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Democratic operative Steve Hildebrand goes rogue

By Jason Horowitz
Washington Post Staff Writer
Thursday, April 1, 2010; C01

On a recent afternoon in his exposed-brick office, Steve Hildebrand coolly explains why his latest target is the woman down the hall.

"She voted against health care because she thought it was bad politically," Hildebrand says, referring to South Dakota's Democratic congresswoman Stephanie Herseth Sandlin, whose office is located on the other side of the Coke machine in a four-story brick building near the Big Sioux River.

Over the past year, Hildebrand, the soft-spoken deputy campaign manager for Barack Obama's 2008 campaign, has repeatedly raised his voice to rebuke Democratic leaders, including the president, for compromising on the principles and promises that got them elected. When he speaks up, the national media come running, eager to portray his spirited critiques as dissension within the Obama ranks.

But in the Obama universe, Hildebrand is a volatile element.

"I'm definitely stabilized," says Hildebrand, who at 47 sports a graying goatee, light stonewashed jeans and a black polo shirt stretched over his belly. "But I'm not over depression."

A progressive true believer who rose to national prominence as the political director of the Democratic Senatorial Campaign Committee, campaign manager for Tom Daschle and the architect of Obama's fearsome ground game, Hildebrand has for years suffered from the debilitating disorder. As Hildebrand shuttles his dog, Cooper, around town, he speaks openly, and at times painfully, about his low moments: The months spent staring blankly at computer screens during the 2008 primary battle, his cycle of resignation and rehiring from the campaign, his caustic e-mails to Hillary Clinton staffers, his unshakable torpor during the general election. Since Obama took office, Hildebrand thinks he has snapped out of it; with his newfound energy, he expresses "disdain for the officials in my own party" and acts as "a progressive voice from the outside."

Obama officials -- mindful that the Hildebrand Strategies Web site promotes the consultant's connection to the president -- see Hildebrand's new phase differently and dismiss his admonishments as the ravings of a sick man.

"You get the good Steve and the bad Steve. When Steve is healthy, he's a world-class operative. And when he's not, things get pretty crazy," says a White House official, who would only speak about a former colleague anonymously. The official, who acknowledges that Hildebrand has never requested to join the White House, adds that given his behavior, "it's tough to see a role internally for Steve."

Into the fray

Hildebrand owns a gray three-bedroom house on a residential stretch of Sioux Falls' main drag with Mike Pierce, his partner of 17 years. On a recent Tuesday, an American flag hangs over the porch, and a spruce wrapped in Christmas lights stands in the front lawn. A repairman works on the vents in the 106-year-old house's renovated kitchen, where Hildebrand likes to make risotto and where Pierce, 57, keeps a collection of salt-and-pepper shakers in the shape of Santa Claus heads and snowmen. Hildebrand opens the door to drop off Cooper, who immediately jumps over Ann Basche, an 80-year-old neighbor who looks after the dog when Hildebrand's at work.

"I'm the nanny," she says.

Hildebrand owns and rents out two of the surrounding houses, and grows tomatoes, cucumbers, squash, peppers, strawberries and raspberries in the combined garden. He and Pierce bottle 150 jars of their own salsa a year.

A photo of Obama by the front door is signed: "To Steve, I wouldn't be here without you!" and hangs above a portrait of the Hildebrand clan beside Lake Superior. Above the stairs are signed photos of Hildebrand shaking Al Gore's hand ("This is when Gore hired me to run the Iowa caucuses," he points out). In the bedroom, wooden block letters on one dresser spell out "Relax."

Presidential candidates secretly gearing up for the election in spring 2006 had a mission in common: sign Hildebrand. He met with Hillary Clinton about the possibility of working as her Iowa state director. In the weeks after, Hildebrand became sickened, he now says, by the American fatalities in Iraq, and grew dismayed by what he considered both Clintons' silence on the matter.

"I was either going to get out of politics or find someone who inspired me," he says.

