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Election Strategy with Soul: Lessons from NY’s Challenger Fights

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A group of 2 white women, a black man and black woman hold their fists in the air on the podium at a rally

This piece was written by a group of campaign organizers from the Cynthia Nixon, Jumaane Williams, and Zephyr Teachout campaigns in New York State in 2018. 


The September 2018 primary elections in New York was a watershed moment that shaped politics across the state. A massive coalition of community organizations and grassroots electoral organizations (like Indivisible and the Democratic Socialists of America) came together in a joint effort to reshape the political terrain of the state. Multiple challenger campaigns came together to form a left electoral flank. They leveraged primary challenges against corporate Democrats, in the State Senate and state-wide campaigns aimed at winning the state Governor (Cynthia Nixon), Lieutenant Governor (Jumaane Williams) and Attorney General (Zephyr Teachout). The State Senate challengers won, by and large, and they took Democratic control of the Senate for the first time in a decade. But the state-wide campaigns ultimately lost in their primary challenges. There are valuable lessons to be gained from these campaigns, and this piece attempts to capture the lessons learned by staff members who came together to debrief the Cynthia Nixon, Jumaane Williams, and Zephyr Teachout campaigns.

Lesson 1: To beat the machine, you need time to build up your forces.

The process of picking a challenger to the political machine in New York was a long and complicated road. One of the major issues with the process of aligning behind a solid candidate and building up endorsements for them is that it take serious time. The seeds of these three campaigns started to germinate in early May 2017. Progressive organizations around the state wanted a challenger to Andrew Cuomo, a corporate Democrat who has a powerful political machine and who was running for a third term. But the prospect of facing Cuomo’s ubiquitous control of New York politics made it difficult to find an experienced political candidate who was willing to take him on. Cynthia Nixon courageously stepped up to the challenge. Jumaane Williams a long-time Working Families Party leader stepped up to the plate to challenge Cuomo’s Lieutenant Governor, Kathy Hochul. Zephyr Teachout who challenged Cuomo in 2014 stepped into the left flank to run a powerful Attorney General race.

Jumaane announced in February 2018, which gave him six months to campaign. Cynthia Nixon announced on March 19th, giving her just five months to run a campaign to challenge the powerful Cuomo machine. Zephyr Teachout’s timeline was even shorter: Eric Schneiderman resigned in May and this triggered an unanticipated election for a new Attorney General, giving Zephyr just over three months to build her campaign.

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Time is money in a campaign. Said another way, lead time can make up for the lack of money in a grassroots campaign. We will never have as much money as the establishment, so we need to take a long-term approach to building our electoral base. That means that our candidates have to announce earlier. Community organizations have to endorse earlier, and infrastructure has be built further in advance. Statewide insurgents should plan to have close to twelve months to build out their campaigns. Grassroots organizing takes much more time than buying millions of dollars in commercials, but it is our only route to victory.

Lesson 2: Unionize campaign staff before you need to.

We organized a debrief for campaign staff so we could take a collective breath in the wake of a hard-fought battle. Campaigns are tough on relationships, and staff conflict is the norm. This election cycle was no different, with one remarkable example: the successful unionization of the staff of the Cynthia Nixon campaign. Supported by Campaign Workers Guild, campaign staff workers won wage increases for under-paid people of color on staff and benefits like one day off per week, and severance pay.

One of the hardest fights was winning a high level staffing change that dramatically improved the day-to-day working conditions for front-line and middle-level staff. This change greatly expanded the Nixon campaign’s capacity to enact a much more coordinated strategy that could work with more integration with the Working Families Party, community organizations, and the campaigns for Jumaane and Zephyr. The union was not only able to win workers’ rights, but also improved Cynthia Nixon’s chances of winning the campaign thanks to increased slate-wide collaboration.

These challenges are not isolated to the Cynthia Nixon campaign. Verbal abuse, sexual harassment and wage theft are rampant in electoral campaigns, making unions essential to both the individual well-being of staff and the broader left electoral project.

A key lesson we drew from these experiences: unionize before you are forced to. Reach out to Campaign Workers Guild, and begin the process while it still feels unnecessary. The amount of time wasted in tense negotiations with management in the final two months of the campaigns and the challenges of organizing a staff that was 45 people strong made the process much harder than it needed to be. Even the most progressive management will often struggle to embody their values internally in organizations where worker exploitation “for the good of the cause” has become the norm. Take the time while the team is small and the working conditions are acceptable to unionize as an essential structure that keeps a campaign team healthy, so that, when you need the union, it is already in place. (For a fuller story and play-by-play of how to unionize your campaign, listen to the Campaign Workers, Unite! There is Power in a Union episode on Healing Justice Podcast.)

Lesson 3: In a statewide race, spend like a small campaign.

