One Great Case

When Online Trolls Target a Community: How the Law Responds w/ Doug Judson

On paper, defamation law looks simple: a false statement is published, a reputation is harmed, and the courts step in to address the damage. The internet has changed that equation. Today, some of the most damaging allegations spread through social media, where accusations can move faster than facts, especially when misinformation about LGBTQ+ people and organizations begins circulating online. Two Ontario defamation cases, Rainbow Alliance Dryden et al. v. Webster and Canadian AIDS Treatment Information Exchange et al. v. Blackwell, exemplify how quickly online accusations can escalate into serious legal battles. Both cases arose after social media posts accused LGBTQ+ organizations and individuals of “grooming” children. What makes these cases especially interesting is how the litigation unfolded. It’s the limits of online speech, the risks of turning cultural narratives into accusations of crime, and how courts determine the real meaning behind words posted on the internet. The result was significant damage awards and an important reminder that anti-SLAPP protections and “public interest” defenses are not a license to publish harmful falsehoods online. To unpack how these cases developed and what they mean for defamation law in the digital age, I sat down with Doug Judson, a lawyer in Northwestern Ontario who represented the plaintiffs and has been involved in a growing number of online defamation cases. Doug shares how a case that started with a single social media post ended up producing one of the largest defamation awards of its kind in Canada. Things you’ll learn; 1. How online accusations of “grooming” against LGBTQ+ organizations turned into major defamation lawsuits 2. Why the court rejected the argument that these posts were protected “public interest” commentary 3. How anti-SLAPP motions work and why the defendant’s motion failed 4. The role of expert evidence in explaining the social meaning of defamatory language 5. Why summary judgment was the right strategy in these cases 6. How courts assess malice in online defamation disputes 7. The challenges of identifying and serving anonymous online defendants 8. Why large defamation awards may matter, even when collecting the money is uncertain Guest Bio Doug Judson practices law with Judson Howie LLP, a firm based in Northwestern Ontario that works with clients across the province. Doug began his practice with a leading Canadian law firm. He has worked with the in-house legal teams of two financial institutions, has held posts in the federal public service in Ottawa, has served as a contract Crown Attorney, and has worked in economic development, health, and justice programming for Treaty #3 First Nations. Doug started his professional career on Parliament Hill as an aide to two former MPs, and has since been involved with federal, provincial, and municipal election campaigns. From 2018-2022, he served on the council of the Town of Fort Frances. Doug maintains a busy volunteer presence in the community. He currently serves on the boards of the Northwest Community Legal Clinic and Borderland Pride. Doug is also currently the President of the Rainy River District Law Association and Past Chair of the Federation of Ontario Law Associations. He has previously served on the executive of the Ontario Bar Association's sexual orientation and gender identity section, on the Law Society of Ontario’s Equity Advisory Group, as President of the Law Students’ Society of Ontario, and on the boards of the Thunder Bay Regional Health Sciences Centre and Start Proud, a non-profit serving 2SLGBTQIA+ students and young professionals. https://www.douglasjudson.ca/ [https://www.douglasjudson.ca/]. About Your Host Areta Lloyd practices estate and trusts litigation, with a particular focus on capacity litigation. She participates in public speaking, mentoring junior lawyers, and presenting courses on the topics of estates law, health law, and law practice management. Areta has written for several publications and wrote a column for the Alzheimer caregiver website ALZlive.com [https://alzlive.com/category/editorial/legal-series/].

