In what was intended to be a lighter moment in the first Democratic primary debate, CNN's Anderson Cooper asked the candidates to name the enemies they were proudest of making over the course of their political careers. The National Rifle Association and pharmaceutical companies were popular answers.
Webb struck a more serious tone in his response, even as he delivered it with a smile.
"I would have to say the enemy soldier that threw the grenade that wounded me but he's not around right now to talk to," he said to scattered laughter.
Webb is a decorated Vietnam war veteran with two Purple Hearts, a Navy Cross and a Silver Star to his name.