Professor & Osler Chair in Business Law

Jackman Law Building
Room J360
78 Queen's Park
Toronto, Ontario M5S 2C5

Tel.: 416-946-8205

Benjamin Alarie is Professor and Osler Chair in Business Law at the University of Toronto Faculty of Law. Widely regarded for his contributions at the intersection of artificial intelligence, law, and taxation, Alarie’s research has helped shape how courts, policymakers, and leading institutions understand the implications of AI for legal reasoning and the future of regulatory frameworks.

Alarie introduced 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 vision has informed both academic debate and the development of new tools for legal analysis, influencing how legal systems might adapt in a rapidly evolving technological landscape.

As co-founder and CEO of Blue J, Alarie has worked to bridge theory and practice. Blue J’s AI-powered tax research platform, developed in close collaboration with experts in law, engineering, and data science, supports more than 2,000 organizations across North America and the UK. Its platform is used by major accounting networks and tax authorities, and forms the backbone of strategic partnerships with institutions such as CPA.com, the National Association of Tax Professionals, CPA Canada, Big 4 accounting firms, and Tax Notes. Blue J’s technology is relied on for tax research and decision-making in contexts where precision, defensibility, and efficiency are paramount.

Alarie’s scholarly work is anchored by a commitment to methodological rigour and practical impact. He is the author or co-author of seven books and more than 65 peer-reviewed articles, spanning tax law, legal theory, judicial behaviour, and the applications of machine learning in law. His most recent book, The Legal Singularity: How Artificial Intelligence Can Make Law Radically Better (with Abdi Aidid), was awarded the PROSE Award and shortlisted for the Donner Prize. His co-authored treatise, Canadian Income Tax Law, is widely cited and has informed jurisprudence at the highest levels, including the Supreme Court of Canada.

He holds an LL.M. from Yale Law School, a J.D. and M.A. (Economics) from the University of Toronto, and a B.A. from Wilfrid Laurier University. He clerked for Justice Louise Arbour at the Supreme Court of Canada, and is a faculty affiliate at the Vector Institute for Artificial Intelligence and the Schwartz Reisman Institute for Technology and Society.

Alarie’s work has received recognition from both academic and professional communities, including the vLex Fastcase 50 award and selection as one of The Globe and Mail’s Top 50 Changemakers. He is a frequent advisor and speaker for courts, government agencies, and global professional networks, contributing to the ongoing conversation about how technology and law can—and should—shape one another in the public interest.

Alarie’s approach combines a respect for legal tradition with an openness to innovation. Through both his research and his work at Blue J, he aims to help legal and tax systems become more accessible, reliable, and responsive to the needs of modern society.

Learn more about Professor Alarie's work at Blue J or connect via LinkedIn.

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
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)
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).