Boxing legend, pop culture megastar, civil rights icon and…hostage negotiator? Muhammad Ali, with his iconic career inside the ring and humanitarian and social justice actions outside it, stands as one of America’s greatest and most celebrated athletes.

His civilian life was marked by activism and celebrity. (He was also a two-time Grammy nominee and, briefly, a Broadway star.) Yet while it made headlines decades ago, Ali’s role as an amateur—and largely unofficial—U.S. envoy to other countries remains a key aspect of his legacy many people have never heard about. 

Here’s how that role developed for Ali, culminating with him traveling to Iraq in 1990 and winning the freedom of 15 American hostages taken after Iraq invaded Kuwait.

Iraq wasn't Ali's first foray into the role of unofficial ambassador. In 1980, President Jimmy Carter tapped him to drum up support in Africa for a boycott of the Moscow Summer Olympics over the former Soviet Union’s invasion of Afghanistan. The former boxer visited Tanzania, Kenya, Nigeria, Liberia and Senegal.

“It is impossible to know whether Ali’s visit to Africa had any effect at all, although it is worth noting that Kenya and Liberia did wind up supporting the U.S. boycott,” writes Michael Ezra, a Sonoma State College professor of American multicultural studies and author of Muhammad Ali: The Making of an Icon.

And in 1985, Ali, arguably America's most high-profile Muslim, traveled to Beirut to try to locate four missing Americans and a Saudi diplomat who were reportedly kidnapped by the Islamic Holy War group. He met with Shia Muslim clergymen but left without learning where the missing people were.

On August 2, 1990, Saddam Hussein’s Iraqi forces invaded the tiny neighboring country of Kuwait. Hussein took hostage thousands of international residents in Iraq and Kuwait—including hundreds of Americans—as de facto bargaining chips. Using them as human shields, Hussein placed the hostages throughout Kuwait and Iraq at strategic locations to deter international forces from bombing and risking civilian casualties. 

U.S. diplomats struggled and failed to secure the hostages’ release. For months, a parade of “graying senior statesmen, publicity-seeking politicians and desperate women and children” traveled to Iraq with the hope of wooing the hostages free from Hussein’s grip, The New York Times reported.

By 1990, Ali hadn’t entered a boxing ring in nearly a decade, after hanging up his gloves for good following his ill-fated final comeback bid against Trevor Berbick in 1981. At age 48, the once-sprite, swaggering and slick-talking Ali was a shell of himself physically. His speech was slurred and he struggled with mobility after suffering from Parkinson’s disease for six years.

While his body was frail, Ali’s reputation as a voice for peace and civil dissent remained strong. His infamous 1967 refusal to be inducted into the U.S. army to fight in Vietnam—and subsequent draft evasion conviction and ban from boxing—established him as someone willing to stand up for his principles. (The Supreme Court ultimately overturned his conviction.)

And with his religious conversion and high-profile support of the Muslim faith—and the Nation of Islam—Ali had also become an enduring figure to Muslims around the globe. 

Despite his illness, Ali set himself a new mission in life: spreading peace and goodwill between the West and the Muslim world, Gene Kilroy, Ali’s former business manager, explains in the 2014 documentary I Am Ali. In that spirit, Ali volunteered to go to Iraq, saying he would bargain for the return of American hostages and a peaceful resolution to the Persian Gulf crisis. 

For Ali, “no journey is considered too distant if he considers the cause just,” author Thomas Hauser writes in Muhammad Ali: His Life and Times.

Ali’s idea was not positively received. “The mass media castigated and ridiculed him,” writes Brian Becker, one of the trip’s organizers. The New York Times, for one, called his bid to help release U.S. hostages "the strangest hostage-release campaign of recent days," noting his "frequent inability to speak clearly."

On November 23, 1990, Ali arrived in Baghdad as a citizen diplomat—"over the objections of President George H. W. Bush," writes biographer Michael Ezra. Without official government support, the mission had been organized by the Coalition to Stop U.S. Intervention in the Middle East, a collection of grassroots peace and community organizations aided by former U.S. Attorney General Ramsey Clark. “[Ali] went to Iraq in defiance of the U.S. government and not on its behalf,” writes Becker.

Ali sought a meeting with Hussein, who kept him waiting. To pass the time, Ali did what came naturally: He took to the streets to mingle with his beloved fans, visiting Baghdad neighborhoods, schools and mosques. The outings went on for a week as Ali bided his time, never protesting. He ran out of his Parkinson’s medication and struggled with bouts of severe speech and mobility impairment.

On November 29, 1990, Hussein finally granted Ali an audience. With media in attendance for their meeting, the former boxer listened as Hussein opined about how well he said the Iraqis treated their American “guests.” 

Then Ali promised Hussein he would bring an honest and positive account of Iraq to Americans back home upon his return—a gesture that reportedly surprised and pleased Hussein. “I’m not going to let Muhammad Ali return to the U.S.,” Hussein said, “without having a number of the American citizens accompanying him.”

On December 2, 1990, Ali flew back to the United States. So did 15 former American hostages. 

Most of the freed U.S. hostages came back on a State Department charter flight. Not being an official envoy, Ali flew commercial.

“He’d made such a torturous trip, he’d secured our release,” hostage Harry Brill-Edwards says in Hauser’s book. “And I said to myself, I can’t do this. We should be in Muhammad Ali’s presence when we go home. In the end, six of us stayed on the flight with Ali. We did it out of sheer gratitude and respect for the man.” 

For Ali, Hauser writes, “the trip was the logical extension of what he had believed for decades. That all life is precious and war is wrong.”

Ali may have won the freedom of 15 of the hostages, but his broader idea of keeping the peace in the Middle East with his visit went nowhere. The First Gulf War started on January 17, 1991, about six weeks after Ali and the hostages made it back to the U.S.

“Ali wasn’t a diplomat,” Hauser tells HISTORY.com. “His geopolitical skills were virtually nonexistent. But his heart was in the right place.”