I Raised $50 Million for the Democrats. This Week, I Voted for Trump.

I was 17 when I started working in Democratic politics. While still in high school, I was an intern for Barack Obama’s first presidential campaign; later, I served as a field organizer for Hillary Clinton. By the time I turned 26, I was a consultant for dozens of U.S. House and Senate campaigns, four George Soros-backed district attorney races, and a wide range of Democratic organizations. I’ve raised at least $50 million for the left. 

And yet, on Tuesday, I voted for Donald Trump. It felt like the biggest middle finger I’ve ever raised to the party I’d supported for most of my adult life. When he won, I was utterly euphoric. 

Let me tell you why. 

I was born and raised in the Kansas City, Missouri area, in the middle of the country. My family floated somewhere between working and middle class. Neither of my parents went to college; my father never even earned a high school diploma. We moved around a lot, to different towns and different accommodations depending on whether my mom was married or not—sometimes a house, other times a trailer park. Many of my relatives were members of either the laborer’s union or the carpenter’s union. Much of my childhood was spent in union halls. My grandfather used to dress up as Santa Claus at the annual union Christmas party. 

My mom and dad divorced when I was only 10 months old. She scrambled as a single mom, often switching jobs through recessions and layoffs. Her most profound regret, she used to tell me, is that she never went to college; it locked her out of so many opportunities. So she pushed me hard to finish. I went to Johnson County Community College and the University of Kansas, and it took me six years to finish. I had a rare lung disease called primary ciliary dyskinesia—it’s similar to cystic fibrosis—and when it put me in the hospital six times during my freshman year, I was ready to quit. But she wouldn’t let me. At one point, she sold all the wedding rings from her six previous marriages to ensure I had the tuition for a semester at the community college. (For many lower-income women, the quickest way out is to get married.) She was adamant that having that piece of paper—that diploma—was the key to my having a better life.

I was close to my stepbrother Charles, who found another path to a better life, one that many working-class young people take. In 2008, he enlisted in the U.S. Navy. He joined to secure credentials that could unlock opportunities he otherwise wouldn’t have had. Before he enlisted, he worked as a janitor in the same office where Barack Obama served as a state senator in Illinois. The navy did beautiful things for him. He truly loved his job and was able to serve and fulfill his true potential as an electronics technician. He provided for his two children and fulfilled his lifelong dream of living in Japan, having taught himself Japanese as a child. 

Then on August 21, 2017, his ship—the USS John S. McCain—collided with another in the South China Sea, killing him and nine other sailors. By then, I had been working in Democratic politics off and on for a decade, and through my connections, I tried to reach out to former president Obama, hoping he might remember my brother and send a letter to his two children. I remember how striking the lack of empathy was from the people I worked with in Democratic politics. Relationships in politics are extremely transactional, and I never heard anything back from Obama.

Two months later, when Halloween came around, a Republican senator asked Trump’s White House to extend an invitation to my brother’s children for the White House party. Eight other members of our family were also invited. Republican senator Pat Roberts sat with my stepsister and her husband for over an hour at his Washington, D.C., office and listened to them tell the story of my brother’s life. John McCain called them personally. The comfort they offered was deeply appreciated.

Nearly one year later, when I visited Alexandria Ocasio-Cortez’s office on behalf of an organization I was working for, I found a packet of crumpled-up American flag stickers in the trash can. I pulled them out quietly, not wanting her staff to see me, and put them in my backpack. I felt sad but thought I would take them to my brother's kids when I saw them again. I knew they would appreciate them. 

I was never happier about a Democratic victory than when Obama won in 2008. Blacks, whites, young and old, women and men rejoiced together, dancing in the streets to Michael Jackson’s “Thriller,” everyone feeling joy, and more importantly, hope. The same was true of my family—I can still remember how excited my mom was to vote for him. After eight years of George W. Bush, of the Iraq War, of repeated job losses, and growing income inequality leading to the financial crisis of 2007, we all thought Obama would return the country’s priorities to jobs for the middle and working class.  

