Advisory Opinions: "Justice Alito’s Next Moves"

Podcast: Advisory Opinions by The Dispatch
Release Date: February 19, 2026
Hosts: David French & Sarah Isgur
Location: Recorded live at Southern Methodist University (SMU)

Episode Overview

This episode focuses on speculation surrounding Justice Samuel Alito’s possible retirement from the U.S. Supreme Court, features a playful "draft" of potential Alito replacements, discusses the challenges and future of liberal legal movements in contrast to the Federalist Society, and analyzes a major judicial opinion regarding attorney-client privilege in the context of AI usage. The hosts, David French and Sarah Isgur, bring their trademark banter and insight into the intersection of law, politics, and legal culture, punctuated with memorable anecdotes and lively audience Q&A.

Key Discussion Points & Insights

1. The Justice Alito Retirement Rumors

[04:49 - 08:40]

• Alito Watch: The legal world is currently abuzz with rumors about Justice Alito’s potential retirement at the end of the 2026 Supreme Court term.
• Normal Timing: Historically, Supreme Court retirements are announced in early July, immediately post-term, considering political factors like midterm elections and Senate control.
• Alito’s Personality:
  • Sarah characterizes Alito as an introvert, not motivated by power or legacy.
  • "He reminds his clerks of this, sort of the Ozymandias version of the Supreme Court: This shall all be forgotten. You shall be forgotten. You're not so special." – Sarah Isgur [06:02]
• Book Speculation:
  • Alito’s book is scheduled for release October 6 — oddly during the week oral arguments resume, not the typical summer vacation slot.
  • This peculiar date has set off speculation that Alito may retire before the new term begins.

Notable Quote:

"It's really thin gruel for a retirement speculation. But it is not too thin gruel for us to talk about..." – David French [08:40]

2. SCOTUS Succession Draft: Who’s Next If Alito Retires?

[08:40 - 19:19]

David and Sarah alternate picks in a lighthearted NBA-style fantasy draft of likely Trump nominees for Alito’s seat. Their criteria focus on recent judicial trends and internal judiciary politics.

Sarah’s Picks

1. Judge Andrew Oldham (5th Circuit)

   • Former Alito clerk; seen as ‘maverick’ on the right.
   • "He is also at the top of that list for writing literal, like, words, opinions. No matter how you break it down, he’s just working harder." – Sarah Isgur [09:32]

2. Judge Jen Mascott (3rd Circuit)

   • Member of the Kavanaugh ‘clerk mafia;’ comes from a powerful network influencing recent Trump judicial picks.

3. Solicitor General John Sauer

   • Noted for argument performance in Trump immunity case; his odds depend on how key cases are decided.

David’s Picks

1. Judge Amul Thapar (6th Circuit)

   • South Asian background, fitness influencer, “Maha Justice” candidacy.
   • "He’s been talked about a lot in the clerk wars that erupted around the nomination of Brett Kavanaugh." – David French [10:53]

2. Judge Patrick Bumatay (9th Circuit)

   • Young, rising, notably openly gay; reflects cultural shifts in right-wing legal world.

3. Judge Naomi Rao (D.C. Circuit)

   • Front and center in Trump’s first term judicial strategies, still a strong contender.

Special Commentary

• The influence of former clerk “mafias” (notably Kavanaugh's and Thomas’s) is noted as a significant factor in current and future judicial appointments.
• Judges are increasingly “auditioning” through prolific opinions, with ambition on display.

3. The American Constitution Society (ACS) vs. The Federalist Society

[21:00 - 35:48]

• Context: Prompted by a listener’s question about judicial philosophies and a NYT article about the ACS’s future.
• FedSoc Strengths:
  • Born grassroots, gave voice to conservative students in unfriendly academic environments.
  • Anchored in clear, easily articulable philosophy: originalism (“rooted in the words on the page” – David French [28:56]).
  • Created cohesion, debate culture, and networking advantages for members.
• ACS Challenges:
  • Modeled as a liberal answer to FedSoc, but struggled with a lack of core philosophy and majority status in legal academia.
  • “Fed Soc was offering sort of social cohesion as much as anything else. I mean, truly, like, my children are FedSoc babies...” – Sarah Isgur [22:29]
  • ACS remains reactive (currently repositioning as explicit opposition to Trump and the Roberts Court), rather than as a proactive intellectual movement.
• The Quest for ‘Liberal Originalism’:
  • French advises ACS to stake out clear ground, suggesting liberal originalism or interpretivism (“dworkinism”) as philosophies centering on text but with different interpretive traditions.
  • “[Originalism] is a pretty easy philosophy to defend when it comes to law because it’s rooted in text...one of the reasons why a lot of the liberal philosophies have not taken hold is because they have de-emphasized text." – David French [28:47]
• Legal Realism:
  • The battle against legal realism (the idea judges are merely politicians in robes) is an ongoing struggle for both sides.
  • “Our podcast is basically a constant war against legal realism.” – Sarah Isgur [33:43]

4. Judicial Opinion: Does AI Break Attorney-Client Privilege?

[35:48 - 45:09]

Case Summary:
Judge Rakoff (SDNY) ruled that documents prepared using a consumer AI (Claude) by a party in anticipation of litigation were NOT protected by attorney-client or work product privilege.

