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Scott Ritter, the former chief UN Special Commission (UNSCOM) inspector, who correctly assessed the absence of weapons of mass destruction in Iraq and predicted a disastrous outcome for the US invasion, observed, "not only has he demonstrated a lack of comprehension when it comes to the complex reality of Afghanistan (not to mention Pakistan), Holbrooke has a history of choosing the military solution over the finesse of diplomacy." Noting how the Dayton Accords were built on the assumption of a major and indefinite NATO military presence, which would obviously be far more problematic in Afghanistan and Pakistan than in Europe, Ritter added: "This does not bode well for the Obama administration."

Ironically, back in 2002-2003, when the United States had temporarily succeeded in marginalizing Taliban and al-Qaeda forces, Holbrooke was a strong supporter of redirecting American military and intelligence assets away from the region in order to invade and occupy Iraq. Obama and many other Democrats presciently criticized this reallocation of resources at that time as likely to lead to the deterioration of the security situation in the country and the resurgence of these extremist groups, but Holbrooke instead sided with the Bush administration in supporting the disastrous invasion and occupation.