Trailblaze 2028

Former New Orleans mayor and Louisiana Lieutenant Governor Mitch Landrieu joins Jamal Simmons and Matt Butler. Mitch led the push to roll out the bipartisan infrastructure law and spent years on the road listening to working-class voters. He explains why America feels "stuck", and why he calls Donald Trump a Cat 5 hurricane. He uses Katrina to show how the country can rebuild "the way it should have been." He also covers healthcare, tariffs, ICE, and voters who backed Trump three times and are now walking away. He shares whether he's running for president in 2028, and he talks about race, diversity and America's future.

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Chapters
0:00 Cold open: "Trump is a Cat 5 hurricane"
0:29 Welcome, Mitch Landrieu
0:52 Getting $800 billion of infrastructure out the door
2:33 280 cities, towns and counties: listening to America
4:07 "We're stuck"
4:24 Why Democrats got no credit for infrastructure
5:54 Why building in America takes so long
8:34 What do we build after the hurricane?
10:42 Katrina: "We're all in the same boat"
12:46 The lesson: Trump is a Cat 5 hurricane
14:02 "Think more Dolly, less Donald"
15:32 Build it back the way it should have been
17:32 Healthcare: one sickness away from bankruptcy
19:25 Old vs crazy: costs, wars and broken promises
20:31 Everyone's a tariff expert now
21:12 ICE, Minneapolis and Hispanic voters walking away
24:04 Is Mitch running for president?
25:19 More presidents with hair
27:25 "We're better than this, and we're better together"
28:18 A DNC chair pitch, and praise for Pete Buttigieg
29:48 Race, diversity and America's future
33:45 Jamal & Matt: is he getting in?
36:10 The Trailblaze staff house

Democratic strategist Chuck Rocha (Latino Vote Podcast) joins Jamal Simmons and Matthew Butler for a midterm gut-check: why working-class Latino voters who backed Trump are swinging back to Democrats, what's fueling the anger behind ICE raids and broken economic promises, and whether Trump's $5,000 "tariff dividend" is real. Then the crew turns to 2028 — Gavin Newsom's fly-fishing-creek interview with Jake Tapper, the decades-long Newsom-Harris relationship, why the VP slot may need to be Latino, and why 20 presidential campaigns quietly staffing up right now could reshape the next generation of Democratic operatives.

Chapters:
0:00 Intro: Midterm Briefing with Chuck Rocha
0:15 The Angriest Voters in 36 Years
1:15 ICE Raids and the Fear Behind the Anger
2:28 How Democrats Keep Latino Voters Past November
3:43 Trump's $5,000 Check: Real or a Scam?
5:19 Newsom, Harris, and the Fly-Fishing Interview
8:47 Why South Carolina Could Decide the Newsom-Harris Standoff
9:34 Inside the Newsom-Harris Relationship
11:21 Does the Party Ever Give a Losing Nominee a Second Shot?
11:54 Texas as the 2028 Preview
12:50 The Case Against "Comeback" Candidates
13:59 What Kind of Candidate Wins Right Now
16:15 Taking On a Powerful Female Candidate
17:40 Why the VP Pick May Need to Be Latino
19:04 Bill Richardson Stories
20:15 The Hidden Opportunity: Staffing Up 20 Campaigns
21:44 Lessons from Staffing the Gore Campaign
23:24 2028 Hopefuls Are Already Quietly Hiring
24:00 Wrap-Up and Chuck's Latino Vote Podcast

Jamal Simmons and Matthew Butler tackle the question hanging over the Democratic Party: what do you actually stand for? They dig into patriotism, a hollowed-out military leadership, structural reforms like expanding the Supreme Court, America's fading global standing, and a economy where a shrinking number of billionaires control a growing share of the wealth — closing with a callback to Mario Cuomo's 1984 convention speech.

00:00 – Why don't Democrats have a clear answer to "why should we be in charge?"
02:43 – What Democrats actually agree on: childcare, healthcare, living wages
04:04 – Patriotism has to run both ways
04:50 – Pete Hegseth's Pentagon is pushing out women and officers of color
08:15 – Structural reform: expanding the Supreme Court, fixing the electoral college
11:24 – Why nobody prosecuted the Epstein files under Biden
13:44 – The left has to celebrate America's wins, not just its faults
17:59 – America's fading standing in the world under Trump
23:03 – The economy is rigged for a shrinking class of billionaires
25:29 – "More millionaires, fewer billionaires" — Jamal's closing pitch
27:09 – Mario Cuomo's 1984 speech and "we have to beat those people"

Jamal Simmons and Matthew Butler dig into the fallout from Jared Kushner's meeting with House Minority Leader Hakeem Jeffries — was it a smart olive branch or a self-inflicted wound days before Democrats need to look like they're ready to fight? Then they turn to the Trailblaze 2028 prediction markets, where AOC is surging, Gavin Newsom is in freefall, and John Ossoff is quietly having the best year of any 2028 hopeful.

