Former Trump Field Staffers Detail Iowa Team’s Dysfunction

Photo by Paige Godden

By Isabella Murray

September 29, 2020

Shekinah Hollingsworth sat crying in her Ford Fiesta outside Cedar Rapids’ Coe College last October.

The Iowa Trump Victory field organizer had just left the school, where she was meeting with a student on behalf of President Trump’s reelection campaign in the state before it was interrupted by a scathing phone call from State Director Carly Miller and Deputy State Director Kerrick Kuder.

Miller and Kuder were upset with Hollingsworth because the Maryland native hadn’t shared with them the fact that she worked a second, early morning job in order to afford being an organizer in the state—as a full-time Trump field organizer, she was earning around $2,100 a month with a stipend of $300 for campaign expenses.

“Carly and Kerrick called me together to berate me and accuse me of dishonesty, laziness, and overall lack of willingness to be committed to this campaign due to their discovery of my part-time job,” Hollingsworth told Starting Line. “I didn’t tell them about my part-time job because I was really afraid of the reaction for good reason … I needed the part-time job. I ended up doing Doordash as well.”

Embarrassed and distressed, Hollingsworth decided that day she would resign from her position with Iowa Trump Victory after only having worked for a month and a half.

“This is not worth the amount of stress and anguish that I’m going through. I’m a very capable person and I’ve been on campaigns before,” Hollingsworth said of the experience, compounded with a number of other factors that caused her to leave.

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Hollingsworth’s complaints of humiliation, stinginess, and isolation while working for Iowa Trump Victory isn’t unique. With an exceptionally high turnover in field staff working for unusually low salaries, three additional former staff members have come forward to Starting Line with disheartening experiences from the campaign to reelect the President in Iowa.

“The turnover was unusually high. That’s putting it lightly,” said a former Southeast Iowa Trump field staffer who requested anonymity. “I mean, obviously in politics you have turnover naturally. But not to the extent that I saw there … I believe Iowa Trump Victory is almost 100% turned over.”

State leadership demanded unattainable doorknocking, phone call and signature goals, every staffer said, while offering little training or expense money and upbraiding field staff for working with local contacts, among other issues.

And during a time when Iowa poll numbers show tightening margins between Trump and Vice President Joe Biden, as well as leads for Democratic Senate candidate Theresa Greenfield, the former Trump staff admitted their lack of confidence in GOP victories in Iowa this November.

“Our drive from our superiors was heavily focused on an arbitrary numbers game, in a state where over 90% of people who are eligible to vote are already registered. Though I was hired as a field organizer, we were still dictated on who to speak to, who to organize with, and to drop anyone who wasn’t deemed useful,” said Hollingsworth.

The Trump campaign itself has pulled four weeks in a row of Iowa TV advertising as the national campaign struggles with a cash crunch near the end of the election, all while Joe Biden’s campaign has recently gone up on TV here.

State Republican Party leaders, though, tout the Iowa Trump operation as one of the best in the country, praising the leadership team and the amount of voter contacts they’ve done throughout the course of the campaign.

Press contacts at the RNC and state party did not respond to Iowa Starting Line’s multiple requests for comment for this story.

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High Turnover

Hollingsworth’s attempt at quitting the campaign ended poorly, she said. After calling her regional field director to tell him she’d be turning in a resignation letter, Hollingsworth said the director seemed “bewildered” on the phone before hanging up on her.

“So I typed up a letter for Carly and Kerrick and I got a response from Carly immediately — she kind of pulled the, you can’t quit, you’re fired kind of thing.”

The former Trump staffers counted about 24 Trump Victory Iowa staff who have quit or were fired since late last year, Hollingsworth said. The three other former staff members who spoke with Starting Line confirmed this number, which is close to what they say is the entirety of the campaign’s Iowa field operation — a team of about 25-30 people right now.

“[Iowa leadership] has run a revolving door campaign that has caused many former staff to just try and forget they were ever part of this poorly structured campaign,” Hollingsworth said.

