Power Forward : My Presidential Education (9781476763361)

by Love, Reggie

  The kid didn’t have I.D., so I couldn’t let him in. “Come on, bro,” he begged, giving me a little smirk.

  “Sorry, I don’t make the rules,” I explained.

  “You think you can tell me what to do?” he spat back, his face suddenly flooding red. He was dressed in khakis, a pastel-pink J.Crew button-down. His friends were all staring at him. But he only had eyes for me. “You think you’re somebody? You trying to push me around?”

  I’ll give it to the guy. It took some stones to pick a fight with somebody three times his size. Of course, he was also drunk. Liquid courage, it is well documented, can convince you that a host of bad ideas are, in fact, good ones.

  And then he swung.

  Thankfully, it was a big windup. I saw his fist coming a mile away and moved out of the way. Cory also noticed what was happening and jumped in, wrapping his arms around the guy’s pink shirt, jerking him forcefully from my reach.

  “How dare you!” he sputtered as his friends tried to drag him away. “You’re just a fucking doorman.”

  Well, now I am, I thought. But a doorman is just a job. Jobs change. Being entitled, with no self-awareness, rarely does.

  I stopped working at McFadden’s shortly after that. I had recently gotten promoted at the senator’s office, and frankly, I was run ragged from being up nearly twenty-two hours every other day. Besides, I couldn’t show up at the Obama office with a black eye. That’s not the kind of operation they were running.

  Thankfully, after six months working for the senator in the mail room, I was promoted from staff assistant to deputy political director for Alyssa Mastromonaco at Obama’s Hope Fund. I would be splitting my time between the Senate office and his PAC. Once again, I landed in a very glamorous position: database management.

  If Senator Obama did a fundraiser, if he was in a TV advertisement to help another candidate, if he sent out an email asking for a contribution for someone else’s campaign, if he appeared at a rally—any communication he had with anybody—I kept a record of it.

  This kind of list is part of a politician’s lifeline. The ability to differentiate an avid supporter from an ambivalent one is of profound value. So when someone requested a photograph with Senator Obama at a Democratic meeting, we’d promise to mail it to that person if he or she would provide an address, and I would make sure that happened and then keep track of that information. The PAC also used postcards to build relationships with the thousands of non-Illinois constituents the senator would meet while campaigning for other Democrats. The team would send a photo of the senator standing in a location that the recipient would immediately recognize as local, and we’d personalize the postcard with a note on the back saying, “Hey, thanks for joining me at the rally in support of Claire McCaskill” or “Debbie Stabenow.” And with the note would be a link to our website.

  The postcard was good PR. But the genius part was collecting names and email addresses. It would become the beginning of the first national list of supporters. It is always the efforts of a couple hundred dedicated individuals that allow a candidate to build broader support, and even before any official declaration of candidacy, the team had started to identify who those few hundred people were.

  In part because of the systems I helped to set up, the campaign was allowed to buy/rent fewer lists in the future, which, in turn, enabled the team to communicate coherent messages and to interact with engaged and likely voters. Identifying and interacting with Democratic activists across the country before officially launching a national campaign was critical. Preparation and forward thinking had the Obama team slightly ahead of the curve. The team could identify among the people we’d mailed, who had already shown up to see the Senator, those who had already demonstrated tangible support. The team was able to put energy into smarter places. The data was solid. Because of that I felt I’d helped to make a difference early on.

  Even so, the process wasn’t easy. There were days when I would have more than a thousand postcards to send. I’d bring them home with me and stamp them one after another, hour after hour in front of the television. Sometimes I’d enlist friends to help. (Bribing them with beer or chips or the use of my pickup truck to move furniture.)

  There was something else the team did differently. In the normal ecosystem of campaigning, interested parties would ask Barack Obama to appear at an event to help with their fundraising. Typically special guests like Obama would do their thing, help draw a crowd to other candidates and causes, then say good luck and God bless. But early on, our approach to events had a longer-term goal in mind.

