Perhaps not the best quality to have in a top strategist, not understanding how the race is won.

Jason Linkins provides the key graph from a Karen Tumulty piece in Time Magazine:

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.