Rob L. Winterstein

The applicant held a third mortgage on a property and challenged the sale of the property by the assignee of the first mortgage, arguing the assignee failed to issue a fresh notice of sale.

The applicant moved to convert the application into an action to add allegations of fraud, while the respondents moved to dismiss the application.

The court granted the motion to convert the application into an action, finding the record insufficient to deny the investors the ability to pursue their claims.

However, the court ruled on the legal issue, holding that under the Mortgages Act, an assignee is not required to issue a fresh notice of sale if the interested parties received written notice of the assignment.

The appellants appealed a Master's order that varied a previous 'last chance' order requiring the respondent to post security for costs.

The previous order stated that if the respondent failed to post security by a specific deadline, the action would be dismissed.

The respondent failed to comply, but the Master subsequently issued a new order extending the deadline and increasing the security amount.

The Superior Court allowed the appeal, finding that the Master was functus officio once the original order was issued, entered, and breached, resulting in the dismissal of the action.

The Master therefore had no jurisdiction to vary the order or grant a stay.

Blackjet Inc. sought summary judgment against Skyline Investments Inc. et al. for unpaid marketing fees under an Agency Agreement.

The defendants disputed the amount, alleging double-billing and Blackjet's breach of contract for failing to provide monthly reconciliations and appoint an account manager.

The court granted summary judgment, finding some double-billing by Blackjet but dismissing the defendants' breach of contract claim as they had waived their right to enforce it.

Blackjet was awarded a reduced amount for unpaid fees and late payment fees, along with pre- and post-judgment interest.

The appellant, a lawyer, appealed from a summary judgment dismissing his counterclaim against his former counsel, Lang Michener LLP.

The counterclaim alleged negligent advice regarding a potential claim against his professional liability insurer (LawPro) for coverage of an Italian judgment based on fraud.

The motion judge found no coverage existed under the policy because the Italian judgment was based on fraud rather than professional negligence or error.

The Court of Appeal upheld the dismissal, finding the Italian court had explicitly declined jurisdiction over professional liability claims and the judgment was based on extra-contractual fraud, not professional services.

The court also upheld the costs award of $45,000 against the appellant.

The tenant appealed a Landlord and Tenant Board review decision that upheld an eviction order for rental arrears.

The tenant argued that his obligation to pay rent was discharged because the landlord's staff mistakenly refused his attempt to pay the arrears in cash.

The Divisional Court dismissed the appeal, finding no error of law in the LTB's conclusion that a refused payment does not erase the debt.

The Court also found the LTB's refusal to set aside the eviction order was reasonable given the tenant's stated refusal to comply with any order to pay arrears.

However, the Court granted the tenant a final opportunity to pay the arrears in cash to avoid eviction.

The applicant in a human rights proceeding sought to amend his Application to correct typographical errors and add subsequent incidents of alleged discrimination.

The respondent did not oppose the request.

The Tribunal granted the request, finding it timely and noting that the additional allegations were of a similar character to the original claims without causing prejudice to the respondent.

The applicants brought an application to declare the respondent a vexatious litigant under section 140 of the Courts of Justice Act.

The court found that the respondent had persistently and without reasonable grounds instituted numerous unmeritorious actions, motions, and appeals over a decade, while failing to pay over $150,000 in costs orders.

The court granted the application, prohibiting the respondent from instituting or continuing any proceedings in Ontario without leave of a judge, and awarded substantial indemnity costs to the applicants.

The self-represented appellant appealed a Master's order dismissing his legal malpractice action for failure to pay costs awards, as well as the Master's award of substantial indemnity costs and refusal to permit cross-examination of an affiant.

The Divisional Court found no factual or legal errors in the Master's decisions, noting the appellant's failure to pay tens of thousands of dollars in costs and his vitriolic submissions.

The appeal was dismissed with costs awarded to the respondents.

The defendants brought a motion to dismiss the plaintiff's legal malpractice action due to his failure to pay multiple costs orders totaling $29,000.

The plaintiff, a self-represented litigant, had a history of unpaid costs awards and had made numerous unproven allegations of bias and corruption against judges and opposing counsel.

The court found that the plaintiff had no intention of paying the outstanding costs and dismissed the action under Rule 60.12, subject to a condition allowing the plaintiff to move to set aside the dismissal if he successfully appealed a related matter to the Supreme Court of Canada.

The moving party sought to review an order of a single judge of the Court of Appeal dismissing a motion to extend the time to file an application for leave to appeal from the Divisional Court.

The panel agreed with the single judge that there was no prospect of success on the merits of the proposed leave to appeal motion.

The motion to review was dismissed with costs fixed at $5,000.

The appellant landlord appealed a Small Claims Court decision dismissing its claim for property damages against a former tenant for lack of jurisdiction.

The Deputy Judge had ruled that the Landlord and Tenant Board (LTB) had exclusive jurisdiction over the matter.

The Divisional Court found that the Deputy Judge erred in law, as section 89(1) of the Residential Tenancies Act requires a tenant to be in possession of the rental unit for the LTB to have jurisdiction over damage claims.

