Executive Summary: Key Legal and Evidentiary Issues

• Tiffany Longarini brought a negligence claim against her legal representatives — Clifford Lloyd, Konstantine Dimakis, and Silkport Capital — for falling below the standard of care in representing her in civil litigation.
• Neither Silkport Capital nor Dimakis were licensed by the Law Society of Ontario to provide legal services, yet both were found to have provided them.
• Affidavits filed on Longarini's behalf were sworn by Dimakis, who had no firsthand knowledge of the material events and failed to identify the source of his information, rendering them inadmissible.
• Failure to advise Longarini of the need to file her own affidavit and to submit to examinations was a central allegation raised in the pleadings and motion materials — not a novel issue introduced by the motion judge.
• Elevated costs of $42,925.10 were awarded against Longarini in the underlying proceedings as a direct consequence of the appellants' conduct.
• On appeal, the Divisional Court found no palpable and overriding error in the motion judge's findings and dismissed the appeal with costs fixed at $2,500.

Facts of the case

Tiffany Longarini retained Clifford Lloyd, Konstantine Dimakis, and their firm Silkport Capital to represent her in litigation against a Mr. Huitema, which involved an Ontario Business Corporations Act (OBCA) application and a defamation action. Lloyd was the only lawyer licensed by the Law Society of Ontario (LSO); Dimakis was neither a lawyer nor a paralegal, and Silkport Capital held no LSO licence. On May 9, 2023, Henderson J. granted an ex parte injunction in favour of Huitema. On May 23, 2023, MacNeil J. continued that order with amendments and adjourned the motion to June 9, 2023. Rather than filing affidavits from Longarini herself, the appellants prepared and served affidavits in Dimakis' name on or about May 22, 2023. On June 2, 2023, Longarini was served with a statement of claim in the defamation action. When Lloyd appeared before Bordin J. on June 9, 2023 in connection with Huitema's OBCA motion, the court noted that the uploaded materials were so disorganized as to be unusable. On June 21, 2023, Lloyd served a Notice of Intent to Defend in the defamation action but did not file the documents with the court. The matter returned before Sheard J. on June 26, 2023 as a hearing de novo, at which the respondent, through Lloyd, refused to submit Longarini or Dimakis to examination or cross-examination.

Contractual and professional obligations at issue

The motion judge found that the conduct of the parties after execution of their agreement made clear that the appellants were engaged to act for Longarini in all litigation with Huitema in which she was involved. The appellants had argued they were providing mergers and acquisitions services rather than legal services, but virtually all the evidence before the court demonstrated otherwise. Lloyd, as the only LSO-licensed lawyer, was understood by all parties to be representing Longarini in court, in court documents, and in communications with opposing counsel. These professional obligations carried with them the duty to provide competent legal advice — including advising a client on the need to put forward her own evidence and to participate in examinations when required.

Reasoning and analysis

Sheard J., following the June 26, 2023 hearing, was highly critical of the appellants' conduct. She found that no weight could be given to Dimakis' affidavits because they addressed material events about which he had no firsthand knowledge and failed to identify the source of his information. She characterised the decision to put forward Longarini's evidence through Dimakis as "at best negligent, and at worst, improper," and concluded that reliance on those affidavits effectively left Longarini without any admissible evidence on the motion. Sheard J. further described a letter from Lloyd to a witness as "threatening" and characterised his conduct as "highly improper and impugns the integrity of opposing counsel and the integrity of the administration of justice." On February 20, 2024, Sheard J. settled the costs payable and awarded Huitema elevated costs — totalling $42,925.10 — against Longarini, citing the disorganised and inadmissible affidavit evidence, the threatening witness letter, the refusal to produce Dimakis or Longarini for examination, vitriolic communications with opposing counsel, Lloyd advancing irrelevant arguments, and the hearing being extended from a scheduled 2.5 hours to a full day.

On the summary judgment motion before Bordin J., the appellants argued that Dimakis' affidavits were filed because Longarini was ill and unavailable. The motion judge rejected this explanation on multiple grounds: it was not disclosed in the Dimakis affidavit itself, it did not explain Dimakis' failure to identify the source of his information, it did not explain his failure to appear for cross-examination, and it provided no basis for why Longarini — said to be ill — was also not produced for examination as a witness. On appeal, the appellants raised a single issue: that the motion judge had decided the case on a "novel theory of liability" by finding a failure to advise, which they claimed had not been raised in the pleadings and denied them a fair opportunity to respond. The Divisional Court rejected this argument entirely, pointing to the Amended Statement of Claim, the Amended Notice of Motion, and the Respondent's factum — all of which expressly alleged that the appellants provided incorrect legal advice and insisted it was unnecessary for Longarini to file her own affidavit. The court further noted that the heightened particularity required in pleadings for intentional torts such as fraud does not apply to negligence claims, and that the deficiencies identified by the motion judge were obvious from the record.

Ruling and overall outcome

The Divisional Court, per Corbett J. (Faieta and Shore JJ. concurring), dismissed the appeal. The court found no palpable and overriding error in the motion judge's factual findings and no error of law in her conclusion that the appellants' conduct fell well below the standard expected of a competent solicitor. Longarini, as the successful party, had previously been awarded damages of $41,000 and costs of $1,606.54 at the summary judgment stage. On appeal, the appellants were further ordered to pay appeal costs of $2,500, inclusive, jointly and severally, within thirty days of the oral decision delivered on October 29, 2025. In total, the amounts ordered in Longarini's favour across both proceedings come to $44,606.54.