But it didn’t turn out that way. As much as anything, he was a Democratic technocrat. Still, in 2016, when Trump ran against Clinton, I was one of those people who laid in bed for three days when the Democrats lost. By then, however, I was an outlier in my family, who had already made the shift to Trump—as had millions of others in Missouri, a former bellwether state that grew redder with every election. For the longest time, I couldn’t understand why.

In 2019, I decided to move to San Francisco, a place where you’re unlikely to hear anything good said about Trump. After that, I got married to a man who worked in the Bay Area, and my circle of acquaintances was virtually all Democrats.

Looking back, I realize I had a foot in two worlds—the world of Democratic politics and the world of my family back home. The gap between these two worlds grew ever wider until it became a chasm—a chasm the Democrats failed to see, even after eight years of Trump as their opponent. 

It began with Bill Clinton championing the North American Free Trade Agreement, which took effect in 1994 and began the outflow of millions of jobs—many of them union jobs—from the U.S. to Mexico, China, and other countries. A slew of free trade policies followed that gutted communities like the one I came from. According to the Bureau of Labor Statistics, Missouri lost 36 percent of its manufacturing jobs between 1990 and 2019. Immigrants, many who came here illegally, replaced Americans in labor-intensive industries like hospitality, construction, and landscaping. Many of my acquaintances in San Francisco couldn’t fathom why Americans would even want these jobs.

“Why wouldn’t they want to make more money?” Democratic donors and Silicon Valley tech bros and Ivy League graduates wondered aloud to me. “Just go to college,” they’d conclude, as if it were that easy.

Exasperated, I tried to explain: “Many people can’t afford college, and honestly, not everyone even wants to attend college.’’ In fact, as of 2022, only 38 percent of Americans over the age of 25 hold a bachelor’s degree.

Meanwhile, I admit I bought into the notion that the right only opposed illegal immigration because they were racists. But recently have I come to see that the influx of immigrants allows companies to pay wages so low their employees are barely above the poverty level. Some in my family are among the seven million men who Vice President-elect J.D. Vance has described as dropping out of the labor force entirely—not because they are lazy or don’t want to work, but because they can’t find decent-paying jobs.

One of my cousins fits into this demographic. He worked at McDonald’s from 2010 to 2017 and never missed a single day of work. But he could barely live on $10 an hour. He needed to make the kind of money union laborers once made—$25 to $35 an hour—a livable wage. However, graduating from college is the only way to earn this income level now. My cousin hasn’t worked in two years because he says there is no point; he doesn’t want to work for wages that won’t allow him to amount to anything. The credentialed gatekeeping championed by Democrats has failed people like my cousin and many others. 

What’s tragic is that there are so few in the Democratic Party able to communicate with the working class and serve their interests effectively. Senator Bernie Sanders ran a populist presidential campaign in 2016 with colossal momentum but was locked out by Democratic elites. Pennsylvania Senator John Fetterman ran an incredibly successful campaign against Dr. Mehmet Oz with a pro-worker populist message. He is now spurned by the elite left as being problematic and not passing their test for ideological purity. 

Last July, when Biden dropped out, during the brief 10 minutes before he handed the nomination to his vice president, I texted a friend of mine high up on Bernie’s team.

“Tell Bernie he has to run and tell him to make Fetterman his running mate.” I thought they could unite the left and moderate flanks of the party and ensure a win in Pennsylvania. 

But when I floated this idea to my other friends in Democratic circles, they laughed at me. Fetterman, they said, was an abomination and a traitor to their left ideals—he supports Israel, after all, and goes on Joe Rogan’s podcast—and Bernie was no more fit to be the nominee than he had been in 2016. Or so they believed.

When you consider what the modern Democratic Party has become, you begin to understand how they lost touch with their base. At the home of a major donor, a billionaire who lives in a mansion overlooking San Francisco Bay, I listened to the speakers hoping to raise funds for the 2022 midterms. Waiters dressed in black with silver trays bounced between wealthy elites. The speakers outlined their strategy for winning the midterms and the 2024 election saying: “We no longer want to win the working class. We don’t need those people anymore. They’re gone forever. The future will be young Latinos and people of color.” 