Since the tenant had vacated the unit, the Small Claims Court had jurisdiction.

The court also found the Deputy Judge made a palpable and overriding error in finding that a second LTB hearing had occurred where damages could have been addressed.

The Federation of Rental-Housing Providers of Ontario intervened.

The appeal was allowed and the matter remitted to the Small Claims Court.

The moving party sought an extension of time to bring an application for leave to appeal from the Divisional Court.

Prior to the hearing, the moving party demanded the presiding judge recuse himself, alleging bias, racism, and corruption based on previous decisions.

The moving party failed to attend the teleconference hearing.

The judge declined to recuse himself, finding no air of reality to the bias claims.

The motion for an extension of time was dismissed on the merits, as the proposed appeal raised no issues of public importance and had no realistic chance of success.

The defendant/moving party sought leave to appeal a decision dismissing his motion for costs.

The motion judge had found that the costs issue was already determined by a prior Master's decision, which was upheld on appeal.

The court dismissed the motion for leave to appeal, finding that the moving party failed to meet the test under Rule 62.02(4) as there was no reason to doubt the correctness of the decision, no conflicting decisions, and the issues did not extend beyond the immediate parties.

Costs were awarded to the responding party on a partial indemnity basis.

The moving party sought leave to appeal an order dismissing his appeal of a Master's order that had stayed his action pending payment of numerous outstanding costs orders.

The court dismissed the motion for leave to appeal, finding that the moving party failed to meet the strict two-part test under Rule 62.02(4).

Specifically, there was no conflicting decision of another judge or court, no reason to doubt the correctness of the order, and the proposed appeal did not involve matters of such importance that leave should be granted.

The plaintiff appealed a Master's order that stayed his action pending the payment of several outstanding costs orders.

The plaintiff argued the Master lacked jurisdiction to vary a previous order to include additional costs awards reinstated by the Divisional Court.

The Superior Court dismissed the appeal, finding the Master had jurisdiction under section 106 of the Courts of Justice Act and Rule 59.06(1) to vary the order based on the changed factual landscape.

The court also reprimanded the self-represented plaintiff for making unauthorized audio recordings of the proceedings in violation of section 136 of the Courts of Justice Act.

A self‑represented defendant brought a motion seeking costs of an action after the action was administratively dismissed for delay under Form 48D.

The responding party argued that the issue of costs had already been determined in earlier proceedings before a master and upheld on appeal to the Divisional Court.

The court held that the doctrines of res judicata and issue estoppel barred the renewed request for costs because the entitlement had already been finally determined.

The administrative dismissal order was issued without knowledge of the prior rulings and did not reopen the issue.

The motion was dismissed and costs were awarded to the responding party on a partial indemnity basis.

Following a successful interlocutory motion extending time to appeal and setting aside portions of a master's direction, the self‑represented moving party sought costs substantially exceeding $3,000 against the opposing parties and their counsel.

The court considered the principles governing cost awards to self‑represented litigants, including the rule that such litigants are generally not entitled to indemnity for legal expenses absent proof of lost income or opportunity cost.

The moving party provided no evidence of income loss and had also received a court fee waiver.

Applying established authority, the court held that only modest disbursements were recoverable.

The court awarded $300 for disbursements and otherwise made no order as to costs.

The appellant law firm appealed a Master's decision that varied an earlier costs order and awarded $1,000 in costs to the self-represented respondent upon the discontinuance of a fee recovery action.

The respondent also appealed, challenging the discontinuance and seeking higher costs.

The Divisional Court allowed the appellant's appeal regarding the variation of the costs order, finding the Master was functus officio and lacked jurisdiction to vary costs orders previously made by superior court judges.

The appeals regarding the $1,000 costs award were dismissed, as the Master reasonably approximated the respondent's disbursements and correctly applied the law regarding self-represented litigants' entitlement to costs for foregone income.

The plaintiff sought an extension of time to appeal portions of a case management direction issued by a master deeming the plaintiff served with a notice of examination for discovery, deeming non‑attendance, and deeming a certificate of non‑attendance obtained.

The court held that the justice of the case required granting the extension, particularly because the merits of the proposed appeal were strong.

The court found that the master lacked jurisdiction under rule 77.04 of the Rules of Civil Procedure to impose deeming provisions effectively finding an anticipatory breach of discovery obligations before a notice had been served and without procedural fairness.

The deeming provisions created an unfair procedural landscape for a future motion concerning the manner of discovery.

The extension of time was granted and the appeal allowed, striking the impugned paragraphs of the case management direction.

The plaintiff brought a motion for summary judgment against his wife, who had been noted in default, for funds she allegedly diverted and stole from him.

The court granted summary judgment for $466,420.22, finding that the debt would survive bankruptcy due to fraud.

However, the court dismissed the plaintiff's requests for a vesting order over the defendant's personal property and for an order redirecting hypothetical future settlement funds, as the legal requirements for such orders were not met.