 to 2006. A former Pentagon official who spent considerable time in Iraq says that Rosen provided “really valuable insights into the thinking of certain entities” in his journalistic and analytic work.

Republican-appointed diplomats and Defense Department officials would not seem to be Rosen’s natural audience, given that he has had almost nothing kind to say about the U.S. or its allies. A 2011 blog post by an Atlantic magazine writer recounts some of Rosen’s greatest hits: On Twitter he voiced his approval of a Taliban-issued 9/11 anniversary statement, hailed a Greek mob beating of a former government minister, and wished “pain and suffering” on Wolf Blitzer. None of this seemed to matter. If anything, Rosen’s growing network of friends and contacts in the foreign policy world learned to price in his various eccentricities or analytic biases, which became more obvious over time. “I gotta respect his knowledge of stuff on the ground. But it’s like talking to an Al-Tikriti about politics in Iraq,” says the former Pentagon official, naming Saddam Hussein’s hometown. “You’ll get a perspective there, but if you talk to someone from the Al-Ubeid tribe you get a different perspective.”

As the U.S. presence in Iraq wound down, Rosen embedded with many of the most notorious armed groups on earth, including the Taliban, Al Shabaab, and Mexican drug cartels. He was also allowed to tag along with fighters from the Lebanese terrorist group Hezbollah who were patrolling West Beirut during a fairly sudden rash of sectarian violence in 2008—an outstanding achievement, by some measures, given the organization’s paranoia. Around that time, Rosen reconnected with someone he had known since mid-decade: Robert Malley, the Clinton-era diplomat who oversaw much of the administration’s Israeli-Palestinian peace efforts, who was then working as the head of the International Crisis Group’s Middle East division. Malley later served as the Middle East director on Obama’s National Security Council during his second term in office, handling the Syria conflict, counter-ISIS efforts, and negotiations with Iran. “Nir is someone who spent much of his adult life on the ground going to war zones and taking inordinate risks most of us would not take,” Malley told me.

Rosen’s anti-establishment bent and penchant for making provocative or outrageous statements still did nothing to slow his integration into the institutional foreign policy world. He was a fellow at the New American Foundation from 2005 to 2008, where he was a favorite of J Street co-founder and former Israeli diplomat Daniel Levy; he was the C.V. Starr distinguished visitor at the American Academy in Berlin for a month in 2007, and received a Pulitzer Center grant for an Afghanistan-related project in 2009. In 2008, he was named a fellow at New York University’s Center on Law and Security, the kind of multiyear posting that hailed Rosen’s ascension within a foreign policy machine he had spent his career denouncing. That posting ended when Rosen tweeted his satisfaction at CBS reporter Lara Logan’s sexual assault in Cairo’s Tahrir Square in 2011, calling her “a major war-monger” in apparent reference to her alleged cheerleading for the U.S. invasion of Iraq. In an interview with MediaBistro, Rosen explained that heheard that Ms. Logan was roughed up like many other journalists” and “had not realized it was something more serious.” CNN’s Anderson Cooper, who had been working alongside Logan when the attack took place, didn’t buy the explanation when Rosen appeared on his show to discuss the controversy. “You … linked to the CBS News statement, which clearly said it was a sexual assault,” a noticably agitated Cooper pointed out. “Yeah, I shoulda read it,” Rosen conceded.  Rosen’s contacts and track record—which by then included In the Belly of the Green Bird and Aftermath, two widely admired accounts of the U.S. campaign in Iraq—were not enough to save his job. He resigned from NYU five days later.

Rosen’s humiliating ejection from the institutional foreign policy community forced him onto an even less orthodox path at precisely the right time. As the Arab Spring unleashed new waves of chaos across the Middle East, the region exploded with possibilities for Arabic-fluent Americans who had little apparent consideration for their personal safety. In March of 2011, protesters took to the streets in the southwestern Syrian city of Deraa, demanding the release of teenagers arrested for spray-painting anti-regime graffiti. By the end of the summer, Syria was in an incipient state of civil war, with government forces massacring anti-regime protesters, who coalesced into a loosely organized armed opposition. Rosen was well positioned to cover the conflagration, which would involve nearly every country in the region, displace over 13 million people, warp the politics of both Europe and the United States, and devolve into the deadliest and most consequential conflict of the 21st century.

Early in the war, Rosen, working largely for Al Jazeera, focused his attention on the country’s armed opposition, for whom he professed sympathy. Robert Ford, the U.S. ambassador to Syria from 2010 to 2014, met Rosen at the ambassadorial residence in Damascus in December of 2011. Ford recalls that Rosen offered a “striking” description of the cross-sectarian character of a protest he had witnessed in southern Damascus. “He asked me at this point whether Americans could provide help to them,” Ford says. Through 2011 Rosen was “quite pro-revolution, almost in a naive way,” one associate recalls.

