United States Court of Appeals 

For the First Circuit 

No. 18-1637 

GARRICK CALANDRO, as Administrator of the Estate of 

Genevieve Calandro, 

Plaintiff, Appellant, 

v. 

SEDGWICK CLAIMS MANAGEMENT SERVICES, INC., 

Defendant, Appellee. 

APPEAL FROM THE UNITED STATES DISTRICT COURT 

FOR THE DISTRICT OF MASSACHUSETTS 

[Hon. Patti B. Saris, U.S. District Judge] 

Before 

Kayatta, Circuit Judge, 

Souter,* Associate Justice, 

and Selya, Circuit Judge. 

 David J. Hoey, with whom Daniel T. Landry and Law Offices of 

David J. Hoey, P.C. were on brief, for appellant. 

 Allen N. David, with whom Jane A. Horne, Catherine M. Scott, 

and Peabody & Arnold LLP were on brief, for appellee. 

March 18, 2019 

 

 

* Hon. David H. Souter, Associate Justice (Ret.) of the Supreme 

Court of the United States, sitting by designation. 
- 2 - 

SELYA, Circuit Judge. A Massachusetts statute, 

familiarly known as Chapter 176D, requires firms that are "in the 

business of insurance" to handle claims in good faith and to 

respond reasonably to the exigencies of the settlement process. 

Mass. Gen. Laws ch. 176D, § 3. But every case has twists and 

turns, and an insurance carrier is not to be held to a duty of 

prescience. 

This case illustrates the point. In it, plaintiffappellant Garrick Calandro, suing in his capacity as administrator 

of the estate of Genevieve Calandro (his late mother), won a multimillion dollar jury verdict for wrongful death and conscious pain 

and suffering against a nursing home. Attempting to add to the 

spoils of that victory, the plaintiff then sued a claims-management 

firm, defendant-appellee Sedgwick Claims Management Services, Inc. 

(Sedgwick), contending that Sedgwick's actions, both pre- and 

post-verdict, violated Chapter 176D.1 That suit was tried to the 

district court which entered a take-nothing judgment. The 

plaintiff appeals, arguing that the district court erred in holding 

 1 As its corporate name implies, Sedgwick is in the claimsmanagement business. It is an open question whether a claimsmanagement firm, as opposed to an insurance carrier, is "in the 

business of insurance," Mass. Gen. Laws ch. 176D, § 3, and 

therefore subject to the provisions of Chapter 176D. We need not 

answer this question today but, rather, follow the district court's 

lead and assume, without deciding, that Sedgwick is subject to the 

strictures of Chapter 176D. 
- 3 - 

that Sedgwick's actions did not constitute unfair claims 

settlement practices. 

Bench trials evoke a deferential standard of review. 

Applying this respectful standard, we affirm the judgment below. 

I. BACKGROUND 

The case at hand involves a tangled web of facts and a 

complicated procedural history. For ease in exposition, we offer 

only a barebones sketch and refer the reader who hungers for the 

full anthology to the district court's opinions. See Calandro v. 

Sedgwick Claims Mgmt. Servs. (Calandro I), 264 F. Supp. 3d 321 (D. 

Mass. 2017); Calandro v. Sedgwick Claims Mgmt. Servs. (Calandro 

II), No. 15-10533, 2017 WL 5593777 (D. Mass. Nov. 21, 2017). 

Sedgwick is a claims-management firm, that is, a thirdparty administrator of insurance claims. At the times material 

hereto, Hartford Insurance Company (Hartford) insured the Radius 

Danvers nursing facility (Radius), located in Danvers, 

Massachusetts. Hartford retained Sedgwick to handle claims 

arising out of Radius's operations. 

During this period, Genevieve Calandro was a resident at 

Radius. While there, she fell from her wheelchair and was taken 

to a local hospital. She never returned to Radius and died at a 

hospice facility on August 16, 2008. 

After securing letters of administration, the plaintiff 

sued Radius in a Massachusetts state court. His complaint 
- 4 - 

adumbrated claims for negligence and wrongful death. Sedgwick 

learned of the suit on October 12, 2011. On the same day, it 

received a letter from the plaintiff's attorney demanding $500,000 

to settle the plaintiff's claims. According to Sedgwick, no 

information that might have facilitated settlement was received 

along with the demand letter. 

