Trailblaze 2028

How Politics and Soccer Collide—And Why It’s Still a Spectator Sport In this episode, we dissect the messy intersection of politics, sports, and public perception through the lens of the World Cup and former President Trump's antics. It’s smart, sharp, and a little sarcastic—because if you’re going to discuss global sport, might as well point out how the game is played off the field. In this episo...

Jamal & Matt are joined by Ari Rabin-Havt and In this episode, they dive into what the 2028 Democratic primary might look like, exploring voter dynamics, candidate strategies, and the cultural divides shaping American politics. This isn't just guesswork—it's a strategic deep-dive meant to challenge your assumptions about what's next. Main Topics Covered: The shifting electorate: understanding...

Jamal Simmons and Matt Butler unpack the complex political maneuvers surrounding Joe Biden’s 2024 Presidential run, Gavin Newsom’s bold stance, and the future of Democratic contenders like Kamala Harris and Pete Buttigieg. They slice through the noise to understand what strategies might work—or blow up—in the volatile landscape leading up to 2028. Key topics: Gavin Newsom’s ‘ride or die’ loyalty t...

The Future of American Politics: Big Ideas, Big Changes & The Role of Hope In this episode, Jamal Simmons and Matt Butler dissect the shifting landscape of American politics, from the importance of bold ideas to the implications of recent events at the Obama Presidential Center. They explore how current political energy might shape future elections and what strategies will define the fight for...

The Future of Democratic Politics: Big Ideas, Big Challenges, and Project 2029 In this episode, Jamal Simmons, Matt Butler, and guest Andrei Cherny dissect the shifting landscape of American politics, focusing on the Democratic Party’s evolving identity, the power of bold policy proposals, and the innovative initiative – Project 2029 – aiming to reshape the party's strategic vision. Key Insights:...

This episode dives into the messy, often contradictory world of American politics as it gears up for the 2028 elections. From campaign controversies to policy issues like immigration detention, we're exploring what truly influences voter behavior and candidate viability—and what seems to be losing or gaining importance in the eyes of the public. And then there is Graham Platner ! In this episode:...

The Democratic Party's Future and the 2028 Outlook: Unpacking Autopsies, Campaign Strategy, and Leadership Matt and Jamal dive into the messy, complex world of Democratic Party politics — from the recent autopsy report of 2024 to the evolving strategy for 2028. If you're confused about who’s really running the show or what the future holds for Democrats, this is your no-nonsense guide through the...

In this episode, we cut through the political noise to explore the strategic shifts, candidate trajectories, and the underlying factors that could shape the 2028 presidential race. Whether you're a political junkie or just trying to understand the spectacle, this discussion offers clarity and insight into what's really at stake. Key Topics: The impact of foreign policy experience on Democratic and...

Unpacking the tangled web of redistricting, voter suppression, and political power—topics that feel more urgent than ever. Joining Jamal & Matt this week is Stephanie Brown James, co-founder of The Collective PAC, she offers a clear eye on how these tactics threaten democracy, especially for Black communities, and what we must do to fight back. Key topics covered: The impact of recent redistri...

Jamal Simmons, Matt Butler, and Jesse Lehrich explore the landscape of potential 2028 Democratic candidates, key political strategies, and the importance of brand and fight in campaigns. They analyze emerging stars like Alexandria Ocasio-Cortez, prominent governors, and the broader ideological battles shaping the party’s future. Main topics include: The presidential lane: Who’s running and who mig...

In this episode, we explore the evolving political landscape, focusing on generational dynamics, candidate authenticity, and strategies for success in upcoming elections. Our guest, Amanda Litman, shares insights from her experience with Run for Something and discusses how future candidates can navigate social media, authenticity, and the issues that matter most to young voters. Key Topics: The im...

The road to 2028 starts long before Election Day — it starts with the rules. In this episode of Trailblaze: The Road to 2028 , hosts Jamal Simmons and Matthew sit down with Leah Daughtry, one of the most seasoned voices in American political organizing, to unpack how the Democratic and Republican parties are reconsidering their primary and convention processes. From delegate math to regional repre...

