David Woodin
Appellate Attorney · Legal Software Developer
Building legal software since 1988. Now building AI-native systems for appellate practice.
About
I’m a New York appellate attorney and legal software developer who has been building technology for legal practice since 1988. I created the original DOS-based Gunga Clerk sentencing system, rebuilt it for the web in 1998, and have continuously developed it into NYSentencing.com, a substantive legal decision-support system for New York criminal practice. My current work focuses on applying generative AI to substantive appellate practice—not simply using AI to draft text, but designing workflows and systems around the way lawyers actually analyze records, identify appellate issues, develop arguments, test counterarguments, prepare for oral argument, and manage active matters. I build my own tools using PHP, JavaScript, HTML/CSS, SQLite, Python where appropriate, and the OpenAI API. My current law-office system combines matter management with AI-assisted legal workflows and is designed around persistent case context rather than isolated chatbot sessions. I also teach lawyers how to use general-purpose AI safely and substantively in legal practice through CLE programs and consulting. My central interest is the architecture of AI-assisted lawyering: what should be automated, what should be verified, and where professional judgment must remain with the lawyer.
2 Projects
A lightweight legal AI platform I developed from scratch using PHP, JavaScript, HTML/CSS, SQLite and the OpenAI API. The project explores how a practicing lawyer can connect LLM capabilities to structured matter data without relying on a proprietary legal-AI platform. Current development includes persistent contextual memory, matter switching, document-oriented workflows, voice interaction, and integration with everyday law-office functions.
https://nysentencing.com/log-in/
NYSentencing.com is a substantive legal decision-support system for New York criminal practice that I have developed continuously for more than three decades. I created its original DOS-based predecessor, Gunga Clerk, in 1988 and rebuilt it as a web application in 1998. The system helps lawyers analyze New York sentencing law, plea restrictions, lesser-included offenses, bail and recognizance issues, and related statutory relationships. Its purpose is not simply to retrieve legal information, but to encode complex legal rules and relationships into software that assists attorneys in working through substantive legal problems. I have continued to maintain and expand the system as New York law has changed. NYSentencing.com reflects my longstanding interest in translating legal reasoning into practical software for lawyers.
Philosophy
"AI should expand a lawyer’s thinking, not replace the lawyer’s judgment."
I use AI to surface possibilities, test arguments, identify patterns, generate competing approaches, and deepen analysis. But the lawyer must remain responsible for purpose, strategy, verification, professional judgment, and the final work product. The value of AI is not that it removes the lawyer from the process; it gives the lawyer more intellectual leverage while keeping accountability human.