Law Restricts Her From Reducing ‘Excessive’ $91M Injured Worker Award, Judge Finds

A Massachusetts judge has declined to reduce the $91 million damages award she approved last September for a construction worker’s personal injury claim, an award she herself characterized as “grossly excessive” but found is required by statute and precedent.

Suffolk Superior Court Justice Debra Squires-Lee found that because Liberty Mutual insurers willfully failed to investigate and make a reasonable offer to injured worker John Rooney, she was obligated under state law to at least double the verdict issued by a jury in August 2021.

The $26.6 million verdict consisted of $1 million for past medical expenses, $2.1 million for past lost earning capacity, $5.5 million for past pain and suffering, and $18 million for future pain and suffering. After inclusion of a hefty pre-judgment interest charge (reflecting unusual delays because of COVID-19), the final compensatory judgment entered was $45.49 million, which ballooned to more than $91 million after doubling.

The judge said she expects that her ruling will be appealed.

In addition to citing the insurer’s failures in investigating and negotiating offers, the judge suggested Liberty was also hurt by failing to argue that such a large award raised constitutional issues even though it was put on notice that it could face such a large award.

Rooney, a mason, was seriously injured while working on the refurbishment of the Longfellow Bridge that spans Boston and Cambridge when he fell on interior scaffolding. Rooney alleged that the construction firm White-Skanska-Consigli was liable for his injuries because the scaffolding was not compliant with Occupational Safety and Health Administration (OSHA) regulations and had not been properly inspected. The insurers involved were Liberty Mutual companies Peerless, Liberty Mutual Fire and Ohio Casualty Insurance Co.

By the time of trial, defense counsel did not challenge the scope of Rooney’s injuries or medical causation or that Rooney’s injuries, multiple surgeries, and permanent damage were related to his fall.

Liberty and the defendant balked at the jury verdict total and sought a new trial or reconsideration of damages. They complained that the “purported compensatory damages awards were grossly disproportionate” to the trial evidence and were “astronomically higher than other comparable Massachusetts verdicts.”

In the meantime, in September 2021, Liberty offered Rooney the policy limits of $19.5 million, which Rooney rejected. In February 2022, after indicating he would settle the claim for Liberty’s policy limits plus $7.5 million from the construction company’s excess carriers (AIG insurers), Rooney changed his mind.

In April 2022, Rooney sent Liberty a written demand alleging unfair and deceptive acts in violation of the state’s unfair insurance practices law (Chapter 176). Rooney stressed that if he proved Liberty acted willfully, he would be entitled to a punitive damage award under the state’s consumer and business protection law (Chapter 93A) of at least two times the underlying judgment.

Liberty filed for a declaratory judgment that it had not violated Chapters 93A or 176 because it “carefully monitored the case prior to trial and reasonably determined that liability was not reasonably clear” and, after judgment, “carefully re-assessed the claim and promptly offered the full limits of the applicable policies.”

In September 2025 after a 10-day trial on Liberty’s declaration, the judge found that the evidence showed the insurer had willfully violated Chapter 176. She noted that the statute and governing law required her, at a minimum, to double the judgment.

In her ruling, she expressed her subjective view that the finding of willfulness resulted in a “grossly excessive punitive damages award against Liberty far in excess of the goals the statute is designed to achieve.” But, upon concluding that the statute and controlling precedent offered her no discretion, she ordered judgment of $91 million, or two times the jury award.

In seeking the declaratory judgment, Liberty did not argue that if the court found willfulness, the doubling or trebling of the underlying tort judgment would be grossly excessive and/or violative of the Due Process Clause of the Fourteenth Amendment. Instead, Liberty argued that any court would likely conclude that the verdict was an “outlier, well beyond the type of verdicts typically returned in cases of this nature.”

Rooney argued that by not arguing the constitutional issues when it knew that if found to have willfully violated the law the damages could be double, Liberty had waived its due process argument.

The judge agreed with Rooney, writing:

“The Insurers are sophisticated corporate entities represented by experienced and capable counsel. When they filed the instant c. 176D case, they well knew of the seemingly eye-popping judgment in the Underlying Case and the potential for a c. 93A punitive damages award of two times that amount. They nonetheless did not argue that such an award would violate their due process rights. Thus, a finding of waiver is appropriate.”

According to the judge, Liberty did not need to await any finding by the court as to the timing and value of a reasonable settlement offer to know that if it was found to have acted willfully the damages would be doubled.

The judge said she was aware that an appeal is “virtually certain” and thus revisited a few points around her finding of willfulness, the first being the “degree of reprehensibility of the conduct” of the insurers:

First, Rooney was seriously injured. No one ever disputed medical causation and, by the time of trial, Rooney had undergone numerous spine and neck surgeries as a result of his fall. He was unable to work. He had incurred $400,000 in medical expenses by December 2018 and would incur more due to additional surgeries pretrial. During the lengthy litigation, Rooney continued to undergo several neck and back surgeries and incur medical expense.

Second, the interior scaffolding was “grossly deficient,” and any review of the photographs taken would have led “every reasonable insurer” to understand they were OSHA non-compliant and presented a high risk of serious injury or death. And— whether or not there was contributory negligence as Liberty argued – the only credible evidence was that Rooney fell into OSHA-deficient gaps of the interior scaffold. Yet, none of the insurers’ roundtable reports discussed the obvious OSHA violations in connection with the scaffolds or the scaffolding photographs showing excessively large gaps.

Third, Liberty developed a theory of defense — that Rooney was contributorily negligent in placing and /or walking on a single plank — in November 2015 and never reevaluated that theory despite the “wealth of contradictory evidence.”

Fourth, there was no evidence of documented safety inspections of the scaffolding and the insurers never grappled with the “absence of documented safety inspections” and were either unaware of or discounted the defendant’s contractual safety obligations including inspections. The judge said the only conclusion is that Liberty “disregarded Rooney’s health, and its conduct was repeated and not accidental.”

“Despite knowing all the above, Liberty failed to make a reasonable offer of settlement. It did so because the principal claims handler failed in his obligation to investigate, assess and properly value the case,” the judge concluded.

The judge also addressed Liberty’s complaint about the “disparity between actual or harm suffered by the plaintiff and the punitive damages award.” Because the statute circumscribes punitive damages to two or three times actual damages, the ratio between compensatory and punitive damages is not excessive, the judge found.

“The amount of the award in this case is driven by the exceedingly large tort verdict which, together with statutory pre-judgment interest which accrued in part due to an unprecedented global pandemic, resulted in an extraordinarily large judgment,” wrote the judge, adding that the insurer was put on notice by Chapter 93A that it could be liable for up to treble damages.

“The very large punitive damage award that will enter as a judgment in this case is a result of two things: the size of the underlying tort judgment and my finding of willfulness,” the judge concluded. Both the size of the tort judgment and the risk that a court would find they acted willfully were known to the Liberty insurers when they sought a declaration that they did not violate the unfair insurance practices law and, since they did not raise their constitutional claim until after her ruling, the insurers waived that claim, she wrote in her summary