Pete Rouse, Daschle's longtime chief of staff who had joined Obama, then a freshman senator, reached out soon after. He told Hildebrand that Obama had decided to headline Iowa Sen. Tom Harkin's Steak Fry in September 2006, and asked him to staff it. If he accepted, Rouse made clear, it would surely "mess with the Clintons."

That Sunday morning, Hildebrand picked Obama up at the airport and watched as the candidate electrified crowds and transfixed reporters at the Steak Fry.

"It was very hard to try and control," Hildebrand says.

Generally, Hildebrand is prone to dry sarcasm. When he finds something amusing, a reluctant smile appears. As he talks about those early days with Obama, a shadow lifts. He exuberantly recalls how he frantically called everyone he could think of to sing Obama's praises on the four-hour drive back from the Steak Fry to Sioux Falls. That next morning he collected all the press clips about Obama's appearance and e-mailed them to everyone in his address book, a practice he repeated every day until Obama's spokesman, Robert Gibbs, told him in mid-December: "Dude, there are times when you're not helpful."

Hildebrand took Gibbs's name off the list and continued sending them anyway.

The Clintons lost Hildebrand, and he notes with delight that this was the period in which people started telling him, "Don't tell mama, I'm for Obama." At the end of 2006, he participated in a series of critical meetings with David Axelrod, Robert Gibbs, Valerie Jarrett and David Plouffe in which Obama decided to run. He and Plouffe, another top operative, debated who should be campaign manager, each making the case for the other.

Problems strike

But as the Obama campaign machinery came together, Hildebrand started falling apart. He had worked for a few candidates in the 2006 cycle he didn't believe in -- Sens. Robert Byrd, Kent Conrad -- and started not to believe in himself, either. A choppy flight home from Hawaii in 1998 had also evolved into a fear of flying, which is problematic for a life-in-a-suitcase campaign professional.

Hildebrand asked his friend Matt Rodriquez, the Obama campaign's New Hampshire state director who suffered a similar phobia, how he coped.

"Drugs, dude," Hildebrand remembers Rodriquez saying, and he recommended Xanax in particular.

Hildebrand researched the drug, and in the list of symptoms -- failure to focus, failure to finish projects, depression, anxiety -- he recognized himself.

"I broke down," Hildebrand says, his blue eyes getting glassy. "I stared at the computer and cried."

In early January 2007, Hildebrand took the deputy campaign manager job at Obama's campaign headquarters in Chicago, reluctantly leaving the comfort of the life he had built with Pierce. Don't worry, Pierce reassured. And referring to the couple's cocker spaniel, he told Hildebrand, "I've got Oliver."

By June 2007, Hildebrand was taking several antidepressants. Then came a call from Hildebrand's business manager, informing him that his firm was in arrears on its tax payments. Hildebrand and Paul Tewes, the campaign's Iowa director and the business partner with whom Hildebrand has since split, returned to Sioux Falls and discovered that the business manager had embezzled a chunk of company funds to cover video gambling debts. The IRS demanded a back payment that nearly sunk the firm. In September, Oliver, the spaniel at home, unexpectedly died.

Obama rose in the Iowa caucuses on the strength of Hildebrand's strategy of using armies of enthusiastic volunteers and social networking tools to register voters and build a dominating grass-roots operation. And yet, the operative was sinking. He had started dozing off in cabs to the campaign's Chicago headquarters and struggling to get through the days. "There were plenty of times when I wasn't doing a good job at all," he says.

The candidate and his wife, Michelle, had become aware of his problem.

"They always had words of encouragement: Pace yourself, take care of yourself," he recalls. Despite the support of the Obamas and the top staff, Hildebrand had ceased to function.

"I would show up to work and stare at my computer screen," he says.

'Someone who is special'

In the beginning of March 2008, Hildebrand cleared his desk, rented out his Chicago apartment and returned home to Sioux Falls. He and Pierce visited San Diego, Palm Springs and San Francisco on a 10-day trip of soul-searching about whether he should return to the campaign or even to politics. During the trip, Plouffe called and asked if he could come back in some less taxing capacity.

Hildebrand told Pierce he doubted he had the strength to return. Pierce, he says, argued that he would regret sitting it out.