Rosen embedded with the anti-Assad Free Syrian Army, impressing his contacts in the rebellion with his willingness to travel through the quickly disintegrating country and his quick mastery of even the most granular facts about both Syrian society and the conflict’s ever-expanding cast of violent actors. Rosen’s work is often thick with such minutiae. “Jumping from the big-picture stuff to the micro details is really effective. It creates the impression that ‘shit, this guy knows everything,’” recalls the associate.

Multiple opposition sources told Tablet that Rosen could Skype or meet with almost all the key figures in the uprising but that not everyone in the growing anti-Assad movement trusted him. Word spread that Rosen had contacts within the regime and seemed to enjoy a suspicious degree of access to government-controlled areas. “Perhaps the only enduring mystery of Mr. Rosen’s four months in Syria is why, as an American working for an Arab satellite channel that Syria accuses of fostering the rebellion, he was granted permission by the government to report inside the country without any oversight,” wrote the New York TimesRobert Mackey in a sympathetic March 2012 blog post about Rosen. Rosen claimed to Mackey that his Arabic skills allowed him to blend in seamlessly with his surroundings, and added that the regime was simply too busy to surveil him. 

One U.S.-based Syrian opposition figure who has met with Rosen in Europe now thinks he was operating in bad faith during the first year of the conflict. “He was embedding himself with the opposition without being honest,” the source says. “And of course he can’t be honest; if he was, they would kill him.”

Rosen’s assessment of the war seems to have undergone a rapid shift by early 2012, and he began predicting the rebellion’s eventual failure. Even before then, he was granted seamless access to regime-controlled Syria at a time when the government was actively hunting foreign journalists in order to kill them. Paul Conroy, the photographer for the war correspondent Marie Colvin, recalls the ordeal of traveling from Beirut to the rebel-controlled side of Homs in early 2012, the city that was then “the heart of everything.” Conroy, who was with Colvin when the regime killed her in a targeted artillery bombardment on the rebel-controlled Bab Al Amr section of the city in February of 2012, says that it took five days to travel from Beirut to Homs using a network of safe houses and then a secret mile-long tunnel into the city, a trip of only three hours in peacetime.

That wasn’t the only hardship they faced. “They’d been tracking us all the time we were there, from getting into the airport in Beirut—they got our names to Damascus,” recalls Conroy. “They used some quite sophisticated Russian tracking equipment for our cell and SAT phone systems. They had a whole unit set up in Homs funded directly by Damascus where they were shipping money to informants and to Shabiha [pro-Assad militant groups] to coordinate the hunt for journalists.”

Rosen traveled wherever he pleased without any such dramatic obstacles; his presence in the rebel side of the city, an isolated and extremely dangerous enclave where journalists and fixers were well aware of their colleague’s movements, was slight verging on nonexistent. “When I was in Bab Al Amr nobody even spoke about him,” Conroy told me. (Conroy and Colvin traveled to Homs multiple times in late 2011 and early 2012, several weeks after Rosen was in the city.) He was largely working from the government-controlled side of the country, for months at a time, with no apparent regime supervision. Oddly, he seemed to be the only person doing so.

In March of 2012, observers got a window into how Rosen might have pulled off such a feat, when Wikileaks published a tranche of emails hacked from Bashar Assad’s personal inbox. An email from Assad adviser Hadeel Al-Ali stated that Rosen had been in Syria for two months, something that was possible because the journalist had gotten “cover from Khaled and his people.” “Khaled” referred to Khaled al-Ahmad, a businessman in his early 30s who almost no one outside or inside of Syria had heard of, but who the email hack revealed to be one of the president’s intimate advisers.

In a November 2011 email, Ahmad, a budding Damascus-area industrialist whose family came from Homs, informed Syria’s dictator of a promising new relationship with a journalist who had provided information about reporters sneaking into the country. “Nir Rosen was also able to enter Baba Amr,” Ahmad wrote to Assad. “He personally informed me that several Western journalists entered the area via illegal routes and from the Lebanese border. Among the media envoys are a French and a German journalist.” As detailed in the Wikileaks emails, Rosen also mentioned the British journalist Paul Wood. 

“He did this to help his own visa application. He named me,” Wood later wrote in the Columbia Journalism Review. “This was not helpful.”

Other information Rosen possessed somehow made its way to regime officials. A senior Syrian opposition source told Tablet that details about the source’s travels and meetings shared during a private conversation with Rosen in a television studio green room in 2012 also wound up in the leaked emails.

Yet these revelations of apparent complicity with the Syrian regime had far less of an effect on Rosen’s career in the Middle East than the Logan controversy did. If anything, the emails proved Rosen had identified a novel route into Damascus through Ahmad, someone whose father had been a leading figure in the 70s and 80s Baath party and a confidante of Hafez Al Assad’s but who was himself unknown to even the closest Syria watchers. “To be honest I’d only heard of him once or twice when I was in Damascus,” recalls Robert Ford, who served as U.S. ambassador to Syria from 2010 to 2014, of Ahmad. “Nobody had ever described him to me as very close to the president.”

