Highway to Hill

Is MAGA red a primary color?

On this week’s episode of Highway to Hill: It’s party primary season across a whole bunch of states. Quite a few high-profile incumbents have been ousted or are clearly in trouble thanks to endorsements (or non endorsements) from Donald Trump. Is the president’s star power in the GOP enough to keep them save in the midterms, or is he just adding to the Republicans’ electoral problems? Plus, some polisci on why the incumbency advantage just ain’t what it used to be. This week’s syllabus 📚 * “Christian Menefee leads Al Green by 7 percentage points in latest poll ahead of TX-18 Democratic runoff [https://www.houstonpublicmedia.org/articles/news/politics/election-2026/2026/05/12/551511/houston-primary-runoff-election-poll-menefee-green-mealer-cain/]” (Andrew Schneider, Texas Public Media) * “Senate advances resolution to end Iran war as GOP Sen. Bill Cassidy flips to support it [https://www.nbcnews.com/politics/congress/senate-advances-resolution-end-iran-war-trump-bill-cassidy-rcna346001]” (Sahil Kapur, NBC News) * “Massie’s primary is the most expensive in history. Pro-Israel groups have played a huge part. [https://www.politico.com/news/2026/05/17/massie-aipac-record-spending-israel-maga-trump-primary-00925375?user_id=66c4bd1e5d78644b3a9af247&utm_medium=email&utm_placement=newsletter&utm_source=join1440]” (Lisa Kashinsky, POLITICO) * “Republican Senators Are Livid at Trump’s Endorsement of Paxton [https://www.nytimes.com/2026/05/19/us/politics/republican-senators-trump-paxton.html]” (Michael GoldMegan Mineiro and Carl Hulse, The New York Times) * “How Andy Barr out-maneuvered Kentucky’s warring factions to win Trump’s endorsement — and probably a Senate seat [https://www.politico.com/news/2026/05/19/kentucky-senate-seat-andy-barr-00927068]” (, POLITICO) * “GOP Senate primaries in Georgia and Alabama head to June runoffs [https://rollcall.com/2026/05/20/gop-senate-primaries-in-georgia-and-alabama-head-to-june-runoffs/]” (Daniela Altimari and Mary Ellen McIntire, Roll Call) * “It’s Nothing Personal: The Decline of the Incumbency Advantage in US House Elections [https://www.journals.uchicago.edu/doi/abs/10.1086/681670]” (Gary Jacobson, The Journal of Politics) * “Former Rep. Barney Frank dead at 86 [https://rollcall.com/2026/05/20/former-rep-barney-frank-dead-at-86/]” (Niels Lesniewski, Roll Call) * “Mysterious Meddling in Democratic Primaries Has G.O.P. Fingerprints [https://www.nytimes.com/2026/05/12/us/politics/gop-mystery-pac-midterms.html]” (Shane Goldmacher, The New York Times) This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit highwaytohill.substack.com [https://highwaytohill.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Ballroom dance with the devil