Sedgwick engaged Attorney Lawrence Kenney as Radius's 

defense counsel. It also engaged an independent adjuster, Paul 

Bistany, and instructed him to "assess the liability and injuries 

for possible resolution." Bistany's first report, dated October 

24, 2011, noted that the cause of death seemed to be related to 

ongoing medical conditions and, thus, did not necessarily evince 

any negligence on Radius's part. In the same report, Bistany noted 

that some of the documents that he expected to find (such as the 

incident report following the fall) were missing from Radius's 

files. Finally, Bistany explained that he had experienced 

difficulty in locating witnesses (apparently because Radius's 

parent company was in the process of closing the facility). 

Bistany furnished a second report to Sedgwick in January 

of 2012. This report recounted, inter alia, his success in 

locating and interviewing two nurses who had cared for Genevieve 

Calandro. Their information proved unhelpful, though, as they 

offered inconsistent recollections of what transpired before and 

after Genevieve fell from her wheelchair. In July of 2012, the 
- 5 - 

plaintiff added Dr. David Wahl, who was both Radius's medical 

director and Genevieve's attending physician, as a defendant in 

the state-court suit. 

We fast-forward to May 1, 2013. On that date, a hearing 

was held before a medical malpractice tribunal (MMT). See Mass. 

Gen. Laws ch. 231, § 60B. During the MMT proceeding, the plaintiff 

tendered an offer of proof, which included Genevieve's death 

certificate and some form of opinion evidence from a retained 

expert, Dr. Paul Genecin. The record of the MMT proceeding is not 

in evidence, and the parties dispute what quantum of information 

Sedgwick received at that time. Sedgwick maintains that the 

plaintiff's offer of proof was simply an outline of Dr. Genecin's 

opinion and, as such, was insufficient to make liability reasonably 

clear. It adds that it did not receive Dr. Genecin's full report 

until April 27, 2014. The plaintiff disagrees: he asserts — based 

on his interpretation of a note handwritten by Mary Blair (the 

Sedgwick official in charge of the case) — that Sedgwick was given 

Dr. Genecin's full report in anticipation of the MMT proceeding 

(May of 2013) and that, therefore, the MMT proceeding yielded 

information that established Radius's liability for the death of 

Genevieve Calandro. 

The MMT allowed the state-court suit to proceed, see 

Mass. Gen. Laws ch. 231, § 60B, and discovery continued. During 

Dr. Wahl's deposition, taken on November 13, 2013, the plaintiff 
- 6 - 

offered to settle all claims against Radius and Dr. Wahl for 

$500,000. The defendants responded on February 6, 2014, extending 

a joint settlement offer of $275,000. Of this amount, Radius was 

to contribute $125,000. Around the same time (February 7, 2014), 

Attorney Kenney wrote a report to Sedgwick, in which he forecast 

the defendants' exposure at verdict to be in the $300,000 to 

$500,000 range. 

The plaintiff rejected the defendants' February 6 

counter-offer, but the parties persisted in their efforts to settle 

the state-court suit. Nevertheless, the gap grew wider when, in 

April of 2014, the plaintiff increased his demand to $1,000,000. 

The next month, the defendants put a joint counter-offer of 

$300,000 on the table. In a letter dated June 4, 2014, Attorney 

David Hoey, representing the plaintiff, rejected this counteroffer and began efforts to get separate offers from each of the 

defendants. 

In mid-June of 2014, Blair called Attorney Hoey and 

voiced her desire to settle the matter. Before Blair got around 

to proposing a settlement amount, Attorney Hoey ended the call, 

saying that he needed to speak with his client. Blair heard back, 

albeit indirectly, when Attorney Hoey emailed Attorney Kenney on 

June 17, that the case could not be resolved in the range of the 

last previous offer. Dr. Wahl's counsel found a more receptive 

audience: he settled the plaintiff's claims against his client 
- 7 - 

for $250,000 — a settlement in which the plaintiff reserved all 

rights against Radius. Neither Sedgwick nor Attorney Kenney was 

privy to these negotiations. 

