Trailblaze 2028
Trailblaze: The Road to 2028 is your insider’s guide to the next great American political showdown. As both parties begin lining up their runners and riders for the 2028 presidential election, this podcast pulls back the curtain on the candidates, the strategists behind them, and the high-stakes decisions that will shape the race long before the first votes are cast. With sharp insight, behind-the-scenes reporting, and a healthy dose of fun, hosts Jamal Simmons and Matthew Butler explore the personalities, power plays, and pivotal moments that will define the road to the White House—making sense of the politics while never losing sight of the passion. Jamal Simmons has spent years inside the rooms where presidential politics actually happen—and now he’s pulling back the curtain. A veteran strategist and former senior White House adviser, Jamal knows how campaigns are built, how messages break through, and how small decisions can change the course of history. He’s equal parts insider, storyteller, and straight-talker, bringing sharp insight, humor, and a deep love of the political game. Matthew Butler lives at the intersection of politics, media, and strategy. He’s worked behind the scenes helping campaigns and political brands find their voice, build momentum, and survive the chaos of modern elections. With a knack for spotting patterns, personalities, and power plays, Matthew brings clarity to the decisions and dynamics that shape the road to the White House.
Episodes
Jamal Simmons and Matt Butler are joined by longtime Wisconsin operative Joe Zepecki to break down one of the wildest primaries of the cycle: David Crowley's stunning comeback from 20 points down to beat Francesca Hong for the Democratic nomination for governor. Zepecki explains how the Crowley campaign clawed back, why the polls weren't as wrong as they looked, and what it'll take to unite Hong and Crowley voters ahead of a ...
Would Barack Obama actually take the job? Jamal Simmons and Matt Butler make the case for drafting the former president as DNC chair — a "crazy idea" that just might solve the party's fundraising crisis overnight. But first, the news that got them there: the 2028 Democratic primary calendar has arrived, and it's a shakeup. South Carolina goes first, New Hampshire gets bumped to third (and may not survive the move at all...
Will AOC run for President? A Deep Dive Into Her Political Future
We explore whether Alexandria Ocasio-Cortez is gearing up for a presidential run and what factors could influence her decision. From poll numbers to campaign mechanics, we break down the strategic landscape of her potential bid and the broader Democratic race dynamics.
Key topics covered include:
The rising poll numbers for AOC in New Hampshire and their i...
This episode takes a smattering of current political chaos—think Kentucky's senate saga, Iowa's early maneuverings, and the twilight saga of Mitch McConnell—and slices through the noise to reveal what it all means for the 2028 presidential chess game. Whether you're a political junkie or just tired of the same old bullshit, this discussion offers a sharper lens on the future of U.S. politics.
In this episode:
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 episod...
Main Topics Covered:
- The shifting electorate: understanding "beer track...
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&r...
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 a stronger democracy.
Key ...
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:
The 20...
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 political signifi...
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 chaos, sprinkled w...
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 Republican candidates 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 redistricting decisions on Af...
Main topics include:
- The presidential lane: Who’s running and who might?
- T...
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 importance of authenti...
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 representation, Daughtry expl...
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
00:00 Project 2029: New Ideas f...
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 political landscap...
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 Harnessing Protest Energy fo...
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