Bolton, fired by Trump as national security adviser last week, was a well-known figure in Washington when he was appointed to the White House last year. Though he held a number of diplomatic positions in prior administrations, he was ultimately known as someone who fervently opposed multilateral agreements — an uber-hawk who proposed military strikes on both North Korea and Iran before joining the Trump administration.
O’Brien may be lesser known, but the indications are he knows how to broker deals rather than just break them. A practicing lawyer, he had worked with the State Department in roles in Afghanistan and the Middle East under two secretaries of state, Condoleezza Rice in the Bush administration and Hillary Clinton in the Obama administration. He even served with Bolton at the United Nations.
But O’Brien’s highest billing came in May 2018, when the administration nominated him as a special presidential envoy for hostage affairs. It was an unusually high-profile role under Trump, who had slammed President Barack Obama for not doing enough to get hostages home and had long portrayed himself as a master negotiator, willing to do anything to help an American in trouble.
The president claimed in April that O’Brien had called him the “greatest hostage negotiator” in the “history of the United States.” On Tuesday, the day before he announced O’Brien as national security adviser, Trump suggested that the United States’ success rate for freeing hostages under his administration was 38 to zero.
Like much in the Trump world, this figure may involve some creative accounting. The State Department did not respond to a question about who has been released during the Trump administration, but some cases — most notably, the A$AP Rocky case — stretched the definition of both a hostage and also a success, with little indication U.S. government involvement was wanted or needed.
Meanwhile, there are thought to be a number of U.S. citizens who languish in foreign countries. Some, such as Austin Tice, a U.S. journalist who went missing in Syria in 2012, predate the Trump administration, but there are other cases, such as that of Paul Whelan, a U.S. citizen held in Russia since earlier this year, that do not.
Keeping score is hard to do. James O’Brien (no relation), a special presidential envoy for hostage affairs between 2015 and 2016, said the Obama administration freed about a hundred Americans in that time, but added that each case has a unique set of circumstances. “I find the boasting odious,” O’Brien told The Washington Post earlier this year. “Every day an American is held abroad is a loss."
Trump’s highly public approach does have its admirers. Under Obama, the United States codified a long-standing practice of not paying ransoms to terrorist organizations. Some families felt that Obama was too distant from their plight, his government unable to improvise in cases that were often life or death.
But by elevating the importance of American hostages held abroad, Trump may have also increased their value and provided incentive for potential hostage-takers. “You know it will get the president’s attention” if you capture a U.S. citizen, Joel Simon, the executive director of the Committee to Protect Journalists and author of a book on hostage negotiations, told The Post earlier this year.
Indeed, you may get more than attention. The Washington Post reported in April that the president authorized a U.S. official to sign a pledge to pay $2 million in medical fees for Otto Warmbier, a University of Virginia student imprisoned in North Korea, before the comatose 22-year-old could be released. Warmbier died soon after he was released in June 2017. Though there is no evidence that the North Korean bill was ever paid, Otto’s father told The Post that it sounded like a “ransom” for his son.
Despite Trump’s ultimate decision to fire Bolton, his way of thinking is not so alien. The president is still best known for the deals he has wrecked than those he has created: The Iran nuclear deal, the Paris climate change agreement, the Trans-Pacific Partnership Trade Deal, to name a few. He is deeply suspicious of multilateralism, preferring to view the world as a zero- sum game that can be either won or lost.
That game may extend even to hostages. Trump has mused that foreign citizens held by the United States held in criminal cases could be part of political negotiations between nations. He has referred to prisoners of war as hostages. “We have 1,800 ISIS Prisoners taken hostage in our final battles to destroy 100% of the Caliphate in Syria,” he tweeted in April.
There’s little indication that O’Brien feels the same way. By many accounts, he has been hard-working and sincere in his position as hostage negotiator; he converted to Mormonism in his 20s and is frequently described as a nice guy. Though he wrote a 2016 book excoriating Obama’s foreign policy, he skews toward a traditional Republican, with a focus on alliances, engagement and rule of law.
Before the 2016 election, when he advised the campaigns of Wisconsin Gov. Scott Walker (R) and Sen. Ted Cruz (R-Tex.), O’Brien had criticized Trump on these grounds, but later shifted to praising the new president effusively after he won the election. When he was sent to Stockholm with the dubious task of freeing A$AP Rocky, he offered a simple explanation: “The president asked me to come here and support these American citizens."
O’Brien, like Bolton and others before him, is now a captive to the whims of the American president.