Publications

The complete record.

A short selection first, then every publication in the curriculum vitae (July 2026), in its own wording: 9 books and edited collections, 15 book chapters, 69 articles, and a book review. Reverse chronological within each group. Titles link to the DOI, the SSRN abstract, an open repository record, or the publisher’s page, in that order of preference; two pieces with no public record stand as citations. The SSRN author page and Google Scholar carry the citation counts.

Selected Books Chapters Articles Review

Selected 11

2026
Superjustice: Law in the Age of Artificial Intelligence, Introduction
With Samuel I. Becher. SSRN; the complete Introduction, free.
2026
Cognitive Infrastructure for Public Revenue Systems
Canadian Tax Journal.
2026
Legal Order in the Age of AI Agents
With Samuel I. Becher. University of Toronto Law Journal.
2025
LexOptima: The Promise of AI-Enabled Legal Systems
With Samuel I. Becher. University of Toronto Law Journal.
2024
Generative AI for Tax: Looking Back, Looking Ahead
Tax Notes Federal.
2023
The Rise of Generative AI for Tax Research
With Condon, Massey, and Yan. Tax Notes Federal.
2018
How Artificial Intelligence Will Affect the Practice of Law
With Anthony Niblett and Albert Yoon. University of Toronto Law Journal.
2017
Commitment and Cooperation on High Courts
Book, with Andrew Green. Oxford University Press.
2016
The Path of the Law: Towards Legal Singularity
University of Toronto Law Journal. The paper that coined the term.
2016
Regulation by Machine
With Anthony Niblett and Albert Yoon. NeurIPS; Clifford Chance Prize, Barcelona.
2016
Using Machine Learning to Predict Outcomes in Tax Law
With Anthony Niblett and Albert Yoon. Canadian Business Law Journal.

A curated reading list: the recent and forthcoming work alongside the 2016 foundations. The complete groups follow.

Books and edited collections 9

2026
Superjustice
With Samuel Becher. (Oxford University Press, 2026).
2025
Law in a Changing World: The Climate Crisis
Edited with Jutta Brunnée, Brenda Cossman, and Andrew Green. (University of Toronto Press, 2025).
2023
The Legal Singularity
With Abdi Aidid. (University of Toronto Press, 2023).
2018
Canadian Income Tax Law, 6th ed.
With David Duff, Geoffrey Loomer and Lisa Philipps. (LexisNexis Butterworths, 2018).
2017
Commitment and Cooperation on High Courts: A Cross-Country Examination of the Institutional Constraints on Judicial Decision-Making
With Andrew Green. (Oxford University Press, 2017).
2015
Canadian Income Tax Law, 5th ed.
With David Duff, Kim Brooks, Geoffrey Loomer and Lisa Philipps. (LexisNexis Butterworths, 2015).
2012
Canadian Income Tax Law, 4th ed.
With David Duff, Kim Brooks, Geoffrey Loomer and Lisa Philipps. (LexisNexis Butterworths, 2012).
2009
Canadian Income Tax Law, 3rd ed.
With David Duff, Kim Brooks, and Lisa Philipps. (LexisNexis Butterworths, 2009).
2006
Canadian Income Tax Law, 2nd ed.
With David Duff, Kim Brooks, and Lisa Philipps. (LexisNexis Butterworths, 2006).