On this week’s episode of Highway to Hill: After demolishing the East Wing of the White House last year, President Trump wants Congress to fund his massive ballroom project — to the tune of $1 billion. Charlie and SoRelle break down why Trump needs congressional approval (a judge ruled construction can’t continue without “express authorization”), how Republicans are trying to sneak ballroom funding into a Secret Service security package through budget reconciliation, and whether this has anything to do with actual security concerns or if it’s just about rubber-stamping a vanity project. What’s in that billion dollars anyway? Then, in the Gavel Drop: SoRelle catches us up on the Senate’s latest attempt to stymie the president with a War Powers Resolution; plus, Nebraska Democrats are trying a Hail Mary strategy by dropping out of the Senate race entirely to support an independent candidate. Will ditching the toxic party brand work, or is this just giving up on party-building in red states? This week’s syllabus 📚 * “Americans oppose Trump ballroom 2-to-1; even more oppose his signature on money [https://abcnews.com/Politics/americans-oppose-trump-ballroom-2-1-oppose-signature/story?id=132503095&cid=eml_npd_nws_nbcp_05112026&tpcc=eml_npd_nws_nbcp_05112026]” (Emily Guskin, ABC News) * “Beyond Ideology: Politics, Principles, and Partisanship in the U. S. Senate [https://press.uchicago.edu/ucp/books/book/chicago/B/bo8158910.html]” (Frances Lee, University of Chicago Press) * “Senate G.O.P. Stands by Security Money for Trump’s Ballroom [https://www.nytimes.com/2026/05/11/us/politics/trump-white-house-ballroom.html]” (Carl Husle, New York Times) * “Republicans are sweating about the White House ballroom project [https://www.axios.com/2026/05/13/republicans-trump-white-house-ballroom]” (Hans Nichols, Axios) * “Federal judge orders Trump pause construction on White House ballroom [https://www.politico.com/news/2026/03/31/trump-white-house-ballroom-lawsuit-order-00852455]” (Jacob Wendler and Cheyanne M. Daniels, POLITICO) * “3 Republicans Join Democrats in Closest Senate Vote Yet to Halt Iran War [https://time.com/article/2026/05/13/iran-war-vote-senate-murkowski-closest-vote-yet/?utm_source=firefox-newtab-en-us]” (Nik Popli, Time Magazine) * “❓What happened last night: Nebraska gets the Ricketts-Osborn Senate showdown [https://decisiondeskhq.substack.com/p/nebraska-primary-ricketts-osborn-democrats]” (Geoffrey Skelley, DecisionDeskHQ) This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit highwaytohill.substack.com [https://highwaytohill.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

An artificially intelligent Congress?

On this week's episode of Highway to Hill: The generative AI revolution is coming to Congress — or is it? Charlie and SoRelle are joined by Aubrey Wilson from POPVOX Foundation [https://substack.com/profile/284520536-popvox-foundation] to break down how Congress is (or isn't) using AI right now. Why is adoption so mixed across offices, and what are the biggest barriers to using these tools safely and effectively? Aubrey explains how AI could help solve Congress's capacity crisis by processing information faster, drafting better constituent responses, and freeing up staff time for actual constituent service. But she also warns about the risks: hallucinations, privacy concerns, shadow AI users who don't know the rules, and the lack of institutional training and oversight. Plus, why does Congress need its own custom-built AI tools instead of just using ChatGPT? This week’s syllabus 📚 * The Call to Create the Congressional Capacity and Technology Office [https://www.popvox.org/blog/c-tech] (Aubrey Wilson, POPVOX Foundation) * Where the House and Senate are on Internal Use of AI — POPVOX Foundation [https://www.popvox.org/blog/house-senate-ai] (Aubrey Wilson, POPVOX Foundation) This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit highwaytohill.substack.com [https://highwaytohill.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Packing, cracking, and gerrymander reacting

