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By Justin Webb
BBC News North America editor
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The loss of a friend gives Mrs Clinton a chance to turn round her campaign
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Mark Penn, who resigned from Hillary Clinton's campaign for the Democratic presidential nomination on Sunday, was one of her most trusted advisers and friends.
But he had been blamed by many within the Clinton inner circle for the failure of her campaign to overcome support for Barack Obama.
Mrs Clinton is still behind in the race - with the important Pennsylvania primary due at the end of this month.
The immediate cause of the resignation was a meeting Mr Penn held on behalf of his lobby firm with representatives of the Colombian government - which is trying to press the US Congress to sign a free trade agreement.
Mrs Clinton opposes the agreement - support for free trade is unpopular on the campaign trail - and although Mr Penn apologised for an error in judgement, he was left with little choice but to resign.
11th hour
His departure is a blow for Mrs Clinton, but also an opportunity.
He is a good friend, so his resignation and the rows surrounding it will be keenly felt.
But his presence in her inner circle was little short of poisonous. He is greatly disliked by several key figures, and blamed for the mistakes in strategy and tactics that see the Clinton campaign holding on to its chances of victory only by a slender thread.
His resignation is an opportunity for an 11th hour rethink for a troubled senior team.
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