Book chapters 15

2025
Markets, Mobilization, and Transformation: Approaches to Innovation in Addressing Climate Change
in Jutta Brunnée, Brenda Cossman, Andrew Green, and Benjamin Alarie, eds., Law in a Changing World: The Climate Crisis (University of Toronto Press, 2025) 293-307, with Andrew Green.
Peer reviewed
2025
Introduction: How Climate Change Is Affecting Law and What to Do about It
in Jutta Brunnée, Brenda Cossman, Andrew Green, and Benjamin Alarie, eds., Law in a Changing World: The Climate Crisis (University of Toronto Press, 2025) 3-18, with Jutta Brunnée, Brenda Cossman, and Andrew Green.
2023
Explainable AI and Taxation: A Real-Life Application
in Dennis Weber, ed., The Implications of Online Platforms and Technology for Taxation (IBFD, 2023), pp. 283-305, with Anthony Niblett.
Peer reviewed
2022
Technology and the Future of Tax Dispute Resolution Processes and Practices
in Pooja Mihailovich and John Sorensen, eds., Tax Disputes and Litigation in Canada (Canadian Tax Foundation, 2022), with Arthur Cockfield.
Peer reviewed
2021
Quantitative Analysis of Judicial Voting
in David Law et al., eds., Research Methods in Constitutional Law (Elgar), with Andrew Green.
Peer reviewed
2021
Data Analytics and Tax Law
in Roland Vogl et al., eds., Research Handbook on Big Data Law (Edward Elgar, 2021), with Anthony Niblett and Albert Yoon.
Peer reviewed
2018
Legislated Interpretation and Tax Avoidance in Canadian Income Tax Law
in Christopher Hunt et al., eds., Legislating Statutory Interpretation: Perspectives from the Common Law World (Carswell, 2018) at 75-110, with David Duff.
Peer reviewed
2015
The Challenge of Tax Avoidance for Social Justice in Taxation
in H.P. Gaisbauer, G. Schweiger, and C. Sedmak, eds., Philosophical Explorations of Justice and Taxation (Springer International, 2015) 83-100.
2011
Tax Aspects of Canadian Fiscal Federalism
in Gianluigi Bizioli, ed., Tax Aspects of Fiscal Federalism: A Comparative Analysis (Kluwer Law International, 2011) 79-136, with Richard M. Bird.
2011
The VAT Treatment of Real and Immovable Property in Canada
in Robert van Brederode, ed., Immovable Property under VAT: A Comparative Global Analysis (Kluwer Law International, 2011), at 83-121, with Pierre-Pascal Gendron.
2008
National Report Canada
in Michael Lang et al., eds., Tax Compliance Costs for Companies in an Enlarged European Community (Kluwer Law International / Linde Verlag, 2008) at 133-156, with Alan Macnaughton.
2008
Bet on It: The Taxation of Online Gaming
in David Chodikoff and James Horvath, eds., The Taxation and Valuation of Technology (Irwin Law, 2008) at 115-138, with Alex Igelman.
Reprinted with permission in A. Usha, ed., Tax Laws: Global Perspectives (Amicus Books, 2007) at 162-190.
Reprinted with permission in L. Padmavathi, ed., Online Gambling and Law (Amicus Books, 2009) at 127-155.
2007
Retroactivity and the General Anti-Avoidance Rule
in David Duff and Harry Erlichman, eds., Tax Avoidance in Canada after Canada Trustco and Mathew (Irwin Law, 2007) 197-219.
2005
An Income-Contingent Financing Program for Ontario
in Frank Iacobucci and Carolyn Tuohy, eds., Taking Public Universities Seriously (University of Toronto Press, 2005) at 555-596, with David Duff.
2003
State Regulatory Competition and the Threat to Corporate Governance
in Thomas J. Courchene and Donald J. Savoie, eds., Art of the State: Governance in a World Without Frontiers (McGill-Queen’s University Press, 2003) at 165-202, with Ronald J. Daniels.

