Most likely, too, we won't know his final or dominant assessment of the strategy Obama charted in Afghanistan. Perhaps it was something of a kaleidoscope, as most people's would be, shifting with the daily flicker of events. He was by all accounts a man of extraordinarily intense will, with an optimism fed by a refusal to not succeed.
But there is a constant hue to Bob Woodward's portrayal in Obama's Wars of Holbrooke's assessment of the emerging strategy, and the possibility of the U.S. securing stability in Afghanistan: gray-to-black. Throughout Woodward's exhaustive account of the Obama team's exhausting deliberations from September through November 2009, and once more in retrospect in May 2010, Holbrooke knocks down several core assumptions regarding the rationale, progress to date, and prospects for success of U.S. attempts to stand up the Karzai regime. Below, a sampling.
The Taliban will not harbor al Qaeda (Sept. 13, 2009)
Like Biden, Holbrooke believed that even if the Taliban retook large parts of Afghanistan, al Qaeda would not come with them. That be "the single most important intellectual insight of the year," Holbrooke remarked hours after the first meeting. Al Qaeda was much safer in Pakistan. Why go back to Afghanistan, where there were nearly 68,000 U.S. troops and 30,000 from other NATO counties? [sic]...
Astonishingly to Holbrooke, that key insight had neither been in [Bruce] Riedel's report [presented in March '09], nor had it been discussed that Sunday morning [Sept. 13]. Where was the no-holds-barred debate? The president had told them not to bite their tongues. Holbrooke had to bite his because he worked for the secretary of state, who was unsure of what course to recommend. But where were the others? (170)