The Fight for Competitive Elections in Massachusetts with Jessee Littlewood

In this week’s episode, Jennifer welcomes Jesse Littlewood, the campaign manager for the Coalition for a Healthy Democracy. Jesse has extensive experience working on democratic reforms, particularly focusing on increasing civic engagement and advancing policies that make elections fairer and more competitive. Raised in Oregon, Jesse brings insight from strong ballot initiative states and is now leading efforts to put all party primaries, also known as "top two" or "jungle primaries,” on the Massachusetts ballot in 2026. His work centers on improving legislative accountability and making the electoral process more accessible for all citizens.

Jennifer and Jesse discuss the ineffectiveness of the Massachusetts legislature, which has seen a growing trend of citizen-driven ballot initiatives as a response to legislative gridlock. They examine the mechanics behind the all-party primary proposal, the barriers faced by unaffiliated voters (who make up the majority in Massachusetts), and why the current partisan system is failing to address the needs of moderate and independent voters. Controversial topics include the diminished impact of minority parties, low voter turnout in primaries, concerns about empowering moderates at the expense of party ideologues, and arguments about whether these reforms would “kill” party politics or, instead, revitalize them. Jesse counters criticism from progressive and conservative factions, arguing that broad-based competition leads to more responsive governance and dismantles entrenched power structures. With endorsements crossing party lines and strong polling numbers, the conversation highlights why disruption is necessary and why many establishment figures fear meaningful electoral reform.

“To my Republican friends, I say you have nothing to lose but your chains.”

–Jesse Littlewood

This week on Political Contessa:

• The role and process of citizen-driven ballot initiatives in Massachusetts
• The mechanics and implications of all-party primaries (“top two”)
• The high percentage of unenrolled voters and its effect on competition
• The lack of legislative action and increasing reliance on ballot measures
• The declining rate of registered party voters and the rise of independents
• The impact of current primary systems on moderate and young voters
• Arguments from party purists and how reforms could strengthen parties
• Cross-partisan endorsements and the coalition behind all-party primaries

Connect with Jesse Littlewood:

• Coalition for a Healthy Democracy
• Jesse Littlewood on X

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