On July 3, 2014, one of Attorney Hoey's associates emailed Attorney Kenney, informed him of the separate settlement 

with Dr. Wahl, and demanded $1,000,000 to settle the plaintiff's 

claims against Radius. The e-mail indicated that unless an offer 

exceeding $500,000 was extended by July 9, settlement negotiations 

would be terminated and the case would proceed to trial. Due to 

the July 4 holiday, Attorney Kenney did not see the e-mail until 

July 8. No counter-offer was made within the stipulated time 

frame. On July 14, though, Attorney Kenney offered the plaintiff 

$250,000 and communicated his belief that there was some room to 

negotiate. Attorney Hoey turned down the offer and eschewed 

further negotiations. 

The state-court trial commenced on July 17, 2014, 

lasting for four days. Radius admitted to breaching the standard 

of care and tried the case on the issues of causation and damages. 

The jury found Radius grossly negligent and held it liable both 

for Genevieve Calandro's wrongful death and for her conscious pain 

and suffering, awarded the plaintiff $1,425,000 in compensatory 

damages, and also awarded him $12,514,605 in punitive damages. 

Hartford's policy limit — $1,000,000 — was inadequate to 

satisfy the verdict. Not surprisingly, Attorney Hoey notified 
- 8 - 

both Hartford and Sedgwick that the plaintiff planned to seek 

damages under Chapter 176D and Chapter 93A. In response, Sedgwick 

offered just under $2,000,000 to settle the claims against it, but 

the plaintiff spurned that offer. Thereafter, Hartford began 

negotiating separately and made its peace with the plaintiff. The 

details of that arrangement need not concern us. 

In due course, the plaintiff sued Sedgwick in a 

Massachusetts state court. Citing diversity of citizenship2 and 

the existence of a controversy in the requisite amount, Sedgwick 

removed the action to the federal district court. See 28 U.S.C. 

§§ 1332(a), 1441(b). Once a litany of pretrial issues were 

resolved, see, e.g., Calandro I, 264 F. Supp. 3d at 325, the 

district court convened a bench trial. Following the taking of 

testimony, post-trial briefing, and arguments of counsel, the 

court ruled in Sedgwick's favor. It concluded that "reasonable 

offers" were made "at key points leading up to trial" in the state 

court, and that the plaintiff had rejected all of those offers. 

Calandro II, 2017 WL 5593777, at *5. Moreover, "causation and 

damages were hotly contested" throughout the proceedings, at least 

with respect to the wrongful death claim. Id. Viewed in context, 

 2 The plaintiff is a citizen of Massachusetts, as was 

Genevieve Calandro at the time of her death. Sedgwick is an 

Illinois corporation, which maintains its principal place of 

business in Tennessee. 
- 9 - 

Sedgwick's conduct did not transgress Chapter 176D. See id. at 

*8. This timely appeal ensued. 

II. ANALYSIS 

Following a bench trial, we review the district court's 

legal determinations de novo. See Smith v. F.W. Morse & Co., 76 

F.3d 413, 420 (1st Cir. 1996). In contrast, we accept the court's 

factual findings, including reasonable inferences drawn from raw 

facts, unless those findings are clearly erroneous. See United 

States v. U.S. Gypsum Co., 333 U.S. 364, 394-95 (1948); Smith, 76 

F.3d at 420. Put another way, the district court's findings of 

fact must be honored unless, "after careful evaluation of the 

evidence, we are left with an abiding conviction that those 

determinations and findings are simply wrong." State Police Ass'n 

of Mass. v. Comm'r of Internal Revenue, 125 F.3d 1, 5 (1st Cir. 

1997); see Fed. R. Civ. P. 52(a). Where, as here, an appellate 

court is called upon to review findings of fact made at a bench 

trial, this deference makes perfect sense: in such a situation, 

the trial court "sees and hears the witnesses at first hand and 

comes to appreciate the nuances of the litigation in a way which 

appellate courts cannot hope to replicate." Cumpiano v. Banco 

Santander P.R., 902 F.2d 148, 152 (1st Cir. 1990); Reliance Steel 

Prods. Co. v. Nat'l Fire Ins. Co. of Hartford, 880 F.2d 575, 576 

(1st Cir. 1989) (observing that "[d]isputes of this nature are the 
- 10 - 

staples of a trial court's diet, and comprise an unappetizing, 

usually unnourishing, bill of fare for appellate digestion"). 

