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Trailblaze 2028: Daily Summaries Delivered
by 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
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- Oct 1, 202637 min
94: Mitch Landrieu: "Donald Trump Is a Cat 5 Hurricane"
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.More from Politicon: https://www.politicon.comChapters0:00 Cold open: "Trump is a Cat 5 hurricane"0:29 Welcome, Mitch Landrieu0:52 Getting $800 billion of infrastructure out the door2:33 280 cities, towns and counties: listening to America4:07 "We're stuck"4:24 Why Democrats got no credit for infrastructure5:54 Why building in America takes so long8:34 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 hurricane14:02 "Think more Dolly, less Donald"15:32 Build it back the way it should have been17:32 Healthcare: one sickness away from bankruptcy19:25 Old vs crazy: costs, wars and broken promises20:31 Everyone's a tariff expert now21:12 ICE, Minneapolis and Hispanic voters walking away24:04 Is Mitch running for president?25:19 More presidents with hair27:25 "We're better than this, and we're better together"28:18 A DNC chair pitch, and praise for Pete Buttigieg29:48 Race, diversity and America's future33:45 Jamal & Matt: is he getting in?36:10 The Trailblaze staff house
- Sep 15, 202625 min
93: Why Latinos Are Turning on Trump
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 Rocha0:15 The Angriest Voters in 36 Years1:15 ICE Raids and the Fear Behind the Anger2:28 How Democrats Keep Latino Voters Past November3:43 Trump's $5,000 Check: Real or a Scam?5:19 Newsom, Harris, and the Fly-Fishing Interview8:47 Why South Carolina Could Decide the Newsom-Harris Standoff9:34 Inside the Newsom-Harris Relationship11:21 Does the Party Ever Give a Losing Nominee a Second Shot?11:54 Texas as the 2028 Preview12:50 The Case Against "Comeback" Candidates13:59 What Kind of Candidate Wins Right Now16:15 Taking On a Powerful Female Candidate17:40 Why the VP Pick May Need to Be Latino19:04 Bill Richardson Stories20:15 The Hidden Opportunity: Staffing Up 20 Campaigns21:44 Lessons from Staffing the Gore Campaign23:24 2028 Hopefuls Are Already Quietly Hiring24:00 Wrap-Up and Chuck's Latino Vote Podcast
- Sep 8, 202627 min
92: Who Are the Dems? And What The Party Actually Stands For
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 wages04:04 – Patriotism has to run both ways04:50 – Pete Hegseth's Pentagon is pushing out women and officers of color08:15 – Structural reform: expanding the Supreme Court, fixing the electoral college11:24 – Why nobody prosecuted the Epstein files under Biden13:44 – The left has to celebrate America's wins, not just its faults17:59 – America's fading standing in the world under Trump23:03 – The economy is rigged for a shrinking class of billionaires25:29 – "More millionaires, fewer billionaires" — Jamal's closing pitch27:09 – Mario Cuomo's 1984 speech and "we have to beat those people"
- Aug 26, 202615 min
91: BACKLASH: The Jared Kushner and Hakeem Jeffries Meeting
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-deafJamal's read: "don't confuse position with power" — Kushner has no official job but is clearly running plays inside Trump's orbitThe 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 passedJamal'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 fightThe "get even" lane vs. the "get ahead" lane — accountability for "the crooks" vs. delivering lower costs, and Jeffries has to run both at onceWatch for "the princelings" — Witkoff's kid, Lutnick's kid, Trump's kids — as the likely targets who "catch the brick" firstTrailblaze 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 airtimeReal 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 registersAn 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 marginsAOC's electability question hinges partly on Abdul El-Sayed's Michigan race and the DSA candidate's long-shot bid in FloridaSouth 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
- Aug 13, 202621 min
90: The Polls, The Upset, and Wisconsin's Road to 2028
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 CoveredDavid Crowley's comeback from 20 points down to beat Francesca Hong in the Wisconsin governor primaryWhy the polls weren't as far off as the final margin suggestedThe 3,850-vote margin and how razor-thin the race really wasUniting Hong and Crowley voters into one coalition for the fallWisconsin's stakes: certifying the 2028 election and winning a blue trifectaTom Tiffany's record — supporting Ken Paxton's 2020 election lawsuit and voting against certifying Arizona and Pennsylvania's electorsWhy polling primaries is harder than polling general electionsState Navigate's polling methodology and the debate over weighting young votersBernie Sanders and AOC staying out of the primaryRebecca Cooke's rematch against Derek Van Orden in Wisconsin's 3rd DistrictPete Buttigieg's town hall for Cooke and his "Win the Era" PACWhich 2028 hopefuls need to prove themselves in WisconsinThe history of Wisconsin's primary calendar and why it moved to April
- Jul 28, 202619 min
89: Obama for DNC Chair - We Said It Here First
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.TopicsThe New 2028 DNC Primary Calendar — South Carolina, Nevada, New Hampshire, New Mexico, Michigan, and VirginiaNew Hampshire's First-in-the-Nation Fight — the state law standoff and the Delaware backup planWinners and Losers in the New Map — Michigan as kingmaker, New Mexico's wildcard status, and a boost for Mark Kelly and Ruben GallegoThe DNC's Money Problems — debt, fundraising gaps, and pressure on chair Ken MartinThe Crazy Idea — drafting Barack Obama to serve as DNC chairYouTube Timeline
- Jul 23, 202614 min
88: AOC To Be Or Not To Be
Will AOC run for President? A Deep Dive Into Her Political FutureWe 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 implicationsThe importance of the four M's—Money, Media, Message, Mechanics—and the addition of AuthenticityHow AOC’s fundraising success, including over $32 million raised, supports her ambitionsThe significance of her authenticity and progressive stance amid intra-party conflictsThe potential influence of swing states like Michigan and Wisconsin on her presidential prospectsThe impact of progressive candidates in local races and how they could reshape national politicsHistorical parallels with other insurgent candidates and cycle repeats in political ideology shiftsThe strategic value of campaign tours in rural and diverse regionsThe importance of voters craving real change and how AOC taps into that desireThe age factor, and whether grassroots support could propel her from Senate to the presidency
- Jul 14, 202626 min
87: Lindsey Graham: The Aftermath
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: The implications of Lindsey Graham's death for South Carolina's Senate race and the GOP's outlook. How Democrats are maneuvering through the Iowa caucus's evolving rules and the undercurrent of electoral strategy. The bizarre spectacle of Kentucky’s senator crisis and Bashir’s bold move to potentially appoint a new senator The age dilemma in Congress and whether new, younger faces will finally shake up the old boys' club. The potential alliance of Gov. Bashir and AOC for a progressive fuse that could shake the Democratic primary scene. A deep dive into the systemic change fever sweeping across America—what it means for candidates, incumbents, and the political establishment.
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About 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
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