From a very early point in the conflict, Rosen was apparently on to something that absolutely everyone else seems to have missed. The obscure presidential advisor “was among the Bashar cronies whom Rosen was regularly meeting and corresponding with as early as 2011 in order to share information about the opposition and assure them that the United States and its European allies were incapable of referring Bashar’s atrocities against protesters to the International Criminal Court,” Wall Street Journal reporter Sam Dagher writes in his recent book Assad Or We Burn The Country. (“What is in Dagher’s book about me and about Steve Simon is not accurate at all, and is dishonest” Rosen wrote to Tablet by email, although he would not elaborate any further)

In 2012, after the email controversy subsided, Rosen scored a new job, with the Geneva-based Centre for Humanitarian Dialogue, one of the world’s leading conflict resolution NGOs. He was no longer a journalist, or even an analyst. For the next several years, Rosen would act as a kind of shadow diplomat, working under a cloud of secrecy with a seemingly limitless budget and an arsenal of high-level contacts in Damascus and Washington. “He’s kind of passed the line from journalism to being a kind of operator,” says Ford. “It’s different.”

***

The Centre for Humanitarian Dialogue, or HD, was founded in 1999. Although it is an NGO, it receives significant funding from state sources, most prominently the E.U. and the Norwegian government; the group’s office space is a gift of the municipality of Geneva. The organization’s employees are prohibited from speaking to the media. “HD is just a mechanism for parties to any violent conflict to connect with each other and without the pressure of time or physical security or publicity,” explains David Harland, a former high-level U.N. official from New Zealand who had served in Sarajevo for much of the city’s over-1,400-day siege in the mid-’90s and the organization’s executive director since 2011. The center has assisted in brokering the first agreement between the Indonesian government and the Aceh separatist movement, helped reach humanitarian access deals with the Taliban, and negotiated the total disarmament of the Euskadi Ta Askatasuna, which the Basque terrorist organization announced in 2017—a rare instance in which a major nonstate armed group permanently renounced violence.

Syria was a likely theater for HD’s approach to conflict, a steely realism that holds the reduction of violence to be a categorical imperative and avoids drawing moral distinctions between combatants. Like Rosen, HD had an unromantic and decidedly 21st-century understanding of how global events are shaped. It is little surprise that Harland and the organization have given Rosen so much freedom and have stuck by him through moments of controversy. HD gave Rosen the ability to travel wherever he liked with relatively little oversight—he would disappear to Washington on almost a monthly basis, for reasons that remained mysterious to most of his colleagues.

In Syria, HD faced an especially stark challenge. The organization “doesn’t have any substantive view on the outcome of conflict,” says Harland. Yet the Syrian war has always been defined by dramatic battlefield disparities. The Assad regime has an air force, a system of torture camps, chemical weapons, and a host of brutal state and nonstate allies, including Hezbollah, Russia, and Iran. The regime’s atrocities deepened the moral hazards of diplomacy: One side’s ceasefire could mean another side’s sectarian or ethnic cleansing.

Rosen’s well-advertised views on the war didn’t seem to bother his bosses. “It’s public knowledge he says he felt that the most likely outcome for the war would be a government victory of some sort, presiding over a largely destroyed country without much of a formal process,” Harland allowed. “I think he was more right than most.”

HD initially had Rosen organizing what are known as Track IIs— informal, nonbinding diplomatic-style meetings between prominent individuals who typically are out of government. But both the regime and the opposition were wary of Track IIs: The regime feared that the talks legitimized the opposition, while the anti-Assadists viewed the process as a “scam,” according to one senior Syrian opposition leader. According to an associate of Rosen’s, he didn’t have much use for Track IIs either. “He always saw Track II as being ‘for white people,’” the source recalls. “That was his derogatory term.”

Khaled Ahmad had a use for them though. Since he was not under U.S. or EU sanctions, HD could operate as Ahmad’s travel agency. Rosen’s organization secured Ahmad visas that would allow him to attend their meetings and then travel widely throughout Western Europe, according to a source familiar with Ahmad’s travel arrangements.

Though Ahmad has never held an official title within the regime, and never served in the military or Syrian government in any official capacity, there are some who see him as one of the conflict’s pivotal figures. Landis, of the University of Oklahoma, calls Ahmad “the father of the reconciliation process,” someone whose success in brokering local ceasefires in Homs gave him the respect and influence needed to sell the idea of targeted micro-agreements to a skeptical regime, thus pointing a way out of Syria’s morass. If this is true, then Nir Rosen had turned himself into the preferred Western contact for one of the key figures in the regime.