In this diversity case, the substantive law of 

Massachusetts controls. See Erie R.R. v. Tompkins, 304 U.S. 64, 

78 (1938). Under Massachusetts law, a firm that is in the business 

of insurance commits an "[u]nfair claim settlement practice[]" by 

"[f]ailing to effectuate prompt, fair and equitable settlements of 

claims in which liability has become reasonably clear," Mass. Gen. 

Laws ch. 176D, § 3(9)(f), or by "[r]efusing to pay claims without 

conducting a reasonable investigation," id. § 3(9)(d). A party 

whose rights are abridged by a violation of Chapter 176D is 

"entitled to bring an action to recover for the violation under 

[Mass. Gen. Laws Chapter 93A section 9]." Rhodes v. AIG Domestic 

Claims, Inc., 961 N.E.2d 1067, 1075 (Mass. 2012); see McDermott v. 

Marcus, Errico, Emmer & Brooks, P.C., 775 F.3d 109, 117 (1st Cir. 

2014). "Together, the[se] statutes require an insurer . . . 

'promptly to put a fair and reasonable offer on the table when 

liability and damages become clear . . . .'" Bobick v. U.S. Fid. 

& Guar. Co., 790 N.E.2d 653, 658 (Mass. 2003). It bears emphasis, 

however, that the duty to settle arises only when liability and 

damages for the underlying claim have become reasonably clear. 

See id. at 659; Clegg v. Butler, 676 N.E.2d 1134, 1140 (Mass. 

1997). Liability is not reasonably clear if an element in the 

underlying claim is subject to good-faith disagreement. See Clegg, 
- 11 - 

676 N.E.2d at 1138. An insurer who has investigated a claim and 

has a good-faith basis for concluding that liability is not 

reasonably clear does not violate Chapter 176D either by delaying 

a settlement offer or for withholding one altogether.3 See id. at 

1140. 

With this framework in place, we turn to the district 

court's conclusion that Sedgwick did not violate Chapter 176D. 

This conclusion rests on a foundation of subsidiary findings: that 

Sedgwick investigated the claim in a timeous manner and in good 

faith by, among other things, engaging Bistany and retaining 

Attorney Kenney, requiring serial reports, and hiring a medical 

expert; that, based (at least in part) on this investigation, the 

causation element of the wrongful death claim was not reasonably 

clear and, thus, Sedgwick had adequate reason to contest liability 

thereon; and that, even assuming that liability was reasonably 

clear with respect to the claim for conscious pain and suffering, 

Sedgwick did not violate Chapter 176D because it made reasonable 

settlement offers at appropriate times. See Calandro II, 2017 WL 

5593777, at *7. 

 3 To be sure, an insurer cannot avoid liability under Chapter 

176D by playing the ostrich and burying its head in the sand. The 

insurer's investigation must itself be carried out expeditiously 

and in good faith, see Clegg, 676 N.E.2d at 1140, thus ensuring a 

degree of accountability. 
- 12 - 

In this venue, the plaintiff comes out swinging. Hoping 

to land a knockout blow, he pummels many of the district court's 

conclusions. For one thing, he submits that liability was 

reasonably clear as to both the conscious pain and suffering and 

wrongful death claims in October of 2011 (when Sedgwick received 

Bistany's initial report). For another thing, he challenges the 

district court's finding that causation was always a contested 

issue with respect to the wrongful death claim. Finally, he 

challenges Sedgwick's good faith and says, among other things, 

that the district court erred in deeming Sedgwick's settlement 

offers reasonable and prompt. 

