SIOUX FALLS, S.D.—Steve Hildebrand is sitting, laptop open, outside a coffee shop in downtown Sioux Falls. It’s just a few days before November’s election. He’s looking at an Electoral College vote calculator, changing some marginal states from red to blue, blue to red, watching the numbers.
It’ll be over 300 electoral votes for President Obama, he predicts. Looking up, before he closes his Mac and walks back inside to meet his customers Hildebrand says, “It’s all about organization.”
In 2008, Hildebrand was Obama’s deputy campaign manager, David Plouffe’s right hand, a fundraising surrogate, and after a historic win, a draw on the national speaking circuit. Now he owns and runs Josiah’s, a 1,500-square-foot coffee shop named for Josiah Phillips, the Civil War surgeon who helped found Sioux Falls. Philips’ portrait hangs over a stone hearth next to the barista bar.
“This is my first cycle when I’ve been completely out of it,” says Hildebrand, who’s both relaxed and frank with how he feels about the state of the consulting business. “There’s so much bullshit. Too many candidates are in it for themselves. It’s not about accomplishing important things, making hard decisions. And I’m happy to say that to their face.”
For the better part of the past two decades, Hildebrand says he’s given just about everything to his clients, and the decision to move out of politics was in large part based on “whether or not continuing to give up a lot in my personal life and putting my health through hell was worth it for these candidates, who weren’t solving the problems.”
Hildebrand watched Obama make his 2008 election night victory speech with the crowds in Chicago’s Grant Park. He almost missed the moment.
As the presidential field took shape, Hildebrand sought work with Hillary Clinton. After an unproductive meeting between the two in Washington in 2006, he decided against it. When Pete Rouse, whom he knew from Tom Daschle’s circles, called and asked if he’d staff Obama at Sen. Tom Harkin’s 2006 Iowa steak fry, Hildebrand agreed. From then on he was in Obama’s inner circle. Locked into the race, Hildebrand handled an ever-growing list of tasks.
“I had huge responsibilities within the campaign that in hindsight were probably overwhelming,” he says.
He ran the national field operation, the state field operations. When the primary season ended, Plouffe told him he needed to budget for $400 million as the campaign transitioned to the general.
“Nothing I had ever done had prepared me to do something of that magnitude,” Hildebrand says. “It was a different campaign. Nobody’s ever fought a 50-state primary before. Nobody’s ever had the tens of millions of dollars that we had and Hillary had.” Hildebrand wasn’t stuck behind a desk in Chicago. “There were weeks and weeks and weeks and weeks when I was on six-to-eight fights a week,” he says. “And I don’t fly well.”
A colleague recommended Xanax. Hildebrand went online in early 2007 to learn more about it. “There was a section on the site about depression and I read the symptoms, and I sat at my computer and cried because it was the first time I realized I had depression,” he says.
The stress of the campaign only served to make it worse.
“Everyone was fucked up,” he says. “You’re working eighty-to-ninety hours a week, you have no time with your family, you have no time to exercise, eat right; you’re not sleeping at night. Your stress level is at the highest it’s ever been. And so then you add depression to it.”
Hildebrand’s beloved cocker spaniel died. The business manager at his firm called and admitted that he’d been stealing money to support his gambling addiction. Now the company faced IRS scrutiny.
Without a way to cope and stay on the job, Hildebrand left the campaign, left Chicago and took his partner on a 10-day trip to California. It was March 2008. As they were riding bikes along Mission Beach in San Diego, Plouffe called and invited Hildebrand back. With his partner’s blessing, he returned to Chicago. Months later he was watching Obama bask in the cheers of his supporters.
“All the senior staff was supposed to come and be in a private area with Barack and Michelle after his speech, and I decided not to go,” Hildebrand recalls. “I decided to literally run the two miles back to my apartment and start packing.”