Clinton and her senior staff warned the White House multiple times before she left office that the Syrian civil war was getting worse, that working with the civilian opposition was not enough, and that the extremists were gaining ground. The United States needed to engage directly with the Free Syrian Army, they argued; the loose conglomeration of armed rebel groups was more moderate than the Islamic forces—and begging for help from the United States. According to several administration officials who were there, her State Department also warned the White House that Iraq could fall victim to the growing instability in Syria. It was all part of a State Department plea to the president to pursue a different policy.

“The State Department warned as early as 2012 that extremists in eastern Syria would link up with extremists in Iraq. We warned in 2012 that Iraq and Syria would become one conflict,” said former U.S. ambassador to Syria Robert Ford. “We highlighted the competition between rebel groups on the ground, and we warned if we didn’t help the moderates, the extremists would gain.”

But the warnings, which also came from other senior officials—including then-CIA chief David Petraeus and Defense Secretary Leon Panetta—fell on deaf ears. Obama’s small circle of White House foreign policy advisers resisted efforts to make connections with rebel fighters on the ground until 2013, when the administration began to train and equip a few select vetted brigades.