Chiang (Trustee of) v. Chiang: The Dark Side of Civil Contempt w/ Tom Curry

We like to believe that contempt of court is simple: you break the rules, face the consequences, and if you comply, you earn your way back out. The law, we tell ourselves, is precise, structured, and fair. But what happens when the very order meant to restore accountability becomes the trap itself? This case, Chiang (Trustee of) v. Chiang, forces us to confront a deeply uncomfortable reality: that even systems designed to enforce justice can spiral into something coercive, endless, and structurally impossible to escape. What began as a routine commercial debt dispute in California evolved into one of the most complex and punishing contempt proceedings in Canadian legal history. A family chased across borders. A consent order that functioned more like a contract with no exit. A process where the “keys to the cell” were no longer in the hands of the people being punished, but in the hands of their creditors. A use of contempt that was alarming and structurally unsound. And a long odyssey of litigation that took over eight years to resolve. At the center of this story is a haunting paradox. The court wanted answers, but the mechanism it created to extract those answers required cooperation from third parties in another jurisdiction. The result was a legal maze where effort was never enough, compliance was never complete, and the definition of “purging contempt” remained perpetually out of reach. The result was a system that punished without a clear path to redemption, where time, effort, and even compliance could not guarantee release. The lesson for litigators is that precision is not a technical detail; it is a safeguard against harm. To unpack how this happened (and why it still matters), I sat down with Tom Curry, a veteran litigation lawyer in Toronto who was brought into the case at its darkest point. Together, we explored how a single consent order reshaped the trajectory of an entire family’s life, why the Court of Appeal eventually intervened, and what this case teaches us about power, perseverance, and the limits of coercive justice. You’ll also learn: 1. How a routine business dispute turned into a decade-long legal odyssey 2. How a consent order became the most powerful lever in the case 3. What happens when the keys to freedom are held by creditor/plaintiff instead of the contemnor 4. Why “best efforts” can become an impossible legal standard 5. How coercive sentences cross the line into punishment 6. What this case reveals about power, persistence, and human resilience 7. Why structure, not pressure, is the real engine of accountability Guest Bio Tom Curry is a litigation lawyer in Toronto, a partner at Lenczner Slaght, and a speaker. He is recognized as one of the most experienced trial and appellate advocates of his generation in Canada. Tom has a long record of success in high-profile commercial litigation, class actions, arbitrations, business disputes, administrative law, judicial review, intellectual property, competition, and professional liability cases. Tom is a Fellow of the American College of Trial Lawyers and the International Academy of Trial Lawyers and is certified as a specialist in civil litigation by the Law Society of Ontario. He is a regular speaker on a wide variety of subjects relating to trial practice and substantive law. He has been recognized with the prestigious Law Society Medal, the Catzman Award, the Advocates’ Society Award for Excellence in Teaching, and, most recently, the OBA Award for Excellence in Civil Litigation. Connect with him on LinkedIn [http://linkedin.com/in/tom-curry-7268b8b5?originalSubdomain=ca/]. About Your Host Areta Lloyd practices estate and trusts litigation, with a particular focus on capacity litigation. She participates in public speaking, mentoring junior lawyers, and presenting courses on estates law, health law, and law practice management. Areta has written for several publications and wrote a column for the Alzheimer caregiver website ALZlive.com [https://alzlive.com/category/editorial/legal-series/]. Have a suggestion for a great case to feature on the show? Email me at hello@onegreatcase.com Looking for support in your legal career? The Toronto Lawyers Association offers resources, networking, and legal research at no cost. Visit http://tla.orghttps://www.tlaonline.ca/ [https://www.tlaonline.ca/].

