How could this guy siphon so much money from the Clinton campaign? Why wasn't he fired on the spot?
Clinton picked people for her team primarily for their loyalty to her, instead of their mastery of the game. That became abundantly clear in a strategy session last year, according to two people who were there. As aides looked over the campaign calendar, chief strategist Mark Penn confidently predicted that an early win in California would put her over the top because she would pick up all the state's 370 delegates. It sounded smart, but as every high school civics student now knows, Penn was wrong: Democrats, unlike the Republicans, apportion their delegates according to vote totals, rather than allowing any state to award them winner-take-all. Sitting nearby, veteran Democratic insider Harold M. Ickes, who had helped write those rules, was horrified — and let Penn know it. "How can it possibly be," Ickes asked, "that the much vaunted chief strategist doesn't understand proportional allocation?" And yet the strategy remained the same, with the campaign making its bet on big-state victories. Even now, it can seem as if they don't get it. Both Bill and Hillary have noted plaintively that if Democrats had the same winner-take-all rules as Republicans, she'd be the nominee.
[From The Five Mistakes Clinton Made - TIME]
Senator Clinton lost because of stupidity like this, probably a good thing. Running a presidential campaign is nothing like running the country, but it is the closest thing. Clinton's campaign was poorly managed, poorly strategized, poorly conducted, all in all not a good indicator of future success.