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Yes We Can: A Nostalgic Trip to the 08 Campaign

Tonight, CNN aired it’s latest episode of “The 2000s,” the latest decade the news network has profiled since starting with “The 1960s” a few years back. Hopefully, they take their time with the 2010s since history tends to take a while to render its verdict on events, but I digress. The purpose of this post is to focus on the inspiration for tonight’s episode, entitled “Yes We Can.”

For a lot of people, the 2008 presidential campaign was one of the most exciting political experiences of their lives. It was the culmination of so much societal change that happened so fast – largely a result of the expansion of Internet access and use – that it felt like we were in the midst of transformational period whose direction really would be dependent on us as Americans getting that particular election right. For supporters of then-Illinois Senator Barack Obama, for volunteers, and especially for staff, 2007 and 2008 was like being part of political revolution. I know Bernie Sanders supporters will roll their eyes, but that’s partly a result of the position they see themselves in as a result of the hard work we put in a decade ago. I knew that this campaign would be important; my family had collectively been convinced after Obama’s spellbinding keynote address at the 2004 Democratic National Convention that we had just watched the first black president. Afterwards, perhaps the only thing my parents ever agreed on again was that conviction and we monitored Obama’s progress from that moment on. I remember vividly arriving home late one night to both of my parents intently watching Obama’s U.S. Senate debate against Alan Keyes, a race that had no significance to a small family in Louisiana other than the belief that we were watching the future.

So in January of 2007, when Barack Obama finally announced that he was exploring a run for the presidency, I knew exactly where I wanted to be and what I wanted to do for the next two years. I didn’t care who else was running – Hillary Clinton had effectively announced the same intentions earlier in the month – I was on Team Obama before there was one.

I remember how determined I was to join the campaign and how equally daunted I was by the task required to do so. I don’t come from a particularly well-connected family, didn’t know anyone who’d ever worked on a campaign at that level, didn’t know anyone who knew anyone on the campaign, and, well, I lived in Louisiana, which wasn’t going to be fertile territory for the campaign’s recruitment of staffers. Moreover, I knew almost nothing about presidential politics at the campaign level, so I didn’t even know what job I wanted or how to do whatever job I might get.

Didn’t matter. I was getting on that campaign one way or another. And luckily, that determination and tenacity paid off. Just not immediately.

Obama officially announced his candidacy on February 10, 2007 in Springfield, Illinois at the Old State Capitol. It wouldn’t be until later that summer that I finally got my chance encounter with his official campaign. I’d found out in June that Obama was a late addition to the slate of “performers” at the annual Essence Music Festival in New Orleans in July. While generally speaking the evenings were reserved for musical artists, Obama obviously was speaking to a crowd that – while not necessarily politically supportive yet – wanted to give the young, ambitious brotha seeking the presidency as many opportunities to share his message as possible. So he’d be on the main stage (to be introduced by Ludacris, no less) and I knew that meant that his campaign would have a presence at the event (first lesson of politics is to use every public appearance to collect data). So I followed the future-president down to New Orleans and I badgered his campaign staff who were there for any help or advice regarding how to get a campaign job. They were largely dismissive – I’d later learn that presidential politics often employed a lot assholes who thought their mere presence there was validation of their importance – but nonetheless I resigned myself to volunteering for the campaign every day at Essence Fest. They had a table set up in the exhibition hall during the daytime sessions where the staff was collecting voter information and signing up campaign volunteers. The campaign had incentivized volunteers signing others up and getting data that weekend by saying whoever signed up the most people each day would receive complimentary floor seats to that night’s concert. Since this felt like my one and only shot to make an impression on the folks in Chicago, I took the competition as a direct challenge from God: this is your moment, Q – work hard and go get what I have for you.

Needless to say, I got floor seats two of the three days I was there.

As a result, one of the Obama for America staffers recommended me to the campaign’s “Camp Obama” training in Chicago. I knew it was kind of a gimmicky way of recruiting and training volunteers, but it was also held at campaign headquarters in Chicago – so using the same logic that brought me down to Essence Fest and ultimately had me rubbing shoulders with field organizers from the campaign, I figured while this wasn’t the opportunity, it was probably close in sequence with the one I was looking for. If I wanted a job with the campaign, going to Camp Obama would at least check off two important boxes on my path their: another opportunity to make an impression on someone within the official campaign and being at the mothership, where the campaign’s literal human resource department was located. That wouldn’t be an opportunity I’d likely get in Louisiana.

