The Massachusetts Appeals Court examined whether a jury finding of negligent misrepresentation, coupled with a defendant’s later refusal to honor indemnification, supports treble damages and attorney’s fees under G.L. c. 93A.

Robert Shaw, representing 25 TO Holdings LLC and the Cape Club of Sharon LLC, told the panel the trial court erred in converting negligent misrepresentation into an actionable 93A violation. "A material breach is not a 93A violation," Shaw argued, stressing that the judge’s legal synthesis of the facts raises a legal question suitable for de novo review.

Opposing counsel countered that the trial judge—who had the benefit of hearing live testimony and weighing credibility—reasonably concluded the totality of the record showed egregious conduct. Donald Schroeder and other respondents pointed to the judge’s findings that the defendants were on notice of liabilities and later refused to perform, which the judge treated as more than ordinary contract breach.

The parties also debated successor liability and whether the indemnity at issue arose from a contract-based transaction or as an intra‑enterprise dispute. Shaw emphasized the absence of an express obligation at the time the alleged misrepresentation was made and urged the court to limit 93A extensions where the record does not show willful or knowing misrepresentations.

The panel probed both sides on precedent—Shaw asked the court to distinguish Anthony Pier 4 and related duty‑of‑good‑faith jurisprudence; respondents cited trial findings and collateral evidence they said showed a repeated pattern of misleading statements and concealment.

No ruling was issued at argument; the court took the matter under advisement.