It started with a cordial phone call to the Swedish prime minister. It escalated into a series of tweets that expressed disappointment, first with the prime minister, then with Sweden itself.
Now President Trump’s bid to rescue a rap star, ASAP Rocky, who is being held in a Stockholm jail, has spiraled into a situation the administration has apparently decided requires a diplomat typically used to free hostages from war-torn countries.
But the country in question has not been touched by war in more than 70 years, and Rocky is not a hostage — or, in any case, not by any commonly accepted definition of the term. He is a defendant in a criminal case, accused of assaulting a man on a Stockholm street a month ago.
[ASAP Rocky claims self-defense at his trial.]
Mr. Trump’s special presidential envoy for hostage affairs, Robert C. O’Brien, first appeared on Tuesday in the courtroom in Stockholm, where Rocky and two members of his entourage are standing trial. Mr. O’Brien said in an interview on Tuesday that President Trump had asked him to come to support the defendants.
“I’ll be here until they come home,” he said.
It’s an uncommon task for a diplomat whose job is to advise senior government officials on hostage situations overseas. Mr. O’Brien has spent his tenure trying to free Americans from places like Afghanistan, Yemen, Libya and Syria.
His unlikely path to Sweden is the result of two ultra-famous celebrities having a direct line to Mr. Trump, a commander-in-chief who has been otherwise shunned by the entertainment elite. Mr. Trump views the opportunity to free Rocky as a way to earn praise from critics and news outlets he feels treat him unfairly, as well as add another American to his list of released captives, according to two people familiar with the situation. The latest bruising news cycle includes widespread criticism of his Twitter posts that attacked several congresswomen of color and a veteran congressional leader who is black.
The mission in which Mr. O’Brien is now involved began in early July when the rapper Kanye West suggested to his wife, Kim Kardashian West, who has made frequent visits to the White House in the name of criminal justice reform, that she reach out to the White House on Rocky’s behalf, according to two people familiar with the process. In recent weeks, Rocky’s team has also had a direct line to Jared Kushner, the president’s son-in-law and senior adviser, who delivers progress updates to the president.
Embracing the rapper’s case, Mr. Trump deployed his diplomatic and social media influence. He tasked his secretary of state, Mike Pompeo, who oversees Mr. O’Brien, to work with the Swedish authorities; urged the Swedish prime minister, Stefan Lofven, to intervene in the case; and circulated the hashtag “#FreeRocky” on his Twitter account.
But Mr. Lofven declined to get involved, and so Mr. O’Brien, hostage affairs specialist, was in court to observe the trial of a 30-year-old Grammy-nominated rapper whose real name is Rakim Mayers and who says he and his entourage beat up a man on a Stockholm street because they feared he was going to attack them.
Whether appropriate or not, the framing of Rocky’s case as akin to a hostage situation appears to have taken hold at the White House. A senior administration official said the main motivation for Mr. Trump is continuing his track record of getting hostages freed. Mr. Trump has taken pride in the freeing of hostages from Iran, North Korea and Turkey, including Andrew Brunson, a pastor who had been held by Turkish authorities for years.
Engaging in Rocky’s case, according to another person familiar with Mr. Trump’s past hostage-release efforts, is less about getting attention from two celebrities who are kind to him and more about its being “something he can do that no one can really criticize him for.”
In the courtroom Thursday, as Rocky gave his account of the street brawl, saying he was acting in self-defense, Mr. O’Brien sat in a gray suit next to his chief of staff. Asked whether this case was appropriate for a hostage affairs envoy to oversee, he said, “The president sent me here, so it’s totally appropriate.”
“I also help free people that are held by governments,” Mr. O’Brien told reporters, “so unjustly detained Americans.”
When asked whether he’d ever previously been sent to monitor a criminal case, he responded: “When foreign governments hold Americans they always claim it’s a criminal case.”
He was more conciliatory in a Twitter post he sent Thursday.
Mr. O’Brien is the second person to serve as hostage affairs envoy, a position President Obama created in 2015 as part of an overhaul of how the U.S. government handled hostages. Starting in mid-2014 when the Islamic State was beheading captives, family members of hostages complained of confusing policies and dysfunctional communication by various government agencies and urged the government to create a single, senior-level “hostage czar.”
