Appeals court hears dispute over insurer’s investigation and delay after 2016 motorcycle crash

An appellate panel heard oral argument in Gerald Leahy v. Courtney Tyler over whether Progressive’s handling of a 2016 motorcycle-injury claim violated duties on insurers to investigate and make a prompt, fair settlement offer, counsel said; the court took the case under advisement.

Appellant’s attorney Albert Grady said the motorcycle wreck occurred Aug. 29, 2016, Progressive conceded fault for the crash, and the dispute centers on causation and whether Progressive conducted a timely, reasonable investigation under Massachusetts law. Grady told the panel the carrier initially set reserves at about $5,000, received a demand package in October 2017 that included roughly $10,500 in medical bills, and within two weeks “moved their reserves … up to $25,000.” He said Progressive did not make a settlement offer until August (the first offer was $4,137, according to the record) and paid the claimant $25,000 only after counsel-signed medical releases in November 2019.

“The issue is … whether the carrier investigated all circumstances and made a prompt, fair, and equitable claim settlement offer,” Grady told the panel, citing the statutory duties discussed at argument (transcript references to G.L. c. 176D appear in the record). He argued Plymouth Rock, the insured’s underinsured motorist carrier, assessed the same medical record evidence and offered $48,000, which Grady said shows how other insurers valuated the claim; Grady later clarified timing questions about when Plymouth Rock and Progressive exchanged information during the litigation.

Counsel for Progressive argued the case turns on causation and the reasonableness of Progressive’s investigation. “There’s really only two issues in the case: if and when liability became reasonably clear … and whether Progressive’s investigation was reasonable,” counsel said, stressing that a third‑party liability carrier like Progressive has different rights and investigative tools than a first‑party or underinsured motorist carrier. Defense counsel told the panel Progressive repeatedly sought medical records from plaintiff’s counsel and that Progressive lacked authority to compel records the plaintiff declined to provide earlier in the process.

Panel members repeatedly questioned counsel about timing and what documents Progressive had when it adjusted reserves and made settlement decisions. One judge asked, “Doesn’t this whole case come down to causation?” Another asked why Progressive did not request medical releases until about two years after the accident; counsel for Progressive answered that the claim notes show continuous contact and requests for records and that insurers generally relied on records plaintiffs provide prior to suit.

Appellate argument touched on several factual points in the record at trial: an operative procedure in 2018 for the plaintiff’s right wrist (the operating orthopedist’s report appears in the appendix), roughly $23,000 in medical bills cited in a later demand, notes of emotional symptoms such as nightmares, and testimony that Progressive’s claim handlers who reviewed the file did not have medical training. Counsel debated whether moving reserves to $25,000 demonstrated acceptance of the demand package or was merely a business decision reflecting a worst‑case assessment.

No decision was announced from the bench; the panel said the case is under advisement. The oral-argument record shows the dispute centers on (1) when liability and causation were reasonably clear for purposes of settlement under the insurance‑law duties discussed at argument, and (2) whether Progressive’s investigative steps were reasonable given the records it had or could obtain.

The appeals court’s written decision will resolve the legal standard the panel applies to those facts and whether the trial court erred in its findings or legal conclusions.