And now there are five. The former U.S. Senator from Virginia and Reagan administration Naval Secretary joined the four other announced Democratic presidential candidates, promising to challenge the “shadow elites” of federal government. Famous for wearing his Navy boots inside the Capitol, Webb can be unpredictable in his policies. On Wednesday, he hinted at decriminalizing drugs if elected but last week caused a stir defending the Confederate Flag’s heritage. Webb faces a steep uphill climb against his Democratic colleagues but is already a presence on the campaign trail in early primary states.