“I have called you together so we can resolve your indifferences.”

• Chief Justice Warren Winkler, 2010

I have been formulating this blog in my mind for some time, but what finally moved me to write it was a post on LinkedIn^[1] that led me to an address, of which I was not previously aware, by Chief Justice Warren Winkler at the University of Western Ontario’s Faculty of Law on March 24, 2010. In his lecture, “Some Reflections on Judicial Mediation: Reality or Fantasy?”^[2], Chief Justice Winkler traced the rise of mediation in Ontario, sketched its uneasy place within the courts, and candidly assessed its limits. His words ring true even fifteen years later, particularly now as Ontario prepares to expand mandatory mediation province-wide in 2026 as part of Phase 2 of the Civil Rules Reform^[3].

What follows is a reflection on His Honour’s speech, the stark contrasts between private and judicial mediation, and what the coming reforms may mean for the culture of dispute resolution in Ontario.

A Chief Justice’s Reflections on Judicial Mediation 

Winkler C.J.’s central insight was simple yet profound. Mediation is not a science, but an art. Its effectiveness depends not on rigid formulas, but on the intuition, patience, and creativity of the mediator. Some judges and lawyers have those qualities. Others most definitely do not. He admitted that while mediation can be taught, it cannot be fully learned. It is in many respects a personal craft.

Chief Justice Winkler described how judicial mediation had deeper roots in Ontario than many realized. He traces judicial mediation back to Justice Edson Haines (One of the Founding Partners of what is now Thomson Rogers), humorously describing him thus:

“Edson Haines had been a high-profile plaintiff’s personal injury counsel, and he had an unforgettably flamboyant style and presence that suggested that he loved to call attention to himself. He was a dashing figure, dressed elegantly, wore his flowing, blond hair in the style of a British barrister, and drove a Rolls-Royce”.

Justice Haines in the 1960s became notorious for calling counsel into his chambers mid-trial and sending them back out with a settlement. What went on behind closed doors was never recorded, but Chief Justice Winkler suspected it closely resembled the techniques of modern mediation.

By the 1980s, pre-trials had become formalized under the Rules of Civil Procedure^[4]. In the 1990s, mandatory private mediation was introduced in Toronto, Ottawa, and Windsor. By the 2000s, the system had developed “designated hitters”, judges hand-picked to mediate especially difficult cases immediately before trial for their effectiveness. But Winkler also emphasized the structural tension. Many judges resisted the role. Their vocation, they argued, was to decide cases, not broker deals. Mediation, to them, was a descent into “the arena.” Others embraced it as an essential adaptation to litigants’ needs in an era when trial delays and costs were spiraling. Winkler’s conclusion was that judicial mediation was both a reality and a fantasy. It existed, but its availability was inconsistent. Equal access remained elusive. Courts lacked the infrastructure—breakout rooms, technology, scheduling flexibility—and many judges lacked either the desire or the aptitude.

His view was pragmatic. Mediation should be expanded, but it must supplement, not supplant, the Courts’ fundamental role of deciding disputes. Not every judge should mediate. Those who do must be willing and able. Mediation, in his words, should be “where necessary, but not necessarily mediation.”

The Limits of Judicial Mediation

The limits of judicial mediation are not theoretical. They emerge in practice every day. Judges can certainly influence parties, but they cannot compel agreement. They rarely have the time to let settlement discussions mature. Pre-trials are typically scheduled for less than an hour, and even when they run long, they seldom carry the same depth, intensity, or persistence that a full-day private mediation affords.

The judicial role itself creates tension. Judges are trained to resolve disputes by applying law to facts, not by coaxing creative, interest-based solutions. Their interventions can sometimes carry unintended coercive weight. Parties may settle not because they have genuinely reached consensus, but because “the judge said so.” The risk in such cases is a fragile agreement, more likely to unravel under strain.

Judicial mediation, then, is best understood as a tool of limited scope. It can provide valuable pressure points within the litigation process, especially on the eve of trial, but it cannot replicate the patience, flexibility, and creativity that skilled private mediators bring to the table. The line is delicate: judicial encouragement is appropriate, but judicial strong-arming is not.

The Designated Hitter Judge: A Hail Mary on the Eve of Trial

One of Ontario’s most distinctive innovations has been the “designated hitter.” These are judges selected for their subject-matter expertise, brought in on the eve of trial for a last-ditch settlement attempt. The metaphor is apt: it is a Hail Mary pass, a final swing before the expense and uncertainty of a trial.

I  appeared on a handful of these “designated hitter” judicial mediation over my career. Some resolved, some didn’t. I’d say 50/50.  One of them before a judge, very well-known for her tenacity, lasted from 10am to 7pm on a Friday, and was reconvened on Sunday morning, only to settle after the judge kicked all of the lawyers out of the room to speak alone with the litigants.