This episode covers the upcoming 2028 presidential race, the strategic implications of Project 2029, fundraising insights, and the emerging world of prediction markets and their impact on politics. Key Topics Project 2029 and its implications Fundraising trends for 2028 candidates The role of prediction markets in politics Political scandals and candidate vetting Chapters 00:00 Project 2029: New I...

Join Jamal & Matthew for an insightful panel discussion on current political trends, campaign strategies, and the future of Democratic politics. Featuring Chuck Rocha we explore election results, candidate authenticity, digital campaigning, and the path to 2028. Topics: Election results interpretation Candidate authenticity and communication Digital campaign strategies and social media Future...

In this episode, hosts Jamal and Matt analyze the latest Democratic campaign strategies, potential 2028 presidential candidates, and the significance of political books and campaigns. They explore the impact of campaign resources, candidate travel, and the importance of grassroots organizing in shaping the future of American politics. Chapters 00:00 The DNC Playbook and Its Implications 04:33 Harn...

Jamal Simmons, Matthew Butler and Adrienne Elrod discuss the challenges of managing convention signs, the invisible primary, potential presidential candidates, insights into campaign managers and consultants, the importance of campaign staff and loyalty, the impact of reelection on presidential primaries, and the consultant primary and staff dynamics.

Jamal Simmons & Matthew Butler are joined by Adam Green from the Progressive Change Campaign Committee discusses the potential of progressive candidates like James Tallarico in the 2028 race, the importance of a forward-looking vision, and strategies for winning swing states. The conversation covers electoral dynamics, candidate credibility, and the impact of emerging issues like crypto and AI...

Jamal & Matthew explore the current political landscape, focusing on potential 2028 presidential candidates, the impact of recent foreign conflicts, and the influence of Trump and other key figures on the Republican race. Key Topics: 2028 presidential candidates JD Vance and Marco Rubio Impact of recent foreign conflicts on US politics Trump's influence on the Republican primary Prediction mar...

Jamal Simmons & Matthew Butler delve into the historical context of national security, the impact of military experience on presidential elections, the Democratic response to the Iran conflict, and the importance of foreign policy in shaping America's global standing. It also explores the Democratic strategy and positioning on national security issues. Chapters 00:00 Introduction and Setting t...

Jamal & Matt discuss the dynamics of the 2028 presidential campaign, focusing on the emerging trend of candidates embarking on book tours as a means of gaining visibility and support. They discuss various potential candidates, including Gavin Newsom, Alexandria Ocasio-Cortez, and Kamala Harris, weighing their chances of running for president and the implications of their decisions. The convers...

This week Jamal Simmons and Matthew Butler are joined by democratic strategist Rodell Mollineau, they  reflect on the legacy of Rev. Jesse Jackson and his impact on the Democratic Party, particularly in the context of presidential nominations. They discuss the recent Munich Security Conference, where AOC and Gavin Newsom made headlines, and analyze the implications of their statements. The convers...

Jamal Simmons & Matthew Butler discuss the recent rebranding of Kamala Harris's campaign platform, the challenges of engaging younger voters, and the identity crisis within the Democratic Party. They explore the racial dynamics in American politics and the importance of addressing these issues head-on. The discussion also touches on polling and prediction markets, highlighting the current poli...

Jamal and Matthew discuss the current political landscape as it pertains to the 2028 campaign. They delve into the fundraising disparities between the Republican and Democratic parties, the importance of infrastructure spending, and the role of individual candidates in shaping the political narrative. The conversation also touches on Westmore's redistricting efforts in Maryland and the challenges...

Jamal and Matthew discuss Gavin Newsom's recent appearance at Davos, his political strategies, and the implications for the Democratic Party. They then zoom into the Republican responses to current events, particularly in light of the protests in Minnesota, and the potential candidates for the 2028 election. The discussion highlights the evolving political landscape and the importance of authentic...

Will Jon Stewart run for President? That’s the big question as Jamal Simmons & Matthew Butler analyze the dynamics of the Democratic Party, they explore the contrasting strategies between establishment candidates and progressive voices, highlighting the challenges faced by candidates like Bernie Sanders. The discussion extends to the importance of addressing pressing issues such as wealth ineq...