The effect of these choices in Iowa became jarringly clear when Penn conducted a poll just after Clinton’s Senate reelection that showed her running a very distant third, barely ahead of the state’s governor, Tom Vilsack. The poll produced a curious revelation: Iowans rated Clinton at the top of the field on questions of leadership, strength, and experience—but most did not plan to vote for her, because they didn’t like her. This presented a basic conundrum: Should Clinton run a positive campaign, to persuade Iowans to reconsider her? Or should she run a negative campaign that would accuse her opponents of being untrustworthy and under-qualified? Clinton’s top advisers never agreed on the answer. Over the course of the campaign, they split into competing factions that drifted in and out of Clinton’s favor but always seemed to work at cross purposes. And Clinton herself could never quite decide who was right.

March 2007: The Strategy

Penn had won the trust of both Clintons by guiding Bill Clinton to reelection in 1996 and through the impeachment saga that followed. But his poll-tested centrism and brusque manner aroused suspicion and contempt among many of their advisers. In the White House and during Hillary’s Senate races, Penn often prevailed in internal disputes by brandishing his own poll numbers (which his opponents distrusted) and pointing out that he had delivered a Clinton to the White House once before.

In light of this history, he got off to an inauspicious start when Clinton entered the race in January 2007, by demanding the title “chief strategist” (previously he had been one of several “senior advisers”) and presenting each of his senior colleagues with a silver bowl inscribed with the words of Horace Mann: “Be ashamed to die until you have won some victory for humanity.”

Penn had clear ideas about how to engineer a win for Clinton, in Iowa and beyond. Obama had eclipsed Edwards right out of the gate and was experiencing the full measure of “next JFK” hype. In a memo dated March 19, 2007, Penn laid out an “Overall Strategy for Winning” built upon a coalition of voters he called “Invisible Americans,” a sort of reprise of Bill Clinton’s “forgotten middle class”:

As this race unfolds, the winning coalition for us is clearer and clearer. There are three demographic variables that explain almost all of the voters in the primary—gender, party, and income. Race is a factor as well, but we are fighting hard to neutralize it.

We are the candidate of people with needs.

We win women, lower classes, and Democrats (about 3 to 1 in our favor).

Obama wins men, upper class, and independents (about 2 to 1 in his favor).

Edwards draws from these groups as well.

Our winning strategy builds from a base of women, builds on top of that a lower and middle class constituency, and seeks to minimize his advantages with the high class democrats.

If we double perform with WOMEN, LOWER AND MIDDLE CLASS VOTERS, then we have about 55% of the voters.

The reason the Invisible Americans is so powerful is that it speaks to exactly how you can be a champion for those in needs [sic]. He may be the JFK in the race, but you are the Bobby.

Clinton was already under attack for an attitude of “inevitability”—the charge being that she imperiously viewed the primary process as a ratifying formality and would not deign to compete for what she felt she was owed. Penn’s memo makes clear that what she intended to project was “leadership” and “strength,” and that he had carefully created an image for her with that in mind. He believed that he had identified a winning coalition and knew which buttons to press to mobilize it:

1) Start with a base of women.

a. For these women you represent a breaking of barriers

b. The winnowing out of the most competent and qualified in an unfair, male dominated world

c. The infusion of a woman and a mother’s sensibilities into a world of war and neglect

2) Add on a base of lower and middle class voters

a. You see them; you care about them

b. You were one of them, it is your history

c. You are all about their concerns (healthcare, education, energy, child care, college etc.)

d. Sense of patriotism, Americana

3) Play defensively with the men and upper class voters

a. Strength to end the war the right way

b. Connect on the problems of the global economy, economics

c. Foreign policy expert

d. Unions

Contest the black vote at every opportunity. Keep him pinned down there.

Organize on college campuses. We may not be number 1 there, but we have a lot of fans—more than enough to sustain an organization in every college.

Penn’s prescription is notable because it is the rare instance of a Clinton campaign goal that panned out—the coalition she ended up winning a year later is the one described here. Penn’s memo is also notable for its tone: it reinforces rather than confronts the Clintons’ biases. “The biggest problem we have is the troika that has been set up to tear Hillary down,” he wrote.

It is a vast right and left wing conspiracy. Listening to Brit Hume say that Obama is surging while Hillary failed to do X is almost comical and certainly transparent. The right knows Obama is unelectable except perhaps against Attila the Hun, and a third party would come in then anyway.

By contrast, top consultants like Karl Rove usually aim to temper their clients’ biases with a cold dose of realism. I suspect the damaging persecution complex that both Clintons displayed drew much of its sustenance from memos like this one.