I was infuriated by this talk. I also thought: That is going to be a good way to get Donald Trump reelected.

Meanwhile, through the loss of my brother, I knew enough about the military to realize what a mistake it was for the Kamala Harris campaign to trot Liz Cheney all across the Rust Belt. The campaign fundamentally misunderstood all of the middle-class and working-class families who had sent their sons and daughters off to fight the wars of Cheney’s father. True, my brother did not die in combat. He died in a preventable tragic accident, but my heart was ripped to shreds nonetheless when I watched the Biden administration pull out of Afghanistan. It felt so reckless how American soldiers’ lives were thrown away and discarded, knowing the brutal sting of their families’ grief all too well. These were also preventable deaths. How could the Democratic elites so fundamentally misunderstand the pain of the American people? How dare they?

The truth is, I’d been slowly disconnecting from the party. When I volunteered to work at the Democratic National Convention this year, I was hoping to feel inspired again. Instead, when I got there, I encountered the same social snobbery as always, with consultants and higher-ups looking down on volunteers. Donor suites and corporate media suites intermingled in the same area, and extremely rich people mindlessly chanted “joy” and “respect.” Harris had no policies or programs on her website, and yet, an arena of tens of thousands seemed deliriously high, spellbound by her identity as a woman of color running for president. Her political emptiness allowed them to project their own hopes and desires onto her.

The final straw was Oprah Winfrey’s tone-deaf speech. A larger than life Hollywood billionaire so far removed from the experience of average Americans—indeed, from her own experience growing up poor in rural Mississippi—her presence was dumbfounding to me. She said nothing that spoke to the Americans who had once constituted the Democratic base. People like my mom and grandmother, who now must live together because the rents are too high, who live solely on their Social Security checks, who can eat only one meal a day for most weeks because they literally can’t afford to buy as many groceries as they used to. I had seen enough. I was done.

The Democratic Party has evolved into a group that signals virtue but lacks real values. It’s a group that panders but never produces. Advancing LGBTQ rights and a woman’s right to choose are essential freedoms in our country, but when it’s all you have to offer because your constituency is so far removed from the material conditions of regular people, what you get is a candidate who stands for nothing, who could never articulate her vision for America.

Thus I found myself at Donald Trump’s official election night party at the Palm Beach Convention Center. I could scarcely believe I was cheering with the crowd as each swing state turned red. But I was, and I felt the same sense of elation I felt when Obama won in 2008. It was clear that evening, and in the subsequent days as the data came in, that my former friends among the Democratic elite could no longer claim the “racist” white working class put Donald Trump back in the White House. Not when 16 percent of black voters and 45 percent of Latino voters broke for Trump. 

I still don’t consider myself a Republican. I am now an independent and could potentially vote for a Democrat in four years if the right one comes along—a candidate who will speak and listen to the working class. 

My decision to vote for Trump and to publicly express my frustrations with the Democratic Party has been incredibly difficult. I’ve lost many friends, and I know I am going to lose future professional opportunities because of my willingness to speak about this publicly. The one thing holding me back from voting for Trump was the worry he might try to overthrow Obamacare again, as my illness continues to be a significant part of my life. But Trump has promised he’ll keep it, and I believe him. My hope is that if other factions of the Republican Party start to pressure him to do otherwise, he will remember voters like me, and the new coalition he has built.

Still, I have no regrets. The Democratic Party turned its back on me and my family long before I turned my back on it.

As the night in Palm Beach, Florida, melded into Wednesday morning, and dawn neared on a new day in America, I crawled into the backseat of my cab to return to my hotel. My cabbie was a middle-aged black man. I asked him how he felt about the night. Giddily, he exclaimed: “READY to make America great again!”

When I asked him why he didn’t vote for Kamala Harris, he answered: “She just didn’t speak to me. It’s like she was pretending to speak like a black person. It felt fake.”

“Trump,” he concluded, “speaks to all of us the same.” 

Evan Barker, a writer living in San Francisco, is a former Democratic campaign operative. Listen to her podcast, “Rolling in the Deep State,” and follow her on X @Evanwch.

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