When Sean Butterfield started door knocking for the re-election campaign of Seattle’s only socialist city council representative, Kshama Sawant, earlier this year, he knew his task was not easy. Last year Sawant took on one of the world’s biggest corporations, Amazon, with a tax intended to fund public housing, and nearly won.

Butterfield reasoned that Amazon, along with the rest of Seattle’s formidable business sector, would make its presence felt as the primary election day on 6 August drew closer.

So it has happened. Well over a million dollars in political action committee money has poured into Seattle’s local elections, with the city’s Chamber of Commerce Pac alone spending $1.1m (Amazon contributed $250,000), and two other Pacs pouring in another $477,00.

Together, the Pacs have spent over $312,000 on Sawant’s race alone, much of it coming in the form of attack mailers.

More than a dozen of Amazon’s top executives have also now donated to one of Sawant’s primary opponents, Egan Orion. The list includes Jay Carney, the former press secretary for the Obama administration who is the PR and policy chief for Amazon. Two of Amazon’s three CEOs have donated to Orion as well, with Jeff Bezos being the only one not to have personally chipped in, according to numbers from the Seattle Ethics and Elections Commission.

Butterfield, a 35-year-old healthcare worker, was surprised at just how effective the money was, even when spent on campaign mailers. Dozens have hit mailboxes in the district since mid July, and he didn’t grasp their impact until he started seeing – and hearing – it as he went from door to door.

“It’s just shocking when you go knock on somebody’s door, and it’s just a barrage of these talking points,” Butterfield said. “It’s not too hard to untie these knots, the arguments these talking points rest on, but you can’t do that with everybody. We can’t knock on every door.”

But while the mailers might be effective, the role of business money and Amazon in the race could play well for Sawant, who is facing five other candidates besides Orion, with the top two going on to the general election on 5 November.

“This race and indeed all of the city’s elections this year will be a referendum on one fundamental question: who gets to run Seattle? Big business like Amazon and real estate corporations, or working people?” Sawant told the Guardian.

A 46-year-old former tech worker who left the field to obtain a PhD in economics and enter grassroots organizing, Sawant has built her political career on championing social movements and taking on big business. Her message has resonated in Seattle, a city with one of the highest rates of gentrification in the country, and where residents have become increasingly skeptical of the influence of Amazon and its large downtown campus.

Sawant, a member of the Socialist Alternative party, drew national attention in 2015 as one of the driving forces that led Seattle to become the first major city to adopt a $15 minimum wage, and again was in the spotlight in 2018 as she pushed for the so-called “Amazon tax”.

The proposal would have levied a $275-per-employee “head tax” on corporations making over $20m a year to fund new public housing and homeless services. Seattle has the third-highest homeless population in the US, behind only New York and LA.

The tax initially passed, but was repealed only a month later after Amazon threatened to move jobs out of the city and teamed up with labor unions, who were afraid of job losses, in a campaign that attacked the plan as a job-killer that could drive the city’s largest private employer out of town.

The differences between Sawant and Orion, both ideological and strategic, are telling in that they echo conflicts occurring between progressives across the country. While the two agree on the problems facing the city, like homelessness and affordable housing, they offer radically different ways of solving them.

Sawant’s uncompromising style of confrontational, movement-driven politics has made her enemies – including some in labor – and critics often accuse her of being divisive. Orion, an entrepreneur known for saving the city’s pride festival, PrideFest, says he represents a different approach.

As the executive director of a neighborhood chamber of commerce, he accepts that business is backing his campaign. He criticizes Sawant for receiving a substantial amount of individual donations from people outside the state – and she’s raised more money than other candidates, reflecting the fact that she’s an incumbent with a national profile. For his part, Orion sees the support he gets from business as a sign of the effectiveness of his less confrontational, more partnership-driven model of politics.”

“Kshama Sawant is the worst partner for our large businesses. You know, a bologna sandwich would be a better partner,” he told the Guardian.

On homelessness, Orion argues the city doesn’t need more tax revenue from business but instead should focus on “getting better outcomes”, with the funds currently being distributed to non-profits who work with the homeless population.

The two also differ on how the city should create more affordable housing. Orion favors increasing urban density and cutting regulations to encourage developers to build more housing, arguing that would increase housing supply, and therefore lower prices.

Sawant advocates for rent control, an idea, that despite its many critics in academia, is resurfacing as a force in Europe, with some traction in the US as well. Like the yimbys, she supports density and upzoning, but thinks the government and not the private sector should be doing most of the building, saying that purely market-based solutions are “naive at best”.

For Rich Smith, a reporter covering the race for Seattle’s alternative weekly, the Stranger, a Sawant v Orion matchup, if it happens in the general election, would reflect a larger clash happening in the city between more well-off residents who identify as progressive on cultural issues like gay marriage or immigration, but are more moderate on economic issues like taxes or housing, and younger, working-class voters who are generally more willing to embrace the ideas of socialist candidates like Sawant.

“There is a whole contingent of people in Seattle who typically have money, who are Democrats or consider themselves progressive, and think that Seattle is the most progressive place on the planet,” he said. “And so they don’t like it when people point out that there’s huge issues, at least structurally in terms of homelessness, transit, economic inequality, housing or other crises that we’re facing,” he said.

Butterfield, the Sawant campaign volunteer, thinks her direct style makes existing conflicts more visible, and he welcomes it.

“That’s why people call her divisive and claim that she won’t bring everyone to the table,” he said. “As though Amazon doesn’t have a voice in Seattle politics, it’s preposterous, right? I mean, they own the damn table.”