"You establish a relationship and keep going back, and people become friendlier and let down their guard," Ickes said, describing the campaign's methods. "And before you know it, you can pick up useful information. None of this is insidious information; it's information about what makes a person tick politically."
Ready to pounce
In the case of Shay, Ickes remembered that Shay had wanted to increase the representation of gays and lesbians within the national party. Ickes helped him over the years, speaking out in favor of Shay's project at DNC meetings.
Initially, Shay committed to former North Carolina Sen. John Edwards, so Ickes issued a standing order to his staff: Make sure that when Edwards dropped out, Ickes -- and only Ickes -- called Shay. As Edwards' fortunes sagged, Ickes began calling to chat up Shay every couple of weeks.
And on Jan. 30, just before Edwards publicly quit the race, Ickes pounced.
"Look, personal relationships, especially when you're dealing with this at the individual level, are sometimes very helpful," Ickes said later. "I have no reservations about calling in a chit. I don't know if I had a chit with him to call in, but I do think that our prior relationship and the fact that I was helpful may have been helpful in persuading him to be for Hillary."
Shay, for his part, says several factors played into his decision, including the fact that he liked Clinton's performance in the Los Angeles debate and that Barack Obama never called him. But he credits Ickes with keeping Clinton "within the forefront" of his mind, and in fact he committed to her very soon after Ickes placed the critical call.
"In politics, you try to move and close the deal quickly," Ickes said.
Eyeing the inconceivable
Only months ago, most people gave little thought to the superdelegates. Clinton seemed invincible. And for Democrats at least, the idea of uncommitted delegates picking the nominee evoked images of political bosses in smoke-filled rooms. Returning to that era was inconceivable.
But 2008 may be the year of the inconceivable -- not just the year a woman or an African American might be elected president, but the year the Democratic nominee was chosen by delegates unconstrained by the popular vote.
Ickes recognized early on how important those delegates might be. And, in assigning him responsibility for them, Clinton chose a veteran whose loyalty was proven -- and whose iron focus on the goal at hand matched her own.
Both the loyalty and the focus were on display in February 1999, when the Senate voted not to remove Bill Clinton from office.
In the White House residence, Ickes and the first lady were poring over New York state maps in preparation for her Senate bid.
A call came in informing the first lady that her husband had been acquitted, Ickes recalled. "She puts down the phone and says, 'Harold, we were talking about Buffalo.' "
With that, they went back to work.
What mere superdelegate could withstand determination like that?