[Wilson Burman is the pen name for a New York City financial executive who writes The Cunning Realist blog. ]

If Alexis de Tocqueville had sat in the bleacher seats at Yankee Stadium for an entire summer, he would have been an even more interesting read. Fortunately, we had our own master observer of Americana. That the essence of the nation’s character resides in its grandest pursuits as well as its simplest rituals is the legacy of David Halberstam.

Halberstam’s death on April 23 was a terrible loss. He was a graceful and compelling writer. His gift was taking a subject—sometimes complex, sometimes mundane or over-covered—and distilling it for readers into immediacy and timelessness. His insight was linked inextricably to his effortless, after-midnight type of eloquence. The Best and the Brightest, his seminal work on the Vietnam War, combines these qualities, and the topic seemed uniquely suited for his sense of style. What better way to capture the mission creep, the corruption, the maddening incapacity of the Diem regime and its successors, or the intellectual rot in Washington, than with one of Halberstam’s meandering, sparsely punctuated sentences?

Any meaningful discussion of Halberstam, and The Best and the Brightest in particular, means quoting at least some of his writing. It also requires thinking about the topic’s relevance and lingering lessons. After four years, the Iraq-as-Vietnam analogy is more than a bit tired. But despite its exhaustive details on the Vietnam War, the book’s real message is that the failures that led to the quagmire are an integral part of the nation’s identity. The main players—Kennedy, Johnson, Bundy, McNamara, Rostow, Rusk, Taylor, Westmoreland—are almost allegorical symbols of the brilliance, determination, hubris, myopia, and hypocrisy that both account for the nation’s greatness and cause periodic disasters. They were indeed the best and the brightest. But when “events are in the saddle and ride mankind,” as Emerson wrote, strengths can become fatal flaws. To Halberstam, General Westmoreland embodied that:

He liked the Vietnamese and was genuinely committed to their cause, but there was never a real sense or feeling for their frailties, fallibilities, their corruption, their loss of innocence (had they ever been innocent?). He was, finally, too American, too successful in the American and Western sense, too much a sterling product of a success-oriented country to feel the rhythms and nuances of this particularly failed society; he was the finest product of an uncorrupted country where doing good was always rewarded, one worked hard, played by the rules, went by the book, and succeeded. Success. Theirs was a corrupted, cynical society where the bribe, the lie, the decadence had become a way of life, where Vietnamese officers lied frequently and readily to their American counterparts. ... The Americans, particularly the military, were so straight and Westy was the classic example; he was so American, like all Americans in Vietnam he wanted the Vietnamese to be Americans, he saw them in American terms, he could never seem to see them as themselves.

Substitute a few words here and there—leaving in “corrupted” and “bribe” and “this particularly failed society”—and it’s just as relevant now in Baghdad’s alleys and marketplaces as it was a generation ago when the Ivy League, spreadsheets, and flowcharts met their match in the jungles and rice paddies....