James C. O’Brien, no relation and the first person to hold the position, said in a phone interview that his successor’s efforts in Sweden did not fit the job’s original framework. The envoy, he said, should work to free Americans being held without good reason, oftentimes when there are no diplomatic alternatives.
There has to have been another way of handing the situation, James O’Brien said, especially since Sweden is an ally who could be a partner in working to release an actual hostage.
“The envoy’s presence in Sweden is a tweet come to life,” James O’Brien, the vice chairman of Albright Stonebridge Group, a global consulting firm, said.
On Wednesday, the United States Embassy in Stockholm asked that the three defendants be released from detention and allowed to reside at a hotel for the duration of the trial, according to a spokeswoman for the Swedish Prosecution Authority, who called the request unusual.
The prosecutors responded in a letter that the embassy will receive Friday, the spokeswoman, Karin Rosander, said.
“The letter states that this is not how it works in Sweden,” Ms. Rosander continued.
In an administration bent on unraveling many of Mr. Obama’s legacies, the hostage affairs envoy is one Mr. Trump has kept. Robert O’Brien and the Trump administration have managed to free about a dozen hostages held in captivity overseas, using diplomatic leverage or relying on countries such as France and the United Arab Emirates to carry out high-risk military raids in Africa and Yemen.
In working on the release of the U.S. Air Force veteran Jamie Sponaugle from Libya, Mr. O’Brien, 53, negotiated with Khalifa Haftar, commander of the Libyan National Army. He was also involved with the freeing of Luis Andrade, an American citizen who served as the head of the Colombian government’s infrastructure agency before he was put on house arrest.
Joe Miller, whose brother-in-law remains missing after his abduction in Afghanistan in 2016, said that he has dealt with Mr. O’Brien and that he appears to genuinely care about the hostages and their families. A central part of the envoy’s role is communicating with the family members of hostages to make sure they’re getting clear information about the status of their relative.
“He has a tough job,” Mr. Miller said. “He’s not only trying to negotiate with foreign powers and criminal organizations but he has to navigate his government’s bureaucracy.”
Mr. O’Brien, a founding partner of a boutique law firm based in Los Angeles, had served in various foreign affairs positions under other presidents. In 2005, President George W. Bush nominated him as a representative to the United Nations General Assembly, where he worked with John Bolton, Mr. Trump’s national security adviser, who was then the U.N. ambassador. Under both the Bush and Obama administrations, Mr. O’Brien worked on an initiative to train lawyers and judges in Afghanistan.
In his 2016 book, “While America Slept: Restoring American Leadership to a World in Crisis,” Mr. O’Brien details what he deems to be the foreign policy failures of the Obama administration and the potential for the Republican Party to regain power. Mr. O’Brien — who said he advised the presidential candidacies of Mitt Romney, Scott Walker and Ted Cruz — can sometimes sound like Mr. Trump in his prose, writing in the book, “The GOP is winning and will win in the future because it promotes freedom.”
Mr. Trump has been particularly sensitive to criticism over his hostage-negotiation methods. When a story in April said the administration had been billed $2 million for the release of Otto Warmbier, a student who died just days after being returned in a coma by North Korea in 2017, he responded on Twitter.
“No money was paid to North Korea for Otto Warmbier, not two Million Dollars, not anything else,” the tweet said.
The president added that the country’s “cheif” hostage negotiator — who would have been Mr. O’Brien at the time — had praised his abilities.
“‘President Donald J. Trump is the greatest hostage negotiator that I know of in the history of the United States. 20 hostages, many in impossible circumstances, have been released in last two years,’” Mr. Trump wrote on Twitter, seemingly quoting Mr. O’Brien. “‘No money was paid.’ Cheif Hostage Negotiator, USA!”
On Thursday, the State Department said Mr. O’Brien had indeed called the president the greatest hostage negotiator in American history.
“We confirm,” a spokeswoman said in an email.
Christina Anderson contributed reporting from Stockholm.