Now, as Trump’s national security chief, O’Brien must leverage that relationship as he tackles a host of broader, more politically fraught issues, including tensions with Iran and strained relations with European allies.
People close to some of the hostages freed and their families say they believe his appointment might bring more attention to their plight.
“We are hopeful that, given his prior focus on hostage affairs, his appointment will help to continue to make the safe return of Americans held hostage and unlawfully detained abroad a priority for our government, as the NSC’s role in this is so critical,” the James W. Foley Legacy Foundation said in a statement, referring to the National Security Council. The group was set up to honor journalist James Foley, who was murdered by the Islamic State, and to advocate on behalf of those still held overseas.
Since the beginning of the Trump administration, some 20 Americans have been released from imprisonment or captivity abroad, though it is difficult to say whether O’Brien’s efforts were pivotal in the release of those freed under his watch. Those individuals include Andrew Brunson, a pastor held in Turkey; Danny Burch, an engineer jailed in Yemen; and Jamie Sponaugle, a former Air Force service member who was accused of acting as a mercenary in Libya’s civil war.
O’Brien has shown himself to be a skilled bureaucrat, developing a strong channel to top administration officials and securing a role in policy deliberations beyond hostage issues, the people close to the families said.
But some from the families of hostages have faulted O’Brien, and the Trump administration, for trumpeting the release of others, including prominent athletes and musicians, who are detained by foreign governments but aren’t considered hostages in the same way that those whose lives are at risk in the custody of militant groups or hostile regimes.
Family members of American hostages, some of whose identities are not widely known, were furious when O’Brien spent a week in Sweden monitoring the trial of American rapper A$AP Rocky, who was accused of violent assault following a street fight in June. His trial became a media circus and attracted the attention of celebrities and Trump, who took personal interest in the issue after hearing from some of his famous friends.
The family members said O’Brien, who has part-time status at the State Department, could have devoted the energy he spent monitoring the rapper’s public trial working to free people held without any official acknowledgment, whose cases have vanished from the headlines, said a person who worked with O’Brien.
The incident may say less about O’Brien’s personal views about the rapper and more about how he, like other senior officials across the government, have found themselves immersed in initiatives that have seized the president’s attention.
The rapper and two of his associates were allowed to leave Sweden and were later found guilty and given conditional sentences, meaning they faced no prison time in Sweden unless they committed another similar offense there.
Trump appeared to take some credit for the release and sent tweets about the case, including one in which he said he would call Sweden’s prime minister “to see what we can do about helping A$AP Rocky.”
A native of Los Angeles, O’Brien grew up Catholic but converted to Mormonism in his 20s after meeting his South African-born wife. During the George W. Bush administration, he served in several diplomatic and international positions, working for a time with John Bolton, his predecessor as national security adviser, at the United Nations.
A former major in the Army Reserve, O’Brien has also dabbled in politics, serving as an adviser to Republicans Mitt Romney, Scott Walker and Ted Cruz.
In his 2016 book on American foreign policy, O’Brien described an erosion of U.S. influence under President Barack Obama, deriding what he depicted as a “wishful thinking foreign policy approach” that had atrophied the military and ceded power to China and Russia.
“I am certain the American people still believe in winning; that they still see our land as the ‘shining city on a hill,’ ” he wrote, predicting the United States was on the cusp of a “comeback” like the one he said occurred after the election of Ronald Reagan in 1980.
(O’Brien’s book received a positive review from Richard Grenell, the then-Fox News contributor who is now Trump’s ambassador to Germany and was another official under consideration for the national security adviser job).
“He’s definitely a conservative, but he’s a California conservative, so there’s a libertarian and humanitarian core to it,” said an individual who has interacted with O’Brien in his hostage envoy role and who, like other people who had worked with him, spoke on the condition of anonymity to speak candidly.
After Trump’s election, according to people who know him and have worked with him, O’Brien was initially hoping to be nominated as secretary of the Navy. Some State Department personnel believed O’Brien, who had spent years working on foreign policy issues and paid especially close attention to naval matters, saw the hostage envoy position, which he eventually assumed in 2018, as a step toward a higher-level, more influential administration post.
As hostage envoy, the person who worked with him said, O’Brien has been seen as sincere and personable in his interactions with families of Americans imprisoned overseas, “suggesting he’s got a high EQ,” or emotional quotient.
At the State Department he became close to Secretary of State Mike Pompeo, whose close ties to Trump may have helped him land the White House job. Pompeo praised O’Brien on Twitter on Wednesday, saying that “to keep America safe we must lead from a posture of strength. If anyone understands that, it’s Robert.”
Carol Morello and Karoun Demirjian contributed to this report.