Part 1: Democrats Can Be Assholes, Too
Coming of age politically in the Bush to Obama years
Politics in America is a gnarly mess. Sometimes it feels like it has always been, and that’s exactly how the founders intended it. But the dimensions of the mess have changed over the last two decades in ways that may be better understood through the lens of personal experience.
I’ve thought a lot (too much) about how to explain what I think about the Democratic Party and its present failures, and I, too, have failed to manage to do this in a succinct and pointed way. So I’m taking the other tack — the longest version of the story that explains my own experience and how it shapes what I think. It probably doesn’t matter to anyone. But here it is, on the internet for you, and anyone else, to read.
This is Part 1 in a multi-part series about Democratic politics in America. This post is long. Apologies in advance.
Growing up, there was very little political discussion in my house that I remember. My grandmother, Marjorie, was a Rockefeller Republican who served on her local town council for almost 30 years. My mother was an emphatic independent, suspicious of politicians. My father just wanted everyone to get along. My first political memory was watching a televised presidential debate among George H.W. Bush, Bill Clinton and Ros Perot at age six, though I don’t recall anyone expressing a clear point of view about who should or shouldn’t be America’s next President.
It wasn’t until 2003 and America’s invasion of Iraq that I began to have a sense of right and wrong in American politics. My father, who had narrowly avoided conscription to fight in Vietnam, was horrified that America was entering another ground war, and was quickly radicalized by left-wing talk radio.
In the summer of 2004, I fell sideways into professional advocacy work, when I found myself living with my high school my best friend in the suburbs of Washington DC. Unable to find a job as a restaurant hostess, I pulled a ticket with a phone number off a flier stuck to a telephone pole that promised I could “Make $400 a week saving the environment,” called the number on the small slip of paper and was invited in for an interview. The operation, it turned out, wasn’t “saving the environment,” but raising money through a door-to-door canvass to support gay marriage. That summer, President Bush was pushing Congress to pass the Defense of Marriage Act, and my prospective employer had been retained by the Human Rights Campaign to raise money to support their counter-lobbying efforts.
(These were the days before online fundraising, when the best way to capture a donation was a face-to-face conversation.)
Walking around the greater DC Metro area knocking on people’s doors to ask them if they had a few minutes for gay marriage taught me a lot about politics in America. Back then, Barack Obama had publicly stated he didn’t support gay marriage as a basic civil right, and the idea that gay marriage could be protected by the constitution was uncertain. My job as a canvasser was to meet a $120 a day fundraising quota, but that also meant persuading people who might not have thought about the issue that gay marriage was something they should support.
The culture in our Eastern Market canvass office was joyful and enthusiastic. The day kicked off with door knocking practice, where people honed their ability to “make the ask” and respond to objections to “close the gift.” A room of more than 50 paid canvassers would gather to hear the top performers of the day before, and celebrate those who were holding records for the summer. We were an army of persuaders on a mission to convince the world that marriage was a human right.
I had always been skilled at talking to strangers, after dozens of hours flying solo on airplanes in my childhood, but that summer, I realized just how powerful it can be to ask strangers to not just have a conversation, but support your cause. People will surprise you with what they’re willing to do. One memorable day, I was canvassing a neighborhood where I hadn’t gotten a lot of support. I’d even seen a few Bush yard signs. I knocked on the door of a house and a man with bulging biceps and a bald head opened the door. He appeared to be sweating, though it wasn’t clear if that was due to exercise or irritation. I gave him my standard greeting:
“Hey, I’m with the Human Rights Campaign,” I said. “We’re out talking to people today to see if we can count on your support to stop the Defense of Marriage Act.”
I had barely finished my breath when he stopped me. “One sec,” he said, and closed the door.
I wasn’t entirely sure he was coming back, but I waited just the same as he’d asked. A few minutes later he opened the door and handed me a piece of paper. I looked down and almost couldn’t believe what I was looking at: a printed check for $200, my all-time highest one-time contribution.
Now, 20 years later, Democrats look back with mixed feelings on the 2004 election. Bush was re-elected, despite the massive failing of the Iraq war, and Democrats lost big in a lot of places, which some people blamed on the elevation of the gay marriage issue, just as some people have blamed the public discussion of trans rights for Kamala Harris’ loss in 2024. In 2004, a winning coalition was able to defeat the Defense of Marriage Act, even though Democrats weren’t able to elect John Kerry. Winning political victories depends on the status quo you’re willing to accept, and the one people are sufficiently motivated to disrupt. And eight years later, President Obama would come out in support of gay marriage, and eleven years later, it would be enshrined as a right by the U.S. Supreme Court.
That fall, the RNC came to Madison Square Garden and I followed other students downtown to observe the protests, though I didn’t feel strongly enough about American politics to make a sign. I wondered why the Republicans had chosen to congregate in a place where so many people would be adamantly against them. It didn’t occur to me, that could be the point.