"It was bad," says Pierce, who remembers the period differently. "I knew he wanted to finish what he started, but if I had my way, I would have yanked him back before the end of the campaign."

Hildebrand returned to Chicago at the end of the month to work on delegate strategy as the electoral math made it increasingly implausible for Clinton to win. At that time, according to several former Clinton campaign officials, Hildebrand sent nasty e-mails doubting whether their campaign had enough money to pay salaries, and besmirching the Clintons, according to several recipients. The e-mails became so vindictive that a Clinton campaign staffer reached out to Anita Dunn, a senior Obama campaign official.

"A close friend of mine, who also cares deeply about Steve and who worked on the Clinton campaign, did come to me about the e-mails during the primaries," Dunn says. "He said he wasn't the only one receiving the e-mails, and it could become an unnecessary story for the Obama campaign, inconsistent with the tone of our campaign. Primarily he was concerned about Steve."

Dunn says she then contacted Rouse. "We all protected him," Dunn adds. "He is somebody who is special, and people care a great deal about him."

Hildebrand, though, says the e-mails had nothing to do with his depression and that he continues to send "terse e-mails" to opponents.

"They were sent when one of the Clintons, or surrogates, were attacking us in ways that were unfair," he says, without a hint of regret. "And at the time, Hillary wouldn't get out of the race. And she was attacking us!"

He laughs at the notion, raised by some of those Clinton staffers, that the e-mails reflected his poor mental health.

"Like any of them are normal?" he bristles.

Clinton dropped out in June 2008, and Plouffe asked Hildebrand to help work on the Democratic convention in Denver. One of his tasks: arranging for Gore to speak at the convention. In a 30-minute heart-to-heart, Tipper Gore empathized with Hildebrand about his depression and advised regular gym visits, healthier food and openness about his problems.

Increasingly toned, Hildebrand was committed to daily visits to the gym, and he was visiting a psychologist weekly, and a psychiatrist monthly, and taking a "cocktail" of drugs, including Wellbutrin.

"I asked my doctor if the Wellbutrin made you more aggressive," he says, after noticing the ease with which he was breaking bad news to staffers hoping for good positions in the general election campaign. "Because I found it very easy to make these decisions. I was always known as passive-aggressive and now I was just aggressive."

As the general election campaign got underway, Hildebrand thought mostly of returning home. He sneaked away with Pierce to Hull, Iowa, to visit a breeder of Vizslas, selected a puppy and promised to collect Cooper in 10 weeks' time.

"I was counting the days," he says.

In the final three weeks of the race, the campaign dispatched him to Obama-friendly South Florida for voter turnout. On Election Day, he took a 4 p.m. flight from Miami to Chicago, where the senior officials had gathered to watch the returns.

"He went from being the deputy campaign manager to basically being the Miami-Dade get-out-the-vote director," says the White House official, testily adding that Hildebrand showed up in Chicago before polls closed. "He walked into the war room -- we were all stunned."

"I was pretty much a zombie," Hildebrand recalls.

That evening, he stood with the masses in Grant Park as Obama delivered his victory speech. "I was out in the audience, and I wasn't listening to a word he said."

After Obama finished speaking, Hildebrand skipped a private meeting with the president-elect and senior campaign staffers, ran two miles to his new Chicago apartment and began packing. The next morning, campaign officials helped ship his belongings home. On Thursday morning he stopped one last time in Obama headquarters, where the only other official present was Bill Burton, who had commandeered his Herman Miller Aeron chair in his absence.

("It was a really nice chair," recalls Burton, now the president's deputy press secretary.)

"Get out of my chair," Hildebrand barked at Burton. "I'm moving home."

Back in Sioux City

The office building shared by Hildebrand Strategies and Herseth Sandlin are located across the street from antique shops and down the road from Deuces Casino, dusty railroad tracks and Ahler's Pro Body Shop. The nearby meatpacking plant emits wafts of a popcornlike odor.

His tongue lolling, Cooper greets visitors and roams the office under posters of George McGovern, Hubert Humphrey and Obama. Hildebrand considered it a good day: Obama had signed health-care reform into law hours earlier.

