WEEK 29: Sarah Isgur on the War Fracturing the Legal Right

Welcome back to Approach the Bench. This week we sit down with Sarah Isgur — SCOTUSblog editor, Advisory Opinions co-host, ABC News legal analyst, and author of Last Branch Standing. Before all of that: Harvard Law '08, Federalist Society president, veteran of three presidential campaigns, DOJ spokesperson during the Mueller investigation, and the subject of one of the more memorable hiring sagas in recent media history.

We open near Harvard Law, where Sarah led the Federalist Society under then-Dean Elena Kagan. What is it actually like holding conservative convictions in an environment that mostly doesn't share them? Sarah walks us through Kagan's reputation for genuine even-handedness, shares a memorable story about Kagan as Attorney General and later as Justice, and reflects on what it means to be openly on the right in the most elite corners of the legal academy.

From there, we get into the core of Sarah's new book and the central fight now consuming the legal right: process vs. outcome. Why does Sarah call the Court the "last branch standing"? We use the recent Alien Enemies Act rulings as a live case study — including Matt Walsh's call for Trump to ignore the Court and the remarkable moment when deportation flights to El Salvador continued after Judge Boasberg's order, met only by the Salvadoran president's "Oopsie — too late." We press Sarah on the strongest version of the outcome-first argument, what process is actually for, and whether a coherent defense of the Court requires accepting results you hate. We also ask her to help two originalists effectively counter Common Good Constitutionalism on campus — Adrian Vermeule's rising alternative to originalism that asks judges to incorporate a Catholic vision of the common good into their reasoning.

Then we shift to our politics. Does it matter if a political leader is decent? Has the discounting of character produced a grifter class on the right, and fueled the rise of figures like Nick Fuentes and the culture of "vice signaling"? We wrestle with whether a kind "heretic" is more dangerous than an indecent ally, what a decency framework offers young people who've only ever known an indecent style of politics, and whether Sarah fears for the future of the GOP.

We close, of course, with Girl Problems. We ask about that date with Ben Shapiro. And we settle a longstanding debate from a Dispatch "Not Worth Your Time" segment: manual transmission — green flag, deal breaker, or doesn't matter?

Email [email protected] with your questions/comments or submit a voice memo at https://www.speakpipe.com/approachthebench for a chance to be featured on the show! You can also submit anonymous comments through this Google Form: https://forms.gle/9Zjxzkpwajivx19z8 

00:00 Introduction

04:35 Two Harvard Laws

14:54 Attorney General Prediction?

16:24 Sarah’s New Book!24:09 Process v. Outcome (A Split in the Legal Right)

51:54 Decency in Politics

01:02:40 Girl Problems

WEEK 28: How to Get Into Harvard Law (with the Dean of Admissions). Welcome to the Charles River. This week, we sit down with Dean Kristi Jobson—the literal Dean of Admissions—to answer the question everyone wants to know: what does it actually take to get into Harvard Law School?

We start with Dean Jobson’s story—how she ended up at Harvard, what law school looked like when she was a student, and how she eventually took on one of the most influential roles in legal education. Along the way, we get a behind-the-scenes look at what it means to shape a class at the highest level.Then we dive into the main topic: the admissions process. We walk step-by-step through how applications are actually reviewed—from the first reader to the second reader to full committee discussions—and what really matters when decisions get made. One of the biggest takeaways: Harvard Law is far more holistic than people think. Numbers matter, but they’re not the whole story—and relying on them alone is a mistake.We break down the key components of an application:- GPA and LSAT (and how much they actually matter today)- Personal statements and how to stand out without sounding manufactured- Letters of recommendation, work experience, and extracurriculars- The interview—and what separates candidates at the highest levelWe also tackle some of the biggest misconceptions about Harvard Law admissions. Should you hide your political views? Can an application be too polished? Along the way, we cover the numbers: nearly 9,000 applicants, an admit rate just over 9%, and a class filled with near-perfect GPAs and LSAT scores. But more importantly, we focus on what those numbers don’t capture—and how applicants can distinguish themselves in a hyper-competitive pool.We also get into some lighter (and surprisingly revealing) moments, like how accurate Legally Blonde actually is.Then, of course, Girl Problems:- What’s the best profession for a lawyer to marry?- And is intra-section dating as a 1L a terrible idea?Email [email protected] with your questions/comments or submit a voice memo at https://www.speakpipe.com/approachthebench for a chance to be featured on the show! You can also submit anonymous comments through this Google Form: https://forms.gle/9Zjxzkpwajivx19z8

