Di Iorio v. MacNamara, 2025 ONSC 4291

minicounsel

Court File No.: CV-19-00620193
Motion Heard: June 23, 2025

Between:
Anthony Di Iorio, Plaintiff
and
Tyler MacNamara, Toronto Standard Condominium Corporation No. 2227, FirstService Residential Property Services Ontario Ltd. o/a FirstService Residential Ontario, Your Community Realty Inc. o/a Royal LePage – Your Community Realty, Jason Silva aka Jay Silva, 500 Ellington West Ltd., Freed Developments Ltd., FirstCon Group Ltd., Service Plus Aquatics Inc. aka SPA, Defendants

Before: L. La Horey, Associate Justice

Counsel:

Joseph Juda, counsel for the moving party defendants Jason Silva aka Jay Silva and Your Community Realty Inc., o/a Royal LePage – Your Community Realty
Pulat Yunusov, counsel for the responding party plaintiff
Alexandra Shelley, counsel for the defendant Tyler MacNamara
Christine Tassopoulos for the defendants Michael Joseph Callahan aka Michael Callahan and Tanzola & Sorbara Professional Corporation in CV-19-00620196

Heard: June 23, 2025

Background and Overview

1The defendants Jason Silva and Your Community Realty Inc., o/a Royal LePage – Your Community Realty (the “Realtors”) bring this motion seeking answers to questions refused at the examination for discovery of the plaintiff held November 3, 2023.

2The plaintiff purchased a luxury condominium that included a swimming pool over which he has exclusive use. The Realtors were his real estate representatives on the purchase. He commenced two actions seeking damages in connection with alleged defects in the swimming pool by issuing two notices of action on the same day.

3In this action, Mr. Di Iorio sues the vendor of the condominium unit, the condominium corporation, the property manager, the Realtors, the condominium developer, and a pool service company. The plaintiff alleges that the Realtors are liable to the plaintiff, among other things, for failing to recommend terms in the agreement of purchase and sale related to the condition of the pool.

4In action CV-19-00620196 (the “companion action”), Mr. Di Iorio sues his real estate lawyer, Michael Joseph Callahan and his firm, Tanzola and Sorbara Professional Corporation as well as his title insurer, Stewart Title Guaranty Company. He alleges that his lawyer was negligent in his advice in connection with the pool including by failing to recommend terms in the agreement of purchase and sale relating to the condition of the pool.

5The parties in both actions consented to an order that the companion action be tried together with this action, or immediately after it, subject to the discretion of the trial judge. The consent order signed by me on February 11, 2025, also addressed the application of the deemed undertaking rule. The order provided that the defendants in the companion action have access to the evidence and information obtained in this action, but left open the question of whether the defendants in this action shall have access to the documents and evidence in the companion action.

6Mr. Di Iorio was examined for discovery by the defendants in this action. During the discovery he admitted that he received legal advice on the real estate transaction in the conditional period, but refused to answer questions about the content of the legal advice. The Realtors move to compel Mr. Di Iorio to answer four questions related to advice he received from Mr. Callahan, including production of Mr. Callahan’s file relating to the purchase of the condominium property. The questions were refused on the basis of solicitor-client privilege. At the hearing, counsel agreed that all four questions rise or fall together depending on my decision on whether solicitor-client privilege has been waived. The plaintiff has already produced the non-privileged part of Mr. Callahan’s file.

7The Realtors submit that any privilege over the lawyer’s advice is deemed to have been waived and that fairness requires the disclosure of the lawyer’s advice and file.

8The plaintiff opposes and contends that there has been no waiver of solicitor-client privilege.

9The defendant Tyler MacNamara supports the motion. Counsel for the defendants Michael Joseph Callahan and Tanzola and Sorbara Professional Corporation in the companion action attended to observe but advised that her clients do not take a position on this motion. I was advised that Service Plus Aquatics Inc., aka SPA does not take a position on the motion.

Preliminary Issues

10The plaintiff takes issue with the timing of this motion, asserting that the motion comes too late and also argues that the moving parties are attempting to circumvent my February 11, 2025 order. I reject these submissions. Although the Realtors were aware of the companion action early on, it was the refusal of the plaintiff to answer questions at his examination for discovery on November 3, 2023, that triggered this motion. The parties then participated in an unsuccessful mediation. On March 27, 2024, the day after the mediation, the Realtors advised that they would move on the refusals in issue. They submitted a long motion request form in December 2024. When I signed the consent order of February 11, 2025, this motion was scheduled and my order left open the privilege issue.

