Editor’s note: This article is part one in a series looking at how the left is organizing in electoral races in western Massachusetts amid Donald Trump’s second term in office. Part two focuses on local candidate in particular.
It wasn’t hard to spot Jeromie Whalen as he drove into the parking lot of Hadley’s Sunraise Printing in late August. His bright yellow, 1988 Toyota Van — “literally, the model is ‘Van'” — immediately drew attention. A big plastic cup of Cumberland Farms iced coffee sweating in his hand, he oozed affable energy as he chatted with the workers who were ready to paste decals on the vintage vehicle.
“Jeromie Whalen for Congress,” the stickers read. “MA-01.”
For as long as Whalen’s van has been on the road, the region has been represented in the U.S. Congress by Richard Neal, a more conservative Democrat who has become one of the party’s most influential representatives. In recent years, three left-leaning challengers have all lost in landslides to Neal, whose campaign account is stuffed with corporate cash that he has wielded to fight off those progressive hopefuls.
But Whalen thinks this time, things will be different. The 38-year-old high school teacher intends to spend nearly a year on the road, driving his 37-year-old car across the state’s largest congressional district — from Williamstown to Springfield to Oxford — in an effort to upset a 36-year incumbent.
“It’s an enormous feat to do something like this,” he conceded.
Whalen isn’t alone in looking to shift politics to the left amid the realities of a second Trump administration. A new wave of progressives have decided to enter electoral politics, running in races big and small across the region.
Some of those candidates, like Whalen, are looking to shake up the political status quo in the Democratic Party. For example, a 26-year-old Wilbraham native, Michael Lachenmeyer, has announced he’ll be challenging state Rep. Angelo J. Puppolo Jr., who has held his seat since 2007.
“People are feeling squeezed right now,” Lachenmeyer told The Shoestring. So he’s running on a platform that includes everything from single-payer health care to increased transparency for state lawmakers.
The progressive energy inside the party is evident statewide. Earlier this month, Democratic activists were shocked when they saw the new platform they were set to vote on at the party convention in Springfield. The party’s platform committee had stripped it of dozens of specific policies that activists had fought to include in the 2021 platform — everything from Medicare for All and the elimination of subminimum wages to protections for immigrants. The word “transgender” had been removed entirely from the document.
The left wing of the party rallied, collecting enough signatures to force a vote on the convention floor to restore the previous language to the platform. Although not a member of the party himself, activist Jon Weissman — a leader in Mass-Care, the movement for single-payer health care in Massachusetts — was helping to collect those signatures.
“This enthusiasm has roots in the alienation from the party as is,” Weissman said. He said the question facing the Democratic Party is whether new leadership will take over and move it in a bolder direction, or whether many of those people will leave the party altogether.
The movement for more progressive representation is sweeping through municipalities, too. In Northampton, a historic 19 people just ran in a preliminary election for City Council and mayor, including one candidate, Vincent “Luke” Rotello, who is the co-chair of the local chapter of the Communist Party USA. The local chapter of the Democratic Socialists of America decided to endorse candidates for the first time in the group’s history. And although two of them already lost City Council races in Northampton, two other DSA-backed candidates are running in November in Agawam and Amherst.
“People have a lot of fight in them. I think people are looking to get organized and for a political home,” said Annie Wood, the electoral chair for River Valley DSA. Some have been inspired by New York City mayoral hopeful and DSA member Zohran Mamdani, she said. Others have channelled their outrage — over everything from Israel’s genocide in Gaza to the Trump administration’s attacks on immigrants — into organizing both inside and outside the electoral system. “I think there’s something really powerful forming.”
Those growing movements can be seen everywhere from immigrant communities and their allies developing mutual aid networks to tenants forming unions to fight back against rent hikes and evictions. Katie Talbot is the organizing director at Springfield No One Leaves, a grassroots housing justice organization. She said that a lot of people are coming to the organization with “no intention of being political,” but, after conversations about power and how it relates to their situation, organizers are “watching them leave with a little light turned on.”
“I think the current political moment is making that possible,” she said.
But will that energy be enough to counter the Trump administration’s evisceration of the social safety net and targeting of immigrants, the transgender community, and others? Talbot said that although working-class movements have been emboldened, so too has the far right. She’s seen it while out collecting signatures for a ballot question on rent control. During that work, she said somebody angrily called a Springfield No One Leaves organizer an immigrant and said they should be deported.
