How to Rig an Election

Simon & Schuster

Though I come from a rather illustrious old American family, politics was certainly not in my blood. In fact, until I became an operative for the Republican Party in the early 1990s, my family had managed to steer clear of that dirty business ever since my great-great-grandfather, Darwin Rush James, retired from Congress in 1887. My maternal great-grandfather was the printer and entrepreneur John Thomas Underwood, who founded the Underwood Typewriter Company, whose products bore one of the great brands in American history. When I was a kid, I could open any closet in any family home and find one of his ancient machines gathering dust. His wife, my great-grandmother Nana, was the kind of classic Yankee matriarch who would refer to people by what they manufactured, saying things like "Singer, they're in sewing machines." It amused her when the electrician hung a light over the wrong masterpiece. "No, no," she had laughed, "the other Monet!"

Of course that was a few generations ago, and my mother always used that old anecdote as an object lesson in how not to conduct myself. It was her considered opinion that the privileged came in two classes: the ones who worked hard to understand the true value of things, and the foolish.

While the Underwood fortune ensured that I'd never go hungry, family pride -- hell, my own pride -- ensured that I'd never be some yacht-hopping scion whose only full-time employment consisted of finding increasingly undignified ways to wrinkle his linen suits. Still, figuring out what I might do with my life was a tricky prospect. My paternal grandfather, Allen Raymond, had been a legendary correspondent for the New York Times, New York Herald, and the International Herald Tribune, so I had always been very aware of current events, particularly politics. But having spent my youth around an endless succession of reporters, I knew too much about them to ever become one myself.

The first thing I tried when I got out of college in 1989 was public relations, working for a New York firm at $21,000 a year. The Underwood money sure came in handy those days, since I was probably spending about $35,000 a year. The money wasn't a big issue for me, but after two years it was clear enough that I wasn't going to make much of an impact on the world doing flack work for BMW and Toshiba. My college buddies were on their way to significant careers in finance, one running the oil trade desk for Morgan Stanley, another trading his own capital from the family seat on the New York Stock Exchange, while I was going nowhere. I wanted to do something remarkable, to leave my imprint some-how. Here I had this legacy that was an American institution and I could never shake the feeling that I had to find some way to measure up to it.

The one thing I found interesting about PR work was that it challenged you to manipulate people's perceptions. Instead of dealing in cold, hard facts, you had supple, yielding elements that you could present in whatever way best suited your needs. Reality was malleable -- it could be made to bend to your will. What, for instance, could the Super Bowl possibly have to do with toilet cleanser? Nothing at all, unless you happened to be the low man on the Ty-D-Bol account, as I was. It seemed a pretty stupid task to me when I spent weeks and weeks gathering data to find out how many gallons of water Americans flushed during the big game each year. But it was suddenly a brilliant bit of mind control when the Super Bowl announcers were discussing my statistics and my client during halftime at the most highly viewed sporting event of the year.

The idea that you could massage people's perceptions so that they saw what you wanted them to see fascinated me. I didn't exactly have a stranglehold on what my own reality even was at the time, but that didn't seem a very big deal. I just knew that if the little bit of mental sleight of hand I'd learned could be expanded upon, I could make something happen. What that was, precisely, I had no idea.

Becoming a salesman seemed an obvious choice, but for a salesman to leave a substantial footprint on the world he needs a pretty extraordinary product. When I failed to locate such a product in my own imagination, I thought I might find it in higher education; I started looking around at grad schools. None of the programs jumped out at me until I came across an ad for a new one-year program at Baruch College called the Graduate School of Political Management (GSPM). "Political management" -- not that I knew what that actually meant, but it sounded cool. With all my youthful anxiety about living up to my heritage, with the full weight of our moneyed history bearing down on me, that's really all the thought I ended up giving the matter: "Politics. That sounds cool." Well, that and, "I'll give it a shot."

If the notion that a politician is little more than a product pitched by salesmen had dawned on me at the time, it was entirely on a subconscious level.

Fortunately for me, the program was only two years old at the time, and its admissions department was still desperate for people who could pay their way in with fifteen grand. It wasn't like getting into Harvard Law by a long shot -- more like getting into community college. (The program did end up moving to George Washington University in Washington, D.C., and has become quite a well-respected institution since I passed through its doors.)

At that time, the Graduate School of Political Management wasn't physically impressive, either. The school occupied a quarter of a floor in a run-down building near City Hall in New York. Literally shoved in a corner, it consisted of a large conference room, two small classrooms, and some staff offices. The rooms smelled moldy, the chairs were broken. What I'd come to learn later is that, at almost every level of American campaigning, low-rent, dank, and dismal is the default setting for all accommodations.

We were a small class, maybe thirty-five students altogether, and my attitude toward the program shifted from give-it-a-shot to win-at-all-costs on day one. High-profile internships for the likes of Roger Ailes and the legendary Democratic image-maker Hank Sheinkopf were being dangled in front of the class and, for a lot of us, the sense of competition was immediately apparent. Unlike college, which hadn't been about much of anything, performance here promised real rewards in the real world.

Just sitting there in our seats it was obvious that everyone was sizing one another up. At orientation, I remember feeling like I was older than the rest of the class by at least three years chronologically, and by a decade in terms of real work experience. Most of my classmates seemed to think this was just an extension of their senior year in college, while I felt like the experience was laying the groundwork for the rest of my life. I was, after all, the only person in the room wearing a suit.

If this is my competition in this industry, I thought, I've got it made. At the same time, I still had a nagging doubt as to whether I was doing the right thing. This felt more to me like learning a trade than entering a profession, as if I'd just spent $15,000 to go to Apex Tech. It was a totally blind gamble for me.

As I scanned the room, nobody looked like anyone I'd want to hang out with. I was just there to go to class and try to start a career, not to make friends. But that was a major flaw in my personality, since half of...