One U.S.-based source who knows both men says it was Ahmad who arranged for Rosen’s open-ended visa to regime-held Syria in 2011. “Nir was surprised at some stage that he was given this visa without any strings attached,” the source recalls. Ahmad had the seeming ability to ask the country’s intelligence or political apparatus to have Rosen’s visa requests expedited, a privilege hardly anyone else enjoyed. “Nir Rosen without Khaled Ahmad is nothing—he would just be another voice,” explained a source who has had contact with both men. “With Khaled Ahmad, he was armed.” In some sense, the two men helped to create one another, using visas and access as the currency of their relationship.

Robert Malley says that he did not know of Ahmad’s existence until Rosen told him about the young presidential adviser in 2014, when Malley was Middle East director on the National Security Council. The two subsequent meetings between Ahmad and Malley were some of the only major, publicly known, face-to-face points of contact between the regime and the U.S. government during Obama’s second term, which coincided with the most decisive years of the war. Ahmad was “a polished interlocutor for a regime that’s hardly that polished,” Malley recalled. “His brief, as far as I understood it, was to try to improve relations between Damascus and the West.”

Earlier in the conflict Ahmad had met with both Ambassador Ford and Steve Simon through Rosen. Simon, who left government in 2012, met with Ahmad at least twice before the spring of 2015 according to The Wall Street Journal, when Ahmad arranged for Simon to travel to Damascus and meet Bashar Assad, a trip on which Simon briefed Malley after he returned to the U.S. The trip cost Simon his position as a paid consultant at the Middle East Institute, which  Simon had not informed of his travel plans according to a report in Bloomberg. (Simon is currently a professor at Amherst College.) 

Rosen and Ahmad were filling a void that Western policy toward the conflict had created. In October of 2011, the U.S. pulled Ford and his team out of Syria amid a worsening security situation in Damascus. As the war progressed, and as the Assad regime used terror and mass murder to crush the burgeoning and increasingly violent and Islamicized uprising, the U.S. and nearly every other Western government opted for a policy of isolation against Damascus. Once relations between the U.S. and Syria were halted, there was no obvious roadmap for restoring them. 

Rosen was especially useful within this context, thanks to the exceptional frequency of his travels to the Syrian capital together with the anonymity and institutional support afforded to him by his Swiss NGO. No one else had his high-level contacts, his Arabic skills, or his risk threshold. According to multiple former U.S. government officials, Rosen was one of the very few people to provide U.S. policymakers with a sense of the Assad regime’s thought process, and of how the security establishment in Damascus viewed their country’s crisis.

Malley estimates that he met Rosen face-to-face a half-dozen times during Obama’s second term. Rosen had a comparable number of meetings at the State Department. As one official put it, he was part of a group of “not hundreds, but tens” of experts and operatives who routinely briefed Foggy Bottom on the war, and one of a very tiny handful—perhaps three or four people total—who could offer an informed, regime-centered perspective on things. At one point, Rosen provided Malley with information suggesting that Russia was talking to the Syrian government about a possible military intervention in the country, a deployment which came in September of 2015 and may very well have prevented the Assad regime’s collapse.

Rosen and HD had an even more active advisory role with Staffan de Mistura, the U.N.’s special envoy in Syria appointed in mid-2014. According to multiple sources, de Mistura, a veteran Middle East diplomat who nevertheless had little specific prior experience in Syria, was supportive of Rosen’s idea that HD could broker a series of localized ceasefires to resolve ongoing fighting in Aleppo, a solution that would have resulted in the effective surrender of opposition forces in the city. The relationship between the two eventually cooled—Rosen’s hoped-for ceasefires were both unpalatable to much of the international community and impractical to negotiate or implement. But at the beginning of his mission de Mistura seemed eager for Rosen’s respect, even if the HD staffer could be critical of the envoy’s performance. Someone who attended meetings that included both men likened de Mistura to a jilted but still hopeful lover.

When reached for comment by email, de Mistura recalled that Rosen “only occasionally engaged with some of my colleagues and only at the very beginning of my mission, mostly in a context of large brainstorming sessions with several other experts and hence never directly with me … I had the impression of a highly intelligent person with a deep knowledge of the Syrian environment and very strong and sometimes controversial opinions regarding the conflict and its players.” De Mistura characterized HD’s role as “useful and helpful.” “We all wanted very much the same thing: to launch an Aleppo ‘freeze,’ de Mistura wrote. “We just had a different approach to it. Neither worked, because both Syrian sides, in turn, just believed tragically at that time that they could ‘win’ the war.”