WEEK 27: Can the GOP Win Women Back? (with Keri Collins). Welcome to the Harvard Salient office. This week, we’re joined by Keri Collins, a freshman at Harvard College, to tackle one of the biggest political questions right now: why are young men and women drifting so far apart—and can the Right actually win women back?

We start with a quick reset after last week’s episode, including strong feedback (both good and… Instagram comments), before jumping into a classic appetizer: rating pickup lines. From confident to cringeworthy, we sort them into “good,” “eh,” or “NEVER say that”—and learn pretty quickly what actually works and what absolutely doesn’t.

Then we get into the main topic: the growing gender divide in politics. We break down the data—huge gaps in party identification, voting patterns, education, mental health, and issue priorities between Gen Z men and women—and try to figure out what’s actually driving it. Why are young women trending left? Why are young men trending right? And are both sides misunderstanding each other in the process?

We also go deeper than just the numbers. We talk about expectations, resentment, and the real cultural tensions playing out online and in dating. From viral posts to personal experiences, we unpack why both men and women increasingly feel frustrated—and sometimes openly hostile—toward each other.

From there, we push toward solutions:- What would it actually take to bring women back to the Right?- Is this a messaging problem, a policy problem, or something deeper?- Are we locked into a permanent divide, or is there a path forward?

This ends up being less about politics alone and more about relationships, expectations, and how an entire generation is trying (and often failing) to understand each other.

We close with Girl Problems:

- What’s the proper order of gifts in a relationship?

- Should a man’s salary matter when dating?

- Are big, expensive weddings morally wrong?

Email [email protected] with your questions/comments or submit a voice memo at https://www.speakpipe.com/approachthebench for a chance to be featured on the show! You can also submit anonymous comments through this Google Form: https://forms.gle/9Zjxzkpwajivx19z8

00:00 Introduction

14:25 Pickup Lines

24:17 Winning Women Back to the GOP

1:16:18 Girl Problems

WEEK 26: The Gay Marriage Debate (with Ripken). Welcome back to the bench. This week, we’re joined by Ripken Holt for one of our most direct and controversial conversations yet: should gay marriage be legal—and how should Christians think about it?

We jump straight into the deep end. No long intro—just the question everyone’s actually asking: what do Christians believe about gay marriage, and what should that mean for law and public policy? But before we get there, we lay the groundwork with a key threshold issue: how should Christians think about LGBTQ+ identity more broadly?

We break down the three major frameworks you’ll hear today: the traditional/orthodox view, the celibate gay Christian perspective, and the affirming/revisionist position. We walk through the biblical texts, the theological reasoning behind each, and the real pastoral implications—especially for how Christians relate to people inside and outside the Church.

From there, we move into the legal side: how marriage actually works in the United States. We explain the state-driven structure of marriage law, the role of the Constitution, and how cases like Obergefell reshaped the entire landscape. We also explore alternative frameworks—what it would look like to return to a pre-Obergefell system, remove the state from marriage entirely, or shift to a civil-union model.

Then we hit the core debate: should Christians support banning gay marriage? We take seriously the argument that even if same-sex relationships are viewed as sinful, it doesn’t follow that the government should prohibit them. We walk through the “two kingdoms” framework, the limited role of law, religious liberty concerns, and the tension between moral conviction and political coercion.