So the following month, off to Chicago I went – and mind you, campaigns don’t spend on what they don’t have to, so this was on my own dime. The training was fairly standard stuff – we got indoctrinated with the talking points, learned some interesting tactics for phone banking and canvassing, and met some key figures in the campaign, including the National Field Director Jon Carson and Chicago-area Catholic priest Father Mike Pfleger, who left me with an old Chicago adage that I’ve taken with me everywhere ever since: “Don’t send me no one no one sent.” Maybe one day I’ll post something more expansive on how salient that phrase really has become as I’ve gotten older and moved ahead in my professional career. But there was no clear opportunity for me slide my resume to someone or get a face-to-face with anyone with enough influence to help me finagle my way onto the campaign. So, again, I had to get creative. I found a few staffers who seemed close in age to myself and sparked up a friendly conversation in which I hinted more than a few times that I wanted to work on the campaign and anything they could do to help me in that quest, I’d greatly appreciate. I was attentive and sharp during the trainings as well, intentionally trying to stand out to the trainers – who also worked at HQ – because I knew I’d need as many friends in the building as possible for this kid that no one sent to still get a chance to join the campaign. I made it clear that I would even take up a janitorial position if it meant I was on payroll and in the fold; I figured once you’re in, you have a lot more options than when you’re out. So anything would suffice.

I returned to Baton Rouge after the training hopeful that I’d planted the seed, determined to continue being a nuisance to everyone who gave me their email address, and absolutely convinced that I was going to be a campaign staffer for Barack Obama sooner rather than later. In fact, I’d been so convinced that this was going to be the outcome that I’d taken a job as a waiter at a local brunch restaurant called Another Broken Egg Cafe earlier that summer and saved every single tip I earned that summer in anticipation that 1) I was getting an offer from the campaign by the fall and 2) it was unlikely to be a paid gig. Or at least not initially.

As fate would have it, both turned out to be true. Around Labor Day, after almost bi-daily email check-ins with my contacts at OFA, the campaign finally extended an offer to me: an unpaid internship in the New Media department of the campaign. Honestly, I don’t remember the rest of the offer because the answer would have been yes even if they’d told me I’d be responsible for keeping up with Obama’s wave caps. I was in. And that’s all that mattered.

I took my modest savings of a couple thousand dollars (which was huge for me at the time), packed a few bags, and immediately headed up to Chicago to take my rightful place as an unpaid pion in a rapidly expanding national campaign. With the help of my dad going half on the rent and my Uncle Ernest helping me survey the neighborhoods, I secured a small, furnished apartment in “nearby” Cicero (the Craigslist ad said it was minutes from the city; when I arrived, I realized they meant that minutes make up an hour so technically speaking, they hadn’t lied) and prepared for my first day at campaign headquarters.

When I arrived for my first day of work, I was just so taken by the overall atmosphere. The campaign was housed in a fancy high rise building in the Chicago Loop on Michigan Avenue; walking into work felt fancy in a way that I’d seen on television before, but until then had never experienced. It really was a place where everyone walked in with a crisp Chicago Times (I typically read The Onion on my hour-long ride into the city on the Pink line) and a fresh Starbucks latte. In hindsight, I realized it was kind of a self-important atmosphere that was neither beneficial or a net negative to the campaign, but I’d later notice other things about the culture at HQ that made me more interested in being on the ground working with voters than being in the office surrounded by Yale, Harvard, and Brown sweaters.

But that first month, I was in awe. I worked right outside of national press secretary Bill Burton’s office (whom I never could tell if he was black or white, but I amused myself every day guessing) and right across from Chris Hughes, a co-founder of Facebook. The office was sleek, modern, and huge. It reminded me more of the corporate environments that I’d seen my dad operate in than the gritty, brown-tinged campaign offices I’d imagined from having watched Primary Colors as a kid. My work wasn’t anything particularly special or important to the overall goal of getting Obama elected – I largely did copy editing for digital press releases, edited minor digital graphics for the website, and responded to questions from visitors to the site about largely technical issues – but I was there, @barackobama.com email address and everything. And that was the first step.

