Penn Strategy Memo, March 19, 2007

More than anything else, this memo captures the full essence of Mark Penn’s campaign strategy—its brilliance and its breathtaking attacks. Penn identified with impressive specificity the very coalition of women and blue-collar workers that Clinton ended up winning a year later. But he also called Obama “unelectable except perhaps against Attila the Hun,” and wrote, “I cannot imagine America electing a president during a time of war who is not at his center fundamentally American in his thinking and in his values.” Penn proposed targeting Obama’s “lack of American roots.”

Karl Rove Strategy Memo to Bill Clements, Jr., September 4, 1985

As a contrast to Mark Penn’s memos, here’s a fun piece of political arcana: a Karl Rove strategy memo written to former Texas governor Bill Clements, Jr., on the eve of the 1986 gubernatorial race. Clements was elected governor in 1978 but lost his bid for reelection. He was attempting a comeback. Note the tone of bracing honesty: Rove lays out his client’s “potentially explosive” weaknesses, including arrogance and bad press relations. Then he explains how they can be overcome. (Let’s forgive Rove the hackneyed Napoleon quote—Clements won the race.)

Harold Ickes Lists the Campaign’s “Key Assumptions,” March 29, 2007

Soon after Clinton’s presidential campaign got underway, senior adviser Harold Ickes circulated this list of “Key Assumptions.” They include his belief that February 5 would decide the nominee; that Clinton could not survive losses in Iowa and New Hampshire (but that John Edwards and Barack Obama could); and that the prevailing view of her as the incumbent was potentially dangerous. Fatefully, Ickes cited the need to maintain a $25 million reserve fund for use after Iowa—but following Clinton’s loss, he confessed to colleagues, “The cupboard is empty.”

Penn Strategy Memo, April 8, 2007

With Obama’s popularity and fund-raising strength becoming clearer by the day, Penn seemed to absorb the public criticism of Clinton as behaving imperiously. “Show more of the happy warrior,” he counseled. He was also becoming attuned to the importance of the “change” theme Obama was touting: “Let’s talk more about a movement for change coming from the people.” He proposed the slogan “America is Ready for a Change, and HRC is Ready to Lead Us.”

The “Kindergarten” Attack, December 2, 2007

On December 2, Clinton exploded at her staff on a morning conference call, frustrated that her campaign wasn’t on the attack. Hours later, in this series of emails, her panicked staff reacted by putting together an ill-advised attack on Obama for having written a kindergarten essay titled “I Want to Become President.”

Harold Ickes Memo on the Delegate System, December 22, 2007

Harold Ickes was the adviser with primary responsibility for the campaign’s delegate and targeting strategy. While the Obama campaign shrewdly exploited the Democratic Party’s complicated system of allotting delegates, Ickes and the Clinton campaign did not. On December 22, just twelve days before the Iowa caucus, Ickes finally laid out the system for the campaign’s senior staff in this somewhat impenetrable memo.