President Donald Trump's withdrawal announcement came two days after James Jeffrey had delivered a high-profile speech forecasting a sustained U.S. role in the Arab country. | Jose Luis Magana/AP Photo Foreign Policy A ‘Never Trumper’ bets on Trump, and loses Trump’s abrupt decision to exit Syria blindsides — and severely undermines — a veteran diplomat who set aside his doubts about Trump to take a thankless job shaping U.S. policy toward the country.

James Jeffrey, President Donald Trump‘s special representative for Syria engagement, probably should have seen it coming.

In August 2016, the well-respected veteran diplomat signed an open letter denouncing then-presidential candidate Trump as a danger to America. “In our experience,” Jeffrey and dozens of fellow “Never Trumpers” wrote, “a president must be willing to listen to his advisers and department heads [and] must encourage consideration of conflicting views.” Trump, they argued, is “erratic” and “acts impetuously.”


This week Trump blindsided his national security team, including Jeffrey, by announcing that he will be pulling U.S. troops from war-torn Syria. Just two days earlier, Jeffrey had delivered a high-profile speech forecasting a sustained U.S. role in the Arab country.

And with that, the 70-something Jeffrey became the latest in a long line of Trump administration officials to be undermined and even humiliated by the president they serve.

In a sign of frustration at the top levels of Trump’s national security team, Defense Secretary James Mattis announced his resignation on Thursday, releasing a letter saying that his views are not “aligned” with Trump’s and specifically citing the U.S. campaign against the Islamic State terrorist group, which has partly been waged in Syria.

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Trump’s decision to exit Syria reminds critics of former President Barack Obama’s pullout of U.S. troops from Iraq in 2011. They fear that it will have similarly dangerous consequences, allowing a nearly defeated Islamic State to reconstitute.

Jeffrey was U.S. ambassador to Baghdad at the time of America’s withdrawal from Iraq, one of several ambassadorial posts he’s held. and is widely believed to have joined the Trump administration in part to prevent a repeat of that disastrous scenario. Now, some fellow foreign policy hands are wondering why he would bother to stick around.

“Jim came into the administration on the understanding that it would remain deeply and aggressively engaged in Syria and that Trump wouldn’t change his mind,” said Rob Malley, a former senior Obama aide. “Jim will have to decide whether what remains of the [Syria] policy makes sense to him, and whether he wants to be the person overseeing it.”

“How can he put his name and reputation behind this policy?” asked another foreign policy expert who keeps a close eye on Syria and requested anonymity to speak frankly. “The president undermined everything he had been working on.”

Jeffrey is not the only Trump administration official burned by the president.

Trump’s decision to withdraw the roughly 2,000 U.S. troops in Syria breaks with the advice and public statements of nearly every one of his foreign policy advisers, including national security adviser John Bolton, the now-resigning Mattis and diplomats such as Brett McGurk, the special envoy to the Global Coalition to Defeat ISIS.

In a briefing last week, McGurk scoffed at the sort of action Trump wound up announcing several days later: “[O]bviously, it would be reckless if we were just to say, well, the physical caliphate is defeated, so we can just leave now,” McGurk told State Department reporters, using an Arabic-derived term to describe the Islamic State’s structure.

But Trump’s decision is a particularly direct blow at Jeffrey, contradicting the mission of “engagement” described in a job title he assumed despite his reservations about Trump.

“He’s the consummate public servant, so it’s never about politics for him,” a former State Department official said. “If he feels he can contribute to help us navigate difficult policy issues he steps up, which he did.”

The salty-tongued Jeffrey has not commented publicly since Trump’s announcement, and he did not reply to emails Thursday from POLITICO. There was no sign that he intends to quit.

Given Trump’s capricious nature, it’s possible Jeffrey, other Trump aides, or even furious Republican lawmakers, could still convince the president to delay or slow down the pullout. And even without ground forces in Syria, the U.S. is likely to stay involved in Syria in some way, at least through diplomatic engagement with the various actors in the country.

But by pulling out the troops, Washington appears to have less leverage as it pushes warring factions to reach peace deals. The departure of U.S. troops is already being seen as a betrayal of U.S. allies in Syria, including Kurdish fighters going to head-to-head with the Islamic State.

“The way this was done is going to make Jim Jeffrey’s job harder because foreign governments and foreign officials are going to wonder whether he genuinely represents the president of the United States,” said Robert Ford, a former U.S. ambassador to Syria and fellow at the Middle East Institute.

