'The Diplomat' Explores Richard Holbrooke's Life and Death in the Foreign Service

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President Barack Obama, Vice President Joe Biden, then-Secretary of State Hillary Clinton and Richard Holbrooke exchange tense words. Pete Souza/HBO

Updated | Like many Great Men, the late diplomat Richard Holbrooke wasn’t a great father. The work-life balance was never a factor in his long foreign service career, spanning a steamy backwoods post in Vietnam at the dawn of that war to his last post, the one that arguably killed him, the diplomatic version of the Augean Stables—solving Afghanistan and Pakistan.

After his death in 2010, his filmmaker son David Holbrooke set out on a personal project, with the aim of trying to understand the life of his often absent father.

The result is HBO’s The Diplomat, a moving and revealing portrait of one of America’s best-known negotiators, a man who devoted himself to settling international disagreements with talk, not bombs, and who literally died trying to negotiate the “Af-Pak” mess.

The thrice-married Holbrooke was larger than life, a man who, besides negotiating historic peace treaties, was a bon vivant and a limelight hog. His stature was such that his son bagged interviews with global figures—Hillary Clinton, former President Bill Clinton, Diane Sawyer (one of Holbrooke’s ex-girlfriends), General Wesley Clark, U.S. Ambassador to the U.N. Samantha Power, the president of Afghanistan and many more American foreign policy leaders, thinkers and journalists.

The film opens with Holbrooke in his boyish early 20s, the classic Kennedy-era American abroad in khakis, Ray-Bans and oxford cloth. Fresh out of college, he was an ambitious young man who had set off to be a journalist but snagged a job in the foreign service first.  

In letters home from Vietnam sent to his first wife, he conceded a childish thrill at the excitement of the air-slapping rotors on the helicopter rides, as well as his growing certainty that the American military strategy wasn’t going to work.

His sharply worded and critical dispatches from the field, unusual from a junior officer, set the tone for his career. Physically large and temperamentally even larger, Holbrooke was a bull in Washington’s delicate diplomatic china shop.

He thrived under Democratic presidents, serving in the Carter, Clinton and Obama administrations in various high-ranking positions, including U.S. representative to the United Nations.

His greatest diplomatic feat was masterminding a peace accord in the Balkans, applying a combination of personal charm and steel on the bully, Serbian President Slobodan Milosevic, as NATO backed him up with bombs. The Diplomat goes behind the scenes, with footage of a haggard Holbrooke and Clark, shuttling by car and plane hour by hour, day by day, through Balkan war zones and between warring leaders, as some Bosnian citizens dodge sniper fire while others end up in mass graves. Most of the Dayton Accords players—American, Serbian, Croatian and Bosnian—share their memories in the film.

Holbrooke was a Democrat and his son leaves out the fact that, in addition to his foreign service career, his dad sat out the Reagan and Bush years in private equity, spending the '80s and the aughts on Wall Street and eventually serving on the board of AIG, the notorious too-big-to-fail insurance multinational that the government propped up with $182 billion in 2008. But money was clearly not his motivation in life.

The film suggests, without stating it, that Holbrooke’s heart was broken by his failure to achieve his deepest career desire—an appointment as secretary of state—and by his inability to solve “AfPak.” Obama gave him arguably the most impossible job in the world, then proceeded to ignore his advice.

For the film, Washington Post journalist Bob Woodward shared tapes of private conversations in the final year of Holbrooke’s life in which he  makes clear his reservations about the Afghan surge strategy. The audio of the soon-to-die negotiator describing his fear that the generals had too much sway, inserting too much “mil-think” on Afghanistan in the Obama administration, is played over images of men in uniform, including General David Petraeus, advising the President at a long table.

In Afghanistan, as in Vietnam, Holbrooke felt that an over-reliance on military solutions would ultimately fail, but as with Vietnam, few heeded him. In fact, the film suggests, even the fact that he had been in Vietnam diminished his relevancy within the Obama administration.

Images of him in The Diplomat on his final, impossible mission show what life and a foreign service career had done to his 69-year-old body: stepping off the tarmac in Kabul, his face haggard, gut enormous, he suffers the disdain of Afghan President Hamid Karzai—one world leader he was never able to charm or strong-arm.

On his last day at work, the day before he died, he tried to get in to see the president at the White House, but didn’t manage to get past David Axelrod. He hurried back to the Department of State to update Hillary Clinton, his boss.

Clinton gives a candid assessment of Holbrooke and Obama’s troubled relationship. “There were very different leadership approaches and they clashed,” she says of Holbrooke’s attempts to relate to Obama. She says she tried to solve the policy, generational and temperamental disagreements between the men without much success. “I was constantly interpreting for him [Holbrooke], translating, arguing. It was very frustrating for me to see and frustrating for him to go through.”

The icy relations are plain in a photograph of the president and veep scowling at Holbrooke, with Hillary Clinton standing between them, clearly the short female peacemaker in the room.

She was fond of “the big man” and always saved “the big chair” in her State Department office for him, she says. That’s where he was sitting when she noticed a deep red flush climbing from his neck up his face. She asked him if he was OK, and he said he wasn’t.

In the ambulance ride to the hospital, dying of an “aortic dissection,” an aide scribbled his last words on a scrap of a Chinese restaurant receipt.  Holbrooke tearfully reads the aide’s notes aloud: “Tell my kids how much I love them.” “I love so many people.” “Career in public service is over.” And: “Don’t let him die here. Die at home with family.”

This poignant film reminds viewers that there are other sorts of heroes in wartime—and, perhaps even more crucially, in peacetime—who never wear the uniform or pin medals on their chests, but who give their lives for their country.

The Diplomat, which had its premiere at the Tribeca Film Festival this year, will air on HBO November 2.

Correction: An earlier version of this article incorrectly referred to Richard Holbrooke seeking to get David  Axelrod to “come down,” when in fact he was referring to David Holbrooke. The reference has been removed. Also, the Augean Stables was misspelled in an earlier version as Aegean.