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As the conflict erupted in March 2011 and intensified, Mr. Obama and others called on Mr. Assad to leave but put no pressure on him, Mr. Phillips said.

Mistaken assessments

Mr. Obama turned to the United Nations, which gave Russia, a strong Syrian ally, and China the opportunity to veto a get-tough resolution.

“The lesson is that when an administration leads from behind, U.S. national interests get left behind,” Mr. Phillips said.

P.J. Crowley, who was Mrs. Clinton’s spokesman early in the administration’s first term, said he thinks Mrs. Clinton’s assessment is correct and that Mr. Assad will fall.

“It is hard to see how he will be able to die in office, after a long life, as his father did,” Mr. Crowley said.

The administration has made mistakes, he said, such as comparing the Syrian revolt to the uprisings in Tunisia and Egypt.

“The Syrian security forces made a different choice, remaining devoted as an institution to the Assad family rather than the Syrian people,” he said. “There have been many defections and there will be many more. The Syrian military is under enormous pressure and is likely to crack at some point. The military leadership might decide to save itself at Assad’s expense, but there is no indication that we are close to that moment.”

Mr. Crowley also said the administration “did underestimate Assad’s dark side.”

But the Syrian military’s devotion validates Mr. Obama’s cautious approach because “if we become an active combatant, it will entail far more effort, risk and cost than we think to dislodge him,” Mr. Crowley said.

Said the naval school’s Mr. Russell: “There’s international pressure to intervene, but how would we intervene exactly? And to what end? This is a civil war, which means we have to back a side, or sides, since there are multiple parties that are fighting each other. Not all the people fighting on the same ‘side’ share the same political objectives. Our recent record in picking winners, so to speak, is pretty mixed.”