Annamaria Enenajor

Partner
B.A., M.Sc., B.C.L., LL.B

Described by the Toronto Star as a “brilliant, young legal mind,” Annamaria is a fearless and skilled advocate who brings deep knowledge, creative thinking, and an exceptional work ethic to all her client files. She practices criminal defence, regulatory, and constitutional law and is the firm’s managing partner.  

Annamaria has argued before all levels of court in Ontario as well as before the Supreme Court of Canada. She advocates for individuals and companies facing criminal investigations and charges, providing strategic advice and client-focused representation both in and out of the courtroom. She also provides comprehensive and practical independent legal advice to organizations on matters related to criminal, quasi-criminal and regulatory compliance.  Annamaria is also a regulatory adjudicator and sits on the Hearing and Appeal Division of the Law Society Tribunal.  

Annamaria is a strong public advocate for civil rights and criminal justice reform in Canada. She frequently writes, consults and speaks to the media as an expert on these issues. In 2018, she founded Cannabis Amnesty, a national, not-for-profit organization that successfully lobbied the federal government to eliminate criminal records related to simple cannabis possession offences.  She has received numerous awards and recognitions for her public advocacy work, including being named one of the 50 most influential Torontonians by Toronto Life magazine and one of the 32 Women of the Year by Chatelaine. 

Annamaria complements her practice with contributions to legal education and scholarship. She was a Visiting Professor at Osgoode Hall Law School for the 2023/24 academic year, where, among other courses, she teaches first-year Criminal Law. She is also an instructor at Queen’s University Faculty of Law where she has been teaching a popular seminar that she designed called Bias and Criminal Justice System Outcomes since 2018. She is also the co-author of the 9th edition of Sentencing (LexisNexis, 2017); author of “Similar Fact Evidence” in The Law of Objections in Canada: A Handbook (LexisNexis, 2019); and is co-editor of the Canadian Rights Reporter (LexisNexis). 

Before building a practice in Toronto, Annamaria worked in civil litigation in the New York office of Ropes & Gray, LLP where she focused on defending government enforcement actions and conducting internal investigations into allegations of corruption and bribery. While in New York, Annamaria maintained an active pro bono practice. She successfully represented LGBT asylum-seekers and staffed a low-income legal clinic for students in the South Bronx. She was also a member of a team of lawyers who brought an unprecedented civil rights class action against New York City to end the use of excessive force against inmates at Rikers Island and other New York City jails. Before that, Annamaria clerked at the Supreme Court of Canada for Justice Richard Wagner, now Chief Justice. She graduated from McGill University’s Faculty of Law as the David L. Johnson Gold Medalist. 

E aenenajor@rubyshiller.com T 416-964-9664 x107 X @AEnenajor

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