Richard Holbrooke was a problem solver, not a diplomat’s diplomat. He never shied away from publicity or the press, making himself a favorite—and frank—background interview subject among journalists. Tough, hyper-energetic and not constrained by niceties, he took on and wore down most adversaries when given a free hand by the State Department—at least until he met Hamid Karzai.

When Holbrooke died on December 13, Afghanistan was still a work in progress, and perhaps, as diplomats with long experience in the region suggest, an assignment he should never have been given. It is a place that defies outsiders who have not put in years in a perplexing and unforgiving land, however stunning the intellect or analytical powers of the interlocutor may be. On top of that, there was Pakistan.

Holbrooke was restless, kinetic and never reluctant to break diplomatic routines. As ambassador to the United Nations in 1999–2000 (an appointment held up for months by a messy confirmation process), he packed a handful of his Security Council colleagues into a chartered Egyptian plane of uncertain vintage and visited all the African capitals whose governments had a hand in the war in the Democratic Republic of Congo. It was one of several innovative steps he took to put the African continent and HIV/AIDS in Africa on the Security Council map.

Sometimes the creativity backfired. In 2000, he invited Senator Jesse Helms, then chairman of the Senate Foreign Relations Committee, to address the Security Council. Helms, who never had a good word to say about the UN, took the opportunity to blow away the organization on a host of charges and threaten it with American withdrawal if it didn’t listen to Congress. After a few days of silence from the Clinton administration, Secretary of State Madeleine Albright finally stepped in to remind the UN, the media (and Holbrooke) that Helms’s embarrassing outburst did not represent US policy.

Holbrooke and Albright had a testy relationship for years. Albright had been the UN ambassador while Holbrooke was assistant secretary of state for Europe. In that job he had cornered Balkans policy and was on the phone day and night to the UN mission, where the Balkans was frequently on the agenda and where Albright herself was an expert on the region. Later, when Albright became secretary of state, in a crisis period for US policy in Iraq at the end of the 1990s, Holbrooke was oddly absent from the center of debate on Iraqi sanctions and Saddam Hussein’s infractions. It was a moment when Holbrooke’s aggressive style (and repeated boast that he would meet with the devil if necessary) could have been put to good use.

When I asked Holbrooke about why he hadn’t taken on this troubled brief that was instead left to foreign diplomats (who mostly pussyfooted around Saddam), he said that he had inherited a dead-end policy and was more interested in the important task of getting Congress to pay American arrears to the UN. It seemed an odd answer. After I wrote about this later, when he was gone from the UN, I received a handwritten note from him saying that he wanted me to know that he basically walked away from Iraq because Albright and Sandy Berger, Clinton’s national security adviser, were “micromanaging” the policy from Washington.

By contrast, Holbrooke had a good relationship with Hillary Clinton, whose presidential candidacy he supported and advised. Clinton was influential in getting him appointed to the top US civilian job in Afghanistan and Pakistan. Knowing that India had to be factored into regional politics, Holbrooke wisely wanted to include Delhi in his territory. India, however, made it clear he would not be welcome if he intended to link the country with Pakistan, especially if the topic turned to the disputed territory of Kashmir. His terrain became limited.   

Triumph and controversy will go hand in hand into the legacy of Richard Holbrooke. That includes the story of Bosnia and the Dayton peace accord, for which he is being hailed this week as a master negotiator. While the 1995 agreement ended the killing in Bosnia—a resident of Sarajevo told me this year that many still think of him as "God"—Holbrooke is also remembered for having left the small country deeply divided between Serbs and largely Muslim Bosniaks, with separate governments working (in theory at least) in a weak federal coalition.

Serbs retained the power to obstruct a healing of ethnic wounds by denying or downplaying atrocities that took place on a scale not seen in Europe since World War II. Bosnian women, targeted for rape by Serbs or widowed in the mass killings of Bosnian men, as in Srebrenica, have suffered most during the past two decades. European institutions, left to finish the job of putting Bosnia and Herzegovina back together again, have not been able to undo this decision, the price of an agreement that has left paralysis in its wake.

Within the UN system, Holbrooke had some achievements that were not often widely recognized. One was ending the pariah status of Israel, a cause of much American criticism. In the UN, nominations to various bodies are made by regional groups, which then usually support their candidates as a voting bloc. Israel’s regional neighbors had barred the country from participation in the large Asian group, which includes the Middle East. Working closely with former Secretary General Kofi Annan, Holbrooke persuaded European UN members to take Israel into their group, known as Western European and Others (WEOG), to which the US, Canada, Australia and New Zealand also belong. That gave Israel a "home" in the UN and the chance to compete for places on various bodies, ending decades of isolation. In return, Israel agreed not to seek seats on major UN councils or be part of European caucuses in Geneva, at least for the foreseeable future. 

Later in 2005, when Kofi Annan was under extreme pressure from Congress because of allegations of scandal around the oil-for-food program, Holbrooke—no longer at the UN—pulled together the secretary general with a group of policy experts and UN officials at his apartment in New York and bluntly told Annan that he needed to make drastic changes to his UN staff, which was bungling a response to criticism in Washington.

There had been calls for Annan’s resignation. Annan had already been absolved of corruption in the oil-for-food program by the investigation led by Paul Volcker, though he was accused of poor management in handling this and other issues, such as reports of prostitution rings run by peacekeepers in Congo. But Annan, physically weakened and deeply troubled by the attacks, seemed to be drifting. That he was able to recover his balance by acting swiftly to shake up his office was due to the advice he got—without frills, characteristically—from Holbrooke.