Benjamin Alarie

Role: Full-Time Faculty - Professor

Education

LL.M. - Yale Law School (2003)
J.D. - University of Toronto (2002), with honours
M.A. - University of Toronto (2002)
B.A. - Wilfrid Laurier University (1999), with high distinction

Overview

Benjamin Alarie is Professor and Osler Chair in Business Law at the University of Toronto Faculty of Law. He is widely recognised for his contributions at the intersection of artificial intelligence, law, and taxation. His research examines how technological change reshapes legal reasoning, the design of tax systems, and the role of courts and regulatory institutions.

He is the originator of the concept of the “legal singularity,” the hypothesis that legal systems may, through advances in machine learning and computational law, move toward far greater clarity and predictability. This idea has influenced debates in jurisprudence, public policy, and computer science, and it has shaped how academics and practitioners think about the future of legal reasoning in a data-rich environment. His scholarship has been published in leading journals, cited by the Supreme Court of Canada, and engaged by policymakers internationally. He has authored or co-authored seven books and more than sixty-five peer-reviewed articles, including The Legal Singularity: How Artificial Intelligence Can Make Law Radically Better (with Abdi Aidid), which was awarded the PROSE Award in Law and Legal Studies and shortlisted for the Donner Prize. He is also co-author of several editions of Canadian Income Tax Law, a leading treatise that has informed jurisprudence at the highest level.

Alarie is also co-founder and CEO of Blue J, a company that translates his scholarly insights into practice. Blue J’s AI-powered platform for “Better Tax Answers” is used by more than 3,000 firms and institutions across North America and the UK, including major accounting networks, tax authorities, and leading universities. Its technology supports strategic partnerships with CPA.com, Tax Notes, the National Association of Tax Professionals, CPA Canada, and the International Bureau of Fiscal Documentation. Blue J has collaborated closely with OpenAI on pioneering applications of large language models in tax law. With an NPS above 80 and industry-leading adoption metrics, the platform produces the most trusted answers in tax and is increasingly recognised as the operating layer for AI-driven tax cognition, helping professionals and governments deliver superior tax analyses with greater consistency, reliability, and defensibility in high-stakes contexts.

Through both his scholarship and his leadership at Blue J, Alarie combines respect for legal tradition with a commitment to innovation. His work seeks to make legal and tax systems more accessible, reliable, and responsive to the needs of modern society. More about his work and collaborations can be found on LinkedIn.

Areas of Interest

  • Tax Law

Selected Publications

The Legal Singularity: How Artificial Intelligence Can Make Law Radically Better (University of Toronto Press, 2023), with Abdi Aidid (Amazon).

“LexOptima: The promise of AI-enabled legal systems” (2025) 75(1) University of Toronto Law Journal 73-121, with Samuel I. Becher(SSRN).

"Generative AI for Tax: Looking Back, Looking Ahead" (February 5, 2024) Tax Notes Federal (SSRN).

"AI and the Future of Tax Avoidance" (December 4, 2023) Tax Notes Federal (SSRN).

"Will AI Replace Tax Practitioners?" (October 30, 2023) Tax Notes Federal (SSRN).

"Automated Tax Planning: Who's Liable When AI Gets It Wrong?" (September 25, 2023) Tax Notes Federal (SSRN).

"The Ethics of Generative AI in Tax Practice" (July 31, 2023) Tax Notes Federal (SSRN).

"The Rise of Generative AI in Tax Research" (May 29, 2023) Tax Notes Federal (SSRN).

"The Rise of the Robotic Tax Analyst" (January 2, 2023) Tax Notes Federal (SSRN).

"How Artificial Intelligence will Affect the Practice of Law" (2018) 68 University of Toronto Law Journal 106, with Anthony Niblett and Albert Yoon (JSTOR).

"The Path of the Law: Towards Legal Singularity" (2016) 66(4) University of Toronto Law Journal 443 (SSRN).

"Using Machine Learning to Predict Outcomes in Tax Law" (2016) 58(3) Canadian Business Law Journal 231, with Anthony Niblett and Albert Yoon (SSRN).


Academic appointments

Faculty Affiliate, Vector Institute for Artificial Intelligence
Faculty Affiliate, Schwartz Reisman Institute for Technology and Society

Awards and distinctions

  • Donner Prize shortlist for "The Legal Singularity: How Artificial Intelligence Can Make Law Radically Better" (2024)"
  • Association of American Publishers (AAP) PROSE Award for "The Legal Singularity: How Artificial Intelligence Can Make Law Radically Better" (2024)
  • vLex Fastcase 50 Honoree (2023)
  • Top 50 Changemaker, Globe & Mail (2022)
  • Alan Mewett QC Prize for Excellence, University of Toronto Faculty of Law Students' Law Society (2009)