Uncompromising Advocacy
Our lawyers set precedent and shape the law
arrow

Visionary justice
Comprehensive service

In Memoriam

Clayton C. Ruby, C.M.
B.A., LL.B., LL.M., LL.D. (honoris causa)
(1942 – 2022)

Clayton C. Ruby was one of Canada’s leading lawyers. For over 50 years, Mr. Ruby was at the forefront of criminal, constitutional, and civil rights advocacy. He was a champion of the underdog and a fearless advocate. Our firm’s ethos is modeled on his unwavering commitment to clients, justice and the public good.

Mr. Ruby passed away peacefully, surrounded by his family on August 2, 2022.

Best Lawyers Badge

Our Team

Brian Shiller
Partner
B.C.L., LL.B

Brian is a founding partner of Ruby Shiller Enenajor, Barristers and leads the firm’s civil litigation practice. Brian has more than three decades of litigation experience in a broad range of practice areas, with a particular emphasis on media and regulatory law. Brian has successfully represented clients in cases involving defamation and police brutality. His skilled advocacy on behalf of clients has resulted in precedent-setting victories in areas such as civil fraud and internet libel. Brian also has extensive experience in all aspects of animal welfare law.

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

Annamaria is a formidable advocate with international experience and a record of success both inside and outside of the courtroom. As a criminal and constitutional lawyer, she has argued cases before all levels of court including the Supreme Court of Canada. She thinks strategically, creatively and ambitiously about solving her clients’ legal problems.

Best Lawyers Badge
Heather Gunter
B.Sc., J.D.

Heather Gunter is a skilled, intelligent and empathetic advocate who has represented clients on a wide range of criminal matters, including driving offences, sexual offences, fraud, and homicide. Ms. Gunter has a special interest in assisting youth who have become involved in the criminal justice system as  well as clients who face mental health challenges. Ms. Gunter has experience seeking Not Criminally Responsible designations before the criminal courts and assisting clients who are before the civil mental health system. 

Sabrina Shillingford
Associate
B.A., J.D.

Sabrina Shillingford is a fearless advocate, dedicated to championing the rights of accused persons in the legal system. Ms. Shillingford has successfully represented clients in a variety of cases, skillfully navigating complex Charter issues and securing full acquittals for her clients at trial. Ms. Shillingford has a particular interest in appeals and has successfully aided in getting bail pending appeals. She also has experience suing the police and has been successful in achieving favourable settlements for her clients.

Our lawyers care deeply about each case and every person. We avoid conventional solutions and instead create an individualized litigation strategy that caters to our client’s unique legal problem and personal situation. We break boundaries by ambitiously pursuing outcomes that exceed expectations. Let us be your champions.

“Underlying all our advocacy is a love of liberty and a yearning for justice.”
CLAYTON RUBY
go to top

Practice Areas

Our lawyers practice at all levels of court in Ontario, other provinces, Federal Court, and at the Supreme Court of Canada. This includes the defence of a variety of criminal offences including homicide, financial crime, violent offences, weapons offences, drug offences, and sexual offences. We defend clients against large and complex prosecutions, such as wiretap, Anti-Organized Crime, and Guns and Gangs prosecutions. We also represent clients in regulatory prosecutions, institutional workplace investigations, and professional disciplinary proceedings. Our civil practice is focused on cases involving breach of contract, fraud, defamation, police brutality, malicious prosecution, and negligent investigation.

We are proud to represent clients in public law cases and in constitutional challenges to government policy or legislation, particularly legislation that is discriminatory or that produces wrongful convictions.

We also advocate outside the courtroom, recognizing that our clients’ needs often involve media relations, crisis management and strategic advice in anticipation of litigation.

Criminal Defence

A criminal charge, whether minor or serious, can be life-altering. At Ruby Shiller Enenajor, we defend every criminal case with diligence, care, and ingenuity. Our lawyers are experienced in handling all types of criminal charges, including homicide, financial crime, white collar crime, violent offences, weapons offences, drug offences, and sexual offences. 

Regulatory Law and Professional Discipline

The lawyers at Ruby Shiller Enenajor are experienced in defending clients within a wide array of regulatory contexts, including disciplinary action against medical professionals, lawyers, and other professionals. Our lawyers also represent individuals in proceedings before financial regulators, such as the Ontario Securities Commission.

Constitutional Law

We are passionate about holding government to account through constitutional litigation at the trial and appellate level. Our practice focuses on Charter litigation which is aimed at pushing government and society towards more just outcomes. We have pursued remedies for breaches of Charter rights, including freedom of expression, Indigenous rights, and equality rights.

Civil Litigation

Ruby Shiller Enenajor, Barristers handles a broad range of civil litigation practice areas, including media law, regulatory law, defamation, and civil fraud. We have a particular interest in holding the state to account through civil actions related to police brutality, investigatory negligence, and malicious prosecution. We are also experienced and passionate in the areas of animal welfare and boundary trees.

Appeals

We are vigorous appellate advocates, particularly in the arenas of criminal law, public law, and constitutional law. We have a decades-long history of advocacy before the Supreme Court of Canada in landmark cases, including Morganthaler v. The Queen, R. v. Morin, R. v. Askov, R. v. Parks, United States v. Burns, R. v. Harbottle, R. v. Arcangioli, R. v. Gardiner, R. v. Ipeelee, R. v. Gladstone, Ward v. Quebec, and R. v. Sullivan and Chan.

Investigations and Crisis Management

We have experience advising individuals who are under investigation by the police, an institutional employer, or a regulatory body. We understand that a single event may lead to multifaceted legal issues, such as concurrent criminal, civil, and regulatory concerns. We are adept at assisting clients in crisis to mitigate their risk on multiple legal fronts. We often work with individuals who have significant public profiles, and with PR firms and management companies, to shape the media message and preserve our clients’ public reputation.

Our Process

Please contact our office to learn more about our rates and retainer requirements. At that time, you can arrange to meet with us for a consultation appointment. At the consultation, we will provide some insight into your case and help you determine whether we are the right team of lawyers to suit your needs. To learn more, contact us today.

* Please note that our firm does not offer free consultations.

News and Media

Ruby Shiller Enenajor has been featured in

Get in Touch

Ruby Shiller
Enenajor
Barristers

197 Spadina Ave. suite 402
Toronto, ON M5T 2C8

Telephone: 416 964-9664
Fax: 416 964-8305
Email: admin@rubyshiller.com
Twitter: @Ruby_Shiller

embedgooglemap.net