Articles 69

2026
Legal Order in the Age of AI Agents
(2026) University of Toronto Law Journal, advance access, doi:10.3138/utlj-2025-0104, with Samuel I. Becher.
Peer reviewed
2026
Policy Forum: Cognitive Infrastructure for Public Revenue Systems
(2026) 74(2) Canadian Tax Journal 367-381.
2025
LexOptima: The promise of AI-enabled legal systems
(2025) 75(1) University of Toronto Law Journal 73-121, with Samuel I. Becher.
2024
Generative AI for Tax: Looking Back, Looking Ahead
(2024) 182(6) Tax Notes Federal 1069-1078.
2023
AI and the Future of Tax Avoidance
(2023) 181(10) Tax Notes Federal 1809-1815.
2023
Automated Tax Planning: Who’s Liable When AI Gets It Wrong?
(2023) 180(13) Tax Notes Federal 2297-2305, with Rory McCreight and C. Tucciarone.
2023
Will AI Replace Tax Practitioners?
(2023) 181(5) Tax Notes Federal 855-861, with Rory McCreight and C. Tucciarone.
2023
The Path of Tax Law: Toward Legal Singularity
(2023) 180(9) Tax Notes Federal 1455-1462, with Rory McCreight and C. Tucciarone.
2023
The Ethics of Generative AI in Tax Practice
(2023) 180(5) Tax Notes Federal 785-793, with Rory McCreight.
2023
The Rise of Generative AI for Tax Research
(2023) 179(9) Tax Notes Federal 1509-1522, with Kim Condon, Susan Massey, and Christopher Yan.
2023
The Rise of the Robotic Tax Analyst
(2023) 178(1) Tax Notes 57-63.
2023
The Intersection Between Tax Credits and Trade or Business
(2023) 178(5) Tax Notes 689-695, with Christopher Yan.
2023
Relief of Innocent Spouses—Not So Podlucky
(2023) 178(9) Tax Notes 1339-1347, with Susan Massey and Christopher Yan.
2023
Overcoming Accuracy-Related Penalties with Reasonable Cause
(2023) 178(13) Tax Notes 1995-2002, with C. Tucciarone and C. Yan.
2022
The Debt-Equity Distinction and Tribune Media
(2022) 175(4) Tax Notes 593-600, with Kathrin Gardhouse.
2022
Disguised Distributions and Management Fees: Aspro Revisited
(2022) 175(9) Tax Notes 1401-1408, with Christopher Yan.
2022
Reserve Mechanical: Microcaptive Insurance Arrangement Denied on Appeal
(2022) 175(13) Tax Notes 2037-2045, with Bettina Xue Griffin.
2022
Situational Awareness: Accurate Financial Recordkeeping and Business Deductions
(2022) 176(5) Tax Notes 713-719, with Kathrin Gardhouse.
2022
Deducting Legal Expenses: Unpacking the IRS’s Appeal in Mylan
(2022) 176(9) Tax Notes 1419-1426, with Kim Condon.
2022
Tax Credits That Bond a Partnership: Revisiting Cross Refined Coal
(2022) 176(13) Tax Notes 2069-2074, with Bettina Xue Griffin.
2022
Chemoil: Economic Substance, Tax Credits, and Unprofitable Ventures
(2022) 177(5) Tax Notes 719-727, with Christopher Yan.
2022
Cashaw: Conflicting Duties and the Trust Fund Recovery Penalty
(2022) 177(9) Tax Notes 1257-1267, with Ann Velez.
2022
Timing is Everything: The Step Transaction Doctrine in GSS Holdings
(2022) 174 Tax Notes Federal 1849, with Stefanie Di Giandomenico.
2022
Using Machine Learning to Evaluate the Existence of a Trade or Business: Olsen
(2022) 174 Tax Notes Federal 1231, with Christopher Yan.
2022
Using Machine Learning to Crack the Tax Code
(2022) 174 Tax Notes Federal 661, with Bettina Xue Griffin.
2021
Predicting Worker Classification in the Gig Economy
(2021) 173 Tax Notes Federal 1733, with Kathrin Gardhouse.
2021
Battling Uphill Against the Assignment of Income Doctrine
(2021) 173 Tax Notes Federal 1253, with Kathrin Gardhouse.
2021
Would Management Fees by Any Other Name Still be Deductible
(2021) 173 Tax Notes Federal 499, with Christopher Yan.
2021
Seventh Circuit Affirms Spouse is Not so Innocent on Appeal
(2021) 172 Tax Notes Federal 2149, with Stefanie Di Giandomenico.
2021
Captive Insurance Appeal in Reserve Mechanical Will Likely Fail
(2021) 172 Tax Notes Federal 1431, with Bettina Xue Griffin.
2021
Economic Substance Doctrine: Still Giving Perrigo Heartburn?
(2021) 172 Tax Notes Federal 599, with Christopher Yan.
2021
Will Machines Replace Us? Machine-Authored Texts and the Future of Scholarship
(2021) 3(2) Law, Technology and Humans 5, with Arthur Cockfield.
Peer reviewed
2021
An Unprofitable Pretax Venture Can Still be a Partnership
(2021) 171 Tax Notes Federal 1951, with Bettina Xue Griffin and Christopher Yan.
2020
Ahead by a Century: Tim Edgar, machine-learning and the future of anti-avoidance
(2020) 68(2) Canadian Tax Journal 613-629.
Peer reviewed
2020
Predicting Economic Substance Cases with Machine Learning
(2020) 22(2) Journal of Tax Practice and Procedure 35-41, with Abdi Aidid.
Peer reviewed
2020
Using AI to characterize financing between related parties
(May 18, 2020) 96(7) Tax Notes State 915-920, with Abdi Aidid and Bettina Xue.
2019
Turning Standards into Rules Part 5: Weighing the Factors in Capital Gains vs. Ordinary Income Decisions
(January 14, 2019) (Bloomberg, Bureau of National Affairs).
2018
Turning Standards into Rules Part 4: Machine Learning and Economic Substance
(December 28, 2018) 249 DTR 11 (Bloomberg, Bureau of National Affairs).