But as I alluded to before, the luster of simply being at HQ had lost of bit of its appeal for me. For starters, $2000 in Chicago didn’t go nearly as far as I’d hoped and I had to remind myself that my ultimate goal was to get a paid position with the campaign. Dwindling funds helped remind of that fairly quickly. But the longer I was at headquarters, the less attached to the energy of the campaign I felt. While there were some high moments – like when I got to be in online campaign ad – the staff’s morale in HQ was sometimes a depressing, volatile variable. I remember one day in late September – maybe early October – after a particularly brutal period in the race that saw our poll numbers plummet and the whole “inevitability” theme around Clinton’s campaign really start to balloon in the national press, Senator Obama decided to pay the staff at HQ a visit to boost morale. Prior to his arrival, morale did often hinge on national press coverage and the chattering political class that made up many of the social circles of the folks in the office. So if a bad poll came out, the office was much more muted than usual. If a rough news cycle clocked us a few more times than we’d expected, you could feel the tension in the office. While I was still excited about being part of the team – the movement – I wasn’t a politico. I was a believer. I was there because I genuinely believed in what we were trying to do and I wasn’t as comfortable with the internal prognostications and perspectives openly discussed and felt that by comparison made me seem naive, idealistic, and perhaps the most disturbing possibility: the only person who truly believed we could pull this off. When Obama arrived, the staff was herded into our largest conference room and Obama spoke for a few minutes, touching on the obvious – our poll numbers – but promising that real progress was being made on the ground and that campaigns, particularly long ones like the one we were engaged in, always had lead changes. When he opened up the floor for questions, I didn’t even realize I’d raised my hand. But I knew even if I didn’t have a question, I was going to say something to the future president. When he called on me, I panicked a bit because I genuinely didn’t have a question I needed answered, so I winged it. I asked him something really stupid and borderline inappropriate about why he hadn’t attacked Hillary Clinton yet, despite our poll numbers dipping. Obviously, he wasn’t going to share the campaign communications strategy with me and even if he had to share, who the fuck was I to hold him accountable? But he was gracious; he smiled at me and gave something of a winding answer that to this day I still can’t remember. But I was happy I’d asked and happier still that he’d answered. I’d only meet Obama two more times again after that, but never quite with his full attention like I’d had for a couple minutes in that crowded room.

After the pep talk, the mood in HQ was noticeably improved. But my determination to go into the field was steeled. Obama himself had said it: the real progress was being made on the ground, in the primary states, and if that was true, that was where I needed to be. For the next few weeks, I badgered Jon Carson for any opportunity to get on the field, emphasizing that I’d love a paid gig, but would be willing to earn it however possible. He entertained my overtures, probably wondering why this kid was so bold to just casually and often pitch myself to him for a job, but also curious about someone with the testicular fortitude to do so (truthfully, at the time, I didn’t know being the National Field Director was a big deal – hell, I didn’t know any of those positions were particularly important) and by late October, he finally had an assignment for me.

Obama was planning his first rally in St. Louis and his rallies typically accompanied the opening of a new field office. Carson’s charge to me was simple: the new Missouri Field Director, Mike Dorsey, would need help socializing the rally and boosting attendance. Moreover, we needed volunteer help to make sure we collected as much information as we could at the rally. Knowing that I had family in the city and many of my familial roots are in the St. Louis area, Carson figured this would be great opportunity for me to be successful and told me that if the rally went well, I’d have earned a paid field organizer position. I agreed with his assessment and accepted the challenge.

In St. Louis, my job around the rally was to manage outreach to the local colleges and Democratic groups. Since Obama was still the candidate that made college-aged kids’ socks roll up and down, the task wasn’t a particularly difficult one. Within a few days, we felt good about attendance and prepared for the boss to arrive to kick off our efforts in the state.

The rally was awesome. Admittedly, I had by then been so familiar with the stump speech I probably could have delivered it myself, but it was cool to finally be out of the stuffiness of HQ and in the midst of the voters who would actually decide the election. The energy was electric, the crowd was huge, and the reception to signing up was remarkably positive. Aside from one minor rookie mistake – I gave an interview to a local news station that wanted reaction to the rally; that’s a no-no for staff on a campaign that aren’t press secretaries – the event was a roaring success. And true to his word, when I arrived back in Chicago, Carson offered me a paid position back in St. Louis, working under Dorsey and handling youth outreach as a field organizer for $2,000 a month. I remember thinking that was way more than enough for me; I framed the receipt of my first check for $852 and to this day, I still have it.

