Obama’s caution on Syria has vexed those in the administration who have seen opportunities, at different moments over the past four years, to tilt the battlefield against Assad. Some thought that Putin’s decision to fight on behalf of Assad would prompt Obama to intensify American efforts to help anti-regime rebels. But Obama, at least as of this writing, would not be moved, in part because he believed that it was not his business to stop Russia from making what he thought was a terrible mistake. “They are overextended. They’re bleeding,” he told me. “And their economy has contracted for three years in a row, drastically.”
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By late winter, though, when it appeared that Russia was making advances in its campaign to solidify Assad’s rule, the White House began discussing ways to deepen support for the rebels, though the president’s ambivalence about more-extensive engagement remained.