2018
Turning Standards into Rules Part 3: Behavioral Control Factors in Employee vs. Independent Contractor Decisions
(December 14, 2018) (Bloomberg, Bureau of National Affairs).
2018
Turning Standards into Rules Part 2: How Do Financial Risk Factors Affect Debt vs. Equity Determinations?
(December 3, 2018) 233 DTR 10 (Bloomberg, Bureau of National Affairs).
2018
Turning Standards into Rules Part 1: Using Machine Learning to Predict Tax Outcomes
(September 18, 2018) 182 DTR 10 (Bloomberg, Bureau of National Affairs).
2018
How Artificial Intelligence will Affect the Practice of Law
(2018) 68(1) University of Toronto Law Journal 106-124, with Anthony Niblett and Albert Yoon.
Peer reviewed
2018
Computational Legal Research and the Advocates of the Future
(2018) 36(4) Advocates’ Quarterly 12-17, with Anthony Niblett and Albert Yoon.
2016
Using Machine Learning to Predict Outcomes in Tax Law
(2016) 58(3) Canadian Business Law Journal 231-254, with Anthony Niblett and Albert Yoon.
Peer reviewed
2016
Law in the Future
(2016) 66(4) University of Toronto Law Journal 423-428, with Anthony Niblett and Albert Yoon.
Peer reviewed
2016
The Path of the Law: Towards Legal Singularity
(2016) 66(4) University of Toronto Law Journal 443-455.
Peer reviewed
2015
Panel Selection on High Courts
(2015) 65(4) University of Toronto Law Journal 335-381, with Andrew Green and Edward Iacobucci.
Peer reviewed
2014
Policy Preferences and Expertise in Canadian Tax Adjudication
(2014) 62(4) Canadian Tax Journal 985-1027, with Andrew Green.
Peer reviewed
2014
Advance Tax Rulings in Perspective: A Theoretical and Comparative Analysis
(2014) 20(4) New Zealand Journal of Taxation Law and Policy 355-384, with Kalmen Datt, Adrian Sawyer and Greg Weeks.
Peer reviewed
2014
Accumulating Wisdom: An Updated Empirical Examination of Class Counsel Fees in Ontario Class Actions
(2014) 9(2) Canadian Class Action Review 355-384, with Peter Flynn.
2014
The Importance of Family Resemblance in ’Series of Transactions’ after Copthorne Holdings
(2014) 62(1) Canadian Tax Journal 69-109, with Julia Lockhart.
Peer reviewed
2011
The Taxation of Winnings from Poker and other Gambling Winnings in Canada
(2011) 59(4) Canadian Tax Journal 731-763.
Peer reviewed
2010
Interventions at the Supreme Court of Canada: Accuracy, Affiliation and Acceptance
48 Osgoode Hall Law Journal 381-410 (2010), with Andrew Green.
Peer reviewed
2010
Trebilcock on Tax Avoidance
60(2) University of Toronto Law Journal 623-642 (2010).
Peer reviewed
2010
Assessing Tax-Free Savings Accounts: Promises and Pressures
57(3) Canadian Tax Journal 504-532 (2009).
Peer reviewed
2009
Charter Decisions the McLachlin Era: Collegiality and Ideology at the Supreme Court of Canada
47 Supreme Court Law Review (2d) 475-511 (2009), with Andrew Green.
2009
Mutual Misunderstanding in Contract
46(4) American Business Law Journal 531-572 (2009).
Peer reviewed
2009
Policy Preference Change and Appointments to the Supreme Court of Canada
47 Osgoode Hall Law Journal 1-46 (2009), with Andrew Green.
Peer reviewed
2008
Should They All Just Get Along? Judicial Ideology, Collegiality, and Appointments to the Supreme Court of Canada
58 University of New Brunswick Law Journal 73-91 (2008), with Andrew Green.
Reprinted with permission in Adam Dodek and Lorne Sossin, eds., Judicial Independence in Context (Irwin Law, 2010).
2008
The Legacy of UK Tax Concepts in Canadian Income Tax Law
[2008] British Tax Review 228-252, with David Duff.
Peer reviewed
2008
Kingstreet Investments: Taking a Pass on the Defence of Passing On
46(1) Canadian Business Law Journal 36-49 (2008).
Peer reviewed
2007
Remedies and Alternative Contracts
44(4) American Business Law Journal 639-671 (2007), with Jim Dinning.
Peer reviewed
2007
Tax Policy, Capital Structure, and Income Trusts
45(1) Canadian Business Law Journal 1-19 (2007), with Edward Iacobucci.
Peer reviewed
2007
Rethinking the Approval of Class Counsel’s Fees in Ontario Class Actions
4(1) Canadian Class Action Review 14-46 (2007).
2007
The Reasonable Justice
57(2) University of Toronto Law Journal 195-226 (2007), with Andrew Green.
Peer reviewed
2006
The Taxation of Strike Pay
54(2) Canadian Tax Journal 426-449 (2006), with Matthew Sudak.
Peer reviewed
2005
Symposium on Tax Avoidance After Canada Trustco and Mathew
53(4) Canadian Tax Journal 1010-1037 (2005), with Sanjana Bhatia and David Duff.
Peer reviewed
2004
Divided Entitlements and Intermediate Default Rules
9(2) Stanford Journal of Law, Business & Finance 135-175 (2004).
2003
Executive Compensation and Tax Policy: Lessons for Canada from the Experience of the United States in the 1990s
61 University of Toronto Faculty of Law Review 39-77 (2003).

Book review 1

2011
The Transformation of the Supreme Court of Canada
review of Donald R. Songer, 61(1) University of Toronto Law Journal 173-178 (2011).
Peer reviewed