The plaintiff is punching above his weight. Most of his 

arguments can be bundled together and dealt with as a single 

strike. The common denominator is that those arguments are 

ineluctably factbound and, taken in the ensemble, boil down to a 

plaint that the district court missed the mark in concluding that 

Sedgwick's conduct did not violate Chapter 176D. While the 

plaintiff acknowledges that these arguments are "factuallyintensive" and subject only to clear-error review, he nonetheless 

invites us to hold that the record as a whole belies the district 

court's findings. We decline the invitation. 

We start with the plaintiff's asseveration that 

liability was reasonably clear on both the wrongful death and the 

conscious pain and suffering claims as early as October of 2011. 
- 13 - 

This asseveration, though, was not articulated in the district 

court and, thus, may well be waived. See Teamsters Union, Local 

No. 59 v. Superline Transp. Co., 953 F.2d 17, 21 (1st Cir. 1992) 

("If any principle is settled in this circuit, it is that, absent 

the most extraordinary circumstances, legal theories not raised 

squarely in the lower court cannot be broached for the first time 

on appeal."). 

In all events, the asservation lacks force. When he 

conducted his investigation in October of 2011, Bistany was unable 

to determine whether or to what extent Radius was liable for the 

death of Genevieve Calandro, partially because certain documents 

were missing and some witnesses had not yet been located. Based 

on the incomplete information available to him, Bistany suggested 

that Genevieve's longstanding health issues seemed to be the most 

likely cause of the difficulties that she experienced. Given his 

report of October 24, 2011, Sedgwick had every reason to continue 

to investigate — as it did — rather than roll over and concede 

that Radius's negligence was the cause of death. Consequently, we 

discern no clear error in the district court's implicit finding 

that, with respect to wrongful death, causation (and, therefore, 

liability) was not reasonably clear in October of 2011. 

The district court's finding that causation (and, 

therefore, liability) was never reasonably clear with respect to 

the wrongful death claim at any time before the state-court jury 
- 14 - 

returned its verdict, see Calandro II, 2017 WL 5593777, at *7, is 

likewise supportable. In assailing this finding, the plaintiff 

points to e-mail exchanges between Blair and Attorney Kenney, which 

he interprets as indicating that liability is likely. Although 

this argument has a patina of plausibility, it cannot withstand 

scrutiny. 

In the course of the bench trial, witnesses clarified 

that "liability," as used by lawyers and claims personnel in the 

insurance industry, typically refers to a breach of the standard 

of care — not to causation. Both Blair and Attorney Kenney 

testified that they used the term in that way. The district court 

credited this account. See id. at *5 n.7. Within wide limits, 

credibility determinations are committed to the sound judgment of 

the trial court, see Fed. Refin. Co. v. Klock, 352 F.3d 16, 29 

(1st Cir. 2003), and the plaintiff has given us no reason to 

deviate from that principle here. 

We add, moreover, that other evidence amply supported 

the district court's finding that Sedgwick continually — and in 

good faith — contested the causation element of the wrongful death 

claim. See Calandro II, 2017 WL 5593777, at *7. As we have 

already noted, Bistany reported to Sedgwick, early on, that the 

cause of Genevieve Calandro's death was unclear. Contrary to the 

plaintiff's importunings, this uncertainty was not dissipated by 

the plaintiff's May 2013 offer of proof to the MMT. The district 
- 15 - 

court supportably found that offer of proof to be no more than an 

outline of the expert opinion evidence that the plaintiff hoped to 

adduce at trial and, thus, too insubstantial to render causation 

(and, therefore, liability) reasonably clear.4 See id. at *7-8 & 

n.9. In this connection, the district court credited Attorney 

Kenney's testimony that Sedgwick did not receive Dr. Genecin's 

complete report (laying out his reasoning about the cause of 

Genevieve Calandro's death) until late April of 2014. See id. at 

*7 n.9. Blair's handwritten note does not undermine these 

findings; the plaintiff himself recognized that whatever Blair 

received served only to make Sedgwick generally "aware of the 

nature of Dr. Genecin's expected testimony." 

In the interval between the MMT proceeding and the 

disclosure of the expert's complete report, the investigation into 

liability continued. It was not until May of 2014 that Sedgwick 

received an opinion on causation from its own medical expert — an 

opinion that differed materially from that of Dr. Genecin. To 

cinch the matter, the verdict form in the underlying state-court 

 4 The fact that the MMT allowed the plaintiff's state-court 

suit to proceed, without more, does not establish that liability 

on the wrongful death claim was reasonably clear. See Mass. Gen. 