  In our scenario, we adopted the philosophy that “Obama’s a Democrat. We are trying to get you reelected because you are a Democrat, and hopefully we can all grow together.” And so, when the senator agreed to appear, we made the request that his participation be contingent on our receiving the list for the event of the candidate he was showing up to support.

  This did not always go over well.

  The Iowa Democratic Party, for example, gave us their list, not digitally, but as labels. The kind your grandmother sticks on envelopes. I had to type thousands of addresses and names into our database. It was a passive-aggressive “screw you.” But we got the data.

  These were the early days. I only knew the senator well enough to say hello coming and going. I felt like to him I was probably still some random staffer who happened to have played basketball at Duke.

  I did get to sit in on one meeting. It was with Baron Davis, the two-time NBA all-star, who came in with his agent, Cash Warren, to talk about his youth development foundation. I was a prop. But it was still cool to have that seat at the table, even if it was only for fifteen minutes. I remember thinking how in awe I was to be in the senator’s office with such an impressive bunch. Baron Davis had the basketball career I always wanted and not only was killing it, he was able to work with his best friend, Cash, on the daily. I was impressed, and a bit jealous.

  At this point, the senator hadn’t yet formally declared an intention to run for the highest office of the land. I was down on the bottom rungs of the office ladder, developing these systems, gathering the data, doing the tedious work, not really having a clear endgame in mind. Little did I know how dramatically everything was about to change. How, in a matter of days, Senator Obama would go from a passing figure to a presidential candidate, and I would play the role of sidekick.

  * * *

  It was Pete Rouse’s idea. It had probably been his plan all along. He brought me into his office, sat me down, and gave me two scenarios.

  “Do you want to go to Iowa?” he asked.

  “Do I?” I asked, not knowing what “going to Iowa” meant—other than the fact that if I did go, the population of black people would increase exponentially.

  Then he brought up the prospect of my being the senator’s personal aide.

  “Is that an option?” I asked, knowing even less about what that job would look like.

  “It is. But I didn’t think you were interested in that position,” Rouse said casually.

  He wasn’t wrong. I was young, ambivalent about almost everything except basketball, but especially about being a personal aide, because I had no notion of what it entailed. On the other hand, there was my desire to shoot hoops. Hang out with my friends. Maybe get a flashy job in finance like some of my old classmates. Or pursue my dream of playing in the NFL one day, something I’d been groomed for since high school and had been actively recruited for after graduating from Duke. Being someone’s personal aide sounded like the very opposite of all of that. But Rouse had never led me astray, and his offer resonated with my instinct to get off the bench and into the game in any way I could make a difference.

  At the time, I was dating a young woman named Erin, who worked as an analyst for Prudential Securities. I’d met her through her sister, Casey, who was in Duke law school while I was an undergrad. Erin was my ambassador to D.C. She was twenty-nine and dialed into the local ethos. She thought I was too immature
for her, and I probably was, but we dated anyway. She ended up being a great advisor to me; an unanticipated inspiration—a friend with actual benefits. If I ever got lost driving in D.C., I would call her, and she would navigate me home. At base, she had figured her shit out. And I hadn’t.

  “Don’t be stupid,” Erin chided, when I told her I was probably going to pass on the traveling personal assistant offer. “This is the biggest opportunity of your life. My last boyfriend was a field organizer in Iowa for Kerry and if your candidate doesn’t win it’s tough. But, as a personal assistant to a candidate, win or lose, you are left with invaluable experience and relationships.”

  Erin was always ten moves ahead of me. She could see the smart play, how the job of PA to Barack Obama would change my life forever, in ways that running a campaign office in Iowa, or working at Goldman Sachs, or training for the Dallas Cowboys would not.

  It was Erin’s voice I heard in my head when I walked into Rouse’s office and told him I wanted the bodyman slot after all. And just like that, I had a new job.

