Legal Lines, Legal Ambiguity with Writers April Dembosky and Jessie Allen

August 1, 2025

On Friday August 1, MacDowell Downtown hosted a thought-provoking evening featuring journalist April Dembosky and law professor Jessie Allen—two artists-in-residence whose current work explores the murky intersections of legal reasoning, mental health, and personal experience. Each, in their own way, is grappling with how culture, subjectivity, and ambiguity shape our understanding of justice.

two women seated in armchairs address an audience while speaking into microphones

(Oriana Camara photo)

April Dembosky, a health journalist with NPR’s San Francisco affiliate, opened the evening by reading from her forthcoming nonfiction book. Blending memoir and investigative reporting, the book follows the murder trial of her former college boyfriend, Steve, who was charged with killing his wife and whose defense hinged on a diagnosis of schizophrenia. The excerpt Dembosky read traced her reentry into Steve’s life after a 15-year silence, recounting the moment a defense attorney reached out to her for help in mounting an insanity plea.

Dembosky’s prose was as emotionally charged as it was intellectually rigorous, examining the limits of the legal system’s ability to parse mental illness from moral character. Did the law really have the ability to separate psychotic symptoms from personality? The presentation closed on a poignant note with a song Steve had once recorded for her—his voice and guitar echoing through Bass Hall, lending a human dimension to a case often reduced to clinical or criminal terms.

Jessie Allen followed with a reading from her own project: a genre-blending reinterpretation of Sir William Blackstone’s Commentaries on the Laws of England, an 18th-century legal text that has seen renewed relevance in U.S. Supreme Court decisions, particularly in recent rulings. But rather than approaching Blackstone as a traditional legal scholar, Allen—who has a background in performance art—read him as an emotional, intuitive outsider.

What began as a series of blog essays has evolved into a book-in-progress that weaves together personal narrative, legal analysis, and cultural commentary. Her project, Law, Actually touches everything from Brooklyn real estate and voting rights to sexual harassment, elder law, and even Halloween costume dilemmas, illustrating how ancient legal ideas continue to shape the most ordinary aspects of contemporary life. In Allen’s hands, Blackstone is reclaimed not as a rigid relic, but as a surprisingly radical thinker whose work invites reinterpretation.

The evening offered a compelling reminder that law is not simply a system of rules, but a living dialogue between abstract principles and the complexities of human experience. From the courtroom to the classroom, from psychiatric diagnoses to historical legal texts, Dembosky and Allen are each illuminating the personal dimensions of justice—and challenging audiences to think critically about the forces that shape it.

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