“It’s always darkest before the dawn,” she said. But whether those movements have success will depend on how much organizing happens in the next year. “There’s still a lot of work to go with that hopefulness.”
State Rep. Lindsay Sabadosa is part of the progressive wing of the state’s Democratic Party. A former co-chair of the Bernie Sanders presidential campaign in Massachusetts and the sponsor of the statewide Medicare for All bill, she said she’s concerned by the devastating impacts of Republicans’ cuts to Medicaid and more. She’s encouraged by grassroots organizing — tenants fighting against rent hikes, for example — but wants to see far more people engaged in that kind of work across the region.
“I don’t see what I would hope to see, which is how do we take care of each other to get through this,” she said. Political candidates need to be running on a vision of the future they want to see, she said, and organizers need to be doubling down on efforts to make sure people have access to the basics: housing, enough food, safety, and the right to speak out against the Trump regime.
“I think the fights are about to get a lot bigger and we’re not ready for them,” she said.
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When Tahirah Amatul-Wadud announced her campaign for Congress against Richard Neal, it was the end of 2017 — just a little more than a year after Bernie Sanders had staged an improbable, but ultimately unsuccessful, campaign for president against presumed Democratic nominee Hillary Clinton. The four members of “The Squad,” including Massachusetts’ Ayanna Pressley, were about to shock the country by winning election to the U.S. House as the party’s furthest left coalition.
There were “no real models for doing what we did,” Amatul-Wadud told The Shoestring about her campaign. “We were challenging a very strong incumbent, we were grossly underfunded, we didn’t match the … larger demographics of the district.”
Amatul-Wadud forged ahead, championing some of the same issues as Sanders, like Medicare for All. But Neal pulled in $3.5 million during the election cycle, most of it from corporate interests, and spent nearly as much. In the end, he handily defeated Amatul-Wadud. She watched, though, as in the subsequent years, candidates continued to run against Neal, who rarely faced serious challenges before her campaign.
“To realize there’s an enduring legacy from that experience is amazing,” she said.
Amatul-Wadud, who is now the executive director of the Massachusetts chapter of the Council on American–Islamic Relations, said that she was one of a wave of political candidates — many of them women and people of color — who entered their races feeling frustrated with the Trump administration. She said she’s seeing the same happen again with the second Trump administration. But she’s also seeing people get more involved on the local level, going to city council meetings or calling their school boards for the first time.
“This is the moment. Nobody is sleeping,” she said. “To see people find their voice and feet … it’s so empowering, it’s so beautiful. To see people feeling strong and capable to engage in a political process.”
One of those people is Lachenmeyer, who got his start in politics by organizing for the Indivisible movement on his college campus and working on Amatul-Wadud’s congressional campaign.
Originally, Lachenmeyer said he had no intention of running for office, having become disillusioned with how establishment Democrats “botched” the 2024 election against Trump. But he said he took issue with some of the actions and statements of his own state representative, Angelo Puppolo, including when he was quoted earlier this year in The Reminder saying that the “migrant issue” is “the elephant in the room” in Massachusetts.
“I felt he was unacceptable as the representative in my home district,” Lachenmeyer said.
So he decided to jump into the race. He faces an uphill battle against Puppolo, who ended last month with almost a quarter million dollars in his campaign account, according to state campaign finance records. Lachenmeyer said he has been buoyed by the success of left-leaning Democrats who have shifted the political landscape in Minnesota, where they’ve passed a slew of progressive bills including free public college tuition for lower-income families and stronger protections for unionizing workers.
“Getting more progressives elected at lower levels will help us start changing the policy outcomes in the region, and as people get more excited about what politics can do for them, that will create a landscape that’s more generally favorable to progressives overall,” he said.
Tom Hendrickson also has hope for the future of the left in western Massachusetts. A political operative who has worked on campaigns in the region since 2019, he is himself running for re-election to the Agawam City Council in November. He’s also been endorsed by the local chapter of the Democratic Socialists of America — a badge of honor for somebody who was inspired to pursue a career in politics by Sanders during his first run for president.
“We’re seeing the local progressives and the left wing here in the greater Springfield area getting more organized, getting better at campaigning, getting more active, and, you know, learning the strategies that lead to success,” he said.