Discussion Points

• Hypothetical Example:
  • If a client uses AI to understand or revise a document prepared by their attorney and then shares the AI’s output with that attorney, is it still privileged?
• Core Legal Analogy:
  • AI use is like Googling your lawyer’s contract, NOT like getting a second legal opinion.
  • “If you’re a client...your Google search history is a discoverable thing. It absolutely is.” – David French [38:00]
• Key Factors:
  • Open AI systems (like public Claude or ChatGPT) may not ensure privacy—the user’s expectation of privacy is critical.
  • Rakoff was particularly concerned about open models using inputs for future training, effectively making the information quasi-public.
• Practical Implication:
  • Lawyers should warn clients: Don’t expect privilege for anything entered into a public AI system.
  • “Don’t use ChatGPT as your backup attorney and expect it to be privileged.” – David French [44:34]

Q&A Segment – Deep Dive

[51:56 - 55:15]

• If the attorney, not the client, uses AI?
  • Work product privilege becomes the key issue; using open AI could jeopardize protection, especially if info is shared or used to benefit the model’s creators.
  • Caution and understanding of new tech are now essential legal skills.

5. Boneless Chicken Wings Lawsuit & Judicial Voice

[45:29 - 51:05]

• Case Recap:
  • Lawsuit over Buffalo Wild Wings’ "boneless wings" (which are saucy nuggets, not actually deboned wings) dismissed with playful, pun-laden opinion.
• Quote:

  "His complaint has no meat on its bones." – Read aloud by David French from the judicial opinion [46:15].

• Discussion:
  • When, if ever, is humor or flourish appropriate in judicial writing?
    • It’s fine in ‘humble cases’ (low stakes/frivolous), but should be avoided in opinions heavy with political consequence.
    • “Taking joy in humble cases is a good thing. Yeah, snark and sarcasm are a bad thing.” – Sarah Isgur [50:02]

6. Audience Q&A Highlights

Europe’s Approach to Free Speech vs. US Trends

[55:19 - 60:06]

• David’s Take:
  • Dislikes the European state-centered, value-oriented limits on free speech.
  • Notes recent, troubling movement in the U.S. toward similar censorship trends—now from both left and right.
  • Warns that when the state "sets the values" for citizens, the temptation to censor becomes overwhelming.
  • “Whenever you take that as an approach...the temptation towards authoritarianism is overwhelming.” – David French [59:40]

Memorable Moments & Quotes

• On Judicial Legacies:

  “You shall be forgotten. You’re not so special. Nobody’s gonna be sitting around, you know, talking about Sherman Minton in 2026 except me...” – Sarah Isgur [06:02]

• On Judge Oldham:

  "He is also at the top of that list for writing literal, like, words, opinions...He’s just working harder." – Sarah Isgur [09:32]

• On Legal Movements:

  “FedSoc was actually willing to say, here’s what we believe in, and you can attack it and criticize it, but we’re actually going to stand for something. And ACS has been unwilling to do that.” – Sarah Isgur [25:06]

• On Privilege & AI:

  “Don’t use ChatGPT as your backup attorney and expect it to be privileged.” – David French [44:34]

• On Free Speech:

  “I am really not in love with the European framework of free speech...Sadly, I think we’re moving...more towards that regime at the moment, and it’s very distressing to me.” – David French [56:06]

Timestamps for Key Segments

• Justice Alito Retirement Speculation: 04:49 – 08:40
• SCOTUS Draft: Alito’s Replacement: 08:40 – 19:19
• ACS vs. Federalist Society, Judicial Philosophies: 21:00 – 35:48
• AI & Attorney-Client Privilege: 35:48 – 45:09
• Saucy Nuggets Lawsuit & Opinion Style: 45:29 – 51:05
• Q&A (AI as Attorney Tool, Free Speech in Europe): 51:56 – 60:06

Episode Takeaways

• Legal Culture: The episode blends serious judicial speculation with inside-baseball legal humor, exposing the personalities, politics, and power networks that shape American courts.
• Tech & Law: Modern lawyering now requires tech literacy: what you ask an AI might wind up discoverable in court.
• Free Speech: Both legal history and policy are cyclical; current trends signal concerns for civil liberties from both left and right.
• Legal Community: Much of modern legal movement-building relies on clear principles, collaborative networks, and a willingness to take intellectual risks.

For listeners seeking both a primer on current legal events and an insider’s tour of law’s evolving landscape, this episode delivers both wit and wisdom.