The Clinton/Holbrooke alliance was not enough to break through a risk averse White House according to Vali Nasr, dean of SAIS and a senior advisor on Afghanistan:
The White House, however, did not want to try anything as audacious as diplomacy. It was an art lost on Americas top decision-makers. They had no experience with it and were daunted by the idea of it.
While running for president, Obama had promised a new chapter in U.S. foreign policy: America would move away from Bushs militarized foreign policy and take engagement seriously. When it came down to brass tacks in Afghanistan and Pakistan, however, Clinton was the lonely voice making the case for diplomacy….
But Clinton shared Holbrookes belief that the purpose of hard power is to facilitate diplomatic breakthroughs. During many meetings I attended with her, she would ask us to make the case for diplomacy and would then quiz us on our assumptions and plan of action. At the end of these drills she would ask us to put it all in writing for the benefit of the White House
Holbrooke and Clinton had a tight partnership. They were friends. Clinton trusted Holbrooke’s judgment and valued his counsel. They conferred often (not just on Afghanistan and Pakistan), and Clinton protected Holbrooke from an obdurate White House.