Highway to Hill

Today on Highway to Hill: Some news you can use as we barrel towards Election Day! We figured you didn’t need yet another podcast to regurgitate the latest polls or handicap one Senate race or another. So instead, we’re gonna run through some of the most talked about claims of possible election theft, and give some expert context on what are the really big concerns; what’s possible, but not that likely; and then what is just straight up fiction.This week’s syllabus 📚* “Trump administration to send election monitors to Idaho’s largest county” (Idaho Capital Sun)* “Exclusive: National Guard Mobilizes for Election” (Ken Klippenstein)* “Judge denies the Justice Department’s bid to stop processing California ballots” (NPR)* “Everyone Thinks They’re Going to Win” (Gabe Fleischer, Wake Up to Politics)* “Election Officials Fear Trump Administration’s Interference in Midterms Voting” (The New York Times)* “‘Lisa is Lisa’: Murkowski endorses a Democrat as she faces 2028 dilemma” (POLITICO)* “How Tennessee would replace Marsha Blackburn in the U.S. Senate if she becomes governor” (Tennessee Lookout) 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

Today on Highway to Hill: Congress has passed legislation to heavily sanction Russia in the midst of its ongoing aggression towards Ukraine, but the president is taking as… more of a suggestion, even though he signed the law! What is in the “Lindsey O. Graham Sanctioning Russia Act of 2026”, why is Trump suddenly ignoring the entire point of the bill, plus the return of our least favorite villain from Season 1 of the second Trump administration: Elon Musk.This week’s syllabus 📚* “Elon Musk’s Secret Conversations With Vladimir Putin” (Thomas Grove, Warren P. Strobel, Aruna Viswanatha, Gordon Lubold and Sam Schechner, Wall Street Journal)* “Pentagon awards SpaceX with Ukraine contract for Starlink satellite internet” (Amanda Macias and Michael Sheetz, CNBC)* “Order to limit Starshield for Ukraine came from inside White House, sources say” (Erin Banco and Gram Slattery, Reuters)* “Did Ukrainian strikes on Russian datacentres reduce online disinformation?” (Aisha Down, The Guardian)* “H.R.5334 - Lindsey O. Graham Sanctioning Russia and Iran Act of 2026”* Zivotofsky v. Kerry (2015)* Raines v. Byrd | 521 U.S. 811 (1997) (Justia U.S. Supreme Court Center)* “Scandalized” on NPR 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

Today on Highway to Hill: The 2026 midterms are shaping up to be the most expensive in history. Both parties are raising and spending boatloads… but are any of these dollars making a difference? What is all this money telling us about which seats the two parties are targeting, and which they’re triaging? Finally, the Republicans have a big spending advantage, but are their dollars going as far as the Democrats’ are?This week’s syllabus 📚* “Republicans enter triage mode as their election hopes continue to dim” (Andrew Howard, Erin Doherty and Lisa Kashinsky, POLITICO)* “Top G.O.P. Groups Pull Support From First House Incumbents” (Shane Goldmacher, The New York Times)* “John Thune hopes to flood a ‘big map’ with a GOP money wave” (Jordain Carney, POLITICO)* “Big Money Breaks Records, Boosts GOP: 5 Things to Know About the Midterms” (Ian Vandewalker, Brennan Center for Justice)* “Why the GOP’s spending advantage is nowhere near as big as it looks” (David Nir, The Downballot)* “The Multipath Money Trail: Financing Congressional Elections from 1990 to 2024” (Charlie Hunt and Jaclyn Kettler, The Forum)* “Omar home search raises fears about election season probes” (Michael Macagnone, Roll Call) 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

Today on Highway to Hill: It’s time to talk about money, and I don’t mean the gobs of cash being spent in the midterm elections — maybe another week on that one. We are talking about all of the unorthodox ways the Trump administration is spending, or not spending, taxpayer money in ways ranging from questionable to downright illegal. Diverted Ukraine aid, weird cult-y campaign ads, and recissions are all being tossed around; and Congress, sadly, is nowhere to be found.This week’s syllabus 📚* “Homeland Security spending $20M in taxpayer funds for pro-Trump ads” (PBS NewsHour)* “Trump diverts Ukraine aid to authoritarian countries in Latin America” (Andrew Feinberg, The Independent)* “Trump chooses the worst way to cut federal spending” (Editorial Board, The Washington Post)* “GOP lawmakers challenge Trump’s nearly $1B funding clawback” (Helen Huiskes and Sudiksha Kochi, The Hill)* “The Obscure Tool Trump Is Using to Snatch the Power of the Purse” (Gabe Fleischer, Wake up to Politics)* “Russ Vought Insists He Has a Neat Trick to Override Congress. It’s More ‘a Confession,’ Experts Say” (Emine Yücel, TPM)* “Time for yet another debate over daylight, spurred by Trump” (Mike Magner and Mark Schoeff Jr., Roll Call)* “Dennis Hastert, Powerful Politician Disgraced by Child Sexual Abuse, Dies” (Carl Hulse, New York Times)* “Surge in Taxpayer-Funded Ads from Congress Blurs Campaign Lines” (Chris Cioffi, Jon Meltzer and Irfan Uraizee, Bloomberg) 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

Today on Highway to Hill: Charlie is joined by Avery Davis Roberts and Sarah Cooper of The Carter Center. Avery and Sarah are the director and associate director respectively of the Carter Center’s Democracy program. We talk about the work the Carter Center does around the world, their crucial nonpartisan election observation program, and why democracy and nonviolence still matter in a polarized age.This week’s syllabus 📚* Carter Center website: https://www.cartercenter.org/* Avery and Sarah’s work on democracy: https://www.cartercenter.org/programs/democracy/* We don’t have to agree to get along, PSA: https://www.cartercenter.org/news/international-day-of-democracy/ 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