  What I didn’t have was a job description. To this day I still haven’t been able to track it down, because there never was one. Each bodyman job is unique to the principal. Every boss is peculiar. Like snowflakes, the bosses come with their own distinct characteristics (and needs). And more likely than not, they don’t even know what those needs are—until you don’t meet them.

  On that note, to any future PA candidates out there, know this: nobody is going to tell you what you are supposed to do. There is no training. There is no manual. There is no human resource department to provide you with a helpful itemized sheet of responsibilities. If you dare to ask what your job actually is, the folks in charge will likely say, “Handle stuff.”

  That’s it. “Handle stuff.”

  Thus was the true beginning of my presidential education. Learning the ropes of life at the heel of the man who was out to change the course of this great nation.

  As for how you “handle stuff ”? You’re on your own. You will be clueless. You will panic. On more than one occasion, said “stuff ” will most definitely not be handled. You will mess it up. Royally.

  I know I did.

  3

  * * *

  * * *

  EVERY LAYUP ISN’T EASY

  * * *

  * * *

  On February 1, 2007, the night before my first official trip as bodyman, I was walking the aisles of pharmacy-turned-supermarket Harris Teeter in something of a fog. I had black and silver Sharpies in my basket, black Pilot G2 Gel Roller pens, Trident chewing gum. I was thinking I should throw in some trail mix, in case the guy was starving or something.

  So I headed to the nut section and confronted how much I did not know about Senator Obama. Considering all the options—salted or dry roasted? sweet or spicy? with or without dried fruit or candy?—I realized I hadn’t a clue what the man would like. I also had an accompanying thought: how much could it possibly matter? The contingency I was planning for was a starving candidate. He’d be grateful regardless, right?

  I snagged a bag of Planters Trail Mix Fruit & Nut with M&M’s.

  Back in my apartment, I couldn’t relax. I was anxious. I tried to watch some TV to distract myself, and before I knew it, I woke up at 1:00 A.M. and realized I’d been drooling all across my shoulder. I walked to the bedroom to try to catch some real sleep, all too aware that in four and a half hours I would be boarding a commercial flight from D.C. to LaGuardia with the senator. He had just formed an exploratory committee to test his viability for becoming the President of the United States. And we were heading to New York City for three fundraisers—cocktails, a dinner, and a late-night meet and greet.

  I’d already gotten my feet wet doing some advance work in Washington. I’d been the point of contact for the “Families USA” conference, where the senator delivered one of his first speeches on health care in the U.S., articulating his belief that our country needed to create a supplementary system for the traditional employer-based insurance system, which he hoped would act as a transition to universal health coverage.

  As part of the advance team, I’d arrived at the venue, the Mayflower Hotel, early enough to absorb the layout, confirming that the entrance and exit routes wouldn’t be too congested for the senator to travel through. The narrower a route, the more time it took for him to leave a building. In my short time as a newly minted PA, I’d observed that Senator Obama was a man of the people and he never turned his back on an opportunity to hear another point of view. Which could make for a prolonged exit.

  The day prior to our trip to New York, I worked advance for the National Prayer Breakfast at the Washington Hilton. My responsibility was to make sure that the Senator got from the breakfast to the car in a timely manner, so that he wasn’t late to his next scheduled event. It seemed simple enough. The prayer breakfast officially ended at 9 A.M., so at about eight-fifty, I walked toward the entrance of the ballroom in anticipation of the senator’s exit. It was then that I noticed he was not at his table. After a thorough search around the room, I realized that he wasn’t there at all.

  I tried my best to stay composed. It was my trial run before my first travel assignment with the candidate, and I’d already misplaced him. Aha! I know. I’ll just call him on his cell phone.

  I rang the number I had in my cell and got a voicemail saying that his number had been changed. Panic began to set in. I’d lost Barack Obama. I called Nick Colvin, another team member.

  “Nick,” I said, trying to feign calm, “what’s the senator’s cell phone number? I can’t seem to locate him.”