Jeffrey’s mid-August appointment, announced by Secretary of State Mike Pompeo, surprised Washington’s foreign policy community. Trump had blackballed “Never Trumpers” from serving his administration. But Jeffrey is believed to be the first of any prominence to get a slot, because Pompeo, who has maintained a solid relationship with Trump, was willing to vouch for him.

A month later, Trump agreed to abandon his previous desire to quickly remove the U.S. troops. At the time, Jeffrey said U.S. troops would stay in Syria to ensure the lasting defeat of the Islamic State terrorist group and the departure of Iranian troops, a timeline that could prove indefinite.

“I am confident the president is on-board with this,” Jeffrey said.

On Wednesday, Trump justified his about-face by saying he’s fulfilling a campaign promise in bringing home the troops because his only goal in Syria, defeating the Islamic State, has been achieved.

But Trump aides have repeatedly said the terrorist group, also known as ISIS, though much diminished, is not yet fully vanquished. Aside from that, Syria’s other major conflict — the nearly 8-year-old war between the regime of Bashar Assad and rebels trying to oust him — is not over.

The Syrian morass has also drawn in Iran, Russia, Turkey, Israel and other actors. Jeffrey’s mission has included trying to devise a coherent strategy for a diabolically vexing situation. He is one of three special envoys based at the State Department who deal directly or indirectly with Syria.

Aside from Jeffrey, there’s McGurk, who took his post under the Obama administration and is rumored to be leaving soon. There’s also Joel Rayburn, who holds the title of special envoy to Syria as well as deputy assistant secretary for Levant affairs; he joined the State Department after serving at the National Security Council and has kept a low profile.

Jeffrey has taken the opposite tack. He has held press conferences, given speeches and otherwise privately and publicly assured U.S. allies that America won‘t abandon Syria.

He often cites Iraq, where a U.S. troop pullout in 2011 allowed the Islamic State to overpower a weak Iraqi military. Obama had to redeploy troops to the country to beat back the terrorist group, which also snatched territory in neighboring Syria.

Jeffrey has repeatedly said U.S. goals should include what he calls the Islamic State’s “enduring” defeat.

“The enduring defeat means not simply smashing the last of ISIS’s conventional military units holding terrain, but ensuring that ISIS doesn’t immediately come back and sleeper cells come back as an insurgent movement,” Jeffrey told reporters in mid-November.

Jeffrey is in many ways the ideal candidate for his current role.

He has held multiple diplomatic posts in Iraq and was in the country during some of the most violent years following the 2003 U.S. invasion. That has made him deeply familiar with Sunni Muslim militant movements.

His experience as the U.S. ambassador to Turkey has helped him navigate the political tensions between U.S.-backed Kurds fighting the Islamic State in Syria and Turkish government threats against those Kurds, whom Ankara fears will embolden Kurdish separatists in Turkey.

Jeffrey also understands how to wend through Washington, having held posts such as deputy national security adviser under then-president George W. Bush. Before taking his current job, he spent several years as an analyst at the Washington Institute for Near East Policy.

He’s familiar with the military, too. He was a former Army infantry officer who served in Germany and Vietnam from 1969 to 1976 before joining the U.S. Foreign Service, according to his official biographies online.

Jeffrey, a father of two who holds degrees from Northeastern and Boston universities, has a gruff manner, a booming voice and a killer glare. During his briefings on Syria, he displays near-granular knowledge of the situation on the ground as well as the political process intended to end the conflict.

Jeffrey has an appreciation for nuance. For instance, he’s careful to remind critics of Obama about the complex reasons the former president decided to pull troops out of Iraq, including the crucial fact that the Iraqi government refused to exempt U.S. forces from Iraqi prosecution.

But Jeffrey also has some strong views about the Middle East. In particular, he sees Iran’s Islamist government as a menace to the region, if not the world, and he worries about the long-term impact of the Iranian presence in Syria. Israel has also counted on the U.S. to act as a check against Tehran in neighboring Syria.

One of the main goals of the Trump administration, Jeffrey has repeatedly said, is “the withdrawal of all Iranian-commanded forces from the entirety of Syria.”

“We don’t see why it is in the interest of anyone to have Iranian forces, particularly power projection forces — long-range missiles and other systems that can threaten other countries — present in Syria if we have resolved the underlying conflict,” Jeffrey said in mid-November.

In that same session with reporters, Jeffrey said the U.S. military presence “has indirect impact” on reigning in Iran’s “malign” activities in Syria.

But, like any diplomat, Jeffrey is always mindful of who’s ultimately in charge of what the U.S. does.

During the mid-November briefing, Jeffrey was asked point blank: “When do you foresee U.S. forces actually leaving Syria? Can you give us a guesstimate?”

His answer? “When the president decides.”