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