Clinton's Superdelegate Hunter

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In 1988 Ickes was at it again, negotiating a change in party rules that would not be tested until 2008. In return for Jackson's support at the convention that summer, Michael Dukakis endorsed a complex plan that awarded delegates based on a candidate's proportion of the vote in every state. By doing away with winner-take-all primaries, the new rules prevented a front runner from wrapping up the nomination with a handful of wins in big, delegate-rich states. Underdog candidates could stay alive through the primaries, and perhaps even win the nomination, by collecting delegates in every contest, whether they won it or not. It would be two decades before an underdog turned front runner named Barack Obama would take full advantage of those rules. If Clinton's victories in big states like New York, California, Pennsylvania and Ohio had been winner-take-all, she would be the nominee today. Of course, if superdelegates didn't exist, Obama's delegate lead would be foolproof. Such are the ironic consequences of the rules Ickes helped write.

It has not gone unnoticed that Ickes, after a generation of maneuvering behind the scenes for insurgent candidates, is working for the Establishment contender this time, in exactly the kind of stodgy corporate campaign he once took a special pleasure in trying to destroy. But as Obama surged and Clinton fell behind, Ickes settled into a more familiar role as sideman to a long shot. Even inside Hillaryland, Ickes is something of a rebel. One part of that is simply his years: at 68, he is twice (and in a few cases, three times) the age of his colleagues. He is allergic to e-mail and loads his pockets down each morning with extra cell-phone batteries to keep up with the pace of modern campaign communications. In a suite of offices where black is de rigueur for women as well as men, Ickes is a somewhat diverting figure who favors a colorful Carnaby Street fashion sense--purple dress shirts and floral ties are his trademarks--that is as brash and unapologetic as he is.

More important, Ickes has never hidden his disdain for the way Clinton's campaign for President was run through the early primaries and has expressed special contempt for Mark Penn, the erstwhile chief strategist who was demoted in early April. Ickes loves to refer to the rest of the campaign's high command as "the thought police" for its habit of denying reality for the sake of message discipline.

He has few illusions about the Clintons. As deputy White House chief of staff in Bill Clinton's first term, he handled the President's dirty work--everything from managing the Whitewater scandal to fund-raising for his re-election campaign. In addition to a pile of personal legal bills, Ickes' reward was learning from the front page of the Wall Street Journal that he'd been fired, three days after the 1996 election. But he was back with the Clintons a few years later, this time helping direct Hillary's 2000 race for the Senate. And he is again at their side now, in the latest impossible fight of their lives. It's a loyalty few can match.

Would he work for the ultimate insurgent, Obama, if this last-ditch effort on Hillary's behalf falls short? Ickes says he would, "although not with the same intensity." As if, for Harold Ickes, that were even possible.