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Are Skidmore students literate in politics and government? Lessons in democracy
Students rock the vote New voters, new media, new energy
Road to the White House Melissa Winter '89 staffs the First Lady
McCain-Obama: Fair fight? Reviewing the 2008 presidential race
Growing the grassroots Scott Kennedy '87 films urban citizen action



On the campaign trail with Michelle Obama

by Susan Rosenberg

On Inauguration Day
the New York Times reported that First Lady Michelle Obama was expected to bring “a sense of youth and style” to the White House. She was also bringing what Times sources called a “cream of the crop” staff of “politically seasoned” advisors and operatives. Among that corps of young urbane professionals is Melissa Winter ’89, deputy chief of staff.

Winter was Michelle Obama’s first hire, back when then-Senator Barack Obama’s campaign got rolling in early 2007. After a Skidmore career that included two summer internships on Capitol Hill, Winter was hired as an assistant to Congressman Norman Mineta. Later she joined Sen. Joe Lieberman’s office, serving as his traveling aide during his 2000 vice-presidential run, his scheduling director for his 2004 presidential bid, and his executive assistant in the Senate. It was at a routine meeting of Senate executive aides that she was invited by Sen. Obama’s assistant to meet with Michelle.

After a 90-minute conversation in Obama’s Chicago living room, “it was crystal clear to me that the Obamas were in this for the right reasons,” Winter says. Their desire to change public discourse and to help Americans get involved in democracy struck her as genuine and inspiring. She had recently been through a “brutal” re-election campaign with Sen. Lieberman, who had lost the Democratic primary but persevered and won as an Indepen­dent. The party politics had left Winter “a little out of sorts with the whole process,” she says, and “the Obamas’ ap­proach seemed wonderfully re-­freshing.” She quit her Senate job and moved to Chicago.

Michelle Obama proved to be such a campaign asset that a second person was soon hired to cover her office while Winter staffed her on the road. Once the nomination was clinched, her staff quadrupled, with Winter serving as her traveling chief of staff. “The best part of the job,” Winter says, “was how much fun we had. We spent hours and hours in vans or airplanes, yet we spent most of those hours laughing.” Amid the demands and pressures, “we made a point of—well, the laughing came naturally—but also of tasting all the local cuisine. We had some great barbecue, the nation’s best cheeseburgers… It’s amazing none of us gained 400 pounds!” She confesses her diet didn’t improve much between road trips, but she says Obama returned to her disciplined eating and exercise.

The Obamas’ young daughters, Malia and Sasha, also “kept us laughing,” says Winter. The girls were huge campaign crowd-pleasers, but staff and family worked to keep their schedules reasonable. “Sometimes we were on buses with refrigerators and TVs, so they could eat as a family on board, and the girls could come into the events or stay be­hind. Sometimes we got to play games with them. They were just delightful and fun to be with.” Winter credits that in large part to their mom: “I was so proud of how she made sure to keep them well-grounded.” Organization was crucial too. Winter says that she and Obama and the second staffer “complemented each other well, because we’re all planners—we don’t like to be late, or find spelling errors, or leave things to the last minute.” They tried to outline their travel dates two weeks in advance, so that Obama could accommodate the kids’ activities. “We built her schedules around ballet recitals and parent-teacher conferences.”

Planning and humor can’t fend off the crush of campaigning forever, and Winter allows, “The Democratic convention almost killed us. I’ve never been quite so exhausted in my life.” First came Michelle Obama’s opening-night speech, which had been tweaked and rehearsed for two solid weeks because “her introduction to the American people was so important,” Winter says. Then the Obama staff attended five to seven events each day, before going to the convention hall each evening. She recalls, “In five days, I ate maybe five meals total. The choice was often food or sleep, and I would pick sleep.”

Now in her East Wing office, Winter notes that her road-trip days of jeans and boots are over. Dressing down during Senate recesses doesn’t apply either. The Obamas’ style may be relatively informal, but “this is the White House; I dress to show my respect for the place where I work,” she says. While she and her colleagues are trying to keep to a six-day work week, rather than seven, she admits, “I’m still readjusting to having any downtime. I’m not very good at it yet.” She adds, “Keeping up this pace will be daunting.”

In another world, how would she spend her time? “What would make me happy, although I’d never be able to pay my bills, would be to own a bookstore,” she says. “I love reading, and I love to buy books and help people choose books.” With all her political experience, what about running for office? “Nope,” she replies flatly, adding with a laugh, “I’ve had my ulcer!” The fact is, despite the pace and pressure, “This is why I moved to Washington after college—to work in the White House. Very few people actually achieve their dream job, and I did.”