My first campaign job was in 2004. I was hanging around Ohio State University’s campus during the summer, getting young people to pledge to vote. After graduating, I did a variety of campaigns. I spent time in Virginia, did a race there in ’05 and then a congressional race in ’06. Then I went back there for Barack Obama in ’08 and then went into Texas with Organizing for America in 2009. And from Texas I went to Nevada for the reelection. I was in Nevada for a year and a half for the reelection. After that, I came back to New York just as I was burnt out.

I got out of campaigns just because I wanted to be back home around family. And then Donald Trump’s election pulled me back in, because there was a sense of “Holy shit — it actually happened.” I was thinking about how to reengage, which is why I became a member of Democratic Socialists of American [DSA] in the beginning of 2017. I actually started — through you — volunteering locally and with national groups to bring some campaign experience to the discussion.

In 2018, with all that was going on, especially after Alexandria Ocasio-Cortez [AOC] won, I was like, “Oh, there’s something happening in New York.” A lot of people interpreted it as this fluke, but those of us in New York political circles knew that just doesn’t happen. You could sense that this was not a one-off. The post-Trump rage was getting directed rather effectively to some of these local races. It was like, “Why do we have these representatives who are terrible, like the Independent Democratic Conference [IDC]?” [The IDC was a caucus of eight NY State Senate Democrats that joined with the Republican minority to block progressive reform.]

So I jumped on with Alessandra Biaggi [a center-left political operative who successfully challenged former state senator Jeffrey Klein, the IDC leader. Coincidentally, Eliot Engel defeated her grandfather Mario Biaggi in 1988 to win his congressional seat] because I grew up in the district. That was another amazing race. People got fed up with the status quo. You saw it with AOC; you saw it with the IDC challengers like Biaggi and Jessica Ramos and others. Then Tiffany Cabán was another, further cementing my idea that there were disparate forces of progressive pushback in New York: the progressive caucus in the City Council, the Working Families Party (WFP), New York Communities for Change. DSA was a nice fusion of new people and energy that got into this critical mass.

Prior to Bernie Sanders’s presidential run, national membership was around seven thousand people. Then there was this explosion. I think DSA and Bernie spoke to people who thought, “Capitalism isn’t getting the job done on health care or education.” DSA gave a cohesive vision and platform on issues like Medicare for All.

For me, that was the appeal of DSA. Early in 2017, it was impressive to see people being very strategic about who they were going to back and why, being on the electoral committee. Sometimes there’s an impulse to primary everyone everywhere. I get that desire to take on the establishment. But it was also nice to see a realization that you need money to run campaigns, district demographics matter, who the incumbent is matters.

I started with the Cabán campaign about ten weeks out. I had heard a lot of buzz about her, and I sat down and interviewed with her and came away really impressed. What was interesting about the Cabán campaign is that it was very unapologetic. She was straightforward. She said, “We’re ending cash bail.” And other candidates were like, “We’re ending cash bail, but with this scenario, and with this hypothetical, and this caveat applies.”

That was a tough one. We lost by fifty-five votes. I’ve replayed in my mind all the things I could have done differently. When it’s such a narrow margin, there are a lot of things you can second-guess yourself on. One thing you learn is that in many ways, the fix was already in before the ballots were recounted.

The process of voting in New York City, in New York state, across America — for a country that prides itself on being the first democracy, we can’t seem to pull off a basic thing like an election without serious problems like long lines and machines breaking, and confusion about the ballots, and not getting a ballot that you applied for. These are the fundamentals of democracy. With the recount, you saw the flaws.

They make it hard to do this because they don’t want a broad amount of people voting. It’s made to discourage people. They’ve clearly decided to make this a little bit harder than it needs to be, and for enough people, it’s like, “Why bother? I can’t wait in line for an hour because I have things to do.”

The process afterward, you learn. DSA plugged in to do this whole canvass. We had photocopies of every ballot cast. It was this very complicated filing system to try to find any way to get that margin — it was intense.

I started with Bowman in the beginning of December, so I had seven months [as a head start]. Having more time on the campaign helped to shape and anticipate things. Also, with Bowman, I was familiar [with the district] — I grew up in Riverdale, my parents’ house is still there, the polling place where Eliot Engel voted is where I went to middle school.

Yeah, actually, I volunteered for his campaign in 2000, when Larry Seabrook challenged him in the primary. I think that was the last competitive primary he had. So with the Bowman campaign, I had a familiarity with the borough, and particularly with the North Bronx. My brother went to MS 181 for a year or two. I had a familiarity with the turf.

Also, with Bowman, familiarity with Engel and having a good foil helps. It’s not a machine — it’s this individual that has a record that there was a lot to pick apart on. His absence from the district was real. I remember him living in Maryland even back in the ’90s. I remember his kids went to school in Maryland.

