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Can Harold Ickes Make It Rain for Obama?

The Democratic operative has cussed, clawed, and outsmarted his way through three dozen elections. His new fight: Stop Karl Rove and Co. from steamrolling Obama.

ONE EVENING SOON AFTER THE 2002 midterm elections, Ickes and a group of Democratic political honchos gathered at BeDuCi, a posh Mediterranean restaurant near his office. Seated around the table were EMILY's List founder Ellen Malcolm, Service Employees International Union (SEIU) president Andy Stern, Stern's adviser Gina Glantz, AFL-CIO political director Steve Rosenthal, Sierra Club director Carl Pope, Ickes, and Enright. The group discussed the upcoming election, and how best to marshal their manpower and money to defeat President George W. Bush. The newly enacted McCain-Feingold law had banned soft money, Ickes' weapon of choice in 1996. The BeDuCi crowd drafted up a new strategy: They would train their firepower on a handful of battleground states, and they would raise money using an obscure type of tax-exempt organization, the 527 committee.

So goes the origin story of America Coming Together (ACT), one of the most sophisticated get-out-the-vote operations in the history of Democratic politics. Ickes also created another 527 dubbed the Media Fund to hammer Bush with TV and radio ads between the end of the Democratic primary fight and the Democratic convention, a vulnerable period for a presidential challenger. When it came to fundraising, the groups acted in unison; Ickes and Malcolm were the rainmakers. Ickes told me, "We traveled all over hell's half acre...It was Ellen and I running around with our PowerPoint and our fucking tin cups."

Their tin cups filled up fast. Ickes says he'd never heard of billionaire financier George Soros—until Soros pledged an initial $10 million to ACT. He didn't know a thing about Progressive Insurance chairman Peter Lewis, who matched Soros' $10 million. Then Andy Stern's SEIU kicked in $32 million in manpower and cash. Republicans howled that Soros' donation "had purchased the Democratic Party" and—in stark contrast to the deregulatory approach to campaign finance currently favored by many GOPers—urged the Federal Election Commission to outlaw 527s. "We were in pig heaven," Ickes recalls. "We never had this kind of money to deal with."

ACT and the Media Fund trounced the competition when it came to fundraising. All told, Democratic-leaning 527s outspent conservative ones by a 3-1 margin, $320 million to $109 million. ACT and the Media Fund together hauled in $202 million. Nearly half of that sum came from just five donors—Soros, Lewis, Hollywood producer Steve Bing, the SEIU, and the AFL-CIO. Democrats had never raised that much money for an independent effort, and never so much from such a small cadre of donors. (The Federal Election Commission later slapped ACT and the Media Fund with a combined $1.4 million in fines for illegal campaign spending.)

Democrats, of course, still failed to knock Bush out of office. But from the ashes of ACT emerged Catalist, a cutting-edge national voter database akin to the one Republicans had put in place more than a decade before. The final decision of ACT's board was to create Catalist. Ickes agreed to raise the initial $5 million to make it a reality.

"You can't go and ask for a million dollars from someone who can't get a White House tour for his daughter," says one wealthy donor's adviser.

Then, on a bright, clear October day in 2005, a car swerved in front of Ickes as he guided his Vespa scooter down Pennsylvania Avenue. The collision threw him into the air before he came down on his right hip, shattering the socket. Without his helmet, Ickes says today, "I'd be six feet under."

Ickes spent 16 days bedridden at George Washington University Hospital. One orthopedic surgeon said he might never walk again. As Ickes recovered, Enright set up a mobile office in his hospital room. He wanted to get back to work on Catalist: "There was money to be raised!"


NOT LONG AFTER LEAVING THE
Obama White House in February 2011, Sean Sweeney paid a visit to his old friend Ickes. He wanted Ickes' advice about raising big money. Seated around the wooden conference room table, the two men talked for an hour and a half as Ickes detailed the dance needed to woo the biggest donors in Democratic politics. Fundraising, he stressed, is no cakewalk: You build a list of carefully selected donors to court, research their giving histories and personal interests, pitch their advisers or "gatekeepers," and travel all over the country asking for money. Presidential-level fundraising is nothing like how people imagine it, Ickes says; rarely do you meet donors like Franklin Haney who buy in right away.

