Flattery will get you everywhere with Donald Trump. The President demonstrated this powerfully on Wednesday, when he named the State Department’s little-known hostage negotiator, Robert O’Brien, to be his latest national-security adviser, despite O’Brien having less relevant experience than anyone who’s held the post in the nearly seven decades since it was created. In O’Brien’s case, his ability to lavish praise on the boss was explicitly cited by the President as a factor in his appointment to one of the most powerful unelected positions in the world. There wasn’t anything subtle about it.
On Tuesday, speaking with reporters on Air Force One, Trump said that O’Brien was one of five finalists, then quoted O’Brien as having told him, “Trump is the greatest hostage negotiator that I know of in the history of the United States.” “He happens to be right,” Trump added. The next morning, O’Brien got the job, barely a week after Trump’s acrimonious parting with his previous national-security adviser, John Bolton, for what Trump said was the sin of disagreeing with his foreign policy. When O’Brien appeared alongside the President on the airport tarmac in California after his appointment, O’Brien praised the “tremendous foreign-policy successes under President Trump’s leadership.”
Trump is now on his fourth national-security adviser, the most ever for a President in his first term, but, even with O’Brien, he is no closer to finding one who agrees with his world view. Judging from quick studies of his writings and public pronouncements, O’Brien is not a bring-the-troops-home-and-pull-up-the-drawbridge America Firster. He is a classic, conventional Republican hawk with a pro-military bent, “Bolton lite,” as a conservative magazine put it: wary of China’s rise, skeptical of Russian President Vladimir Putin, in favor of muscular American internationalism and bigger defense budgets, and most decidedly against the foreign policy of Trump’s predecessor, Barack Obama. Indeed, the title of the book of foreign-policy essays that O’Brien published in 2016 is “While America Slept: Restoring American Leadership to a World in Crisis,” and it includes chapters such as “Obama’s Folly: the Iran Deal Disaster” and “Is the Benghazi Attack Obama’s Madrid Train Bombings?” In a chapter called “Obama’s Falklands Failure,” O’Brien claims that the Obama Administration failed to take a little-noted 2012 crisis in the Falklands seriously and, in doing so, made “the United States an unreliable ally for our closest friends.” As the nod to Churchill in his book title suggests, O’Brien fashioned himself as a herald of American decline, comparing the Obama Iran nuclear deal to the appeasement of Hitler. Bolton, with whom O’Brien served in a mid-level job at the United Nations during the George W. Bush Administration, blurbed the book, calling it “required reading.”
Like virtually everyone else in the G.O.P. establishment, O’Brien was against Trump in 2016 before he was for him. For O’Brien, as for many Republican national-security hawks, his critique of Trump appears to have been largely built on foreign-policy grounds. In a 2015 Politico Magazine piece, he urged Senator Ted Cruz to attack Trump’s suspect world view, and specifically to bring up Trump’s disturbingly “chummy” view of Putin. O’Brien then became an adviser to Cruz’s campaign. But, as soon as Trump won, O’Brien was on board, and by December of 2016 he appeared to be openly courting the new Administration. “We may be witnessing the most impressive presidential transition from a national-security standpoint in history,” O’Brien wrote on The National Interest’s Web site that month.
If O’Brien’s public praise for the incoming Trump Administration was meant as an audition, it worked. A lawyer who started his own firm in Los Angeles, O’Brien was named the special envoy for hostage negotiations (a position that Obama created) in May of 2018 and immediately set about elevating the relatively obscure position’s profile by appealing directly to the publicity-loving President. “From the moment he came, it was clear that he works very well with the President,” Mickey Bergman, the executive director of the Richardson Center for Global Engagement, said. Bergman, who helped negotiate the release of a number of U.S. political prisoners, including the late Otto Warmbier, from North Korea, worked as an outside adviser to the government’s interagency hostage task force with O’Brien. Bergman told me that O’Brien “speaks the President’s language, and I think Trump picked a national-security adviser who will make him feel very comfortable.”
Several others who, like Bergman, are familiar with O’Brien’s hostage work praised him for his skill and empathy in engaging with hostages’ families and the zeal with which he tried to bring their loved ones home. They also agreed that O’Brien, no matter how much his policy views align with Bolton’s, will almost certainly emphasize pleasing the President rather than pushing an agenda in his new position, just as he has in his present one. In August, during an episode that may have sealed O’Brien’s unlikely ascendance to the top of America’s national-security bureaucracy, he offered a particularly revealing glimpse of how he viewed his role. Trump had become obsessed with the case of an American rapper, A$AP Rocky, who was accused of criminal assault in Sweden, and demanded that O’Brien fly there to attend his trial, although the rapper was clearly not a political prisoner or hostage of any kind. O’Brien not only raised no objections but also appeared to wholly endorse a very Trump-centric view of his State Department job. “The President sent me here,” O’Brien told reporters, “so it’s totally appropriate.”
