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.

  1. 5d ago

    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

  2. Aug 13

    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

About

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.

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