Will's Resources:

Rebecca McLaughlin & Rachel Gilson Resources on Orthodox Approaches to HomosexualityPodcasts

https://open.spotify.com/episode/2IjFDBoB9BJpVSHgXFLpnD?si=ojnWwQ4FTAOWK8cCN1oXLQ

https://open.spotify.com/episode/4C8ArxaAY9qjE35p4l5oK8?si=PscLPwtJQ6i_IhoR-cESKA

https://open.spotify.com/episode/1lTw8CM1kUAfhvlI2hbWgh?si=_0vKk6qwQa-TGSrp0gUgZA

https://open.spotify.com/episode/6xHAFfGgcb7mbBRJFhdQCl?si=1fOeG5Z9S6ifUqdLgxGn4A

Books

Does the Bible Affirm Same-Sex Relationships?: Examining 10 Claims about Scripture and Sexuality" (2024) - Rebecca McLaughlin

Born Again This Way: Coming Out, Coming to Faith, and What Comes Next (2020) - Rachel Gilson

Along the way, we keep it grounded (and a little lighter) with some classic segments:

- Ranking the best and worst fast food spots (yes, Chick-fil-A makes an appearance)

- And some honest tension about what Christian relationships should actually look like

We close with Girl Problems:

- How Christian is “Christian enough” to date?

- Should you call out friends for secular relationships?- Dating apps—with Ripken’s take

This is one of those episodes where we don’t dodge the hard parts. Whether you agree or disagree, we try to lay out the arguments clearly, seriously, and without pretending the answers are easy.

Email [email protected] with your questions/comments or submit a voice memo at https://www.speakpipe.com/approachthebench for a chance to be featured on the show! You can also submit anonymous comments through this Google Form: https://forms.gle/9Zjxzkpwajivx19z8

00:00 Introduction

03:49: The Christian View on Homosexuality

18:27 Gay Marriage: Should it be legal?

1:03:04 Fast Food Restaurants

1:10:01 Feedback

1:11:04 Girl Problems

WEEK 25: The Singleness Special

Welcome to Will’s house. This week, we slow things down after a run of politics-heavy episodes to ask a different kind of question: what if singleness isn’t just a temporary inconvenience—but actually a meaningful, even good, way to live?

We kick things off with some spring break recap and listener feedback. Then we jump into a fun but revealing appetizer: Green Flag or Red Flag? From texting habits to family closeness to political intensity, we test our instincts on what actually matters in dating—and where people might be overthinking it.

From there, we turn to the core topic: should you just stay single? We take a serious look at whether modern Christian culture has overpromised marriage—especially in the wake of purity culture—and whether that has set people up for disappointment. We walk through the biblical tension: marriage as a creational good, singleness as a real and sometimes advantageous calling, and the reality that neither is guaranteed.

We break down the real advantages of singleness—time, flexibility, risk tolerance, and undivided focus—and distinguish between temporary and lifelong singleness. We also push back where needed: when “the gift of singleness” becomes an excuse to avoid growth, vulnerability, or rejection.

Along the way, we tackle some uncomfortable but necessary questions: Are Christians subtly equating marriage with maturity? Why does Christian dating feel so intense and high-stakes? In what situations might someone actually be called to remain single long-term?

We close by reframing the goal: not “find a spouse,” but “become a faithful, integrated Christian adult”—whether that leads to marriage or not.

Then, of course, we finish with Girl Problems:

• How to handle it when someone seems interested—but they’re already in a relationship
• Do girls actually like nice guys? (what the data says vs. reality)
• Do guys really have “types”?And one question we probably shouldn’t have answered

Email [email protected] with your questions/comments or submit a voice memo at https://www.speakpipe.com/approachthebench for a chance to be featured on the show! You can also submit anonymous comments through this Google Form: https://forms.gle/9Zjxzkpwajivx19z8

00:00 Introduction, Spring Break, Homeless People

08:16 Where are We? And Feedback.

