Teaching Judges: Appellate Expert Cherise Bacalski on Brief Writing and the Human Side of Law

Appellate specialist Cherise Bacalski teaches appellate writing at NYU Law's New Appellate Judges Program, and in this interview we discuss her insights from both sides of the bench and how her background in rhetoric shapes her approach to appellate advocacy.

• Training new judges: At NYU, Cherise teaches newly appointed appellate judges how to make their opinions more readable through proper structure, headings, and organization—skills that help both judges and practitioners.
• The rule is king: What is the rule in your case? Cherise explains that, whatever it is, that rule should inform every part of your brief.
• Write for a “hostile reader”: Reading your brief—your trenchant, brilliant, erudite, sparkling brief—is the last thing any judge wants to do. Forget being brilliant. Just be clear, concise, skimmable, and easy to digest.
• Lead with old information: One of the most effective writing principles is beginning each new point with familiar information to propel readers forward at the speed of thought, reducing the need for excessive explanation.
• The human element: Cherise views the law as fundamentally human. Understand you are talking to humans, not picking a lock.
• AI is an amazing tool, but not a replacement: Use AI to test arguments and identify weaknesses in briefs. But AI sometimes misses critical "smoking gun" evidence in case analysis.

Tune in for a masterclass in appellate advocacy that bridges the gap between academic rhetoric and practical legal persuasion from an attorney who's seen the system from multiple perspectives.

Appealing in the 9th Circuit? Your deadline is 30 days. Don’t let Rule 58’s “separate document” extension lead you astray. Appellate specialists Tim Kowal and Jeff Lewis also discuss ChatGPT 5 (a “market disruptor”), and sanctions strategies in federal court.

• Appeal Deadline Alert: The 9th Circuit in McNeil v. Guitare held that Rule 58's 150-day extension for appeal deadlines applies only to final judgments, not collateral orders like qualified immunity denials.
• Anti-SLAPP Motion Timing: Mora v. Menjivar confirms that filing just a notice of anti-SLAPP motion within the 60-day deadline is insufficient—supporting documents must be filed concurrently.
• Out: Res Judicata. In: Claim Preclusion.
• Sanctions Strategy: 28 U.S.C. § 1927 can be used for sanctions without Rule 11's cumbersome 21-day safe harbor.
• AI Ethics: California courts confirmed in Nolan v. Land of the Free that attorneys must personally read all cited authorities, regardless of whether AI tools were used in brief preparation.

And more practical insights on navigating procedural pitfalls, avoiding sanctions, and ethically incorporating AI tools into your appellate practice.

Failing to cite your secondary sources in briefs is poor form. But is it plagiarism? Jeff and Tim debate. And when the Supreme Court The publishes a case, should it explain itself? PJ Gilbert and Tim say yes, Supreme Court and Jeff disagree.

Also in this episode:

• Can copying from a CLE article really get you sanctioned? Kelly v. Tao suggests… maybe.
• Presiding Justice Gilbert rails (again) against the Court's silent de-publishing practices.
• Deny a request for admission in a one-way fee-shifting case? You might still owe fees—Gammo v. Morrell.
• $105k in sanctions after failing to abandon claims disproven in discovery—Atlantic v. Baroness.
• The perils of citing the wrong fee statute—Martin v. Hogue.
• Gibson Dunn bills $1.8M for May alone in public interest litigation over LA homelessness.
• Can ChatGPT testify against you? OpenAI’s CEO says maybe.
• How AI tools are reshaping billing, ethics, and expectations for appellate lawyers.

Tune in for AI ethics, briefing blunders, and why even your RFA denials could cost you.