Analysis

11Solicitor-client privilege is a cornerstone of our legal system.[1] It may be waived expressly or by implication.[2] However, the privilege is “as close to absolute as possible” and the privilege will be deemed to have been waived only in the “clearest of cases”.[3]

12The plaintiff and the Realtors agree that the issue on this motion is whether the plaintiff waived solicitor-client privilege by implication.

13I was directed to no case that is on all fours with the circumstances before me.

14Both sides rely on the decision of Justice Perell in Creative Career Systems Inc. v. Ontario.[4] In that decision, Justice Perell commenced his review of the law of waiver of privilege by referencing the oft-cited decision of Justice McLachlin, as she then was, in S. & K. Processors Ltd. v. Campbell Ave. Herring Producers Ltd.[5] In S. & K. Processors, Justice McLachlin held:[6]

Waiver of privilege is ordinarily established where it is shown that the possessor of the privilege (1) knows of the existence of the privilege, and (2) voluntarily evinces an intention to waive that privilege. However, waiver may also occur in the absence of an intention to waive, where fairness and consistency so require. Thus waiver of privilege as to part of a communication, will be held to be waiver as to the entire communication. Similarly, where a litigant relies on legal advice as an element of his claim or defence, the privilege which would otherwise attach to that advice is lost: Hunter v. Rogers, [1982] 2 W.W.R. 189.

... can it be said that in the interests of fairness and consistency the doctrine of waiver requires their disclosure? As pointed out in Wigmore on Evidence (McNaughton Rev., 1961), vol. 8, pp. 635-36, relied on by Meredith J. in Hunter v. Rogers supra, double elements are predicated in every waiver--implied intention and the element of fairness and consistency. In the cases where fairness has been held to require implied waiver, there is always some manifestation of a voluntary intention to waive the privilege at least to a limited extent. The law then says that in fairness and consistency, it must be entirely waived. In Hunter v. Rogers, supra, the intention to partially waive was inferred from the defendant's act of pleading reliance on legal advice. In Harich v. Stamp (1979), 27 O.R. (2d) 395, it was inferred from the accused's reliance on alleged inadequate legal advice in seeking to explain why he had pleaded guilty to a charge of dangerous driving. In both cases, the plaintiff chose to raise the issue. Having raised it, he could not in fairness be permitted to use privilege to prevent his opponent exploring its validity.

15Following his analysis of the case law, Justice Perell concluded:[7]

Thus, a deemed waiver and an obligation to disclose a privileged communication requires two elements; namely: (1) the presence or absence of legal advice is relevant to the existence or non-existence of a claim or defence; which is to say that the presence or absence of legal advice is material to the lawsuit; and (2) the party who received the legal advice must make the receipt of it an issue in the claim or defence.

16The plaintiff acknowledges that the presence or absence of legal advice is relevant and material to this action. However, he does not agree that he has made receipt of legal advice an issue in this action, even though he has made it an issue in the companion action. In other words, the plaintiff accepts that he has waived privilege vis-à-vis Mr. Callahan’s advice in the companion action but maintains that he has not waived it in this action.

17I disagree. I find that the criteria for implied waiver have been met and that fairness and consistency require a finding that the privilege has been waived.

18As noted by Justice McLachlin: “In the cases where fairness has been held to require implied waiver, there is always some manifestation of a voluntary intention to waive the privilege at least to a limited extent.”[8] In this case, the voluntary intention to waive privilege to a limited extent is the commencement of a companion action in which the plaintiff makes virtually identical allegations of negligent advice (in connection with the terms of the agreement of purchase and sale as regards the pool) as against the lawyer in the companion action that he makes against the real estate agent in this action. In both actions, the plaintiff pleads that but for the negligent advice of (the realtor in this action, the lawyer in the companion action), the plaintiff would not have purchased the property or would have offered a lower amount for the property. These allegations are at the heart of the claims against the Realtors and the lawyer.

19In Armstrong v. Penny, Justice Boswell explained that implied waiver arises where “the holder of the privilege takes some action or position inconsistent with the maintenance of the privilege.”[9] In my view, that is the situation here. In commencing two actions with virtually identical allegations against his lawyer and another professional that the plaintiff says resulted in the same damage, the plaintiff has taken action that is inconsistent with the maintenance of confidentiality over the lawyer’s advice, and thus inconsistent with the maintenance of the privilege. He has waived the privilege by his conduct.

