Described by the Toronto Star as a “brilliant, young legal mind,” Annamaria Enenajor is a partner at Ruby Shiller Enenajor DiGiuseppe, Barristers, where she practices criminal defence, regulatory, constitutional law and civil law where it intersects with state accountability. She defends clients accused of criminal misconduct in a variety of cases, including white collar crime, murder and manslaughter, drug offences, human trafficking offences, sexual offences, and fraud. She also acts for clients in professional misconduct and quasi-criminal/regulatory matters. She has argued before all levels of court in Ontario and before the Supreme Court of Canada. 

Ms. Enenajor is also deeply committed to community service and is an outspoken public advocate for evidence-based and compassionate criminal justice reform. She is the founder and Executive Director of the Campaign for Cannabis Amnesty and sits on the Board of Directors of the Open Democracy Project. Her work has been profiled in The Toronto Star, Globe & Mail, and in Toronto Life magazine. She has received numerous awards and recognitions for her public advocacy, including being named one of the 50 most influential Torontonians of 2018 by Toronto Life magazine and one of the 32 Women of the Year in 2018 by Chatelaine

Prior to joining the firm, Annamaria practiced litigation in the New York office of the international law firm, Ropes & Gray, LLP. There, she focused on government enforcement actions and 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. For this work, she was awarded a 2014 Pro Bono Publico Award by the New York Legal Aid Society.

From 2012 to 2013, Annamaria clerked at the Supreme Court of Canada for Justice Richard Wagner, now the Chief Justice of Canada.

Annamaria graduated from McGill Faculty of Law as the David L. Johnson gold medalist, obtaining both civil and common law degrees. During her studies, she was the recipient of numerous awards including prizes for the highest standing in Jurisprudence, Evidence and Public International Law. She also served as the Editor-in-Chief of the McGill International Journal of Sustainable Development Law and Policy and was a legal researcher at the McGill International Criminal Justice Clinic, supporting the Defense Office of the Special Tribunal for Lebanon.


Annamaria Enenajor pens an Op Ed in the Toronto Star

Annamaria Enenajor is profiled in Toronto Life Magazine on her cannabis advocacy: “She’s a partner at Clayton Ruby’s law firm, fighting for the erasure of records for personal possession.”

Annamaria Enenajor speaks to the Toronto Star about how our outdated criminal justice system creates frustrating delays. 

Annamaria Enenajor speaks to Vice Media about how the federal government’s new crime bill could result in more wrongful convictions.

Annamaria Enenajor is profiled in Precedent Magazine: “She has become a go-to media pundit on the criminal justice system.”

Annamaria Enenajor is interviewed for hit legal podcast, Of Counsel: “Annamaria Enenajor is a legal phenom and inspiration among her peers.”

Annamaria Enenajor is featured on TVO’s The Agenda, discussing the legalities of those currently incarcerated for issues related to marijuana.

Annamaria Enenajor is profiled in the Young Advocates’ Standing Committee Newsletter. (October 2015).


Practice AreasCriminal Defence, Constitutional Law, Civil Rights Law
DegreesB.A., M.Sc., B.C.L., LL.B
Address171 John Street, Suite 101
Suite 101
Toronto, ON M5T 1X3