***

Rosen touted his contacts with the regime’s senior intelligence and national security leadership, which is one of the unspoken reasons officials in Washington and elsewhere took him so seriously. “In the summer of 2014, Rosen boasted about his access to the regime’s most notorious mukhabarat chiefs and his regular meetings with them in Damascus,” Dagher writes in Assad Or We Burn The Country, based off of a converastion he had with Rosen in the Syrian capital in August of that year. In meetings with U.S. government officials, Rosen presented himself as being especially close with Dieb Zeitoun, the head of Syria’s General Security Directorate, one of the regime’s four major intelligence agencies. “He says he was working in cooperation with Dieb Zeitoun and that it was Zeitoun who facilitated his work in Damascus,” Ford says of a meeting with Rosen in Geneva during the late summer of 2013. “Nir was getting in and out of Damascus and presenting himself later as an unofficial envoy of the Syrian government. That’s what he presented himself as when he was talking to U.S. officials in late 2013 and 2014,” Ford recalls.

A Middle East-based Syrian opposition figure who met fairly frequently with Rosen says Rosen told him he “met many times with Ali Mamluk,” another one of the regime’s intelligence chiefs. “In a way our meetings developed to me meeting him to sense how Ali Mamluk was feeling and he met me to sense how the opposition is feeling and what we are doing. I would be debriefed and he would be debriefed,” the source says.

One of the many mysteries regarding Rosen is the question of how he won the trust of some of the hardest and most brutal people in one of the most paranoid regimes on earth. One possibility is that Rosen knowingly spread pro-regime spin to Western audiences. The strongest evidence for that claim is the allegation made by multiple experts on the conflict and Rosen associates who spoke with Tablet that Rosen was the author of a controversial essay published by War on the Rocks in August 2016 under the pseudonym Cyrus Mahboubian (which was later changed to Cyrus Malik). That essay, titled “Washington’s Sunni Myth and the Middle East Undone,” stressed the prevalence of Sunnis in Syria’s military and intelligence apparatus in order to argue that the regime was nonsectarian in nature—without noting that the heads of Syria’s two most powerful intelligence branches are always Alawite, or that senior Sunni officers often serve in noncombat roles, or that the regime’s elite combat forces skew heavily Alawite.

Yet at the same time, it is almost impossible to find statements in which Rosen offers full-throated praise to the Syrian government, even if he gave the impression that he trusted the regime and its intentions more than most other analysts did. Rosen told a Syrian opposition figure in a 2015 meeting in a European city that he was certain the government would not bomb rebel positions after agreeing to local ceasefires. In reality, nearly every ceasefire preceded a fresh regime onslaught, regardless of the substance of the agreement supposedly governing the area.

Another possibility for how Rosen won over potentially skeptical hardcore Assadists is that he already had the kind of pedigree that would steady the nerves of regime apparatchiks. In the late 2000s, according to multiple sources familiar with the late-2000s Beirut press corps, Rosen became acquainted with Michel Samaha, a now-disgraced Lebanese politician. Samaha emerged as one of his country’s leading pro-Syria Christians during Lebanon’s long civil war. He was expelled from Lebanon in the 1980s, but returned as the country’s information and tourism minister with Syrian backing in the ’90s and 2000s. In mid- and late-2000s, around the time Rosen had moved from covering Iraq to working out of Lebanon, Samaha was serving as a shortcut into Syria for a cadre of international journalists and analysts sympathetic to the regime, including Seymour Hersh.

As one of the Assad regime’s most prominent long-term operatives in its western neighbor, Samaha enjoyed a close relationship with both Ali Mamluk and Bashar Assad. “Even if you’re pro-Hezbollah you think of him as a lowlife,” one Beirut-based source says of Samaha. “But he’s a good lowlife to have on your side.”

Multiple sources spoke to me about Rosen’s relationship with Samaha: “He was vouched for by another made guy, which is Michel Samaha,” a former associate of Rosen’s says of the one-time analyst’s work in Syria. At least two informed sources told Tablet that Samaha connected Rosen to Khaled Ahmad. The U.S. designated Samaha as a terrorist in 2012 after he was caught importing explosives from Syria as part of a terror plot that Ali Mamluk allegedly orchestrated. Samaha was released from prison in 2016, although he still appears on the U.S. sanctions list.

“How do you win the trust of those people? I’m not sure you ever really do. So it’s all about manipulation,” says Ford. “I’d think of Dieb [Zeitoun] using Nir almost as an agent. Agent implies spying—I’m not saying Nir was spying. He was using him as someone to execute orders as part of an initiative or part of a plan or some kind of an operation, tugging on the Obama administration—pulling on a thread, seeing if it leads anywhere. That’s very much how the Syrians operate.”

While several sources consulted for this article characterize Ahmad as someone who had little ground-level impact but was useful in pleading the regime’s case abroad, his two meetings with Robert Malley, then the Middle East director on the second Obama administration’s National Security Council, still represent some of the highest-level known contacts between the U.S. government and the Assad regime during the war.

