Clinton's Superdelegate Hunter

Harold M. Ickes was midway through a typical profanity-laced cell-phone call on the inch-by-inch battle for the Democratic presidential nomination recently, when he peered over his glasses and demanded, "This call is off the record, O.K.?"

Would anyone want to pick a fight with Ickes, the famously ill-tempered bad boy of the Democratic Party who once bit a rival political operative on the leg? Who once got so mad at having to remove his shoes at an airport security line that he marched off to his plane, yelling "Keep them!" over his shoulder, and flew home in his socks? Who sometimes answers reporters' phone calls with a curt "I'm sorry, Mr. Ickes isn't here now," and then simply hangs up?

As it happened, most of what Ickes uttered into his phone in a Virginia hotel lounge that recent afternoon was punctuated with so many expletives that it was unquotable in this magazine. But that call was like hundreds he is making each week now as Hillary Clinton's top superdelegate hunter, the person stalking, hectoring and sometimes winning over new supporters from among the nearly 800 elected officials, party leaders and activists who will almost certainly choose the next Democratic nominee.

Ickes' superdelegate search had the feel of utter futility only a few weeks ago, when both math and momentum seemed to rule Clinton out of contention. But then came her 9-point win in Pennsylvania, highlighting Barack Obama's persistent weakness among Catholics, senior women, Hispanics and blue-collar workers, and the self-aggrandizing return of the Rev. Jeremiah Wright to the political spotlight. These two events have played perfectly into a pitch Ickes had been making to superdelegates for months: that "we don't know enough about Obama" to make him the nominee. "The one thing we Democrats don't need is an October surprise," insists Ickes. "And the last five weeks have shown us that there may still be much to learn about him. With Hillary, there's not much left to learn."

Gone too, argues Ickes, is the other big strike against Clinton: that she's not as electable as Obama in a matchup against John McCain. Polls have lately shown Clinton faring better than Obama against McCain--in one recent poll, 7 points better--in part, Ickes says, because of her enduring popularity with key Democratic constituencies in the states that matter the most in a general-election campaign.

Ickes isn't fazed by those who accuse him of damaging the party by trying to wrest the nomination away from the first viable African-American contender. "Everyone says, 'You can't take this away from a strong black candidate,'" Ickes says. "Well, how about the first woman candidate of consequence? That's been almost swept under the rug while people have been mesmerized by Obama. Yes, he's a very strong candidate. But so is Hillary. She's a pretty big deal too."

Still, the math remains prohibitive. For all of Ickes' efforts, it is Obama who has been steadily chipping away at Clinton's lead among superdelegates. Meanwhile, almost every scenario has Obama maintaining his slim but stable lead among pledged delegates through the May 6 contests in Indiana and North Carolina--and the final primaries on June 3. The idea that Clinton can narrow her deficit among all delegates and then vault over Obama with a rush of support from uncommitted superdelegates is still remote. But it no longer seems impossible. There are fresh signs that the dispute over the rogue primaries held by Florida and Michigan may be resolved in a way that delivers more delegates to her than to Obama. Ickes has been in charge of those negotiations too. "Everyone over there was pretty much convinced this thing was finished," says another senior Clinton adviser, referring to the somber mood at Hillary's campaign headquarters. "We were going through the motions. But not Harold. He's been focused on those delegates like a madman. And there's a chance it may actually pay off."

How much of a chance? The perpetually sly Ickes of course won't say, preferring instead to marvel that the game isn't over yet--and he might have as long as four more months to caper on her behalf (although he predicts the fight will be resolved by mid-June). "For those of us who have been hanging around presidential politics for years," says Ickes, "there's never been a nominating process quite like this."

How to Win When Losing Which is an ironic comment, to say the least, since Harold McEwen Ickes has done so much over the past 30 years to make this moment possible. Son of an irascible Franklin Delano Roosevelt Cabinet member (whose nickname was the Old Curmudgeon), the younger Ickes was raised in the Washington bubble of his time--but he migrated West, worked as a cowboy on a ranch in Northern California and harbored little interest in the kind of work done by his father, who died when the boy was 12. That changed in the summer of 1964, after graduating from college, when Ickes headed south to work for the civil rights movement. The next year, he was beaten so severely by a gang of whites in Louisiana that he lost a kidney. Ickes has been a practicing political operative ever since.

Though he has played many roles since his first campaign, in 1968, Ickes is known best as a closer, the master of the bitter end who can wring important victories from defeat. He fought pitched, sometimes noble, usually hopeless battles on behalf of Eugene McCarthy, Ed Muskie, Ted Kennedy and Jesse Jackson. And in most cases, he took the fight for his underdog candidate all the way to the party's convention, where he tried every trick the rules allowed--and some they didn't--in the hope a miracle would happen. It never did. But in the process, Ickes helped rewrite those rules into the ones that now govern the way Democrats choose a nominee. At the 1980 convention, Kennedy trailed President Jimmy Carter by more than 750 delegates, all of whom were bound by the existing rules to vote for the candidate they were pledged to. So Ickes orchestrated a floor vote on Kennedy's call to "free the delegates"--let them exercise their own judgment as to who should be the nominee--a tool that could come in handy again this year in Denver. "We lost; the nomination was Carter's--we all knew what was going to happen," Ickes says now. But the 1980 showdown gave rise to the Hunt Commission, which re-introduced superdelegates into the process of selecting a Democratic nominee. It is on these superdelegates that so much for the Clinton campaign rests.