10:19 Red, Yellow, or Green Flag?

14:08 Singleness

44:52 Girl Problems

Week 24: The Spring Break Special

Shooting at the Harvard Radcliffe Institute, Mason and Will take a bit of a break from the typical content flow to have a heart-to-heart on the bench. They discuss the positives and negatives of podcasting in a social media age and open up about their active debates about what to focus on, how to share their views, and whether to continue doing the podcast at all. 

If you want an inside look at the Christian Conservative Harvard Bachelor podcasting space, this episode is for you.

Email [email protected] with your questions/comments or submit a voice memo at https://www.speakpipe.com/approachthebench for a chance to be featured on the show! You can also submit anonymous comments through this Google Form: https://forms.gle/9Zjxzkpwajivx19z8

00:00 Introduction

1:17 Problems with Podcasting and Priorities

13:01 Reflecting on ‘Political Podcasting’

24:10 Spring Break Plans!

25:50 Girl Problems: The Thirty-Three Percent Rule

WEEK 23: American Empire & Progressive Christian Nationalism.

This week, we take the bench to the Radcliffe Gardens across from Cambridge Common and are joined by Frank, another Harvard student with a sharp interest in politics, law, and the role of religion in public life. We open with a quick introduction to Frank’s background — from Bates College to Harvard — and talk about what drew him into debates about politics, faith, and American power. For the appetizer, we come prepared with a classic law-student exercise: our top three best and worst Supreme Court decisions. We debate cases ranging from Brown v. Board and Dobbs v. Jackson Women’s Health Organization to infamous decisions like Dred Scott, Buck v. Bell, and Wickard v. Filburn, arguing about which rulings most strengthened — or most damaged — the American constitutional system.

The main topic turns to one of the most urgent geopolitical questions right now: Iran, U.S. power, and the rules of international law. We walk through the basic legal framework governing war between states under the United Nations Charter, including the prohibition on the use of force, the doctrine of self-defense under Article 51, and the principles of necessity and proportionality that are supposed to limit military action. Using the latest escalation between Iran, Israel, and the United States as a case study, we ask whether American involvement fits within international law — or whether the modern system has simply broken down when major powers decide to act.

From there, we pivot to the growing political figure James Talarico, the Texas Democrat whose viral speeches combine progressive politics with overtly theological language. We unpack the idea of “progressive Christian nationalism,” look at some of Talarico’s more controversial statements about faith and identity, and debate whether his approach represents a genuine theological vision or a political repackaging of Christianity.

We then turn briefly to the Texas Senate race, breaking down the contrast between John Cornyn’s institutional Republican career and Ken Paxton’s confrontational, populist brand of conservatism, and what that fight says about the future direction of the GOP.

Finally, we close with Girl Problems, where things get a little more personal: Should you ever settle for anything less than the best in a spouse? What are the top traits to look for in a husband or wife — and which traits are the biggest red flags? We each give our lists and debate what actually matters when choosing someone to build a life with.

Email [email protected] with your questions/comments or submit a voice memo at https://www.speakpipe.com/approachthebench for a chance to be featured on the show! You can also submit anonymous comments through this Google Form: https://forms.gle/9Zjxzkpwajivx19z8

00:00 Introducing Frank

12:27 Best and Worst Supreme Court Opinions

22:56 Iran and the American Empire

51:05 Progressive Christian Nationalism

1:08:32 Girl Problems: Best and Worst Traits in a Spouse

WEEK 22: The Pastor Calling Harvard Law Back to Christianity

Recorded in Hastings Hall, the oldest dorm at Harvard Law School, this week we sit down with Justin Yim — the pastor serving HLS students — to talk about something that may be quietly happening across American campuses: a renewed hunger for Christianity.