"It's something we've waited too long for," he says, as video of Obama signing the bill plays on a TV in the room's corner. He talks about how, when he was 5 years old and growing up the youngest of nine children in nearby Mitchell, his father died without health insurance when a tree he was bulldozing fell backward and punctured his lung. Several of his sisters are medical practitioners, and Hildebrand himself originally majored in nursing at South Dakota State before switching to political science.

But Hildebrand doesn't pretend he is satisfied, either.

"I'm disappointed that there's not a public option," he says, convinced it was an achievable goal if there had been "a serious push for it internally from Pelosi, Reid and the president."

The president is not absolved from blame, in Hildebrand's view, on a host of legislation.

"I didn't see him as rising to the occasion," Hildebrand says. "I didn't see him as bold. I hadn't seen him persuading the American people to the extent that he could have. If he was that person, Congress would follow suit. Instead, Congress held him back. He was bogged down."

He is especially frustrated about the lack of progress on gay rights, and he thinks a nationwide recognition of gay marriage is decades away.

"You think the president is going to get this Congress to do it? They're not going to," he says, adding he was disappointed by the president's failure to defend gay marriage during a referendum in Maine. "His leadership and voice could have made a difference."

When Hildebrand ran into the president in the West Wing last month, he did thank him for advocating a repeal of "don't ask, don't tell," in his State of the Union speech, he says. A few days later, he returned to Washington to meet with Herseth Sandlin regarding "don't ask, don't tell." After a few minutes of conversation, Hildebrand says, she told him, "I didn't think that I was coming in here to be interrogated. I have other people in the gay community who I trust and I don't trust you."

She got up to leave and turned around.

"And I suppose I'll be reading this on a blog," she said, according to Hildebrand.

Soon after, Hildebrand made headlines by threatening to run against Herseth Sandlin himself if she cast a nay vote on health care.

"She irritated me to a point where I made the decision to defeat her," says Hildebrand, watching Cooper disembowel a stuffed animal.

But when she voted against Obama's bill, Hildebrand suddenly reneged. The reason, he says, is that he is working pro-bono to elect a liberal doctor from Rapid City. "He's a stronger candidate than me," he says.

This week, that candidate dropped out 20 minutes before the filing deadline.

The Recovery Room

Hildebrand is certainly aware that revealing his story could alter his stature. CNN might not play his pronouncements on a loop. Potential candidates might not seek his services. Obama's strategists may decide they can do without him in 2012. In short, Hildebrand's political impact may be diminished.

He seems fine with that. With the exception of unseating Herseth Sandlin, he says he has no more interest in working for federal candidates, whom he dismisses as "chuckleheads." The bulk of his business is now centered on issues he is passionate about -- climate change, campaign finance reform, gay rights. And personally, he is happier at home in Sioux Falls, where he is committed to living a normal life with his partner and content to speak his mind about the things he believes in.

After a lunch of enchiladas, Hildebrand climbs back into his black GMC Yukon, the rear window of which is adorned with an Obama '08 bumper sticker. ("The first ever," he boasts.) He drives past the old courthouse and then the gay bar where he and Pierce occasionally grab a pizza and beer. He pulls into a parking lot outside the Recovery Room, a neighborhood dive near the hospital, to join Pierce, who is drinking Buds with two old friends, Mary Von Bockren, 56, and her husband, Trent, 58.

The bar-size pool table in the corner of the room is empty and a woman puffs her cigarette next to a screen tuned to CNN ("Pres: 'It isn't always tidy.' ") They talk about how weird it is to see Hildebrand whenever he shows up on television.

"It's like, 'What?' " says Mary.

"It's a Jekyll and Hyde sort of thing," says Pierce.

They banter about the conversation Friday, which centered on whether Hildebrand would actually run against Herseth Sandlin ("He had no intention of running," says Pierce) and jokes about how much beer the Von Bockrens drank on St. Patrick's Day. Under fluorescent beer signs, Pierce teases Hildebrand, who had just gotten over a cold, that he is an especially needy patient.

"There's no place like home when you're not feeling well," says Mary.

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