 

 

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

 

Awaken Your Inner Political Contessa

 

Thanks for tuning into this week’s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.

 

Spotify I Stitcher I Apple Podcasts I iHeart Radio I TuneIn I Google Podcasts

 

Be sure to share your favorite episodes on social media. And if you’ve ever considered running for office – or know a woman who should – head over to politicalcontessa.com to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you’re ready to enter the political arena.

 

&nbsp;
&nbsp;
In this week&rsquo;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,&rdquo; 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 &ldquo;kill&rdquo; 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. 
&ldquo;To my Republican friends, I say you have nothing to lose but your chains.&rdquo; ~Jesse Littlewood 
This week on Political Contessa:
<ul>
<li>The role and process of citizen-driven ballot initiatives in Massachusetts</li>
<li>The mechanics and implications of all-party primaries (&ldquo;top two&rdquo;)</li>
<li>The high percentage of unenrolled voters and its effect on competition</li>
<li>The lack of legislative action and increasing reliance on ballot measures</li>
<li>The declining rate of registered party voters and the rise of independents</li>
<li>The impact of current primary systems on moderate and young voters</li>
<li>Arguments from party purists and how reforms could strengthen parties</li>
<li>Cross-partisan endorsements and the coalition behind all-party primaries </li>
</ul>
Connect with Jesse Littlewood:
<a href="https://coalitionforhealthydemocracy.org/">Coalition for a Healthy Democracy</a>
<a href="https://x.com/jesselittlewood">Jesse Littlewood on X</a>
&nbsp;
Awaken Your Inner Political Contessa
&nbsp;
Thanks for tuning into this week&rsquo;s episode of Political Contessa. If you enjoyed this episode, please subscribe and leave a review wherever you get your podcasts.
&nbsp;
<a href="https://open.spotify.com/show/6ImzVp6n3MBUcMBP8jsZhu">Spotify</a> I <a href="https://www.stitcher.com/s?fid=656529">Stitcher</a> I <a href="https://podcasts.apple.com/us/podcast/political-contessa/id1588917810">Apple Podcasts</a> I <a href="https://www.iheart.com/podcast/1300-political-contessa-87658237/">iHeart Radio</a> I <a href="https://tunein.com/podcasts/News--Politics-Podcasts/Political-Contessa-p1531739/">TuneIn</a> I <a href="https://www.google.com/podcasts?feed=aHR0cHM6Ly93d3cub21ueWNvbnRlbnQuY29tL2QvcGxheWxpc3QvZGFlMDZlNGItMGQ0YS00YmZjLTljZGEtYWRhMjAwZmFjMjNlL2Y5ODQwODQzLWIyNjUtNDI0Mi05MWFiLWFkYWYwMGFlODZmOC9jYzc1YWM1MS1hZGU1LTQwYmEtYmY5My1hZGFmMDBiMmM5NjMvcG9kY2FzdC5yc3M%3d">Google Podcasts</a>
&nbsp;
Be sure to share your favorite episodes on social media. And if you&rsquo;ve ever considered running for office &ndash; or know a woman who should &ndash; head over to <a href="http://politicalcontessa.com/">politicalcontessa.com</a> to grab my quick guide, Secrets from the Campaign Trail. It will show you five signs to tell you you&rsquo;re ready to enter the political arena.
&nbsp;

Women on the right need a safe space to discuss politics, policy, news, and ownership over the fact that it is ok to agree to disagree. It is our First Amendment right to free speech. Before we can even out the number of women in our local, state, & federal governments, we need to empower women to feel comfortable and confident discussing these and other topics.

My name is Jennifer. I’m a single mom of three girls living in Boston. I’m a lawyer with two political science degrees, and I have no problem talking politics with people who disagree with me.

I spent three years as the Chairman of the Massachusetts GOP and ran for the very liberal Boston City Council. I’m a frequent analyst on Newsmax, Fox News Radio, and Boston Media. As a Republican in a blue state, I know a few things about how to disagree agreeably.

Join me for fascinating conversations that engage and clarify every week. For more information and resources, visit Political Contessa.

Women on the right need a safe space to discuss politics, policy, news, and ownership over the fact that it is ok to agree to disagree. It is our First Amendment right to free speech. Before we can even out the number of women in our local, state, &amp; federal governments, we need to empower women to feel comfortable and confident discussing these and other topics.
My name is Jennifer. I’m a single mom of three girls living in Boston. I’m a lawyer with two political science degrees, and I have no problem talking politics with people who disagree with me.
I spent three years as the Chairman of the Massachusetts GOP and ran for the very liberal Boston City Council. I’m a frequent analyst on Newsmax, Fox News Radio, and Boston Media. As a Republican in a blue state, I know a few things about how to disagree agreeably.
Join me for fascinating conversations that engage and clarify every week. For more information and resources, visit <a href="https://www.politicalcontessa.com">Political Contessa.</a>

Women on the right need a safe space to discuss politics, policy, news, and ownership over the fact that it is ok to agree to disagree. It is our First Amendment right to free speech. Before we can even out the number of women in our local, state, & federal governments, we need to empower women to feel comfortable and confident discussing these and other topics.  My name is Jennifer. I’m a single mom of three girls living in Boston. I’m a lawyer with two political science degrees, and I have no problem talking politics with people who disagree with me.  I spent three years as the Chairman of the Massachusetts GOP and ran for the very liberal Boston City Council. I’m a frequent analyst on Newsmax, Fox News Radio, and Boston Media. As a Republican in a blue state, I know a few things about how to disagree agreeably.  Join me for fascinating conversations that engage and clarify every week. For more information and resources, visit Political Contessa.

Political Contessa

Women on the right need a safe space to discuss politics, policy and news, and ownership over the fact that it is ok to agree to disagree. It is our First Amendment right to free speech.

Before we can even out the number of women in our local, state, & federal governments, we need to empower women to feel comfortable and confident discussing these and other topics.

I’m Jennifer. I’m a single mom of 3 girls living in Boston. I’m a lawyer with 2 political science degrees and I have NO problem talking politics with people who disagree with me.

I spent 3 years as the Chairman of the Massachusetts GOP and ran for the very liberal Boston City Council. I’m a frequent analyst on Newsmax, Fox News Radio, and Boston media. And as a Republican in a blue state, I know a few things about how to disagree agreeably.

Join me for fascinating conversations that engage and clarify every week and for more information and resources visit Political Contessa.

Women on the right need a safe space to discuss politics, policy and news, and ownership over the fact that it is ok to agree to disagree. It is our First Amendment right to free speech.
Before we can even out the number of women in our local, state, &amp; federal governments, we need to empower women to feel comfortable and confident discussing these and other topics.
I&rsquo;m Jennifer. I&rsquo;m a single mom of 3 girls living in Boston. I&rsquo;m a lawyer with 2 political science degrees and I have NO problem talking politics with people who disagree with me.
I spent 3 years as the Chairman of the Massachusetts GOP and ran for the very liberal Boston City Council. I&rsquo;m a frequent analyst on Newsmax, Fox News Radio, and Boston media. And as a Republican in a blue state, I know a few things about how to disagree agreeably.
Join me for fascinating conversations that engage and clarify every week and for more information and resources visit <a href="https://www.politicalcontessa.com">Political Contessa.</a>

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