  “He’s been in the car for ten minutes,” Nick replied.

  “Oh, okay, cool,” I stammered, though cool was the last thing I felt. Especially since I was about to formally begin my tenure as the bodyman in less than twenty-four hours.

  Turns out, I had been right to be anxious. Losing the soon-to-be presidential candidate was the opening chapter in a long catalog of errors I would commit over the next six years. Another memorable, if insignificant, error occurred on the flight into LaGuardia, when the senator opened the bag of trail mix I’d bought and proceeded to pick out every M&M, holding them all in his palm like pieces of candy-coated toxic waste.

  “I’m not going to eat these,” he said, pushing his hand in my general direction. Clearly, I thought. “Do you want them?” he asked, wrinkling his nose.

  “No thank you, sir,” I answered, then made the first of what would be thousands of notes to self: No candy with the trail mix.

  This list would also come to include:

  No gum wrapped in tiny papers. (He preferred Dentyne Ice.)

  No energy bars with fruit. (Likewise, he preferred MET-Rx Protein Plus.)

  Salads only in emergencies, because you can’t eat salad in a car.

  Nothing battered and fried.

  Always have extra hand sanitizer, because after a day spent on a rope line you go through that stuff like oxygen.

  Don’t forget the silverware.

  Or the napkins.

  Or the water.

  Or the green tea.

  Nicorette. Normal flavor, two milligrams. (Like Sharpies and regular gum, I would buy that stuff by the case.)

  And heading the list: Little things matter. Subhead: Sometimes they make all the difference.

  * * *

  Traveling to New York always feels magical to me—ever since my first trip to the Big Apple in December 2001, when Duke played Kentucky in Madison Square Garden and Coach K led our team to Ground Zero. On this inaugural trip to New York for the campaign the city still had a sense of grandeur to me. We would be attending a couple of fundraisers and then an event hosted by Tracy Maitland, one of the most powerful African-American men in media, someone I had long admired and respected.

  Maitland had put together a who’s who of African-American moguls, including Russell Simmons, Pepsi guru Frank Cooper, financier Brian Mathis, L.A. Reid, Andre Harrell, and about fif
teen others who were set to meet Obama in Maitland’s swanky West Village apartment.

  I was inspired just breathing in the same oxygen. I mean, these were men of color who had broken barriers in corporate America and crushed it in everything they’d tried in life. I was still very much a small-town boy from North Carolina. The only super-successful black men I’d known until then were in the sports world. Meeting these kingmakers and seeing all these alternate paths to achievement gave me a perspective that I’d never had before.

  Despite the fact that most of these men had overcome racial challenges in their own careers, many of them were not as eager to jump on the Obama bandwagon as I thought they would have been, especially given that executives and boards of directors at Fortune 500 companies were even less diverse than the executive, legislative, and judicial branches of government. To say this group was rough on Obama is like saying the Pistons were rough on Jordan. Forget the Jordan rules. These were the Obama rules. It seemed like I was watching a trial. The candidate was seated in the front of the room, and everyone else was lined up across from him, grilling him like a steak.

  Why was he the man for the job? They didn’t see what Obama had done specifically for the black community. African-Americans had loved Bill Clinton, who over the years had forged relationships of reciprocal trust with concrete action, and this group of heavy hitters wasn’t certain Obama would have their back the way that Clinton had. There was a lot of hand-wringing over the fact that the senator hadn’t spent enough time in the African-American churches, or courting nationally prominent African-American politicians and leaders and their organizations.

  Over the next couple of hours, the candidate gave the men detailed descriptions of all the things he had worked on up to that point and explained why he might be unfamiliar to them. “I’ve only been a United States senator for two years,” he offered. And he spelled out in detail how he had spent his time among his constituents—the African-American community on Chicago’s South Side. He’d also helped the Democrats win back the Senate in 2006, a feat that promised tangible benefits for millions of Americans, African-Americans included.