In late December, Obama went with his family to his native Hawaii. He took long walks, ate lots of food, and spent a good deal of time with his family as he inched closer to a decision. On Tuesday, January 2, he spent four hours with Axelrod in his Chicago office. On Sunday, Obama called Daschle at home and broke the news: He was going to run.
One of the mysteries of this presidential cycle is how the Clinton operation, with its vaunted foresight, failed to see Obama coming. Politically, the Clinton presidential team did very little early on, aside from holding a series of meetings among a very small group of advisers: Penn, campaign manager Patti Solis Doyle, communications adviser Howard Wolfson, media strategist Mandy Grunwald, and occasionally the veteran Democratic operative Harold Ickes and a few other confidants. In the spring of 2006, they were still eyeing John Edwards. After Edwards took a far more aggressive policy approach than Team Clinton had anticipated, Hillary Clinton responded by delivering a series of policy speeches, now largely forgotten. (Aides insisted she was not responding to Edwards, but many Clinton insiders say otherwise.) Barack Obama barely registered. Penn had not yet included him in his occasional surreptitious polls of the primary electorate.
A few Clinton advisers did detect danger. On September 17, 2006, when Obama gave the keynote address at Senator Tom Harkin’s annual steak fry in Iowa, Steve Hildebrand was spotted shepherding Obama through the crowd. The next day, Solis Doyle e-mailed Hildebrand to make clear that she knew he had been there.
One Clinton adviser admitted to me that it wasn’t until late January of this year when, in a short period of time, Obama got fund-raising pledges from four of the party’s top fund-raisers—Orin Kramer, a New York hedge-fund manager; Alan Solomont, a Boston venture capitalist; Mark Gorenberg, who was one of John Kerry’s top bundlers; and Steve Westly, the former California controller—that Clinton’s inner circle finally understood the threat Obama posed.
Obama’s rise was particularly worrisome for two reasons. First, money is the mechanism by which the Clintons exert leverage over the party. Some Clinton supporters believed the couple’s sway over the party’s money machinery is even more important than their popularity with the Democratic base. So the defection of major fund-raisers was a serious blow.
Second, part of the grand strategy for Hillary Clinton’s run at the White House was to build a movement around her gender and the possibility of electing the first female president. Penn, the campaign’s visionary, believed that presenting Clinton’s candidacy as a historic occasion would reinspire voters badly disillusioned after eight years of George W. Bush. But Obama, the first credible black candidate, assumed the symbolic role that Clinton’s team had in mind for her. His reception by voters and the media was rapturous. Obama’s potential appeal had occurred to Clinton’s advisers, but as several of them later admitted, they failed to anticipate the intensity with which the Democratic Party and the national media would embrace him.