The Most Interesting Race in Massachusetts Politics

Young vs. old. Incumbency vs. insurgency. Money vs. grassroots. Establishment vs., well, grassroots.

The most interesting story in Massachusetts politics isn’t at the top of the ticket – it’s the congressional primary to represent Western Mass. There, 38-year incumbent Richie Neal is facing a surprisingly robust challenge from first-time candidate Jeromie Whalen in the Democratic primary for Massachusetts’ First Congressional District.

The race touches almost every major fault line in Democratic politics this cycle.

Money in politics? Neal is one of Congress’ leading recipients of corporate PAC money – Whalen takes none, and has signed the Political Integrity Pledge.

Is Congress too old? Neal is 77, Whalen is 39.

Base frustration with Democratic leadership? Neal is the leading Democrat on the powerful Ways and Means Committee. If Whalen wins, Neal would be the highest-ranking Representative of either party to lose a primary since Alexandria Ocasio-Cortez beat the No. 4 House Democrat in 2018.

Moderates vs. progressives? You could accurately predict both candidates’ positions on most issues, with Neal in the centrist lane, and Whalen on the left. One example: Neal was one of the 75 Democrats who voted to thank ICE last year, while Whalen is in favor of abolishing ICE.

Congressional self-dealing? Neal has used campaign money to spend millions on luxury restaurants and hotels during cycles when he had no opponent, and has paid his son nearly $300,000 over the past five years.

But none of that explains why the race is competitive.

On paper, it shouldn’t be.

By conventional measures, this shouldn’t be much of a contest. Neal is the former mayor of Springfield, where almost one-third of the voters in the district live. He’s got the second-biggest campaign war chest in Massachusetts – larger than both Senate candidates. Last time he faced a serious primary challenge, Neal won by double-digits against a well-funded, experienced local politician. In that race, Holyoke Mayor Alex Morse enjoyed support from multiple national progressive groups, including Justice Democrats and Sunrise Movement. Whalen has no comparable national support, experience, or funding. By the traditional rules of congressional politics, this story would end there.

But Neal is largely absent from the district. Even before Whalen entered the race, local Democratic activists often joked that Neal represented Martha’s Vineyard – where he frequently hosts fundraisers – more than Springfield or Pittsfield.

The very factors that made Whalen look easy to dismiss may have created the opportunity he needed. While Whalen was spending his days at events across the district, Neal’s campaign seemed to be evaluating the race from a distance. The numbers said Whalen was less formidable than Morse. The ground told a different story.

The contrast was clearest during this spring’s Democratic caucuses. Over 28 days, local activists gathered across the district to select delegates to the state convention. Whalen’s campaign had a representative at all 45 caucuses, and Whalen personally attended 25. Neal attended none, even though the House was out of session for 16 of those 28 days.

But Whalen isn’t only showing up at political events. He’s a staple in local parades, festivals, grand openings, and community events. When a food truck vendor had a permitting problem, Whalen was there, calling attention to the issue – and directing his social media followers to a good meal.

That kind of visibility does more than build familiarity. In a district where the incumbent has a reputation for absence, Whalen has begun doing some of the small, unglamorous things an engaged representative normally would: showing up, noticing local problems, and making himself useful.

While watching Whalen campaign volunteers hand out flyers at a festival earlier this summer, I heard one recipient say, “save the paper, I love that guy.” One festival comment is hardly polling data. But it captures what Whalen’s campaign has spent a year trying to create: enough familiarity that voters no longer need an introduction.

His frequent appearances contributed to his steadily growing base of support. Whalen has the support of every local activist group that has picked a side in the race, including Progressive Mass, Progressive Victory, six Indivisible chapters, and more. By late July, more than 1,000 Whalen yard signs were up around the district – a striking footprint for a campaign operating on a fraction of Neal’s budget.

But the largely uncontested phase of Whalen’s insurgency is ending.

Neal began airing ads in early August and has made more in-district appearances in recent weeks. After declining several debate and forum invitations, Neal agreed to one debate on August 26 – six days before the primary, and after early voting had already begun. After months of dormancy, Neal’s campaign is finally becoming visible on the ground.

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And this is where the financial disparity starts to matter. Neal has outraised Whalen seven to one this cycle, and the cash-on-hand gap is even more stark: as of the last reporting period, Neal had $4 million available, while Whalen had just $40,000.

For most of the race, that advantage was largely latent. Now Neal has begun putting it to work.

For months, one of Whalen’s biggest advantages was that Neal was barely campaigning against him.

That is changing.

Whalen has shown what a congressional campaign built on personal appearances, volunteers, and word of mouth can accomplish. Now comes the harder test. Neal has millions of dollars available and has finally begun spending them. Whalen has thousands of dollars and the grassroots network he spent a year building.

We’re about to find out whether that’s enough.

Follow Alex Rikleen on Bluesky at @rikleen.bsky.social.