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The clearest articulation of the Assad regime’s actual compromise position for ending the war came in the form of an unpublished 66-page paper Rosen himself wrote and then distributed in Washington in late 2014, notably to staffers on the National Security Council, including Malley. The paper was eventually published in full under Rosen’s name at the Grayzone Project in August of 2018. The paper argues that in spite of the Assad regime’s brutality, the only conceivable path to peace in the country was through a sequence of ceasefires through which pockets of armed opposition would give up their ambitions of overthrowing the government in exchange for a local halt in fighting. To supporters of the opposition, the paper and the “local ceasefire” paradigm were a roadmap to Assadist victory and a license for human-rights abuses. The ceasefires allowed for the regime to sequence its wins with international backing while saving Assad from having to fight on a national scale.

“There is nothing wrong with the goal of reducing violence,” says Rafif Jouejati, a Syrian-American management consultant active in anti-Assad activism in the U.S. “The question is who was doing the negotiations and what were their intentions … if you are working with a mass murderer, violence prevention takes on a whole new meaning.”

Throughout 2014 and 2015 and prior to the Russian military intervention, Assad faced a frightening manpower shortage—local-level de-escalation meant he could focus his scarce remaining forces on the areas of most urgent need. In theory, the ceasefires would grant local autonomy and amnesty, or even integration into state-allied security forces, to rebels that gave up their fight against the regime. In practice, the agreements often went into effect in areas the regime had placed under harsh siege conditions for extended periods of time, meaning that the deals effectively rewarded the government for starving out entire cities. Jouejati, like many others in the anti-regime camp, view the word “ceasefire” as “a euphemism”—for them, the agreements allowed Assad to achieve his war aims under the guise of civilized diplomacy.

Rosen’s paper ignited controversy when Washington Post columnist David Ignatius first reported its existence in November of 2014. Later reporting in Foreign Policy magazine indicated that the document had spread throughout the U.S. government, including on the National Security Council. HD did not authorize the paper’s distribution, and the document itself wasn’t published in full until August of 2018, when it was embedded at the end of a Grayzone Project article about Khaled Ahmad. Despite speculation that Rosen himself gave the paper to Ignatius with an eye toward influencing U.S. policy, evidence suggests that Rosen panicked when news of his work became public.

But in retrospect, the paper is, and was, entirely consistent with HD’s ground-level approach to the war. In a March 2017 email that Tablet has obtained, Harland boasted that HD had “facilitated an agreement to restore water supplies to some three million people in and around Damascus, and for the evacuation of 700 Opposition fighters and their families to safety.” The deal, reached “between the Syrian regime and Armed Opposition Groups,” ended opposition control over a water station at Wadi Barada that served 70% of the greater Damascus area. The area had been under siege since 2013, and the regime’s reconquest, aided through a “torrent of airstrikes, barrel bombs, tank shells, mortar fire and snipers,” according to the nonprofit news project Syria Direct, came as a result of a ceasefire agreement in which HD now acknowledged its involvement. One source told Tablet that the email resulted in the curtailment of E.U. funding for HD’s Syria programs, something that Harland did not deny when asked about it. In a year-end message in 2018 that Tablet has also obtained, Harland wrote that Syria was an area of “regret.”

In that email, Harland goes on to echo one of the key themes of Rosen’s paper four years earlier, which argued against pushing for national-level reconciliation, the aim of U.S.-supported negotiations held in Geneva. “While always insisting that HD would do nothing to cross wires with the official process, I was also too blunt in saying that the Geneva process couldn’t succeed,” Harland wrote, “and that it just prolonged the agony, by providing cover for the prosecution of the war, or for not doing very much.”

Five years later, what is most striking about Rosen’s paper isn’t its conclusions or its advocacy—at a time when the Assadists’ survival was far from assured, before Russia’s military intervention—but its many lengthy block quotes from unnamed regime officials whose identities would surely have been transparent to the paper’s readers in Washington, and which are not hard for an attuned layperson to decode. It should be clear to anyone who has slogged through the whole thing that the purpose of the paper wasn’t only to sell U.S. officials on a potentially groundbreaking solution to the world’s most severe crisis, but to communicate an end-state that would be acceptable to comparatively more enlightened figures within the Syrian security and intelligence establishment. The message is clear enough: This is as far as the hard men of Damascus were willing to go.

“The paper circulated throughout the National Security Council, with Malley himself receiving a copy, although it had little apparent impact on his thinking. “I believed our priority was to reduce the violence and end the war, what came to be known as de-escalation,” Malley said, explaining his existing approach to alleviating the Syria crisis. “It doesn’t mean I agreed with the specifics of the plan Nir was advocating.” I remarked to one former Obama administration foreign policy official that Rosen had made it remarkably far for a relative outsider to the Washington policymaking apparatus. “I don’t know how much of an outsider you can call yourself if you can email or call literally every person working on Syria at the NSC,” the source replied. “I don’t know how much of an outsider that makes you.”