While I was technically old enough to vote in the 2004 election, the logistics of registering to vote in my first fall of college were over my head, and no one was waving a voter registration form in my face asking me to do it. The years between the New York Republican convention and what I have come to think of as my true political awakening were strangely apolitical. I voted in my first presidential primary in 2008. I was an intern in Hillary Clinton’s New York Senate office, and couldn’t think of voting for anyone else. Barack Obama’s optimism seemed like a false promise. While my peers screamed “Yes We Can!” I wasn’t so sure.
I spent the years between 2009 and 2016 working in Washington DC, but adjacent to politics, first at a center-right foreign policy think tank and then in an international development nonprofit. While our think tank hosted Senators for public events as “senior statesmen,” we didn’t interact with the legislative process, and I was fairly oblivious to whether and how America’s political representatives might be serving their best interest — or not.
To the Republicans I interacted with, the emergence of the Tea Party was as much an nuisance as it was to Democrats. When I left that organization in 2012, I imagined the future of my career being largely international in scope, and over the next four years, I would travel to more than a dozen countries in the course of my work on behalf of large multinationals, building their social impact footprint in Africa and other emerging markets. I voted in every election because I understood that’s what a “good citizen” did, but I still lacked fundamental awareness of the ways in which America’s leadership was or was not serving the needs of the people.
As the 2016 election heated up, it was increasingly clear the outcome of the election would defy expectations. The Republican field was both too wide and too thin, and Donald Trump had gained support among a strong plurality of voters. It seemed like 30 percent of Republicans shouldn’t have the power to choose their party’s candidate, but with the other 75 split four ways, he cruised to victory. On the other side of the ballot, Hillary Clinton had carefully safeguarded her nomination with a pre-primary agreement with the DNC.
It’s easy now to see the ways that Clinton’s “fixing” of the Democratic nomination may have smelled like injustice to many Democrats, but in that moment, I found her actions seemingly justified. She was a die-hard Democrat who had done her time and given a great deal in service to her party. She had graciously stepped aside to make way for Obama in 2008 and just as graciously served as one of America’s most successful modern Secretaries of State. Bernie Sanders was a lifelong independent who had done very little for Democrats – who was he to claim the party’s mantle? I had been warned early in my career that liberals were notoriously meritocratic, that every level of authority had to be earned. Hadn’t Clinton earned it?
My penchant for meritocracy also helped me (and countless others) undervalue Trump’s viability as a candidate. I had been raised to believe that the best should always win. How could voters ever choose someone with so little relevant experience to run such a big, influential, and complex country? I assumed Trump meant for his presidential campaign to serve as some kind of mega-brand-building exercise that would allow him to further expand his media empire that he could capitalize on after a narrow loss.
It wasn’t until July 2016 that I started to think otherwise. A New York Times headline announced that the Trump campaign was ramping up its field operations in Florida, Ohio, and Pennsylvania. Hmmm, I thought. That sounds like the strategy of someone who actually wants to win. My mind quickly flashed forward to the thought of a Trump victory, and I felt vaguely queasy. I couldn’t stomach the feeling of not doing something to prevent it. Thankfully, a fortuitous series of events somehow helped me get an offer to join the Florida Democratic Party in Broward County a month later.
It’s hard to talk about the 2016 campaign without whining. The world knows so much now that it didn’t know then, especially about the Democratic Party’s massive blind spots, which makes it easy to write the 2016 election off as one big miscalculation. But the truth is, many of the core ideas that guided the 2016 election are still in play.
Campaign strategy had two phases. Phase 1: voter registration or VR. End goal: register 200,000 new voters across the state and hope they were voters who would vote for Clinton. Phase 2, starting in early October: voter turnout. End goal: mobilize all registered Democrats to vote by Election Day.
I joined the campaign at the end of August, imagining that I would show up to an office similar to the HRC Canvass office in DC, but the reality was a lot different. Our team of 12 field organizers was responsible for about 100 square miles of the northeast corner of Broward County, FL. Our “turf” covered the semi-opulent retirement communities of Coconut Creek, through the immigrant enclaves of Pompano Beach, to the wealthy beach dwellers of Deerfield Beach. Our team was a mix of a few college students, some recent college graduates, and several mid-career professions with varying degrees of experience.
For $3000 a month, we were expected to work more than 80 hours a week, from 10am to 10pm Monday through Saturday, and from 12pm to 9pm on Sundays. (No one objected to working that many hours amounted to working for close to minimum wage.) Our job was to call and recruit volunteers from lists of voters and donors who would show up for shifts – phone banking to recruit still more volunteers, registering voters, and knocking doors to help people make a plan to vote. We were personally expected to complete at least 2000 calls to volunteers a week, which meant at least 280 dials a day. (Most people tried for 350 dials on Monday to buffer the rest of the week). Each call was individually dialed from the organizer’s personal cell phone — an auto-dialing system was seemingly considered a waste of money.