Kushner requested the sit-down with Jeffries to talk affordability and pointed him toward Chief of Staff Susie Wiles — Matthew notes Kushner has personally profited more from this administration than almost anyone, making the meeting look tone-deaf
Jamal's read: "don't confuse position with power" — Kushner has no official job but is clearly running plays inside Trump's orbit
The pushback plan: a leak, 24 hours of outrage, then Jamie Raskin expands the House Judiciary probe into Kushner's business dealings — Jeffries says "nobody gets a free pass"
The counter-argument: if Jeffries is actually Speaker, keeping a line open to the White House is how anything affordability-related gets passed
Jamal's verdict: "the right meeting, the wrong timing" — Democrats aren't done girding for battle, and it reads like leadership is planning the negotiation before winning the fight
The "get even" lane vs. the "get ahead" lane — accountability for "the crooks" vs. delivering lower costs, and Jeffries has to run both at once
Watch for "the princelings" — Witkoff's kid, Lutnick's kid, Trump's kids — as the likely targets who "catch the brick" first
Trailblaze 2028 markets: AOC jumps from ~10% to 19%, largely at Newsom's expense (33% → 14%); Ossoff rockets from 6% to 17% on the strength of viral clips and a Senate race giving him constant airtime
Real Clear Politics polling tells a completely different story than the prediction markets — Kamala Harris leads polls at 27.6% on name recognition alone, while Ossoff barely registers
An Emerson poll shows Buttigieg, Ossoff and Newsom all beating Vance and Rubio head-to-head; Harris and AOC are more competitive but not by the same margins
AOC's electability question hinges partly on Abdul El-Sayed's Michigan race and the DSA candidate's long-shot bid in Florida
South Carolina's Black electorate historically plays it more moderate than Michigan or Wisconsin — expect a "lane" dynamic (Black candidate, white non-Southern candidate, Southern candidate) to shape who breaks out

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 must-win fall matchup against MAGA Republican Tom Tiffany. They dig into why this race is about far more than one governorship — it's about who certifies Wisconsin's 2028 presidential results and whether Democrats can finally win a blue trifecta and redraw fairer congressional maps. Plus: lessons on polling primaries versus general elections, Rebecca Cooke's rematch in WI-3, Pete Buttigieg's swing through the state, and why every 2028 hopeful needs to prove they can win in Wisconsin.

Topics Covered
David Crowley's comeback from 20 points down to beat Francesca Hong in the Wisconsin governor primary
Why the polls weren't as far off as the final margin suggested
The 3,850-vote margin and how razor-thin the race really was
Uniting Hong and Crowley voters into one coalition for the fall
Wisconsin's stakes: certifying the 2028 election and winning a blue trifecta
Tom Tiffany's record — supporting Ken Paxton's 2020 election lawsuit and voting against certifying Arizona and Pennsylvania's electors
Why polling primaries is harder than polling general elections
State Navigate's polling methodology and the debate over weighting young voters
Bernie Sanders and AOC staying out of the primary
Rebecca Cooke's rematch against Derek Van Orden in Wisconsin's 3rd District
Pete Buttigieg's town hall for Cooke and his "Win the Era" PAC
Which 2028 hopefuls need to prove themselves in Wisconsin
The history of Wisconsin's primary calendar and why it moved to April

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), and New Mexico crashes the early window for the first time in history. Jamal and Matt break down the delegate penalties, the diversity math, and who wins and loses in the new map before landing on their boldest prediction of the cycle.

Topics
The New 2028 DNC Primary Calendar — South Carolina, Nevada, New Hampshire, New Mexico, Michigan, and Virginia
New Hampshire's First-in-the-Nation Fight — the state law standoff and the Delaware backup plan
Winners and Losers in the New Map — Michigan as kingmaker, New Mexico's wildcard status, and a boost for Mark Kelly and Ruben Gallego
The DNC's Money Problems — debt, fundraising gaps, and pressure on chair Ken Martin
The Crazy Idea — drafting Barack Obama to serve as DNC chair
YouTube Timeline

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 implications
The importance of the four M's—Money, Media, Message, Mechanics—and the addition of Authenticity
How AOC’s fundraising success, including over $32 million raised, supports her ambitions
The significance of her authenticity and progressive stance amid intra-party conflicts
The potential influence of swing states like Michigan and Wisconsin on her presidential prospects
The impact of progressive candidates in local races and how they could reshape national politics
Historical parallels with other insurgent candidates and cycle repeats in political ideology shifts
The strategic value of campaign tours in rural and diverse regions
The importance of voters craving real change and how AOC taps into that desire
The age factor, and whether grassroots support could propel her from Senate to the presidency

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 episode:
The environmental impact of 4th of July fireworks in D.C. and urban air quality
The role of patriotism in political discourse, highlighting historical progress and current challenges
Analysis of potential 2028 Democratic candidates: Westmore, Mamdani, and Gavin Newsom
Inside look at FIFA city negotiations and their impact on host cities’ economics
The politicization of the World Cup and its reflection of domestic political tensions
The importance of active citizenship and service in maintaining American exceptionalism
The humorous yet revealing episode of Trump’s involvement in international soccer, illustrating his tendency to politicize everything
The uplifting celebration of international unity and spirited fan participation in the World Cup