One of the central pieces of our debrief was a deep analysis on the different ways that the three campaigns spent their money. Together we poured over public records, researched consultants and calculated the percentage of money each campaign paid for what types of services. In this analysis we identified two different spending trends.

One strategy – employed by Andrew Cuomo, Sean Patrick Maloney, Tish James, Kathy Hochul and Zephyr Teachout – was to spend 75% or more on digital and TV advertising. This trend illustrates the enormity of the state of New York and the size of the electorate. One and a half million Democrats voted in the September 13th primary, close to double what some of the most experienced political operatives in New York predicted. It is financially and physically impossible to call and knock on the doors of that many people, so there is a strong argument for reserving very large percentages of spending for advertising, for both corporate and grassroots campaigns.

In contrast, the Cynthia Nixon spent a very small proportion of its budget on advertising. Our analysis of the campaign revealed that the campaign spent 33% of its money on staff, 33% of its money on consultants and only 13% of its money on advertising. The argument for spending large amounts of money on advertising could be overcome if we have massive grassroots organizing efforts, extremely inspirational candidates, and enough time to build up our campaigns. These kind of field efforts are possible and, in many ways, preferable, if we have the correct circumstances. We didn’t have those circumstances in these campaigns, so it would have been a more strategic choice in this case to invest more heavily in advertising. This would have been a very hard pill to swallow for field and grassroots organizers, but we need to be real about the conditions we’re working in.

Second, our assessment is that there was an over-investment in consultants in this campaign. Looking deeper than the 33% of campaign funds that was spent, we saw that over 22 total consultants were hired at a cost of $635,000, not including direct purchase of advertising. What drove this spending strategy? The kind of new candidates that we need don’t have deep electoral experience, and there is a tendency to think we must buy that experience in the form of high-priced consultants. You can “buy experience” to an extent, but the math gets tighter and tighter depending on how financially overmatched you are by your opponent. Massive corporate contributions meant that Cuomo had about fifteen times as much money as the Nixon campaign. Because the planning in the early days of the campaign was unclear and because staff upheaval made continuity difficult, the campaign over-relied on a large number of consultants. Twenty-two consultants with differing strategic orientation made coordinating a path to victory very difficult.

Lesson 4: Organize for the long-term.

Our debrief was attended by four different field directors, each of whom had years of grassroots organizing experience. But we are still not sure if our campaigns should have had field programs at all. Why? The money that we spent on field could have been spent on advertising. In the future, without a year-long campaign and clear strategy to integrate volunteers into ongoing community organizing after the election, we would not encourage campaigns to invest such a high proportion of their resources in field programs. Here are a few recommendations for movement-oriented campaign field organizing:

A. Build close relationships with the community organizations that your candidate represents. Strategize ways that campaign volunteers who live near the organization and care about their issues will become the future members of that organization, whether the candidate wins or loses. Organizations like Citizen Action New York were involved in the statewide campaign, and they used data collected to further their membership program. On the flip side, community organizations have to learn to better use the data that is harvested during campaigns to do mass membership drives and grassroots fundraising. Campaigns need to plan for how they will responsibly transition their volunteers to community organizations, whether it’s through building relationships or sharing lists and data.

B. Campaigns must plans to build spaces for their volunteers after the election, win or lose. These spaces could include appreciation parties, trainings and next steps for future involvement. For example, our friends at the Jess King Congressional campaign in PA kept up with leaders through post-election one-on-ones, holiday parties for regional teams that the candidate attended, and mass meetings in multiple cities where the candidate and campaign staff attended and spoke about how it is important for electoral volunteers to also engage in issue-based work. Their campaign staff is also involved long-term with those organizations on the ground. This transfers relationships between the campaign and local organizations and it makes a strong case for hiring locally whenever possible – even if organizations and campaigns can’t coordinate during the campaign itself. They also donated leftover funds from the campaign to local organizations (Lancaster Stands Up, York Stands Up, and the Democratic Party). Our campaigns did a host a joint volunteer thank you call with Working Families Party. But it was late and very brief, and it could have gone much further. It is critical to use our electoral campaigns to intentionally develop grassroots infrastructure for the long term victory of the left.

C. Campaign workers also need long-term support and integration into movement work. After a campaign ends, many campaign workers with incredible talent and drive for justice are left out in the cold. One beginning step is planning for severance pay (which the Cynthia staff received after bargaining for it with the support of Campaign Workers Guild). But two to four weeks of severance pay is a survival plan, not a future plan. The endless churning-through of staff is taking great potential leaders and giving them an experience of the movement that is comparable to working at McDonald’s during rush hour for six months straight. If we care about justice, we better care about people. And these are the people that care the most about this work. They are a resource that we must stop wasting.

Lesson 5: Coordinated slates show promise, but they need work.

