WASHINGTON » In the summer of 2010, Richard C. Holbrooke, the Obama administration’s special representative for Afghanistan and Pakistan, began recording a secret audio diary, detailing his frustrations with a White House that he believed was too willing to listen to the military, and too often mistook domestic political calculations for strategic thinking.

"That really is the way the White House thinks," Holbrooke said in an Aug. 12, 2010, entry in the diary, the existence of which has not been previously reported. "They don’t have a deep understanding of the issues themselves, but increasingly they’re deluding themselves into thinking they do."

Holbrooke, a diplomatic troubleshooter who worked for every president since the 1960s, was widely known to be in conflict with the Obama administration. But the audio notes that he dictated on a near daily basis from August 2010 until his death at age 69 from a torn aorta in December of that year provide an usually candid, if one-sided, record of the internecine battles that troubled the administration over the direction of the war in Afghanistan.

The notes are featured in "The Diplomat," a documentary about Holbrooke that will have its premiere on Thursday at the Tribeca Film Festival and be shown on HBO in the fall. The New York Times viewed the film before its release.

The notes lay bare Holbrooke’s doubts that President Barack Obama’s decision to send tens of thousands of additional troops to Afghanistan would lead to an end of the war. Holbrooke was instead drawing up plans to strike a bargain with the Taliban and Afghanistan’s meddlesome neighbors, including Iran and Pakistan.

But Holbrooke, who 15 years earlier had brokered the peace deal that ended the war in Bosnia, said he believed he could not get a hearing at the highest levels of the Obama administration.

"Went over to the White House to see Tom Donilon, who was extremely agitated and kept saying, ‘You’re going too slow, you don’t have a strategy, the president’s very dissatisfied,’" Holbrooke said in the audio notes on Aug. 11, 2010, referring to Obama’s deputy national security adviser. "I said, ‘Tom, we have a strategy — you guys have never let us lay it out.’ That of course got him even more agitated."

Holbrooke continued: "Tom said things like ‘I’ll write my strategy myself.’ An odd thing to say because he doesn’t have a strategic sense, so what he thinks is strategy is actually political."

Holbrooke had well-known difficulties connecting with Obama — the president once mocked Holbrooke for insisting that he be called Richard, not Dick — but those who worked with Holbrooke at the White House and at the State Department said the resistance he encountered in the administration prompted him to press harder to find common ground with the president.

"Dick was constantly, as you would imagine, pushing very hard on his point of view," Donilon said in an interview. "Some days, we would be in vehement agreement, and some days, we would not be."

Although Donilon praised Holbrooke as energetic — the two were old friends — Holbrooke’s often passionate efforts to make his case did not go over well with many others at the White House.

Holbrooke "made it worse for himself," said David Holbrooke, the diplomat’s son and the director of "The Diplomat." "He was sort of tone deaf on how to connect with the president." Obama was cool and calculating, David Holbrooke said, while his father was "all heat, he was fire and energy."

David Holbrooke said he toyed with naming the film "Undiplomatic" because his father "didn’t have the smooth lines, the elegance, of the classic diplomats."

"But that’s also what worked for him until the Obama administration," David Holbrooke said, "where a lot of what had worked for him previously just didn’t."

Beyond the personal disconnect between the president and Holbrooke, the audio diary reveals conflict with Gen. David H. Petraeus, who was then the commander of the U.S.-led military coalition in Afghanistan.

Just as Holbrooke was seen to have pulled Bosnia out of its civil war, Petraeus was viewed as the architect and the leading advocate for the counterinsurgency strategy that helped salvage the war in Iraq. By 2010, the two were trying to stem a growing debacle in Afghanistan. The general often referred to Holbrooke as his "diplomatic wingman."

Holbrooke did not like the nickname — he considered himself no one’s wingman — but he nonetheless backed up Petraeus in public. In private, Holbrooke was skeptical of the general’s strategy to hold off on peace talks with the Taliban until he could weaken them militarily.

Petraeus "wants to do it when the time is right, which he says will be next year, by which time he’ll have had more military success," Holbrooke said in an Aug. 6 entry. "Frankly, I just don’t believe him."

Whether the Taliban were actually ready to talk at the time remains an open question. And though there was a broad consensus in the administration that a negotiated settlement would eventually be needed to end the war, Holbrooke believed the White House was blindly backing Petraeus’ desire to wait on talks, and the diplomat’s frustration was evident.

Recounting a conversation with David Axelrod, then a senior adviser to the president, Holbrooke said Aug. 12 that he had told Axelrod that the administration had been dominated too long by "military thinking and military domination."

"While I had great respect for the military," Holbrooke continued, "they should not dictate political strategy, which is what’s happening now."

Holbrooke’s views appeared to have been shaped by his experience as a young foreign service officer in Vietnam in the early 1960s. There, he saw firsthand the limits of the U.S. military and how it was often only the narrowest and most optimistic of reports that worked their way from the field back to decision-makers in Washington.

"I’m constantly amazed that so many military men who have been here for so many months can so miss the facts in front of their eyes," he wrote in 1963 in a letter to his first wife, Litty Holbrooke, an excerpt from which is also included in "The Diplomat."

By the time Holbrooke began keeping his audio diary nearly 40 years later, Obama was already reaching a similar conclusion about what was being reported back from Afghanistan.

Still, a determined effort to open peace talks did not begin until early 2011, just months after Holbrooke’s death, and it took another year before the Taliban publicly acknowledged a willingness to negotiate. The peace process ultimately stalled.

"I’m sure they’ll take a tough line at the beginning," Holbrooke said in an Aug. 20 entry in his audio diary. "That’s what negotiations are about."

Matthew Rosenberg, New York Times

© 2015 The New York Times Company