Six weeks after their meeting, Sweeney asked Ickes to join Priorities' board. "You might want to go back and check with your overlords, whoever they happen to be," Ickes told him. The optics weren't good: Ickes was a registered lobbyist who'd represented unions, public utilities, and trade groups. He also suspected that Obamaland blamed him for advising Hillary Clinton to stay in the 2008 race until Puerto Rico's June primary. Ickes denies doing this, but he did scratch and claw to recruit superdelegates for Hillary well after her campaign had been written off; the bitter primary fight had left some lasting enmity between the Clinton and Obama camps. Two days later, Sweeney rang again. Now they wanted to make him Priorities' president.

Ickes says his work with Priorities has been "sobering"—nothing like 1996 and 2004, when the money poured in. He, Sweeney, Burton, and others have crisscrossed the country, hitting up every major donor who'll sit for their PowerPoint spiel. Priorities' fundraising pace has gathered speed in recent months, snagging big donations like Haney's $1 million and $2 million from Qualcomm cofounder Irwin Jacobs and his wife, Joan. (Burton also says Priorities has $20 million in commitments from donors.) Yet even with the uptick, Priorities will be hard-pressed to meet its $100 million target; in July, Ickes told me he'd revised that goal down to $75 million. That pales in comparison to the hundreds of millions Rove- and Koch-linked groups plan to spend.

Priorities and the other Democratic super-PACs have struggled for a number of reasons, say Ickes and other fundraisers. There's the disgust with outside spending, which Obama himself helped fuel. In 2008, his campaign urged outside groups, like strategist Paul Begala's Progressive Media USA PAC, to wind down so the campaign could better control its message. (Ironically, it was Burton who was tasked with conveying the directive.) Obama 2008's message to donors was: If you want to support the campaign, donate to and bundle for the campaign itself. In 2010, the president called super-PACs a "threat to democracy." But after realizing he'd be seriously outspent without outside help, Obama grudgingly blessed Priorities USA Action and dispatched top aides—including David Plouffe, who masterminded the 2008 win—to help pitch donors. Yet many big Obama backers have yet to pony up: By late July, just 15 of his 638 bundlers had given to the Obama super-PAC.

That has made Ickes' job even harder. While the vast majority of major Clinton donors signed on with Obama for the 2008 general election, Ickes told me some are reluctant to fund Priorities when so few of Obama's core backers are giving big. They take his long-standing supporters' hesitance as a cue that either Obama isn't really in trouble or the super-PAC isn't a smart investment. "Why should we put money in if they're not?" these donors tell Ickes.

Ickes faults the Democrats who anonymously suggested to reporters in 2010 that Obama, who beat all presidential fundraising records in 2008, could raise $1 billion for his reelection. Donors are wondering, "What do you need my paltry million for?" he says. "You fucking guys are gonna raise a billion!" He also suspects that some donors shy away from big-check super-PACs because they bought into the Obama campaign's small-donor emphasis and are disenchanted with the post-Citizens United playing field.

Then there's the lack of a nemesis: In 2004, donor anger ran so high, Ickes recalls, that an unknown Philadelphia financier had mailed ACT a million-dollar check—unsolicited. "We had the best fundraiser in 2004 that Democrats had stumbled across since Lyndon Johnson," he says. "It was George W. Bush."

Today a similar dynamic exists—only it's Republicans relying on outrage at Obama to reel in millions. "You can walk into certain rooms and say, 'We've got to get rid of Obama,' and out come the big checks," says Colby College's Anthony Corrado.

Obama's lukewarm rapport with donors hasn't made Ickes' job easier. Unlike Clinton, who mastered connecting with his supporters and stroking their egos, Obama tends to keep his backers at a remove. It shows up in the small things, says one wealthy Democrat's adviser, like asking for $30,000-plus to attend a dinner and then making attendees pay for their picture with the president. "The White House has been too late in reaching out to their donors and making them feel appreciated," this adviser told me. "You can't go and ask for a million dollars from someone who can't get a White House tour for his daughter."

Yet all those factors still don't fully explain the Democratic donor malaise. "You still sort of have to scratch your head and say, 'This is the president of the United States, and he could lose,'" Ickes says. But he's not giving up. "Hope springs eternal, and now Romney's on a roll, he's raising money, and the Republicans really think they can win the White House," Ickes says. "Will things pick up? I think they will."

Enough to reach Priorities' $75 million goal? Enough to swat back the attacks headed Obama's way this fall? Enough to land a few good punches on Romney?

Ickes closes his eyes and shrugs. "Who the hell knows?"

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