Ruby Shiller Enenajor, Barristers

About 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.