20In the recent decision of the Divisional Court in One York Street Inc. v. 2360093 Ontario Ltd., the court expressed the concept of implied waiver as follows:[10]

Waiver is “implied where a party makes its state of mind material to its claim or its defence in such a way that to enforce the privilege would be to confer an unfair litigation advantage on the party claiming it”: Doman Forest Products Ltd. v. GMAC Commercial Credit Corp., 2004 BCCA 512, 245 D.L.R. (4th) 443, at para. 12; ProSuite Software Ltd. v. Infokey Software Inc., 2015 BCCA 52, 382 D.L.R. (4th) 698, at para. 1.

21In this case, the plaintiff has put his state of mind in issue with respect to the advice he received from his professional advisors in his claims, albeit in two separate actions. It would be unfair for the plaintiff to refuse to disclose what advice he received from his lawyer when he also says that the negligent advice from his lawyer on the very same issue caused his losses.

22It would be unfair not to allow the Realtors to test the validity of his claim that “but for” the advice of the real estate representatives (if such advice was given) that he would not have purchased the property or purchased it at a lower rate, when he has made the same allegation in different proceedings against the lawyer. In these circumstances, the plaintiff’s actions (in commencing two actions making the same allegations of negligent advice against his lawyer and the real estate agents) are inconsistent with the maintenance of confidentiality and thus the privilege. I do not accept the plaintiff’s argument that he has not waived privilege because he has not “used” the legal advice in this action.

23There is another way of looking at this issue that leads to the same result. It has been held that where a party puts his state of mind in issue and has received legal help to form that state of mind, privilege is deemed to be waived with respect to that legal advice. There is a caveat to this, and that is that simply putting state of mind in issue without reliance on legal advice does not amount to an implied waiver.[11]

24There is no doubt that the plaintiff has put his state of mind in issue in both actions. There is also no doubt that the plaintiff has pleaded that he had legal help in the action against his lawyer. However, the plaintiff submits because he is not relying upon the contents of the legal advice in his claim against the Realtors, there is no trial fairness or consistency issue that gives rise to a deemed waiver. I disagree. In this particular case (two separate actions in this court with the same allegations), it would be fundamentally unfair to permit the plaintiff to shield behind a claim of solicitor-client privilege, the legal advice he received which may negate a finding that the Realtors’ advice caused the plaintiff’s losses (even if the Realtor’s advice was negligent).

25This is particularly the case where there is a possibility that the Realtors and the lawyer may ultimately be found to be joint tortfeasors.[12]

26If this were one action against all the defendants rather than two actions dividing the defendants, there would be no doubt that the plaintiff waived privilege due to his allegations against the lawyer. It would be a victory of form over substance to conclude that the issuance of two actions instead of one compels a different result in the circumstances of this case.

27The plaintiff relies on the recent decision of the Court of Appeal in SIF Solar Energy Income & Growth Fund v. Aird & Berlis LLP.[13] In that case, the plaintiffs (investment trusts) commenced an action against defendants alleging breach of various trust duties. The plaintiffs commenced a separate action against a law firm, alleging that the law firm was negligent in failing to identify or report the misconduct of the defendants in the main action. The law firm brought a motion to stay the action against it on the ground that it was an abuse of process. The Court of Appeal expressed the issue before it as being whether the motion judge erred in permanently staying an action commenced by the plaintiffs against the law firm “on the basis that the proper procedure was to have moved to add that defendant to an action the appellants were pursuing against other defendants involving the same factual circumstances.”[14]

28At paragraph 49 of the decision, Justice van Rensburg for the court said:[15]

Second, although the A&B Action pleads the facts alleged in the Main Action, and, as the motion judge noted, includes claims against other professionals, the claims that are asserted against A&B are of a different nature. Contrary to A&B’s submissions, the A&B Action does not allege that A&B “participated in” the wrongdoing alleged in the Main Action, nor does it claim that A&B are jointly and severally liable with the defendants to the Main Action. The A&B Action is an action for solicitors’ negligence, breach of contract and breach of fiduciary duty. I agree with the appellants’ submission that it is not unusual for a solicitor’s negligence action to be commenced when there is a separate action against the alleged wrongdoers based on the same factual matrix: see, e.g., 1014864 Ontario Ltd. v. 1721789 Ontario Inc., 2010 ONSC 3306; Gowling Lafleur Henderson LLP v. Meredith, 2011 ONSC 2686, 32 C.P.C. (7th) 209; and Hurst v. Hancock, 2020 ONSC 1216. In such cases, where issues are overlapping and to prevent inconsistent verdicts, procedural orders can be made, including for case management, joint discovery on common issues, and/or for trial together: see e.g., Kelkas v. Kilicaslan et al., 2020 ONSC 3596, 5 C.C.L.I. (6th) 218.