Nuremberg Revisited: When Evil Was Obvious but the Law Wasn’t w/ David Parry

We tend to think of history’s great atrocities as moral failures that are obvious in hindsight. Evil acts, evil people, and clear lines between right and wrong. But the harder question (which still haunts legal systems today) is this: how do you turn moral certainty into legal accountability when the law itself doesn’t yet exist? That question has been back in public conversation recently with the release of the film Nuremberg. But it was never theoretical for the Allies in the wake of World War II. They weren’t just confronting the scale of the crimes; they were operating in an almost impossible legal position. No established crime for what we now call crimes against humanity. No clear roadmap for holding individuals responsible for actions carried out under the color of domestic law. And nowhere was that tension more visible than in the trial of Hermann Göring. What looks, at first glance, like a straightforward prosecution unravels into something far more complex. A courtroom filled with politics, ego, performance, and legal improvisation. A defendant who understood power, optics, and narrative better than many of the people questioning him. And a cross-examination that’s now infamous. This case forces us to confront an uncomfortable truth: accountability doesn’t come from outrage alone. It comes from systems, structure, and the discipline to resist fighting on the wrong terrain. Nuremberg wasn’t just a legal milestone. It was a test of whether law could rise to meet morality without collapsing into vengeance or theater. To unpack all of this, I sat down with criminal lawyer and Crown prosecutor David Parry. He has spent years studying the Nuremberg trials and their legacy. Together, we explored what Göring’s testimony reveals about human nature, why Robert Jackson’s cross-examination still matters, and how the innovations born at Nuremberg continue to shape international law today. You’ll Also Learn 1. Why Nuremberg wasn’t inevitable, and how close the Allies came to abandoning trials altogether 2. How retroactive justice became one of the most controversial but necessary legal innovations of the 20th century 3. Why Göring’s charisma and ego made him such a dangerous witness on the stand 4. What not to do in cross-examination when facing a powerful, combative defendant 5. How “arguing with the witness” quietly hands them control of the courtroom 6. Why structure (not emotion) is the prosecutor’s most powerful tool 7. How film evidence changed the trial when words failed 8. What Nuremberg teaches us about accountability, power, and the fragility of democratic systems 9. Why law is ultimately an attempt to discipline our moral instincts, not replace them About the Guest David Parry is a criminal lawyer and Crown prosecutor who began his career in private practice before moving into public prosecution. He has a long-standing interest in international law, legal ethics, and the history of the Nuremberg Trials—particularly how the International Military Tribunal grappled with accountability, morality, and the limits of law in the aftermath of World War II. His work sits at the intersection of legal theory and real-world courtroom practice, which makes him especially well-placed to unpack what actually happened inside the courtroom at Nuremberg. About Your Host Areta Lloyd practices estate and trusts litigation, with a particular focus on capacity litigation. She participates in public speaking, mentoring junior lawyers, and presenting courses on the topics of estates law, health law, and law practice management. Areta has written for several publications and has written a column for the Alzheimer's caregiver website ALZlive.com [https://alzlive.com/category/editorial/legal-series/]. Have a suggestion for a great case to feature on the show? Email me at hello@onegreatcase.com Looking for support in your legal career? The Toronto Lawyers Association offers resources, networking, and legal research at no cost. Visit http://tla.orghttps://www.tlaonline.ca/ [https://www.tlaonline.ca/].

Ritualistic Repetition or Genuine Intent? Inside a Stunning Undue Influence Case w/ David Delagran & Justice Gilmore

Most people imagine undue influence as overt manipulation: a domineering child, a vulnerable parent, and a will that suddenly changes. But the reality, undue influence often looks like routine caregiving.  That’s what made Abbruzzese v Tucci so striking. At first glance, it looked like a typical estate dispute. Instead, what emerged was a rare, almost textbook convergence of every factor litigators usually struggle to prove: isolation, dependency, capacity concerns, and a sudden transfer of the family home for no consideration. Then, everything changed when a single piece of evidence emerged; something you rarely see in these files. Civil litigator David Delagran walked me through the moment the entire case took a sharp turn. A moment that revealed just how different this file was from the usual “she said / she said” estate dispute. What he uncovered suggested something more deliberate, more structured, and far more difficult to dismiss. Then I sat with Justice Gilmore, the judge who ultimately had to make sense of it all. From her vantage point, this case wasn’t just unusual; it presented a combination of factors she rarely sees align so neatly in one file.  It all pointed to something beneath the surface that only became visible once she started asking the right questions.  Why do some cases that look “clean” on paper unravel the moment you peel back a single layer? What happens when the usual tools for assessing capacity and intent collide with the messy realities of family relationships? In this episode, we explore all of it, from the litigation strategy to the judicial reasoning. We also talk about the deeper lessons this case offers for anyone navigating influence, vulnerability, and the fragile line between care and control. You’ll Also Learn; * How dependence, isolation, and family conflict quietly lay the groundwork for influence * Why repeated phrases and “too-consistent” explanations can be a red flag in capacity cases * How a drafting solicitor’s clean notes can mask deeper dynamics the lawyer never saw * Why contemporaneous medical assessments often reveal what retrospective reports can’t * How judges test whether a testator’s words were their own or shaped by someone else * What credibility looks like when family stories, expert opinions, and documents all clash * Why this case is becoming a reference point for spotting influence that hides in plain sight Guest Bios David Delagran is a civil litigator and partner at Beard Winter LLP in Toronto, with over 25 years of litigation experience across commercial, estates, and employment disputes. In contentious trusts and estates disputes, David represents personal and institutional estate trustees, as well as beneficiaries, in all matters arising out of the administration of trusts and estates, including administration, will challenges, dependent support claims, interpretation issues, and breaches of trust. David works together with the firm’s Estates and Trusts solicitors to form an effective multidisciplinary litigation team. Connect with David on LinkedIn [https://www.linkedin.com/in/david-delagran-4731496a/].  Justice Gilmore is an Estates List judge and a specialist in estates litigation. She sits in Toronto and has presided over a large variety of civil, criminal, and family cases since her appointment. She was the President of the Ontario Superior Court Judges’ Association from December 2014 to June 2017 and sitting Past President until June 2019. Justice Gilmore has passed the Level C civil servant French exam, which permits her to hear trials in French, and has been a regular educational panel member on evidentiary and advocacy issues. Connect with her on LinkedIn [http://linkedin.com/in/madam-justice-cory-gilmore-740a5525?originalSubdomain=ca/].  About Your Host Areta Lloyd practices estate and trusts litigation, with a particular focus on capacity litigation. She participates in public speaking, mentoring junior lawyers, and presenting courses on the topics of estates law, health law, and law practice management. Areta has written for several publications and wrote a column for the Alzheimer caregiver website ALZlive.com [https://alzlive.com/category/editorial/legal-series/].