Our leadership constantly reinforced how important field operations were for the campaign’s ultimate success, and yet, I never felt like the field was the real priority. Early in September, the campaign held a statewide training in Tampa which brought together nearly 600 Field Organizers from across the state for two days of instructions and motivation. Headlines showed Clinton in Tampa for donor meetings, and rumors started circulating that maybe she was planning on swinging by the hotel for a quick motivational meet and greet. But she never showed — the donor meetings were too many and too important for her to find 30 minutes in her schedule for a drive by. Instead, we settled for a two-minute montage video that attempted to capture the energy of Obama’s “Yes We Can!” But “Stronger Together’ never had quite the same energy.
Back in the office, the feeling I could not shake is how hard we were working for so little result, while Trump campaign volunteers easily turned out thousands of people for impromptu rallies all over town. There was very little camaraderie or collective celebration. I remembered back to my HRC summer, the team meetings before launch, the milestone numbers of ranking canvassers applauded by all. Here, everyone put their head down and managed their own time. We were too tired to have the energy for more.
Much of the campaign is a blur, but a few moments stand out in my memory. One evening during voter registration, I was standing outside a Walmart around 8pm wearing a Hillary Clinton for President t-shirt, asking passersby if they were registered to vote, when an older woman walked at me like she was going to run into me, flipping both her middle fingers at me. “I hate you people!” she screamed in my face. I jumped back so she wouldn’t hit me and she continued past me, almost speed walking into the store. I knew that plenty of people didn’t like Clinton. I hadn’t, until that moment, understood just how forcefully so many average Americans really hated her.
Voter registration ended and GOTV (get out the vote) began. I was paired with a young Black field organizer to staff a canvass office in the middle of Pompano Beach. Our job was to recruit retired white ladies from Coconut Creek and send them out to canvass the low-income immigrant and Black neighborhoods of nearby Pompano. Our multiracial staffing was seemingly intended to make sure that everyone could feel safe. We decided a canvass launch event with the Congressional Member from our district could help motivate our volunteers to show up. A former district judge, Alcee Hastings had been impeached for bribery in 1989, but had made a comeback three years later as a Member of the House of Representatives. His staff confirmed that he was available on the Saturday in question and we worked the phones like crazy, ultimately confirming more than 60 volunteers for the canvassing shift.
That morning, my supervisor called to let me know she’d just gotten some bad news: Hastings wouldn’t make it. I couldn’t believe that anything could be so important that he couldn’t spend 30 minutes on a Saturday morning motivating a room full of volunteers who were about to go talk to hundreds of his constituents, four days before Election Day.
“I dunno,” she said, “Maybe donor meetings?”
(Hastings died of pancreatic cancer while still in office in 2021, at 85 years old.)
I stood on a chair and did my level-best to motivate that crowd. It was raining and wet — not a nice day to be walking around knocking doors. And yet, all these people had showed up because they believed.
As GOTV heated up, volunteers would ask me if they could leave voice messages for the people they called. This went against protocol because then volunteers weren’t make as many calls per shift. Another volunteer in an adjacent district would ask his organizer if he could talk to people who lived in his neighborhood who weren’t on his list. The answer was no. The objective was to talk only to true-blue “DDD” Democrats. At no point were we to try to persuade an undecided or independent voter to turn out. The assumption was, if every Democrat in Broward County voted, it could balance the scales against the Republican energy surging across the rest of the state.
In the aftermath of Clinton’s loss, people liked to argue about exactly why the campaign failed. I came to see it as a bag of rocks that sunk the boat — you could argue about their relative size, but at the end of the day, they all played a part in bringing us down, many of them out of the campaign’s control. But there were many things that could have been under Democratic control that went unexercised, many campaign tactics that went untried. Hillary Clinton was trying to win using Barack Obama’s 2012 campaign strategy, and no one seemingly had the courage to undersore all the reasons that probably wouldn’t work.
But Democratic Party infrastructure was degraded and broken long before Hillary Clinton ever self-proclaimed her candidacy and lost to ]Donald Trump. The party of the 1970s has aged and decayed, failing, perhaps by choice, to bring along a new generation of Democratic leadership. The gerontocracy of Democratic politics extends is an active, ongoing choice. Just this week, Pelosi enforced the Democratic meritocracy when she opted to support a 74-year-old Member with a throat cancer diagnosis over Alexandria Ocasio-Cortez to lead the Oversight Committee.
After the campaign, I came back to Brooklyn and discovered an opportunity for a different kind of political action. Instead of frantically knocking on doors just before election day, what happens when you bring people together to talk about the future?
That’s up next.