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Kennedy's top military adviser, Gen. Maxwell Taylor, said later that MacArthur's statement made a "hell of an impression on the President."
Over the next several years, Holbrooke found himself witness to the wisdom of MacArthur's advice. From 1963 to 1966, Holbrooke worked in Vietnam as a rising young diplomat assigned first to the rural Pacification Program, a key component in the war's counterinsurgency strategy, and then to the U.S. Embassy in Saigon.
Next, Holbrooke was summoned to Washington to work on a special White House team headed by a veteran of the infamous Phoenix Program that sought to terrorize and "neutralize" South Vietnamese Communist leaders.
In 1968, Holbrooke was assigned to the peace talks in Paris where special envoy Averill Harriman represented a chastened President Johnson in seeking a negotiated end to the war (only for Johnson to discover in October 1968 that Richard Nixon's presidential campaign had sabotaged those talks by persuading South Vietnam's President Nguyen van Thieu to boycott in exchange for promises of a better deal.)
After narrowly winning the presidency, Nixon continued the war, even expanding it into Cambodia, but to no avail. In 1973, the U.S. "giant" settled for terms that had been available in 1968 and then watched its South Vietnamese allies collapse in 1975.
Failure to Learn
But neither those direct experiences nor his studies in history seemed to have informed Holbrooke's judgment regarding the limits of a giant's powers.
It would have been good if one of Holbrooke's professors at Brown had suggested he read a little Kipling:
It is not wise for the Christian white
To hustle the Asian brown;
For the Christian riles
And the Asian smiles
And weareth the Christian down.
At the end of the fight
Lies a tombstone white
With the name of the late deceased;
And the epitaph drear,
A fool lies here,
Who tried to hustle the East.
Despite the disastrous outcomes from his early endeavors, Holbrooke found that he had earned a place in the Washington Establishment, as an operative who would get his hands dirty on the seamier side of international affairs.
Holbrooke became the Democrats' go-to diplomat for particularly messy conflicts, such as the Balkan wars of the 1990s, situations where a strong moral compass was viewed as something of a disqualifier. Holbrooke was counted on to bulldoze through and over any ethical qualms to achieve what Washington wanted.
Fast forward to the first weeks of the Obama administration.
With the arrival of a new Democratic president, we see Holbrooke waiting in the wings for a senior diplomatic position as something to which he felt entitled. And President Obama came through just two days after taking office by naming Holbrooke special envoy to Afghanistan and Pakistan (Af-Pak).
However, even assuming that Holbrooke had learned lessons from his Vietnam experiences, he didn't show it during Obama's fateful deliberations in his first weeks in office, as the President threw 21,000 more troops into Afghanistan to shore up a collapsing military strategy, rather than start thinking about a coherent exit plan.