Democratic debate: Jim Webb gives the most awkward answer of the evening

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Jim Webb was responsible for one of the most uncomfortable moments of the Democratic debate on Tuesday evening when his dark sense of humour failed to translate.

Webb served in the Marine infantry as a rifle platoon and company commander during the Vietnam War. He was awarded the Navy Cross, the Silver Star Medal, and other military honours for bravery.

The former Virginia senator was asked to name the enemy he was most proud of making in his political career during the debate.

“I’d 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 slowly after the other four candidates gave their answers, his mouth gradually breaking into a grin.

A few members of the audience managed an uneasy chuckle, but Moderator Anderson Cooper was keen to move on from his answer and quickly redirected the debate towards closing statements.

Webb, who was tipped to be the wild-card of the night, also repeatedly complained of not receiving as much attention as the left-winger Bernie Sanders and front-runner Hillary Clinton. When Cooper tried to cut him off for going over his allotted time with an answer, he responded curtly: “I’ve been waiting for 10 minutes. I will say this.” He then finished his point.

His performance during the debate was poorly received overall, with Salon dismissing him as “obstuse, petulant, and out of touch”. He emerged from the debate in fourth place at 0.9 per cent in opinion polls.