Hendrickson said that older, more moderate incumbents in the region haven’t had to face serious challengers in a long time. And so while they may have plenty of campaign cash in their war chests, he doesn’t think they have the “campaign chops to go against progressive challengers.” Voters are also growing tired of “the same old, corrupt politicians,” he said.
“All three of those things have created a political environment out here that is ripe for progressive ascension,” he said.
That’s the zeitgeist that Whalen is hoping will propel him to victory against Neal in the 1st Congressional District. And he said that is, in part, why he believes he’ll be successful where others previously failed.
“We are in a new era in which the Democratic Party can exist in an authentic manner,” he said. In the current political moment, he said that policies that he’s running on — Medicare for All and the Green New Deal, for example — no longer seem like dreams that are too big. “They actually fix the systems that are broken at hand.”
But Whalen isn’t the first candidate to run against Neal as an outsider or on that particular platform. He won’t even be the only one this election cycle.
Nadia Milleron, a Berkshire County farmer-turned-consumer advocate, ran against Neal in 2024 as an independent. Milleron, who confirmed to The Shoestring that she’s running again as an independent in 2026, focused her platform on reviving American-made medicine and food production, lowering the cost of living, and expanding healthcare access. But like many electoral challengers, she faced the prospect of a candidate who could far outspend her and has name recognition across the state.
Milleron said that running outside the two-party system allows her to speak more directly to voter disillusionment.
“A lot of people here feel alienated from politics entirely,” Milleron said. “They don’t trust Democrats or Republicans, but they want someone who understands how policy failures have shaped their everyday lives. That’s who I’m trying to reach.”
Late last month, Quinnipiac University released results from its national poll of registered voters. It found that 54% of them have an unfavorable opinion of the Democratic Party — the lowest favorability rating for the party since Quinnipiac began asking the question in 2008.
One of those who now feels disenchanted with the Democratic Party is Amatul-Wadud, who ran as a Democrat when she challenged Neal. Today, she said that while she’s still a registered Democratic voter, she identifies more as an independent.
“I’m definitely not ‘blue no matter who,’ I’m not loyal to the party,” she said.
Amatul-Wadud said she has watched Democrats fight against progressives in their own party and accept corporate money while opposing policies that are popular with their voters. She also criticized the party for accepting the support of the American Israel Public Affairs Committee while supporting Israel’s actions in Palestine. Not only has that created a humanitarian crisis for Palestinians, she said, but it has also led to a “a marked increase in anti-Muslim sentiment” in the United States, including direct violence toward Muslims.
“I want to say that I’m cautiously optimistic because at some point, things will get better,” she said. “But I’m not sure how, I’m not sure in what ways and what things change. And what systems break to make it happen.”
Amatul-Wadud, like Weissman, predicted that the Democratic Party will either change to reflect its more progressive will, or that the party itself will be what “breaks.”
“Start drafting its obituary if it does not make the change and submit to the policies that the people want,” she said.
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Matt Baron has worked as a political consultant for the last four decades, helping progressive organizations like Indivisible Action and candidates like Amatul-Wadud run their campaigns. But he’s not entirely convinced that the left is going to succeed in Hampden County, south of the “tofu curtain.”
“The progressives are sort of where they are,” he said. “They have their base, which is the Amhersts and the Northamptons and the Greenfields, and the more moderate Dems like Puppolo and people in the other urban cities, they have their political bases, and I don’t really see it changing too much.”
Barron said that Neal’s base, for instance, includes what used to be known as “Reagan Democrats” — older, more conservative voters in the region’s Irish, Italian, and Polish communities. He said that the challenge for any candidate hoping to get elected on a more progressive platform is going to be appealing to the many other voters, especially those in communities of color, who have become “checked out” of a political process that they feel doesn’t represent them.
Barron said that instead of focusing on big public protests like the “No Kings” rallies that turned out thousands of people earlier this year, progressives should be getting out into those communities and registering people to vote. That’s how to seize the levers of power, he said.
“What I would say to progressives is, ‘Stop going to all these rallies,’” he said. “I don’t think it’s doing much. Whereas, if you went down into some of these places where there’s a lot of apathy to try to get people more engaged, that might be more productive in the long run.”
Driving around in his big yellow van, that’s what Whalen is hoping to accomplish. He said he intends to travel to every corner of the district, which contains 83 municipalities and covers nearly one third of the state’s entire landmass.
“You’ve got to be mobile and you’ve got to be willing to travel and put miles on,” Whalen said.