29The plaintiff relies on this passage for the proposition that the Court of Appeal has recognized the propriety of commencing a solicitor’s negligence action even if there is another proceeding based on the same factual matrix.

30The court in SIF Solar referred to the potential issue of waiver of privilege in such situations and stated:[16]

The motion judge briefly referred to and rejected the appellants’ articulated reasons for commencing the A&B Action as a separate proceeding. First, he suggested that there would be an implied waiver of privilege once a client sues the lawyer: that is, that the commencement of the A&B Action would result in the waiver of any privilege the appellants might assert. The appellants’ contention was that any waiver of their privilege in the A&B Action would not extend to the Main Action, since A&B was not a defendant to that action; that was their reason for commencing a separate proceeding. Typically, the waiver of solicitor-client privilege resulting from a client’s lawsuit against their lawyer is for the limited purpose of allowing the lawyer to defend the solicitor’s negligence claim and not for all purposes. This was the case in Kelkas, where, in refusing consolidation of a solicitor’s negligence action with an action against a wrongdoer based on the same facts, the court considered as a factor that the plaintiff had only waived solicitor-client privilege within the confines of the solicitor’s negligence action and not in the other two actions, and gave specific directions for documentary and oral discoveries. [my emphasis]

31The court did not have to decide whether the commencement of a separate action against the law firm would result in a waiver of privilege. The court specifically stated that it was not determining the merits of any claim to solicitor-client privilege and the issue was left open.[17]

32Therefore, SIF Solar does not determine the issue before me.

33The plaintiff also relies on the Kelkas case referenced by the Court of Appeal.[18] In Kelkas, the plaintiff commenced three actions arising from injuries sustained in a motor vehicle accident. In one action the plaintiff sued the driver of the other vehicle in the collision in tort. In the second action, he sued his motor vehicle insurer pursuant to the underinsured coverage afforded by his policy. In the third action, he claimed against his former lawyer, alleging that he had improvidently settled his accident benefit claim. Master Fortier (as her title then was) found that the plaintiff had waived solicitor-client privilege only within the confines of the solicitor’s negligence action. In deciding a motion for consolidation or trial together, she found that because the files in the solicitor’s negligence action were protected by solicitor-client privilege and the deemed undertaking rule applied, discoveries in the solicitor’s negligence action ought to remain separate from the discoveries in the other two actions.

34However, that case is distinguishable in that there were no overlapping or concurrent allegations against the solicitor and the other defendants as in the case at bar. Rather it appears that the common issue that made the solicitor’s file relevant to the other two actions was the issue of damages. In this respect, Master Fortier held:[19]

The moving parties argue that the measure of damages and the evidence required to prove damages will be the same in all three proceedings and the evidence regarding damages will overlap in the proceedings. While this is likely accurate, the moving parties have available to them alternative means to obtain information on the plaintiff’s damages. I agree with the submissions of the plaintiff that any relevant non-privileged productions of the defendant in the solicitor’s negligence action would be properly included as part of the plaintiff’s affidavit of documents in the tort and OPCF actions.

35In the case before me, the main action and the companion action do not just have the same factual matrix and common issues of damage. This case also involves the same and potentially inconsistent allegations against the professionals where it is also alleged that the professionals sued in the two actions caused the same damage.

Disposition and Costs

36The motion is granted. The parties agreed that the successful party on the motion would be entitled to partial indemnity costs in the sum of $6,000. As the moving parties were successful on the motion, the plaintiff shall pay to the moving parties this sum within 30 days.

Di Iorio v. MacNamara, 2025 ONSC 4291

Case Summary

Background and Overview

Preliminary Issues

Analysis

Disposition and Costs

Cited Authorities

Case Law

Legislation

Di Iorio v. MacNamara, 2025 ONSC 4291

Case Summary

Background and Overview

Preliminary Issues

Analysis

Disposition and Costs

Cited Authorities

Case Law

Legislation