Ruby Shiller Enenajor, Barristers
4 lawyers · City of Toronto
One of 2,345 law firms listed in Toronto, and one of 455 handling Criminal Defence.
Free consultation
Free consultationAbout Ruby Shiller Enenajor, Barristers
Ruby Shiller Enenajor, Barristers is a small litigation firm with an office at 197 Spadina Avenue, in Toronto's Fashion District. Clayton Ruby, whose career spanned five decades of criminal, constitutional, and civil rights advocacy, and civil litigator Brian Shiller founded the firm in 2009. Ruby had already argued Supreme Court of Canada cases such as R. v. Askov, which established the constitutional right to a trial within a reasonable time, and served as a Bencher of the Law Society of Upper Canada from 1977 until retirement. Ruby received the Order of Canada in 2006 and died in 2022; the firm still carries the name.
Annamaria Enenajor is the firm's managing partner. A former Supreme Court of Canada law clerk to Chief Justice Richard Wagner and a member of both the Ontario and New York bars, Enenajor was elected a Bencher of the Law Society of Ontario in 2023. The firm's lawyers handle criminal defence, civil litigation, regulatory and professional discipline matters, constitutional and Charter litigation, and appeals, including police accountability and animal welfare cases. The practice doesn't stop at trial; its lawyers argue matters from provincial court through to the Supreme Court of Canada. Best Lawyers named the firm to its Best Law Firms Canada list in both the 2025 and 2026 editions.
Practice areas
Milestones & recognition
- Clayton Ruby served as a Bencher of the Law Society of Upper Canada from 1977 until retirement and received the Order of Canada in 2006.
- Annamaria Enenajor was elected a Bencher of the Law Society of Ontario in 2023, joining Convocation, the body that governs the profession.
- Best Lawyers in Canada has included Enenajor every year since 2022; its 2026 edition recognized Enenajor in Criminal Defence, Administrative and Public Law, Appellate Practice, Cannabis Law, and Professional Malpractice Law, a distinction the publisher describes as going to only 3% of lawyers globally.
- Best Lawyers named Ruby Shiller Enenajor to its Best Law Firms Canada list in the inaugural 2025 edition and again in 2026.
- Sabrina Shillingford won the 2025 Advocacy Award from the Canadian Association of Black Lawyers, announced in November 2025.
In the community
- Enenajor founded Cannabis Amnesty in 2018, advocacy that helped lead to federal legislation expediting pardons for simple cannabis possession.
- Enenajor has taught as a Visiting Professor at Osgoode Hall Law School (2023 to 2024) and an Adjunct Lecturer at Queen's University Faculty of Law since 2018.
- Brian Shiller chairs the Board of Directors at Reconnect Community Health Services and serves on the board of Main Stage Theatre Company.
- Sabrina Shillingford served as President of the Black Law Students Association at Osgoode Hall Law School; the Osgoode Women's Network later established an award in Shillingford's name.
Good to know
Wheelchair accessibleFees & payment
Flat fee
Free consultationLawyers 4
Annamaria Enenajor
Managing Partner
Criminal DefenceAdministrative & Regulatory Law
Brian Shiller
Founding Partner
Civil Litigation & Dispute ResolutionBusiness & Corporate Law
Heather Gunter
Lawyer
Criminal DefenceAdministrative & Regulatory Law
Sabrina Shillingford
Associate
Criminal DefenceAdministrative & Regulatory Law
This firm’s lawyers at a glance
- Law schools
- McGill University (2), Osgoode Hall Law School, University of Ottawa 4 of 4 lawyers
Who handles what
The neighbourhood
The firm's office sits at 197 Spadina Avenue, Suite 402, in what's now called Toronto's Fashion District. The area was long known as the Garment District, home to the city's textile and clothing manufacturers and, for decades, to a large share of Toronto's Jewish community, whose delis, theatres, and synagogues once filled the streets nearby. Many of the old warehouses along Spadina have since been converted into offices, restaurants, and design studios, and it's that kind of building, a converted commercial space in a formerly industrial stretch, that now houses a small litigation practice.
Frequently asked questions
- What areas of law does Ruby Shiller Enenajor handle?
- The firm practices criminal defence, civil litigation, regulatory law and professional discipline, constitutional law, and appeals, from its Toronto office.
- I've been charged with a criminal offence in Toronto. Can Ruby Shiller Enenajor represent me?
- Yes. The firm defends a range of criminal matters, from drug and driving offences to homicide, sexual offence, and financial crime charges, and represents both youth and adults.
- Can the firm bring a civil claim against the police?
- Yes. Its civil litigation practice includes claims for unlawful arrest, malicious prosecution, and negligent investigation, alongside other police accountability work.
- Does Ruby Shiller Enenajor represent professionals facing a discipline hearing?
- Yes. The firm represents doctors, lawyers, and other regulated professionals in regulatory and professional discipline proceedings.
- Does the firm practice animal welfare law?
- Yes. It's one of the firm's civil litigation focuses, with lawyers appearing before regulatory boards and courts on animal welfare matters.
- Where is Ruby Shiller Enenajor located?
- The firm's office is at 197 Spadina Avenue, Suite 402, in Toronto's Fashion District.
Where to find them
197 Spadina Avenue, Suite 402, Toronto, Ontario M5T 2C8 · 416-964-9664
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