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A former Central Iowa field organizer who quit in August 2020, who also requested anonymity, said that her departure from the campaign was followed by a number of others.

“When I quit, five people at least left either in the next couple of days or that week,” she said. “When I left, everybody started leaving. And now they’re pulling people in from different states to work in Iowa. Because [they have] no options,” she said. The Central Iowa organizer said she was one of the few members of Iowa Trump Victory who is from the state.

“They now have field organizers aged 17 and 18, and someone in their 60s.”

Toxic Work Environment

One of the most cited reasons among former Iowa Trump Victory staff for leaving the campaign was the hostile and sometimes malignant work environment.

The Southeast Iowa field organizer lasted the longest with Trump Victory of the four former staff members that Starting Line spoke with. The Illinois native was a field organizer in Southeast Iowa for four months, beginning in February and ending in May.

He quit because he wanted to be back home with his wife and children during the pandemic and was tired of the “toxic work environment” of Iowa Trump Victory.

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The staffer, who had worked before on gubernatorial campaigns and at a political firm, said that like most jobs in politics, the President’s Iowa reelection campaign was intense. But Iowa Trump Victory had an additional layer of isolation and unattainable demands.

“That’s not really unusual, but I guess I could say there is kind of like an extra level of coldness to it, whereas in other campaigns or political work, it’s not quite that ostracizing,” he said. “It’s an around-the-clock kind of operation with any political job, but other campaigns, there’s actual camaraderie, there’s actually an onboarding process that can take days, weeks, not a single day. It was all just about the data, the numbers and nothing else — it almost seemed like inhuman to a point.”

The job’s red flags began to rise as soon as the onboarding process, he said, which was similar to the other three staffers’ experiences.

A 20-year-old field organizer who worked on the campaign for 4 weeks in Des Moines said that upon arriving in the state, he had no direction from leadership, and was simply sent straight out to collect ballot petition signatures.

“The first week went by, and I asked when I would be trained. And they kept saying, ‘it’s really busy right now, keep working,’” the organizer said. He asked leadership some weeks later for some more direction, and they instead cut ties with him.

He spent his four weeks working for the campaign in Central Iowa living in a hotel with limited contact with state leadership. The young organizer did busy work like sign delivery, rally attendance, phone calls and door-knocking but never got trained to be a field organizer, which he was hired onto the campaign to do after having worked on three past GOP campaigns.

“They didn’t tell you what to do or what not to do, but the minute you did something that they didn’t like, you were in big trouble,” he said. “I’ve seen better campaigns run off of less money and better leadership and better coordination. It just felt very sloppy. We had the money, we had the resources. It was horribly used. And it was evident in our numbers. Every single week we would get yelled at because of our numbers.”

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The morale on the team’s daily and nightly calls was also very poor, said the former staffers. All were fearful of being singled out and humiliated on account of their numbers.

“I compare it to when you’re passing notes around a classroom in elementary school and the teacher catches it and reads it in front of the class,” said the former Central Iowa organizer. “They’ll humiliate you.”

She said that at one point in late July, her district was doing particularly poorly with numbers because one of their team members had COVID-19.

“One of our team members got the coronavirus, so all of us were basically in quarantine, and there was no sympathy. They were still making the guy who got COVID [but did not have serious symptoms] do phone calls. They were still making him work,” said the Central Iowa organizer, recounting the day that her boss, the regional field director, quit his job on a phone call.

“[Leadership] was just tearing [the regional field director] apart, saying, ‘What is it? Were there eleven volunteers active? Thirteen? Come on. What is it?’ And he was stuttering because he was put on the spot and she was like, ‘Do you think? Or do you know?’ It’s just these scare tactics to try and intimidate people.”

After the call, the regional field director went silent, she said. After attempts by the team to text and call him, they received news that he had quit.