These sessions can be effective precisely because they occur at the moment of maximum risk. The looming prospect of trial, with its costs and unpredictability, sharpens parties’ focus. But they are also constrained by timing. By that late stage, parties have sunk enormous costs, hardened positions, and often invested emotionally in “having their day in court.” Settlement is possible, but much harder.

This duality is why many litigants and counsel still prefer to engage private mediators earlier in the life of a case. A designated hitter may salvage some files, but it cannot replace the proactive, deliberate work of structured mediation long before trial.

The Capacities of Private Mediators

Private mediators, by contrast, live entirely within the settlement space. They dedicate whole days—and often follow-up days—to a single case. They design processes suited to the dispute, like joint sessions, caucuses, staged offers, apologies, or creative remedies that courts cannot order. They are not bound by court hours or schedules. They can stay late, reconvene, or keep working the phones after the session ends.

Parties choose their mediator, and that choice carries psychological legitimacy. A mediator trusted by both sides enters the room with credibility. Their influence rests not on authority but on persuasion, persistence, and creativity. Because they lack coercive power, they must dig deeper into the parties’ real interests. In doing so, they often uncover solutions that judges—focused on legal rights and obligations—would never propose.

Private mediators also commit to their craft. They train continually on the job in negotiation theory, psychology, and conflict resolution. They bring to bear not just legal expertise, but emotional intelligence and human insight. Their neutrality allows parties to speak more freely. And their confidentiality protections exceed those of court-based settings.

Contrasting the Two Roles

When set side by side, the contrasts are stark. Judicial mediators bring the authority of the court, but are hemmed in by time, tradition, and role. They can move parties by the weight of their opinion, but that very authority can shade into pressure. They cannot follow up, cannot custom-design processes, and often cannot give mediation the space it requires.

Private mediators, lacking official authority, compensate with persistence, adaptability, and depth. They live in the gray zones, exploring remedies outside the binary of win or lose. They follow up, they probe, they persuade, and they build consensus in ways judges cannot. Judicial mediation is episodic; private mediation is immersive. Judicial mediation is an adjunct; private mediation is a vocation.

The Promise of Phase 2 (2026): Mandatory Mediation Expanded

Ontario’s Rules already reflect this hybrid reality. Rule 24.1 established mandatory mediation in Toronto, Ottawa, and Windsor in 1999. Empirical evaluations of Ontario’s mandatory mediation model (under Rule 24.1) demonstrate tangible reductions in both trial rates and litigation costs. One study, covering the first 23 months of operation, found that in approximately 85% of cases, mediation had a positive impact on reducing costs^[5].

But the experiment was never expanded province-wide—largely because of resource concerns. That is what Phase 2 of the Civil Rules Reform, set for 2026, now aims to change.

Ontario now stands on the threshold of a major shift. Phase 2 of the Civil Rules Reform, scheduled for 2026, anticipates expanding mandatory mediation province-wide. This will mark the first comprehensive extension of the Rule 24.1 experiment beyond Toronto, Ottawa, and Windsor. If realized, it will mean that early mediation is no longer a regional anomaly, but a universal expectation.

This reform carries both promise and challenge. On the one hand, it may reduce backlog, lower costs, and expand access to justice. On the other, it will test the capacity of the mediation bar. Will there be enough skilled mediators to handle the volume? Will rural and northern regions have the same access as major urban centres? And how will the bench adapt to a culture where mediation is the norm, not the exception?

The stakes are high. If implemented well, Phase 2 could mark a cultural shift on par with the introduction of mandatory mediation in 1999. If bungled, it could deepen cynicism about mediation as a perfunctory step.

Conclusion

Chief Justice Winkler’s reflections remain as timely now as in 2010. Judicial mediation is both real and illusory—present, but inconsistent. Judges bring authority, but authority alone cannot substitute for the craft of mediation.

Private mediators, by contrast, bring persistence, creativity, and neutrality. They have the luxury of time and the freedom to innovate. They are chosen, not assigned. Their settlements are voluntary, not coerced.

They inhabit the art, not the science, of resolution.

As Ontario looks to 2026 and the province-wide expansion of mandatory mediation, it must remember Winkler’s warning: mediation should supplement, not supplant, the courts’ core role. Judges must remain adjudicators first, mediators only where suited. Private mediators will continue to play the deeper, more flexible role.

Litigants and counsel should recognize the difference. Judicial mediation may be a checkpoint, sometimes a last chance. Private mediation is the real work of resolution, and the earlier it is embraced, the better the chances of avoiding the courthouse steps altogether.