We begin with a quick introduction to Justin and how he ended up doing ministry at one of the most elite and intellectually intense law schools in the world. But before getting into it too much, we open with a rapid-fire parenting debate: at what age should kids be allowed to do various things? Smartphones, social media, dating, R-rated movies, alcohol, jobs, and sleepovers — we each give a number and defend it. It’s a surprisingly revealing way to talk about authority, maturity, and how modern culture has changed childhood.

From there, we dive deeper into Justin’s story. How did he enter ministry? Where did he begin? And how did he end up pastoring students at Harvard Law specifically?

That leads to bigger questions about evangelism in elite institutions. How do you share the gospel with students trained to interrogate every claim? Is Harvard Law spiritually darker than other places — or just intellectually honest? What does the daily life of a Christian law student look like compared to their peers? And what does it mean to faithfully preach the gospel when persuasion is never guaranteed?

Then we turn to the big question: Is a revival beginning among young people?

We play a voice memo from a woman in ministry describing a surge in campus ministry participation and discuss broader signs pointing in the same direction. After decades of decline, new data suggests the rise of the religiously unaffiliated has slowed. Ministries like Cru and InterVarsity report growing attendance, the Asbury revival drew tens of thousands of primarily young worshippers, and Bible sales and Christian content engagement online have surged. We ask Justin what he’s seeing firsthand at Harvard Law: are students actually searching for faith?

Finally, we close with one of the most thoughtful Girl Problems segments we’ve had yet. Several female listeners wrote in responding to our conversation about dating and careers. They raise a serious concern: many women today aren’t choosing ambitious careers out of ideology, but out of necessity. If marriage isn’t guaranteed and dating culture is dysfunctional, financial independence becomes survival. We wrestle with the tension between traditional aspirations for family and the practical realities of modern life.

Email [email protected] with your questions/comments or submit a voice memo at https://www.speakpipe.com/approachthebench for a chance to be featured on the show! You can also submit anonymous comments through this Google Form: https://forms.gle/9Zjxzkpwajivx19z8

00:00 Introduction

3:45 Parenting Advice from a Dad and Two Bachelors

28:31 Justin’s Ministry at Harvard Law

53:40 Is There a Revival Happening?

1:00:05 Girl Problems

WEEK 21: Is Modern Dating Rigged? (With Luis Penichet, HBS & Former Marine)

This week we’re joined by Luis Penichet — second-year Harvard Business School student, former U.S. Marine, and founder working on a new kind of dating app. And we go straight at one of the biggest cultural questions facing our generation:

Is the American dating system fundamentally broken?

We begin with a blunt diagnosis. Dating apps reward dopamine, novelty, and endless optionality — not long-term bonding, sacrifice, or family formation. Swiping trains people to treat each other as consumable profiles rather than covenantal possibilities. We discuss why both men and women are struggling — women facing overwhelming choice and rising expectations, men shaped by pornography and comparison culture — and whether our standards are too high, too low, or just disordered.

Luis then shares the idea behind the app he’s building: instead of scrolling through photos, you scroll through simulated conversations. Users create AI agents trained on their views, personality, and values. Those agents interact with other users’ agents first — and you review the conversations before ever seeing a photo. The goal? Shift attraction toward worldview, communication style, humor, and compatibility before physical filtering takes over. We debate whether this could actually rewire incentives — or whether technology will always drift toward superficiality.

From there, we pivot to Luis’s family story. As the son of Cuban immigrants, he explains why identity politics and Marxist frameworks are so dangerous — not in theory, but in lived history. We discuss how grievance-based politics corrodes gratitude, how America differs from Latin American revolutionary culture, and why economic resentment can quietly become moral justification for state overreach.

Then things get fun.

We run through a lightning round of conspiracy theories — which ones are obviously false, which ones are plausible, and which ones we genuinely don’t know what to do with. Instead of dismissing or embracing them wholesale, we talk about epistemic humility, institutional trust, and how to think without becoming paranoid or naïve.

