Richard Holbrooke's 'Generational and Stylistic Differences' With President Obama

In this video, the filmmaker David Holbrooke engages in a Q&A about his film "The Diplomat." (Alex Leung/Asia Society)

Bold, uncompromising, and indefatigable, the diplomat Richard Holbrooke was a major figure in American foreign policy for nearly half a century. As the Clinton Administration's chief envoy to Yugoslavia, Holbrooke played a crucial role in brokering the Dayton Accords in 1995 — a truce between Serbia, Croatia, and Bosnia & Herzegovina that ended years of bloody warfare. More than a decade later, following a stint as chairman of Asia Society, Holbrooke was named special advisor to the Afghanistan/Pakistan region by President Barack Obama. Sadly, this assignment would be Holbrooke's last. He died on December 13, 2010 of a ruptured aorta while meeting with Secretary of State Hillary Clinton.

Following Holbrooke's death, his eldest son David retraced his father's steps in Ho Chi Minh City, Sarajevo, and Kabul, and interviewed dozens of dignitaries who knew him. This journey formed the basis of The Diplomat, a documentary about Richard Holbrooke's life, now available on HBO. In a question-and-answer session held last week in Hong Kong at the Asia 21 Young Leaders Summit, an event hosted by Asia Society, David Holbrooke engaged in a wide-ranging discussion about his famous father, one whose relationship with family was distant. Richard Holbrooke's devotion to his work and no-nonsense style earned him admirers and enemies in equal measure. "My father pissed a lot of people off," David said. 

Much of the conversation revolved around Richard Holbrooke's unhappy years working for the Obama Administration. A staunch supporter of Hillary Clinton during her contentious (and ultimately unsuccessful) primary campaign against Obama in 2008, Holbrooke had "generational and stylistic differences" with the youthful new president, said David. Following Obama's victory, the relationship got off on the wrong foot when, after the president-elect called Holbrooke by his nickname "Dick," the ambassador asked to be referred to instead as "Richard." 

"He thought his talent, charm, and brilliance would win the day, and he just didn't anticipate he'd have such a nightmarish situation with the White House," said David. "What happened too was that he made it worse, time and again. I think he misstepped many times."

David related an anecdote he heard from Joe Klein, the veteran journalist, about an awkward exchange between his father and the president on the day Obama was awarded the Nobel Peace Prize in 2009.

"The president won the Nobel Prize at 7:30am Washington, D.C. time, and at 8:00 he walked in for his first meeting of the day, about AfPak," David said. "My father starts clapping, and he was the only one. Then everyone sits down and the president says, 'OK, last week we were talking about Kandahar — let's pick it up there.'"

But the difficult years Holbrooke spent in the Obama administration was a mere coda in a career that began when Richard, still in his twenties, emerged as a prominent player in the American war in Vietnam. When an audience member asked David whether there was one lesson that could be derived from his father's life, the younger Holbrooke didn't hesitate.

"Diplomacy matters," he said.

For a look at the full question-and-answer session with David Holbrooke, please watch the above video.