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Since December, I have been hearing a steady stream of worries from Clinton partisans who took Barack Obama's challenge seriously from the start. These loyalists felt her campaign was misreading the nature of the political year, the state of the Democratic Party, the organizational requirements of a long struggle for the nomination, and the complexity of the party's attitudes toward both the candidate herself and former President Clinton.
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Not all of these problems can be laid at Penn's feet. But he did come to symbolize a campaign that was much given to infighting and failed to understand the new energies unleashed in the Democratic Party by the reaction against George W. Bush. It did not grasp early enough how much politics has changed since the Clinton '90s. The post-Penn Clinton campaign has only a little time and a narrow window to make up for these mistakes.
http://www.realclearpolitics.com/articles/2008/04/penn_the_symbol_of_clintons_pr.html