Joshua Green has an interesting post-mortem in The Atlantic looking at what went wrong in the Clinton campaign. The major themes seem to be chronic in-fighting among the senior campaign staff, a tendency to put off tough decisions, and a tendency to burn through money.
I would have liked to see more about just where all their money went. Seems like they just about went broke coming in third place in Iowa, and then were fighting money problems for the rest of the campaign. Since Mark Penn is my preferred villain in this tale, I’ll just assume he was overpaid and took huge chunks of money for ineffective ad buys.