Laws ch. 231, § 60B (stating that purpose of MMT is to distinguish 

claims that are "merely [] unfortunate medical result[s]" from 

claims that are judicially cognizable); Joseph v. Sweet, 125 F. 

Supp. 2d 573, 575 (D. Mass. 2000) ("Essentially, [the MMT] is an 

initial screen, derailing claims with no legal merit from clogging 

already congested civil court dockets and increasing litigation 

costs.") 
- 16 - 

trial revealed that the question of causation was submitted to the 

jury, thus confirming that Sedgwick never conceded the causation 

element of the wrongful death claim. 

To be sure, the evidence admittedly points in 

conflicting directions. What matters, however, is that the record 

as a whole plausibly supports the district court's findings. See 

Fed. Refin., 352 F.3d at 29 (explaining that when there are "two 

permissible views of the evidence . . . the factfinder's choice 

between those competing views cannot be clearly erroneous"). 

Bistany's reports, intra-company correspondence,5 the state 

court's submission of the issue of causation to the jury in the 

suit against Radius, and testimony given at the bench trial combine 

to lend strength to the district court's findings. Reasonableness 

is a construct that depends on the totality of the circumstances 

in a given case, not an absolute. Cf. United States v. Rudíaz, 

529 F.3d 25, 29 (1st Cir. 2008) (concluding, with regard to 

criminal sentencing context that [r]easonableness "is a construct 

that must be judged according to objective criteria"). On this 

record, it was for the trier to determine whether Sedgwick acted 

reasonably in continuing to argue that Radius's breach of the 

 5 For example, Blair e-mailed her supervisor roughly one week 

before the start of the state-court trial, reporting that in light 

of the comorbidity issues that commonly pertain to elderly and 

infirm persons like Genevieve Calandro, "we have a strong argument 

for causation." 
- 17 - 

standard of care did not cause Genevieve Calandro's demise. The 

district court embraced this responsibility, and all of its 

findings on this topic pass muster under clear-error review. Taken 

together, they confirm that the offer of proof did not suffice to 

close the "causation" gap and that liability on the wrongful death 

claim was not reasonably clear at any time before the state-court 

trial. 

The case law cited by the plaintiff does not demand a 

different result. Without exception, those cases are cases in 

which liability was reasonably clear from the inception. See, 

e.g., Rhodes, 961 N.E.2d at 1071; Gore v. Arbella Mut. Ins. Co., 

932 N.E.2d 837, 841 (Mass. 2010). They are, therefore, readily 

distinguishable. 

To the extent that the plaintiff suggests that Sedgwick 

acted in bad faith in contesting causation on wrongful death, he 

is fishing in an empty stream. The plaintiff premises this 

suggestion in large part on Sedgwick's withholding of the 

identities of the two nurses interviewed by Bistany. However, the 

plaintiff sought discovery of the nurses' identities in the state 

court, which refused to compel discovery on the ground that the 

plaintiff's request was untimely.6 Given this ruling, the district 

 6 At any rate, the nurses were not critical witnesses. For 

aught that appears, they were able to offer only vague and 

inconsistent recollections of the wheelchair incident. There is 

no reason to believe that any information Bistany received from 
- 18 - 

court did not clearly err in finding that, although Sedgwick may 

have been uncooperative, its decision not to furnish the names was 

within the bounds of permissible trial strategy and, thus, not a 

suitable predicate for a finding of bad faith. See Calandro II, 

2017 WL 5593777, at *7. A party who chooses to hold its litigation 

adversary to the rules of discovery can scarcely be said to be 

exercising bad faith by doing so. Cf. Mulero-Abreu v. P.R. Police 

Dep't, 675 F.3d 88, 91-93 (1st Cir. 2012) (upholding district 

court's dismissal of action for failure to follow court-ordered 

discovery deadlines). 