Although Cynthia, Jumaane and Zephyr didn’t win, the New York State Senate was reclaimed by the Democrats. The Independent Democratic Conference (IDC) was completely destroyed, as six of their eight members were defeated. In every election district where Cynthia, Jumaane, and Zephyr did well, IDC challengers saw a bump in their vote total. Although we could not take full advantage of the massive turn-out motivated by anti-Trumpism, we mobilized more young people and more new voters than ever. New progressive voters that might not have made it out to vote for a smaller state senate race were motivated by the Gubernatorial, Lieutenant Governor and Attorney General race.

In the future, the progressive slate must be run as an actual slate, not just as the three most progressive candidates working closely together. This is a difficult task, given the particular dynamics of the Attorney General race, in which Tish James, a long-time ally of the Working Families Party and Jumaane Williams, decided to run as part of Governor Cuomo’s slate. This dynamics, combined with the challenging racial implications of endorsing a white candidate, Zephyr Teachout, to run against a Black woman candidate in a majority-people-of-color city, made it difficult for the campaigns to cooperate deeply from the start. In the future, a true candidate slate could go as far as having one joint staff, which would drastically cut expenses and present a powerful new vision for New York.

Lesson 6: Build a Healthy and Expansive Electoral Culture.

Campaign organizers came together for a debrief, and we collaborated on this article to intervene on a toxic culture of electoral organizing. This culture is burning through amazing organizers, and it is not helping us to build the long-term power that we need to win. Going forward, we developed a few recommendations for changing the culture of electoral organizing.

A. First things first: Share Knowledge. This isn’t rocket science, folks. If we keep treating knowledge about electoral organizing like it is a rare commodity, we will never have enough rocket scientists to make it to Mars. If consultants, community organizations and campaign managers continue to hold onto their stories and their learnings from campaigns like they were Gollum hoarding his precious ring, we will never learn from our successes and failures. We will never teach the next generation of organizers. Experts in this field need to provide more free trainings to the public and more mentorship to newer organizers.

B. Have better meetings! The most basic elements of good facilitation and group building practices seem to be completely forgotten when it comes to electoral politics. Elections move fast, but – for a group of people who pride themselves on efficiency – we have been surprised by how inefficient and disorganized meetings can be in the world of electoral organizing. There are often no clear facilitators and no set time limits for agenda points. Because meetings are the places where groups come together, setting good cultural norms in meetings sets a strong foundation for organizations. Quick personal check-ins at the beginning of meetings humanize our coworkers, and they help to create emotional depth within groups that can strengthen bonds, soften conflicts, and allow people to be a little more of their whole selves. We can draw on our own cultural traditions and community practices, incorporating them into our work spaces in the form of song, art, ritual and more.

C. Finally, hold debriefs! All the lessons presented in this article were harvested from a meeting of former campaign staff members. In elections, there are sometimes debriefs, but they are usually only for the most senior staff members and executive directors of organizations. This has far-reaching effects. It diminishes the development of new leadership, because staff members are not given a space to talk about lessons learned, to ask questions of management, or to get an honest assessment of the strengths and weaknesses of their campaign. At the same time, senior staff members lose a great deal of potential knowledge by not hearing about or learning from the experiences of their employees.


The American Left has made great electoral strides in recent years.The left has brought much of its deep knowledge of community organizing and digital organizing to bear on local elections with a high degree of success. In 2016, thirteen million Americans voted for Bernie Sanders, a democratic socialist, who raised class politics more clearly than we’ve seen on the political landscape in decades. Major victories by Alexandria Ocasio Cortez, Rashida Talib, Ayanna Pressley and Ilhan Omar show that we are on a healthy trajectory towards left electoral victories.

Of course, there are many less hopeful signs on the state and national landscape. The losses of Bernie Sanders, Stacey Abrams, Andrew Gillum, Beto O’Rourke and Cynthia Nixon illustrate the difficulties of winning large-scale elections. But victory at these levels is possible if we can integrate electoral organizing with grassroots base-building and if we can develop a culture of care that nourishes organizing for the long haul. Moving forward, membership-based community organizations need to operate more like electoral campaigns, and vice-versa. Community organizations without C4’s or PACs should become a thing of the past.  Serious candidate pipelines should be integrated in leadership development programs. Community organizations need to learn to use voter files and data sets to target new members in the same way that elections target voters.  Member recruitment should utilize targetted Facebook, Instagram and Twitter outreach, as well as mass texting and auto-dialers. At the same time, electoral organizing needs more soul. Electoral campaigns need to take the processes of training, leadership development and building an intentional organizational culture more seriously. Throughout this journey, we must continue to build a beloved community of organizing that grows exponentially with each legislative and election cycle completed. This is the only way that we will create governments that are staffed by members of our organizations and representatives of our communities and movements that can chart a course to a new society.




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