could win in predominantly white areas, which meant they’d often go for the safer bet, the next-best thing. One facet of the challenge for Barack was to shift black voters away from their long-standing allegiance to Bill Clinton, who’d shown unusual ease with the African American community and formed many connections there as a result. Barack had already built goodwill with a diverse range of constituents throughout Illinois, including in the rural white farm areas in the southern part of the state. He’d already proven that he could reach all demographics, but many people didn’t yet understand this about him.
The scrutiny of Barack would be extra intense, the lens always magnified. We knew that as a black candidate he couldn’t afford any sort of stumble. He’d have to do everything twice as well. For Barack, and for every candidate not named Clinton, the only hope for winning the nomination was to raise a lot of money and start spending it fast, hoping that a strong performance in the earliest primaries would give the campaign enough momentum to slingshot past the Clinton machine.
Our hopes were pinned on Iowa. We had to win it or otherwise stand down. Mostly rural and more than 90 percent white, it was a curious state to serve as the nation’s political bellwether and was maybe not the most obvious place for a black guy based in Chicago to try to define himself, but this was the reality. Iowa went first in presidential primaries and had since 1972. Members of both parties cast their votes at precinct-level meetings—caucuses—in the middle of winter, and the whole nation paid attention. If you got yourself noticed in Des Moines and Dubuque, your candidacy automatically mattered in Orlando and L.A. We knew, too, that if we made a good showing in Iowa, it would send the message to black voters nationally that it was okay to start believing. The fact that Barack was a senator in neighboring Illinois, giving him some name recognition and a familiarity with the area’s broader issues, had convinced David Plouffe that we had at least a small advantage in Iowa—one upon which we would now try to capitalize.
This meant that I would be going to Iowa almost weekly, catching early-morning United Airlines flights out of O’Hare, making three or four campaign stops in a day. I told Plouffe early on that while I was happy to campaign, part of the deal had to be that they’d get me back to Chicago in time to put the girls to bed at night. My mother had agreed to cut down her hours at work so that she could be around for the kids more when I was traveling. Barack, too, would be logging many hours in Iowa, though we’d rarely show up there—or anywhere—together. I was now what they call a surrogate for the candidate, a stand-in who could meet with voters at a community center in Iowa City while he campaigned in Cedar Falls or raised money in New York. Only when it really seemed important would the campaign staff put the two of us in the same room.
Barack now traveled with a swarm of attentive aides, and I was allotted funds to hire a two-person staff of my own, which given that I planned to volunteer only two or three days per week to the campaign seemed like plenty to me. I had no idea what I needed in terms of support. Melissa Winter, who was my first hire and would later become my chief of staff, had been recommended by Barack’s scheduler. She’d worked in Senator Joe Lieberman’s office on Capitol Hill and had been involved in his 2000 vice presidential campaign. I interviewed Melissa—blond, bespectacled, and in her late thirties—in our living room in Chicago and was impressed by her irreverent wit and almost obsessive devotion to detail, which I knew would be important as I tried to integrate campaigning into my already-busy schedule at the hospital. She was sharp, highly efficient, and quick moving. She’d also been around politics enough to be unfazed by its intensity and pace. Just a few years younger than I was, Melissa also felt more like a peer and an ally than the much younger campaign workers I’d encountered. She would become someone I trusted—as I do still, to this day—with literally every part of my life.
Katie McCormick Lelyveld rounded out our little trio by coming on board as my communications