The issue that Webb cares about the most, and which could cause serious trouble for Hillary Clinton, is the one that Obama used to defeat her: Clinton’s record on war. In the Obama Administration, Clinton took the more hawkish position in three major debates that divided the President’s national-security team. In 2009, she was an early advocate of the troop surge in Afghanistan. In 2011, along with Samantha Power, who was then a member of the White House National Security Council staff and is now the U.N. Ambassador, she pushed Obama to attack Libyan forces that were threatening the city of Benghazi. That year, Clinton also advocated arming Syrian rebels and intervening militarily in the Syrian civil war, a policy that Obama rejected. Now, as ISIS consolidates its control over parts of the Middle East and Iran’s influence grows, Clinton is still grappling with the consequences of her original vote for the war in Iraq.

Although Webb is by no means an isolationist, much of his appeal in his 2006 campaign was based on his unusual status as a veteran who opposed the Iraq war. “I’ve said for a very long time, since I was Secretary of the Navy, we do not belong as an occupying power in that part of the world,” he told me. “This incredible strategic blunder of invading caused the problems, because it allowed the breakup of Iraq along sectarian lines at the same time that Iran was empowering itself in the region.”

He thinks Obama, Clinton, and Power made things worse by intervening in Libya. “There’s three factions,” he said. “The John McCains of the world, who want to intervene everywhere. Then the people who cooked up this doctrine of humanitarian intervention, including Samantha Power, who don’t think they need to come to Congress if there’s a problem that they define as a humanitarian intervention, which could be anything. That doctrine is so vague.” Webb also disdains liberals who advocate military intervention without understanding the American military. Referring to Syria and Libya, Webb said, “I was saying in hearings at the time, What is going to replace it? What is going to replace the Assad regime? These are tribal countries. Where are all these weapons systems that Qaddafi had? Probably in Syria. Can you get to the airport at Tripoli today? Probably not. It was an enormous destabilizing impact with the Arab Spring.”