On this week’s episode of Highway to Hill: The redistricting wars reach new heights as both sides notch victories in a chaotic week that included a major Supreme Court ruling on race and redistricting. Charlie and SoRelle break down the difference between reapportionment, redistricting, and gerrymandering (they’re not all the same thing!), explain packing versus cracking, and why we’re talking about maps in the middle of a decade when this is supposed to happen every ten years. Plus, what does the Supreme Court’s decision mean for racial gerrymandering going forward? Then, in the Gavel Drop: Republicans are floating a plan to send Arlington and Alexandria — two actual cities in Virginia — over to DC for wild reasons; plus, the House and Senate can’t work together despite being controlled by the same party, and Lauren Boebert announces there are only “two and a half good senators” (who’s the half?). This week’s syllabus 📚 * “Gerrymandering Explained [https://www.brennancenter.org/our-work/research-reports/gerrymandering-explained]” (Michael Li, Brennan Center for Justice) * “Supreme Court invalidates Louisiana congressional map over race [https://rollcall.com/2026/04/29/supreme-court-invalidates-louisiana-congressional-map-over-race/]” (Michael Macagnone, Roll Call) * “DeSantis Proposes Florida House Map That Could Add Four Republican Seats [https://www.nytimes.com/2026/04/27/us/desantis-florida-gop-house-map.html]” (Patricia Mazzei and Nick Corasaniti, New York Times) * Florida passes DeSantis’ redistricting map that could net the GOP 4 seats [https://www.politico.com/news/2026/04/29/florida-legislature-redistricting-map-desantis-gop-00898457] (Gary Fineout and Kylie Williams, POLITICO) * “New Lines, New Districts, New Representation: Institutional Impacts of Congressional Redistricting [https://journals.sagepub.com/doi/10.1177/10659129251408063]” (SoRelle Gaynor and Sam Hayes, Political Research Quarterly) * NCSL, “Changing the Maps: Tracking Mid-Decade Redistricting [https://www.ncsl.org/redistricting-and-census/changing-the-maps-tracking-mid-decade-redistricting]” * “Trump has a bold option to counter Virginia’s new gerrymander scheme [https://www.foxnews.com/opinion/trump-bold-option-counter-virginias-new-gerrymander-scheme?ref=51st.news]” (Chad R. Mizelle, Fox News) * “Make Greater D.C. Again? GOP embraces bid to add Arlington and Alexandria to the capital [https://51st.news/dc-re-retrocession-arlington-alexandria-gop/]” (Martin Austermuhle, The 51st) This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit highwaytohill.substack.com [https://highwaytohill.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Can Republicans clear the bench before November?

On this week’s episode of Highway to Hill: SoRelle is at a conference doing actual political science, so Casey Burgat [https://substack.com/profile/15651679-casey-burgat] steps in to help Charlie break down why Republicans are already talking about replacing Supreme Court Justices Clarence Thomas and Samuel Alito — despite lifetime appointments. What’s driving this push? The nightmare scenario of getting “Ginsburg’d” if Democrats take the Senate in the midterms. Casey and Charlie explain the nomination process, and why Supreme Court fights have gotten so ugly. Then, in the Gavel Drop: We’re following up on the House’s scandal-plagued politicians; plus, FBI Director Kash Patel is suing the Atlantic for $250 million over reporting that he “behaves erratically in a manner that compromises national security” — and discovery is going to be wild. This week’s syllabus 📚 * “Why Trump Allies Want Alito and Thomas to Retire—Right Now [https://www.caseyburgat.com/p/why-trump-allies-want-alito-and-thomas]” (Casey Burgat, Crash Course with Casey Burgat) * “2 Years After His Bruising Hearing, Justice Thomas Can Rarely Be Heard [https://www.nytimes.com/1993/11/27/us/2-years-after-his-bruising-hearing-justice-thomas-can-rarely-be-heard.html]” (Neil A. Lewis, The New York Times) * “Trump’s Fed pick grilled by Senate panel, with confirmation still in limbo [https://www.washingtonpost.com/business/2026/04/21/kevin-warsh-senate-hearing/]” (Andrew Ackerman, The Washington Post) * “Sheila Cherfilus-McCormick Resigns [https://www.notus.org/congress/sheila-cherfilus-mccormick-resigns]” (Reese Gorman, Kadia Goba and Oriana González, NOTUS) * “Why Congress Struggles to Police Itself [https://www.caseyburgat.com/p/why-congress-struggles-to-police]” (Casey Burgat, Crash Course with Casey Burgat) * “The FBI Director is MIA [https://www.theatlantic.com/politics/2026/04/kash-patel-fbi-director-drinking-absences/686839/?gift=sNwnpxg8El-wfD2NC7d5PyVdbKG9PQ_spuUrV_qNNEs&utm_source=copy-link&utm_medium=social&utm_campaign=share]” (Sarah Fitzpatrick, The Atlantic) This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit highwaytohill.substack.com [https://highwaytohill.substack.com?utm_medium=podcast&utm_campaign=CTA_1]