Low Pay

Difficult staff check-in phone calls weren’t the only problem. The Central Iowa organizer said she can remember a traumatic call she had with Miller and Kuder when her living situation became complicated — they remained insensitive about her finances and sudden loss of housing, she said.

“I was like, you guys realize, I don’t know where I’m going to live. I still have to figure this out,” the organizer said. “I was near in tears on a Zoom call with them … And that should have been the time I left. But I kept pushing forward.”

The 20-year-old organizer said that because of Iowa’s status as a swing state, the campaign didn’t have a lack of resources, but they were particularly stingy with organizers, who mostly made around $2,100 monthly.

He said the campaign was what happened when you have “basically an unlimited checkbook with crappy staffing and lack of leadership more concerned about their personal agenda than the race. They’re busier with patting themselves on the back than actually completing stuff.”

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The Southeast Iowa organizer said his salary was not $2,100 a month like the three other Iowa Trump Victory field staff that Starting Line spoke with — his was around $3,000. But he was shocked at how low each organizers’ expense portion was — around $300 each month. Campaign materials had to be paid for by organizers upfront with later reimbursements from the campaign.

“The last campaign I worked on handed out $2,000 for expenses and this one I didn’t have half of that. I would go through the expenses quick,” he said.

Two of the staffers said that health care wasn’t provided separately, but was assumed as part of their salary.

Coordination With Local Campaigns

The Central Iowa field organizer said that she finally quit her job after she was reprimanded by leadership for going to a GOP event outside of her turf to support some friends in the state.

All four of the former Trump field staff who spoke for this story said they were often warned by the campaign when they worked with local GOP county chairs or candidates.

“When I would speak to the Linn County Republicans on the ground, they would tell me how Trump Victory was not providing any resources to the local Republican races going on there. Another thing I found weird was how much they tried to restrict me from working with other Republican candidates,” said Hollingsworth.

After an attempt to collaborate with Rep. Ashley Hinson’s campaign, Hollingsworth said she was told that she wasn’t permitted to do so.

“They would yell at us for not attaining these numbers,” she said. “But when I would try and reach out to find help through these coalitions, then I would also get yelled at.”

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However, several of the Republican county party leaders that Starting Line reached out to strongly disputed this characterization.

Laura Kamienski, the chairperson of Linn County Republicans said she has a “great working relationship” with Trump’s campaign.

“I have a great working relationship with the staff in the Cedar Rapids victory office,” she said. “They have signs for all of our local candidates that have them available. I have no complaints.”

Bill Dahlsten of the Linn County Republican Central Committee also said that his relationship with Iowa Trump Victory was positive.

“I have been an active Republican volunteer for 50 years in Des Moines, Scott and Linn counties. Recently retired, I have been spending more time doing so at the Cedar Rapids office. I have found the Trump campaign staff helpful and easy to work with. Issues come up. They always do. The 2020 Trump crew has been far easier to resolve issues with than some campaigns I have dealt with over the years,” said Dahlsten.

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But the young organizer who worked in Des Moines said that the reason he was given for his firing was that they “couldn’t trust him,” in part because he was reaching out to local parties without their knowledge.

The Southeast Iowa organizer also said that Trump’s Iowa campaign kept isolated from others.

“They definitely weren’t that cooperative with the county organizations or the local organizations. They acted like it was kind of like a one-man team, even though usually you work with the county chairs to get your connections,” he said.

Overall, the former Trump organizers, who all remain Republicans, worry about what the operation they experienced will mean for the party in Iowa up and down the ballot in November.

“In order for the President to win his reelection, he needs a team of dedicated, compassionate leaders, that lead in a way where others want to follow, and not prodded into doing so,” Hollingsworth said.


by Isabella Murray
Posted 9/29/20

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Iowa Starting Line is an independently owned progressive news outlet devoted to providing unique, insightful coverage on Iowa news and politics. We need reader support to continue operating — please donate here. Follow us on Twitter and Facebook for more coverage.

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