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The Obama administration always viewed the Syria conflict with wariness. The Assad regime had committed the worst state atrocities of the 21st century, exactly the kind of crimes that the existence of the U.N. and the U.S.’ postwar global leadership were theoretically meant to prevent. But Barack Obama had been elected president on the promise of not doing “stupid shit” in the foreign policy realm.

By the nadir of the Syria conflict, the president had encountered trouble meeting his own criteria: The U.S.-led intervention in Libya in 2011 had a rash of unforseen geopolitical consequences, ranging from heightened U.S.-Russian tensions to renewed civil conflict in Mali to the Benghazi attack. In Syria, Obama repeatedly called for Assad to step down—while also refusing to provide the rebellion with the assistance needed to tip the conflict in their favor. He authorized a CIA-led train-and-equip mission for anti-Assad forces, and then allowed the initiative to become a disorganized and ineffectual laughingstock. The U.S. provided assistance to secular-minded militant groups, and then seemed unbothered when jihadists wiped them out on the battlefield. Most notably, after the August 2013 sarin attack in Ghouta, Obama opted not to enforce an oft-stated “red line” meant to deter the regime’s use of chemical weapons. The administration’s preferred solution in Syria was to work through a negotiating process in Geneva that was often at an absurd disconnect from events on the ground. “I don’t think any one of us who served in the Obama administration can claim to be proud of our record when it came to Syria,” Malley told me.

The rebellion and Assad’s brutality also threatened to complicate President Obama’s highest objective in the region: a negotiated deal to limit Iran’s nuclear program that would also radically upgrade relations between the U.S. and Iran, “balancing” the power of America’s longtime regional foe against that of allies like Saudi Arabia and Israel. The Obama administration could ill afford to push against Assad to the point of alienating the Iranian regime, to whose support the Syrian dictator owed his continued survival. Obama himself drew an explicit connection between any future outcome in Syria and Iran’s regional stature, saying in a late 2015 press conference that any peace in Syria would have to respect Iranian “equities” in the country.

Malley was the key implementer of the president’s vision. He was Obama’s top adviser on Syria, had an active role in Iran diplomacy, and was in practice the NSC’s leading counter-ISIS official. Malley understood that his boss wanted detente with Iran and as little U.S. strategic investment in Syria as morally or practically possible, and he was successful in making those policies a reality. Since U.S. officials used Rosen to feel out opinion in Damascus, as several freely admitted to Tablet, it stands to reason that Assad regime figures may have used Rosen for a similar purpose: To see if their counterparts in Washington—people like Malley or diplomats on the Syria desk in Foggy Bottom with whom Rosen was meeting—were contemplating a change in strategy. For the US, a soft touch toward Assad preserved a careful negotiation with Iran over the country’s nuclear program, while signaling to the opposition that the Geneva talks were the only path to achieving their political objectives in a war that the president said “had no military solution.” 

Steve Simon thought that President Obama was consistent in telling the opposition not to expect any conflict-shifting American assistance. “Everyone who raises the question of whether it was a mistake for Obama to say Assad should go is, in my experience, generally unfamiliar with the next sentence, which is that the United States isn’t gonna make it happen,” says Simon.

Malley himself suspected from an early point in the conflict that Assad would eventually win, and that an opposition triumph would require more investment in a complex foreign conflict than the U.S. was willing or able to give. The French and Arabic-fluent son of an Egyptian-born father who Malley described as a “militant third-world journalist” and an American mother who worked in the Algerian liberation movement’s U.N. delegation, Malley grew up in Paris and New York. Where Rosen was flamboyant and stridently anti-establishment in his public posturing, Malley was discrete and affable, befitting a Rhodes scholar and a Supreme Court clerk. “He’s a very clever guy. He’s extremely clever,” one European expert on the Syria conflict says of Malley. “He’s clever in a way people in Washington are not.”

While Malley frequently met with representatives of the Syrian opposition during his time in government, his interlocutors, including those who admire Malley, do not remember the meetings fondly. “Rob Malley in general just did not believe at all in the Syrian opposition and it was really obvious he just wanted the opposition to go away,” one activist, a Syrian-American who met with Malley during his time in the White House recalls. “He really didn’t care.” Zaher Sahloul, a West Virginia-based physician and anti-Assad activist, said that over the course of his estimated “30 to 40” meetings with administration officials, “Malley was the most noninterventionist and the most protective of the regime.”

