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Reflecting on his role as Mr. Obama’s special envoy, Mr. Holbrooke wrote in The Washington Post in March 2008 that “the conflict in Afghanistan will be far more costly and much, much longer than Americans realize. This war, already in its seventh year, will eventually become the longest in American history, surpassing even Vietnam.”

Mr. Holbrooke’s relationship with Afghan President Hamid Karzai was strained after their heated meeting in 2009 over the fraud-tainted Afghan presidential election. Mr. Karzai brushed it off, saying he had “no problem at all with Mr. Holbrooke.” But the U.S. military commanders in Afghanistan, not Mr. Holbrooke, were the ones who ended up developed the closest relations with the mercurial Afghan leader. The State Department said Sunday that Mr. Karzai and Pakistani President Asif Ali Zardari were among those calling to wish Mr. Holbrooke well.

With his decades of service and long list of accomplishments in U.S. diplomacy, Mr. Holbrooke missed out on a tour as America’s top diplomat, a job he was known to covet. As U.N. ambassador, he was a member of the Clinton Cabinet but his sometimes brash and combative style contrasted with that of then-Secretary of State Madeleine Albright.

At a ceremony to mark the fifth anniversary of the Dayton Peace Accords, Mr. Holbrooke bristled when asked by a reporter if his views on the future of Kosovo — that it would eventually become independent — matched those of his boss.

“You mean Madeleine?” he replied with a derisive snort, referring to Mrs. Albright, who with others in the administration were publicly neutral on the question.

Mr. Holbrooke rejected direct comparisons between Afghanistan and Vietnam, but acknowledged similarities and repeatedly pressed the administration to do more to win the hearts and minds of both the Afghan and Pakistani people.

At the State Department ceremony in January 2009 when he was introduced as the special envoy to Afghanistan and Pakistan, Mr. Holbrooke spotted an old friend in the audience, John Negroponte, his one-time roommate in Saigon (the former South Vietnamese capital now called Ho Chi Minh City) who later was the first director of national intelligence and a former U.S. ambassador to Iraq.

“We remember those days well, and I hope we will produce a better outcome this time,” Mr. Holbrooke said.

A torn aorta is a rip in the inner wall of the body’s largest artery, allowing blood to enter the vessel wall and weaken it. The result is serious internal bleeding, a loss of normal blood flow and possible complications in organs affected by the resulting lack of blood, according to medical experts. Without surgery it generally leads to rapid death.

“True to form, Richard was a fighter to the end,” Mrs. Clinton said. “His doctors marveled at his strength and his willpower, but to his friends, that was just Richard being Richard.”

Mr. Holbrooke is survived by his wife, author Kati Marton, and two sons from an earlier marriage, David Holbrooke and Anthony Holbrooke.