Trump picks his top hostage negotiator to serve as national security adviser

President Donald Trump has picked America’s top hostage negotiator, Robert C. O’Brien, to serve as his new national security adviser.

Trump announced O’Brien’s appointment in a tweet on Wednesday after telling reporters Tuesday he’d narrowed the list to five top contenders. O’Brien was among them.

“I have worked long & hard with Robert,” Trump tweeted. “He will do a great job!”

Trump’s selection comes a week after John Bolton left the administration on somewhat tense terms. O’Brien will now be Trump’s fourth national security adviser in less than three years, replacing Bolton who replaced H.R. McMaster who replaced Michael Flynn.

O’Brien has worked for the Trump administration since 2018, serving as the US special envoy for Hostage Affairs — basically the ambassador in charge of negotiating the release of Americans held abroad. Trump has placed a lot of emphasis on freeing Americans detained overseas (Andrew Brunson in Turkey, North Korean hostages, Danny Burch in Yemen — just to name a few), and it’s been one of the more successful elements of his foreign policy.

O’Brien himself has said Trump has had “unparalleled success” in bringing Americans home. (Trump claims O’Brien called him the “greatest hostage negotiator” in US history, but that seems to be a stretch). Either way, O’Brien has helped Trump achieve those successes, although he’s also faced criticism for putting partisan battles over the fates of actual hostages, most notably when O’Brien went to Sweden to sit in for A$AP Rocky’s trial because of the president’s personal interest.

O’Brien will inherit the national security adviser job from Bolton, whose hawkish positions on everything from Iran to North Korea to Venezuela clashed with Trump’s style of interpersonal diplomacy and expressed aversion to intervention. That rift between the national security adviser and president led to Bolton’s sidelining and his eventual departure from the administration.

O’Brien worked closely with Bolton in the past, including in 2005 when they both served at the United Nations together during the Bush administration. O’Brien has previously praised Bolton as “the smartest guy in the room.”

But now O’Brien will have to deal with some of the fallout of Bolton’s tenure. That includes an increasingly messy situation in Venezuela, where Bolton led a push to oust President Nicolás Maduro that has largely stalled. And though Bolton was known as the most hawkish of Iran hawks, O’Brien is about to take on one of the administration’s top national security jobs just as tensions are spiking again between Washington and Tehran over an attack on a Saudi oil facility.

O’Brien, though, appears to at least be starting out with a perk that Bolton apparently squandered away: a pretty good working relationship with Trump. Whether that partnership will best serve America’s national security interests will be the test of O’Brien’s tenure.