Of course, there have been many champion Trump flatterers in his Administration, and obsequiousness has proved to be a durable survival strategy for the few senior officials who have remained in Trump’s orbit throughout his tenure. The President is entitled to the staff he wants, and loyalty is a fair requirement for a job in this White House, or any White House. The difference between O’Brien and other Trump suck-uppers is that the sucking up appears to be the primary reason that he got the job. Aside from his short stint with Bolton at the U.N. and appointments to two obscure government commissions, O’Brien’s major foreign-policy experience has been in serving as an unpaid adviser to several Republican Presidential campaigns. He has never served in the White House or at the National Security Council and has little experience with the complex interagency process that runs America’s massive national-security bureaucracy, and none at all leading it.
Within hours of O’Brien’s appointment, Bolton offered a gloomy assessment of the troubles that await his successor. At a luncheon in New York, Bolton mocked the President’s diplomatic initiatives with Iran and North Korea as “doomed to fail” and portrayed Trump as a volatile leader who chickened out of a military response to an Iranian drone attack “at the very last minute,” without telling anyone. His remarks were quickly leaked to Politico.
Trump wants the world to think that O’Brien’s appointment doesn’t matter—that, in fact, none of his foreign-policy appointments matter, because he makes all of the decisions. Trump told reporters last week after Bolton’s exit (they disagree on whether Bolton quit or was fired) that he, nonetheless, had many candidates for the position. “Everybody wants it badly, as you can imagine,” he said. “A lot of people want the job—it’s a great job. It’s great because it’s a lot of fun to work with Donald Trump. It’s very easy, actually, to work with me. You know why it’s easy? Because I make all the decisions. They don’t have to work.”
Trump may not want to claim so much credit. The distracting spectacle of another White House personnel shuffle obscured what a consequential moment this is for Trump’s foreign policy. Often precarious, it now seems to be unravelling altogether, collapsing under the weight of its own contradictions, flawed assumptions, and lack of willing partners. During the past few weeks, Trump’s Afghanistan peace talks fell apart after he withdrew an ill-advised invitation to the Taliban to Camp David; his North Korea nuclear talks appear all but dead, and Pyongyang’s nuclear arsenal is now reported to have grown significantly during Trump’s tenure; and his on-again, off-again trade talks with China have so far resulted only in escalating tariffs that are now unnerving businesses worldwide.
In the Middle East, meanwhile, the events of last week are conspiring to create the major foreign-policy crisis that Trump has so far avoided. Just after O’Brien’s appointment, Secretary of State Mike Pompeo landed in Saudi Arabia and declared an attack on Saudi oil facilities “an act of war” that he blamed on Iran. In Israel, it appeared that Trump’s key ally in the region, Prime Minister Benjamin Netanyahu, had lost Tuesday’s election and might actually find himself out of office. Back in Washington, some Republican hawks with whom Pompeo and O’Brien have long been aligned were pressing a reluctant Trump to order a U.S. military response against Iran. Trump himself sent conflicting signals and complained to a reporter that he did not want a war. On Friday, the National Security Council will meet and present Trump with options—and give O’Brien the most high-stakes possible début.
I asked a Republican who knows O’Brien from both the Bush and Trump Administrations whether he was ready for such an enormous challenge. “Nice guy, but in way, way over his head,” the Republican, a former senior Bush Administration official, told me. “I’ve worked with a series of national-security advisers, and he’s not qualified to be national-security adviser,” he added, pointing out that “he has no experience on Russia or arms control or intelligence or covert action or Latin America. Now he’s got the whole world.” The Republican said that he liked O’Brien and just wished that he had said no to the President, predicting, “I don’t think this will end well.”
As if O’Brien needed a cautionary tale, the week began with perhaps the most painful display possible of life after the Trump Administration. Sean Spicer, Trump’s first White House press secretary, made his début Monday night on the ABC TV show “Dancing with the Stars.” After failing to secure some of the more lucrative work that usually comes after such a prestigious posting, Spicer, dressed in a skintight, neon-green ruffled shirt, awkwardly leapt about the stage and played the bongo drums, prompting a judge to observe, “It’s like you were being attacked by a swarm of wasps.” The Times called Spicer “an avatar for the reputational sacrifice and ritual humiliation” that can follow a stint working for Trump. Whatever happens in the Situation Room in the coming weeks and months, no one can say that Robert O’Brien wasn’t warned.
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