Finally, we close with Girl Problems:
- Luis speaks for the short kings (he is one):How should women think about height preferences?
- Biological clocks and delayed adulthood
- And the infamous Alabama Hypothetical

Email [email protected] with your questions/comments or submit a voice memo at https://www.speakpipe.com/approachthebench for a chance to be featured on the show! You can also submit anonymous comments through this Google Form: https://forms.gle/9Zjxzkpwajivx19z8

00:00 Introduction

2:24 Problems with Dating Culture

18:22 Are the Issues with Dating More Deep-Rooted?

37:54 Luis's Cuban Heritage and the Essence of America

57:27 Conspiracy Theories...

1:10:02 Feedback, real quick!

1:13:22 Girl Problems: Short Kings

1:21:05 Girl Problems: Biological Clock

1:24:34 Girl Problems: The Alabama Hypothetical

WEEK 20: Inside the Life of Three Protestants at Harvard

Welcome to Brian’s apartment. This week, we bring Brian Rath, Harvard Business School student, into the mix and step back from pure politics to talk about something deeper: what it actually looks like to live as Protestants at Harvard.

We begin with a breakdown of the differences between Harvard Law and Harvard Business School — the culture, the people, and the academics. We then move into introductions and testimony — what brought Brian to Harvard, how faith shapes each of our lives, and what spiritual life looks like in a place known more for ambition than confession. We respond to strong listener feedback on our birth control discussion, including a passionate Catholic critique of Protestant sexual ethics, and we wrestle seriously with the differences in moral authority, conscience, and how Christians reason through hard questions.

From there, we answer a thoughtful question from a law student about sharing the Gospel in academic settings: when is it bold witness, when is it unwise, and how should Christians think about appropriateness in professional environments?

In the appetizer, in the spirit of Presidents’ Day, we rank the best and worst Presidents. We’ve got some controversial takes on those (now viewed and debated by over 400,000 people on Instagram). Highly recommend listening to this section!

Then we move to the core topic: what makes Protestant life distinct. We walk through authority (sola Scriptura), conscience, personal responsibility before God, how we confess sin, how we think about moral reasoning, and why Protestantism emphasizes disciplined disagreement over moral delegation. We discuss life issues, dignity, and the difference between intrinsic moral wrongs and matters of prudential judgment.

We close with the classic: Girl Problems.- Thoughts on pre-nups- Dating a non-Christian you genuinely love- And advice for the hopeless romantics who don’t want to settle but don’t want to be alone forever

Here are the links to Brian's Protestant resources:Gavin Ortlund/Truth Unites - https://www.youtube.com/@TruthUnites  https://open.spotify.com/show/5pwOh3BIp7rQaeZpmy8SF8?si=3744ff49a1994446
Anglican Aesthetics - https://www.youtube.com/@anglicanaesthetics  https://open.spotify.com/show/1U8TF897KNNea8PTXpvIsD?si=f84bc76f5e3b4341
Sola Media/White Horse Inn - https://www.youtube.com/@solamediaorg
https://open.spotify.com/show/11CeAFKB1ZF7pAmhGv4fMA?si=bf326f01138949ef
The Daily Office - https://open.spotify.com/show/7ABjzy7Tumx5tczT8LBqX5?si=cd458d56ff1642a0
Mike Winger - https://www.youtube.com/@MikeWinger
https://open.spotify.com/show/57uF3G2X0cUJnUMLyRp5HY?si=8e56eada734a4e35

Email [email protected] with your questions/comments or submit a voice memo at https://www.speakpipe.com/approachthebench for a chance to be featured on the show! You can also submit anonymous comments through this Google Form: https://forms.gle/9Zjxzkpwajivx19z8

00:00 Introduction

1:30 Harvard Business v. Harvard Law School

6:46 Getting to Know Brian

13:50 Feedback!

21:32 Ranking the Best and Worst Presidents

43:49 Very Interesting Discussion of Nuclear Energy!

54:27 The Secret Lives of Protestant Guys

1:34:00 GIRL PROBLEMS