While officially I worked in the Missouri field office, the truth is that everything was about Iowa first. And if you were working in a neighboring state, it was about bringing volunteers into Iowa to help canvass. If we didn’t do well in Iowa, Missouri wouldn’t matter. Neither would any of the other states. So it made sense that much of my job early on was dominated by identifying volunteers willing to travel to Iowa on weekends and coordinating those canvassing trips. As fall turned to winter, as treacherous as those trips became weather-wise (that was the first time I’d heard the phrase “wintery mix”), you could feel the building excitement as we got closer to January 3, the date of the Iowa caucuses. We were polling really well in Iowa, essentially at a 3-way tie with Clinton and John Edwards, so every trip, ever door knock, every card we filled out with voter data felt like it was vitally important to the mission of getting Obama elected. By late December, while I had loft apartment in downtown St. Louis, a block away from our office, I was practically living in Ottumwa, Iowa.

January 3 might as well have been Christmas Day for me. The night before, myself and a few of my volunteers had stayed the night at a campaign supporter’s house in Ottumwa. The house was cozy, but the weather outside was brutal. Iowa in the winter is so cold no one cares about fashion anymore. It’s just about layers and how many you can manage to put on. So when it was time to get started the next morning, we layered up and started phase 1 of our GOTV (get-out-the-vote) plan: standing outside in the freezing cold at major intersections in Ottumwa with signs reminding people to caucus that evening. While we’d run into occasional opposition during our canvassing, I do remember vividly experiencing more than one hateful, vitriolic message from drivers as they passed by. In one case, one driver opened up his window only to toss his cold beverage on otherwise innocent volunteers and staffers who just wanted to express their excitement about their preferred candidate. I remember thinking to myself “My God, we’re just kids. They should be happy that we’re excited to be engaged in the process. Why do they hate us?” I never got a good answer to that, but I let the negative recede in my mind because we had a job to do and we felt good about doing it.

That night, I got to watch a precinct caucus up close and in-person. It was an intriguing ordeal, more akin to a game of four corners than a voting process. There’s so much jockeying and horse-trading going on that it finally made the outreach process make sense. We’d been conditioned to ask voters in Iowa that if they couldn’t commit to Obama as their first choice, would they commit to him as their second? When I finally got into a caucus, I realized why that was important. There were rounds of voting, so if after a round a candidate didn’t get the requisite amount of support in the room, that candidate was eliminated from contention. If I remember correctly, in the precinct I got to watch, Edwards got eliminated and most of his supporters came over to our campaign. I thanked the political gods that we’d been prepared as well as we had for the caucus system; other campaigns seemed to be winging it or at the very least, had only come into the voting with a Plan A.

When I left the caucus and headed back to our field office in Ottumwa, I remember all of us – staff, volunteers, and supporters alike – huddled around a desktop computer, pulled up MSNBC’s live stream of the results, and watched in both awe and pride as the network called the caucus for Obama. We’d done it. We pulled it off. It was the best feeling in the world. I felt like I’d truly been a part of something historic. It was off to the White House.

Or so we thought. The next week, as confident as we were heading into New Hampshire – so much so, that I remember Mike Dorsey telling us in Missouri that we’d likely not have to do anything for the rest of the campaign if we won Iowa – we were blindsided by the loss to Clinton. We went from thinking maybe our campaign was going to cruise to the nomination to acknowledging that we were in a dog fight that could go the distance. Or at least to Super Tuesday, when among other states, Missouri voters would cast their ballots. So we got to work, with a sense of renewed relevance in Missouri and a frenetic pace to our work.

We knocked on every door. I reached out to every school. We registered every voter we could. And when it was all said and done, Missouri was the last of the Super Tuesday states to get called, not getting called until early Wednesday morning and the results were so razor-thin, that they didn’t impact the momentum of the race hardly at all. In fact, I think plenty of folks – on or off the campaign – probably couldn’t have told you who won Missouri.

But I can? We won. And whether it was by 4 votes or 4,000, when it’s your blood, your sweat, and your tears that you put into the effort, a win is a win is a win. And we won.

So as I watch tonight’s episode of “The 2000s,” all of these nostalgic feelings come racing back to me. The primary race was unprecedented. The general election was historic. And in the end, we pulled off one of the most incredible political feats in American history. I will always be proud of my time on that campaign and what we accomplished. We helped change the world. And most importantly to me – and hopefully my future children – we helped show folks of color that this country really was ours. We could do anything we put our minds to and that 2008 campaign was tangible proof. I saw it up front. I was a part of it. And I’ll never forget it.

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