While I do have a general aversion to the idea of using pollsters as general strategists (the skill-sets that make one a good pollster don't necessarily translate to being a good strategist -- though Dick Morris and Pat Caddell would probably disagree), Penn's original strategy was not ridiculously flawed.
Penn's notion of creating a "tough" image, and relying on an early knock-out, seemed plausible six months ago. Granted, it didn't work, that's for certain, but it might have. In any event, it wasn't a ridiculous notion.
Often when strategists are ridiculed, it is in hindsight. But strategists use history as a predictor for the future. Had Hillary's opponent been a standard-issue Democrat, she would likely have prevailed. But Barack Obama hasn't been as easy for Hillary to defeat as, say, John Edwards was.
Of course, Penn was finally pushed out because he met with the Columbian government to promote a policy Clinton disagreed with. Still, Hillary's mistake was not in hiring Penn, but in not identifying the misdiagnosis of her campaign, sooner.
Stumbling isn't necessarily a bad thing. John Kerry famously fired his campaign manager late in 2003 (Hillary fired her campaign manager earlier this year, too). This cycle, John McCain' s campaign stumbled worse -- and sooner -- than Hillary's (this may have been a blessing), yet he was able to correct his strategy. Hillary could probably have righted her ship after Iowa. In fact, I believe that a loss in New Hampshire would have probably resulted in her firing Penn.
McCain's ability to adapt is, perhaps, a sign he would adapt well as president, too. Hillary's inability to adapt, ironically, may remind voters of George W. Bush. Who knows?
As a side note, Penn also failed at the art of office politics. HIs internal mistake was to rely solely on the support of the two principals as his allies.
Penn failed to realize that developing a network of supporters -- within the campaign -- was vital.
For all the talk that goes on in Washington about having a "constituency of one," the truth is that anyone who wants to get something done realizes it's a mistake to fail to develop a network of friends and supporters within a given organization. That means your equals and subordinates -- not just your boss -- must at least respect you. In Penn's case, they did not.