Both Malley and Rosen’s detractors tend to describe them as hard leftists who are ideologically opposed to American power, but such cartoonish descriptions convey a distorted picture of how U.S. foreign policy is actually made. Malley has been working near the top of the U.S. foreign policy community for over two decades and was the president’s leading Middle East adviser; whatever his rebellious image, Rosen is comfortable with establishment figures, and has operated within their world with remarkable longevity despite repeated missteps. Meanwhile, the policies they advocated and affected carried over to Donald Trump’s presidency, implying that they are part of a consensus within the Washington foreign policy and defense elite. For the opposition, and for the hundreds of thousands of Syrians expelled from rebel-held areas under the guise of a negotiated peace, there is little meaningful difference between the Assadist formula of “local ceasefires,” the Obama administration’s commitment to “violence reduction measures,” or the Trump administration’s promotion of “de-escalation zones.” In a way, Rosen’s 2014 paper now looks like one of the more prophetic documents of the war: The regime has gradually reclaimed almost the entirety of the country through exactly the means the document articulated.

Ford remembered meeting Rosen at a Washington Starbucks during the summer of 2015—the ambassador had recently left government, partly out of his dismay at the Obama administration’s Syria policy. “Basically [Rosen’s] message was your rebels—because he knew I had supported arming them—your rebels are going to lose … and the Americans need to accommodate themselves to this fact,” Ford recalls. “And I remember saying to him, it’s a long war of attrition, Nir; who knows who’s going to win. As it turns out Nir was right and I was wrong.”

* * *

There are those who continue to see U.S. policy in Syria as a relative success, at least within the hellish terms that the post-Arab Spring Middle East imposed on Washington decision-makers. “Our interests in the region don’t appear to have suffered terribly much,” Simon says of the Syria conflict. “Jordan is fine, even Lebanon seems to be doing OK. The Lebanese economy is not in flawless condition, but that’s not a function of the civil war in Syria. Iraq—well you know there was ISIS which was pretty vexing, but that was dealt with. So whatever it was that the administration had in mind, the end result for U.S. interests seems to have been not terribly adverse.”

This attitude has carried into the Trump era. Brett McGurk, Obama’s counter-ISIS czar, remained in government until the end of 2018. Michael Ratney, Obama’s final Syria envoy, stayed on at the State Department through the first year of Trump’s term in office. In April, The New Yorker reported that Malley, who’s now the President and CEO of the International Crisis Group, was acting as an adviser to Bernie Sanders on foreign policy. No matter who wins the election in 2020, it seems likely that the U.S.’ Syria policy won’t be affected by the outcome any more than it was by the election of Donald Trump.

Rosen himself has been connected to a range of Syria-related activities over the past two years. In early 2018, according to multiple Syrian expatriates now living in Europe, Rosen and Ahmad attempted to convince Syrian businessmen living in Europe to re-invest in their native country. According to sources with knowledge of the meetings, Rosen presided over the gatherings in London without Ahmad, who met with exiled business leaders in Switzerland and Germany. This marked another instance in which Rosen and Ahmad appeared to be acting in tandem—the meetings were part of a single push to bring investment back to Syria. But Ahmad came in with a weak pitch: “He didn’t have many guarantees to offer,” the source recalls. “He just wanted people to reconcile and go back.” Other sources Tablet has spoken to say that Rosen is now close with Samer Foz, a jet-setting pro-regime businessman who was placed on the U.S. sanctions list this past June. Meanwhile, Ahmad is said to have fallen out of favor with Damascus.

Rosen’s own ambitions are somewhat loftier than bringing capital back to Syria, though. According to multiple sources, he plans on writing a history of the Syrian civil war, a conflict he has seen from angles that almost no other writer has been allowed to glimpse.

“I work on conflict resolution, mediating between warring factions, negotiating the release of hostages and detainees, facilitating the delivery of human aid and basic services as well as returning refugees or the displaced to their homes,” Rosen wrote to me by email, after I informed him that I was working on what I hoped would be a definitive account of his activities in Syria. “I work in various countries, and this work has required that I deal with all stakeholders including governments, both to educate them on the situation and to advise on sensible policies and alternatives to war and bloodshed. I have dealt with U.S. officials just as I have dealt with the U.N., Turks, Russians, Jordanians, Germans, Iraqis, and others. My influence over U.S. policy has been greatly and ridiculously exaggerated. When I was a journalist I was radical and very politically strident because that was my job. That has not been my job for six years and I am a different person now.”

We were not able to speak for this article—at one point, we arranged to meet in Washington. The trip was canceled, on account of his traveling to Iraq, and then to some unspecified location “further east in Asia.” A long interview, I suggested, might be fun for the both of us. Rosen did not strike me as someone who had blindly wandered through his remarkable life without reflection on what he was doing and why.

Eventually he wrote that it would be impossible to talk. “I can only say that I find war to be the greatest evil, and it turns men into monsters and produces all the other evils we have come to know, and so my work is dedicated to reducing war as much as possible,” he wrote. “I have prioritized ending the war above all other considerations as a matter of principle and I find any other position to be abhorrent.”

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