5. What if the Clintonites hadn’t spent their war chest like a bunch of whiskey-addled sailors?
Of all the unexpected developments of 2008, perhaps the most astonishing is that, by the end of January, the Clinton campaign was broke—while the insurgent Obamans were flush, allowing them to outspend Hillary in the states after Super Duper Tuesday by two or three or four to one. One difference was Obama-land’s mastery of the Web as a fund-raising tool, which the Clinton people never got the hang of. But another was the latter side’s grotesque overexpenditures in 2007, a grievous error that must be laid at the feet of her former campaign manager, Patti Solis Doyle, an operative Clinton valued more for her loyalty than her ability to actually do the job. Recipe for disaster.
6. What if the Clintonites hadn’t ignored the other caucus states?
Arguably their single biggest tactical blunder was the decision last fall not to invest in building organizations in places such as Minnesota, Washington, Maine, and Idaho, where Obama would not only win but rack up huge pledged-delegate margins. The decision was rooted in arrogance and complacency; in the faulty premise that by carrying the big states on Super Duper Tuesday, Clinton would be able to bring the race to an early conclusion.
7. What if Clinton had dumped Mark Penn before he shot himself in the head?
No single figure was more influential in the Clinton campaign than her portly, perpetually rumpled supreme Svengali. And no one was a greater source of the instability and infighting that turned what was supposed to have been a well-oiled juggernaut into a leaky, creaky vessel. Roundly despised by colleagues, a walking catalogue of conflicts of interest, and a man with no history of successfully negotiating a Democratic presidental primary, Penn might still have been an asset had his strategic advice been sound. But it wasn’t (see No. 10).
8. What if Clinton had “divorced” her husband after South Carolina?
Bill Clinton is a man of gargantuan political talents, to be sure. But his omnipresence made Clinton fatigue an inescapable facet of the campaign’s thematics. And after the debacle in the Palmetto State, which thoroughly (and maybe permanently) alienated black voters from Hillary’s cause, it was clear to many on her team that he was doing more harm than good to his wife’s electoral prospects. Should she have sidelined him, standing up one day and declaring that she was a big girl and could fight her own fights, thank you very much? Some Clintonites think so. And even those who disagree admit that WJC’s energies should have been more carefully, productively channeled. “There was no way he wasn’t going to play a role,” says one. “But did we ever find the right role for him? I think the answer is obviously no.”
9. What if Clinton had gone magnanimous on Obama and the Reverend Wright?
The GOP strategist Alex Castellanos offers an intriguing theory about how Hillary might have reacted differently, and more effectively, to the issue that threatened to swallow Obama. “After the Reverend Wright controversy, Obama was suffering the worst press month of his campaign,” he says. “Hillary had a choice. She could have gotten bigger, more presidential, less political; she could have risen to defend Obama, saying, ‘This is outrageous and has no place in politics.’ Instead, she chose to become smaller, more political, less presidential. She diminished the value of the attacks on him by making them hers. Her instincts betrayed her. What if she had chosen to soar above a weakened Obama? That was her moment. And I believe she missed her last great opportunity to win this race.”
10. What if Clinton had cast herself as the candidate of change?
At the insistence of Penn, Hillary positioned herself from the outset as the avatar of experience, “ready from day one,” as she liked to say, to become the commander-in-chief. But this strategy profoundly misread the prevailing winds gusting across the political landscape—winds favoring a candidate representing a fundamental break with the past. It’s often said that Clinton, as a dynastic figure, would have found this impossible to pull off. But as the first plausible female president ever, why should this have been so? “There was always a powerful positive case for her as the change candidate,” says Democratic guru Bob Shrum. “Instead, she let herself become the Establishment candidate in a year of change.”
And here lies a final point worth making. In the days ahead, retrospective second-guessing and finger-pointing will be everywhere and vicious in Clinton-land—and God knows, as the list above makes clear, there’s blame enough to go around. But in the end the success or failure of any electoral venture rests mainly on the candidate herself. For Clinton, this will undoubtedly be the hardest truth to grasp. But if she hopes to do better next time—and trust me, there will be a next time—grasping it fully will be essential.