Former secretary of state Henry Kissinger once said of him that if “Richard calls you and asks you for something, just say yes. If you say no, you’ll eventually get to yes, but the journey will be very painful.” Holbrooke quickly earned a reputation for brash but influential memos, earning him the nickname “the Bulldozer”.

His family said his final words, as he was prepped for surgery, were to his Pakistani surgeon: “You’ve got to stop this war in Afghanistan”. Holbrooke had been rushed to hospital last week for a torn aorta and underwent 21 hours of surgery, followed by additional surgery over the weekend, before passing away on Monday.

In his most recent diplomatic heavy lifting, Holbrooke was dealing with the vast interlocking complexities of bringing peace to the Afghanistan/Pakistan region even as fighting continued with a resurgent Taliban, coping with corrupt governments, rigged elections, flailing economies, a major narcotics trade, the presence of nuclear weapons in Pakistan – as well as Al Qaeda’s activity in the frontier tribal lands.

Holbrooke’s most pressing task had been to chivvy Afghanistan President Hamid Karzai into taking responsibility for security even as Holbrooke confronted the corruption that imperils the entire American mission there. The relationship between Karzai and Holbrooke became sufficiently tense that Karzai sometimes refused to meet with him, although the American representative was characteristically undeterred. He told reporters Karzai was “an enormously tough customer. As you’ve heard, so am I.”

Holbrooke was critical in convincing Obama to carry out a surge in troops in Afghanistan, even as he pushed for more funding for development projects to improve America’s image in Afghanistan. However, he will never know if his instincts and policies would ultimately succeed. Holbrooke’s death may well have a serious impact on the Obama administration’s strategy for the war in Afghanistan – an effort that relies on military gains, but also leans on development assistance and diplomatic initiatives with Kabul and Pakistan.

In describing Holbrooke, the New York Times said that throughout his diplomatic career, Holbrooke had earned the reputation as a brilliant, sometimes abrasive infighter. Opponents faced his knowledge of the facts of an issue, his bluffs, whispers, implicit threats, fact-filled lectures and, when necessary, a legendary temper to drive home his position. President Obama said Holbrooke was “simply one of the giants of American foreign policy”. He thrived on a work and travel schedule that wore out much younger aides and assistants and he seemed to live on airplanes. He moved easily from swanky Manhattan, the halls of the White House to the slums of Pakistan.

Holbrooke also had a reputation for overwhelming opponents and colleagues alike at the negotiating table. His detractors could term him a bully and he looked the part – the prominent chin thrust forward, the broad shoulders and a tight, sphinx-like smile that might well mean nearly anything. Admirers that included literally generations of younger state department protégés he mentored and the presidents he served were said to be in awe of his negotiating skills.

More than a decade earlier, after picking Holbrooke as US ambassador to the UN, president Clinton said, “His remarkable diplomacy in Bosnia helped to stop the bloodshed, and at the talks in Dayton the force of his determination was the key to securing peace, restoring hope and saving lives”. Supporters said of Holbrooke that his work in Bosnia should have merited him one of those Nobel Peace Prizes.

After being appointed assistant secretary of state for European affairs, his priority quickly became the increasingly tragic, vicious civil war in the former Yugoslavia. Following months of shuttle diplomacy, Holbrooke reached a breakthrough cease-fire in 1995, as well as a framework for dividing Bosnia into two halves – one for Bosnian Serbs and the other for Croatians and Muslims. The final negotiations brought together Serbian leader Slobodan Milosevic, Franjo Tudjman of Croatia and Alija Izetbegovic of Bosnia at Wright-Patterson Air Force Base outside Dayton, Ohio. Holbrooke conducted the extended hard bargaining that led to the final settlement.

Years after the settlement, when he visited Bosnia again in 2008, he told reporters that memories of his own family history – a Jewish grandfather had fled Germany after Hitler took power and the ethnic cleansing of Muslims in Bosnia – led him to reflect that, “I thought I’m seeing a colour remake of the black-and-white scenes we’d seen in World War II of Jews signing away their property at the point of a gun and then being shipped off to who knows where. I don’t think you have to be Jewish to understand that what you’re seeing was a genuine crime against humanity. The Europeans were doing nothing, and the Americans were doing less.”

Much earlier in his career, Holbrooke dealt with America’s tragic involvement in Vietnam for five years. His first assignment was in the Mekong Delta for the US Agency for International Development, then at the US embassy in Saigon as an aide to two ambassadors – Maxwell Taylor and Henry Cabot Lodge Jr. At the end of the 1960s, Holbrooke served under Averell Harriman and then Cyrus Vance at the 1968-69 Paris peace talks.

Thereafter, he was editor/author of one of the volumes of so-called Pentagon Papers, the secret history of the Vietnam War commissioned by the defence department. This history focused on years of US duplicity in the overlapping Southeast-Asian wars leaked to The New York Times in 1971. After these assignments, Holbrooke also served as Peace Corps director in Morocco for two years before first leaving government.

In the Carter administration, Holbrooke served as the state department’s assistant secretary of state for East-Asian and Pacific affairs where he was central in establishing full diplomatic relations with China in 1979, finessing the US commitment to Taiwan, even as it advanced Richard Nixon and Henry Kissinger’s 1972 China visit.

For Clinton, Holbrooke served first as the US ambassador to Germany, working to enlarge Nato, and then as assistant secretary of state for European affairs in 1994-95 where he worked on the Bosnia accord. Thereafter, he became UN ambassador from 1999 to 2001. But despite a distinguished career, Holbrooke would be frustrated in his obvious ambition to become secretary of state. Clinton picked Madeleine Albright and under Obama, Hillary Clinton pipped him again.

Foreign policy remained his life even outside government. During Republican administrations, Holbrooke undertook various foreign policy missions as a private citizen, visiting the Balkans and the less-glamorous parts of Africa and Asia to investigate the human cost of genocide, civil wars and growing HIV/Aids epidemic.

During these Republican administrations, Holbrooke was editor of Foreign Policy magazine from 1972 to 1977, as a Washington Post columnist and as the author of two books, collaborating with long-time Democratic policy advisor Clark Clifford on his memoir, “Counsel to the President” (1991), as well as his own widely acclaimed memoir, “To End a War” (1998), about his Bosnia service. In between all this, Holbrooke also made a fortune as a Wall Street investment banker with his own consulting firm.

Holbrooke was born in Manhattan on 24 April 1941 and his childhood best friend was the son of Dean Rusk, the man who later became both John Kennedy and Lyndon Johnson’s secretary of state. He studied history at Brown University and then entered the state department as a foreign service officer in 1962. Holbrooke was married three times, most recently to journalist and human rights campaigner Kati Marton.

In his final assignment as Obama’s special envoy to Afghanistan/Pakistan Holbrooke clearly saw his first task as lowering expectations, away from George W Bush’s grand, transformative goals toward something more readily achievable. The future will show if he was right. DM

For more, read The New York Times, The Washington Post, Foreign Policy and CNN.

Photo: U.S. special representative to Pakistan and Afghanistan Richard Holbrooke reacts during a news conference in Kabul October 27, 2010. REUTERS/Omar Sobhani