With Cabán, it was the only primary going on in the city, so if you were a political lefty last summer, looking for something to get involved with, there’s Tiffany Cabán, and that was it. This time around, it was more diffuse, because there were more races. Brooklyn DSA really went all in for Cabán last year. Same with Queens. There were all these primary challenges as well.

Another thing, too, was that Andom Ghebreghiorgis [a former special education teacher and DSA member whose campaign focused on linking foreign policy and domestic policy, who suspended his candidacy on June 1 and endorsed Bowman] was running and was courting the DSA vote. So there was robust discussion among DSA members of the Lower Hudson and the Bronx/Upper Manhattan branches of NYC DSA about, “Who do we endorse?” So I think there was more unity behind Cabán because that was the only race going on citywide, and she was the only candidate to engage with the DSA crowd. Whereas in the Bowman race, there were two different candidates that were courting it actively.

There were several candidates that were nominated by various community members to Justice Democrats, and they ended up on Jamaal. From that, there was work to get local political groups to come on board. The Jewish Vote was our first endorser coming on board, then Working Families Party, Make the Road Action, Community Voices Heard (CVH), New York Communities for Change. So a lot of groups that were involved in the 2018 fight against the IDC also coalesced around us.

In January, we got endorsed by CVH and Make the Road Action on the same day in Yonkers, and a week later it was WFP and [New York City public advocate] Jumaane Williams. The sequence helped coalesce resources and attention around Jamaal’s candidacy.

And other local groups started to take notice and get involved. Also, national groups helped. It was nice to see that momentum build as more and more groups were like, “Oh, something’s going on in the 16th. This Jamaal Bowman character is really impressive.” I’ve got to give him a lot of credit for getting these endorsements because we always got feedback from these community groups that said, “Our members really liked him.” There was a genuine connection, and they liked his vision, his charisma. He earned every endorsement.

Part of what was satisfying about this election night was that you could see the grind of dialing for dollars. When I say dialing for dollars, he was not calling for $2,800 a pop — he was calling people, like, “Can you donate $35?” Just going through a list and working that. Also, engaging with voters in these local political groups: “I’m going to a meeting in tower 17, I’m going to sit down and talk to seventeen people at a time.”

This is a credit to you and other local and national leaders — I think there’s been a very intentional building out the bench. That’s been nice to see over the past few years, having more members go through the process of learning the basics of campaigning. It’s a lot of monotonous work. DSA people are really good about going into it with eyes wide open. They’ve been good about developing a team of people with experience running campaigns.

People are learning the ropes of campaigns. They’re coming up with systems for raising money, what campaign literature looks like, what the message looks like. People learn how to write press releases, how to pitch a story — all the basics of a campaign. DSA has been good about building out that bench. In DSA, you have people who have done five different races, but they’re all very conscious of bringing in new people to take leadership roles on campaigns.

I think success breeds success. What’s coming up in New York, all of the City Council races, will be really fascinating. There’s thirty-six or thirty-seven that are open. It’ll be interesting to see which districts DSA focuses resources on, where they can find candidates. Because I think there’s potential to show how much DSA has grown since 2016, kind of being the new kids on the block, so to speak. I don’t think this is a fad. DSA is building power. We see this not just in New York but in other places.

I remember in 2017 it was like, “Who can we find to run?” Now it’s a year or two later, it’s like, “There are three people who are asking for our endorsement.” That’s significant. It’s less like a novelty. I think that’s a good sign. DSA is seen as a center of power.

We’ll have a better sense of that now that the campaign’s over. We can dig into that on the data end. On the anecdotal and personal level, Jamaal has talked a lot about his interactions with police brutality. It started back when Michael Bloomberg was running for president — Jamaal released his op-ed about one of his unfortunately many experiences with stop-and-frisk and police brutality. He told a story on the campaign trail that always stood out to me about his first time getting roughed up by the cops. He was eleven years old.

I think for him, the recent protests stirred up a lot of memories that he had understandably suppressed. Sometimes he’ll talk and be like, “Oh, yeah, there was that other time I got pulled over,” and I realized that was just something that just happened to him on the regular. That was hard to hear, this repeated trauma.

As far as the ripple effects, Jamaal mentioned this as the government failing us on a very basic level. I think the Black Lives Matter protests recently tapped into this existing anger at the failure of government to prevent a national crisis. There’s no leadership; there’s no sense of security. On top of this, the daily oppression and grind of racism that black and brown communities face every day — that coupled with COVID created this pent-up frustration that needed to be expressed.

People really resonated with his lived experience with police brutality, being a middle school principal of an overwhelmingly black and brown school in the northeast Bronx with a very high poverty rate. This is a man who professionally and personally has dealt with the failings of government and the structural racism, poverty, sexism. It’s hard to engage a sixth-grader when last night they got evicted from their house, or they didn’t have breakfast because they don’t have food.

People are tired of the status quo, and Jamaal Bowman is very much the future of the Democratic Party.