Exploitation at the Ballet: The Case That Redefined Justice in Canada w/ Gillian Hnatiw

When we think of ballet, we think of grace, discipline, and the pursuit of perfection, not precedent-setting litigation. But within the walls of elite ballet institutions, the pursuit of perfection can blur into something darker: a culture of hierarchy, obedience, and silence. That silence is what made this case possible. Behind the curtain of one of Canada’s most prestigious ballet schools, a story unfolded that had nothing to do with art and everything to do with power. When the truth finally surfaced, the women seeking justice faced an even greater challenge…a justice system unequipped to name their harm. This wasn’t just a story about a predator hiding in plain sight. It was a reckoning with how the legal system lags behind the realities of digital-age exploitation and gender-based harm. What happens when centuries-old torts can’t capture the trauma of having your body and trust violated on camera? That’s where lawyer Gillian Hnatiw stepped in. As a leading advocate for victims of gender-based violence, she was able to recognize the deeper systemic failure beneath the case, a legal framework unprepared to address modern forms of harm. In this episode, Gillian unpacks the complexities of the case and the creative lawyering it demanded. She also reflects on how the case reshaped the legal understanding of gender-based harm, and why its lessons remain urgent in an era where technology keeps outpacing the law. Things You’ll Learn in This Episode;  * How the Royal Winnipeg Ballet class action broke new ground in recognizing psychological and gender-based harm from non-consensual image taking and sharing. * Why arts institutions can enable abuse through culture, not just conduct, and how silence becomes complicity. * The creative legal strategy behind a case with no clear precedent, from using privacy torts to invoking occupiers’ liability and breach of confidence. * Why this case signals the next frontier of justice — as the law races to catch up to digital realities like voyeurism, deepfakes, and AI-generated abuse. Guest Bio Gillian is one of Canada's leading advocates for victims of gender-based violence. Although that is not her only area of practice, she maintains a diverse litigation practice at her eponymous law firm located in Toronto, with a national reach. Gillian is talented, fearless, hugely empathetic, and a huge risk-taker. You can learn all about her work on her website, gillianandco.ca [http://gillianandco.ca].  About Your Host Areta Lloyd practices estate and trust litigation, with a particular focus on capacity litigation. She participates in public speaking, mentoring junior lawyers and presenting courses on the topics of estates law, health law, and law practice management. Areta has written for several publications and wrote a column for the Alzheimer caregiver website ALZlive.com [https://alzlive.com/category/editorial/legal-series/]. Resources Have a suggestion for a great case to feature on the show? Email me at onegreatcasepodcast@yahoo.com Looking for support in your legal career? The Toronto Lawyers Association offers resources, networking, and legal research at no cost. Visit TLA.org [http://tla.org] Follow One Great Case on Apple Podcasts, Spotify, or your preferred app to stay up to date with the latest cases and conversations. If you’ve found the show valuable, please leave us a review on Apple Podcasts or share it with a colleague. Each time you do, you help another professional discover insights that can shape their practice.