Of course, Sedgwick concedes that liability was 

reasonably clear with respect to the plaintiff's claim for 

conscious pain and suffering. As to this claim, the district court 

found that Sedgwick comported with its duty under Chapter 176D by 

conducting a good-faith investigation and by making reasonable and 

prompt settlement offers. See Calandro II, 2017 WL 5593777, at 

*7. 

This is not to say that the district court found 

Sedgwick's performance to be a textbook model. The court was 

troubled by some deficiencies in Sedgwick's investigation, but it 

found those deficiencies to be due in large part to the windingup of Radius. In the end, the court concluded that Sedgwick did 

 

the nurses' interviews would have served to make causation 

reasonably clear. 
- 19 - 

what it could, given the circumstances. See id. at *2. Perfection 

is not the standard that Chapter 176D imposes upon the handling of 

a claim. Here, the court supportably found that Sedgwick, on 

balance, investigated the claims in a manner sufficient to satisfy 

the strictures of the statute. See Van Dyke v. St. Paul Fire & 

Marine Ins. Co., 448 N.E.2d 357, 361-62 (Mass. 1983) (concluding 

that receiving independent advice from expert witness and trial 

counsel was sufficient even when specifics of actual investigation 

were unknown). The fact that a qualified investigator was retained 

almost immediately buttressed this finding. See Clegg, 676 N.E.2d 

at 1137 (finding investigation reasonable when, among other 

things, investigator was hired promptly). 

This brings us to the plaintiff's complaint that the 

district court erred in finding that Sedgwick's settlement offers 

were reasonable and prompt. See Calandro II, 2017 WL 5593777, at 

*1. Although the district court did not identify a precise date 

on which liability became reasonably clear with respect to the 

claim for conscious pain and suffering, it indicated during the 

bench trial that liability had become reasonably clear on that 

claim by February of 2014. Thus, in evaluating the reasonableness 

and promptness of Sedgwick's settlement offers, the court focused 

on "the value of the case" as of that time. 

This time line comports with the reality of events. 

Discovery in the state-court suit was ongoing during 2013 and, in 
- 20 - 

November of that year, Dr. Wahl's deposition was taken. It was at 

that time that Attorney Hoey again renewed his demand (originally 

made at the time he filed suit and reiterated on October 12, 2011) 

for a $500,000 settlement. Between December 17, 2013, and January 

30, 2014, e-mail exchanges show that Radius and Dr. Wahl were 

actively considering a joint settlement offer of $300,000. There 

was some lag time due to a death in Blair's family and, on February 

6, the two defendants extended a joint settlement offer of $275,000 

for all claims. Even so, they indicated that they had "some room 

to move." The district court found that this offer, though flatly 

rejected by the plaintiff, was both prompt and reasonable. See 

id. at *7. 

This finding was not clearly erroneous. In this context, 

promptness and reasonableness are judgment calls: offers made at 

divers points during a period of time may be deemed prompt, and a 

range of amounts may be deemed reasonable. See, e.g., Bohn v. Vt. 

Mut. Ins. Co., 922 F. Supp. 2d 138, 147-48 (D. Mass. 2013). 

Especially given the course of discovery, the court below did not 

clearly err in deeming the offer prompt. See, e.g., id. And 

especially given the difficulties inherent in placing a dollar 

value on intangibles such as pain and suffering, the court did not 
- 21 - 

clearly err in deeming the amount of the offer to be within the 

universe of reasonable offers.7 

In addition, the district court found that Sedgwick 

(acting on behalf of Radius) had made other prompt and reasonable 

settlement offers that encompassed the claim for conscious pain 

and suffering. These included its participation in a second joint 

settlement offer — in the amount of $300,000 — made in May of 

2014; its spurned attempt to re-ignite negotiations and make a 

further offer in June of 2014; and — after Dr. Wahl had settled 

separately — its $250,000 offer on behalf of Radius alone (made on 

July 14, 2014). As trial loomed, Attorney Hoey advised Attorney 

Kenney on July 15, 2014, that the plaintiff was unwilling to 

resolve the case in the range of Radius's last offer. In the 

district court's view, these pre-verdict offers were sufficient to 

inoculate Sedgwick against Chapter 176D liability. See Calandro 

II, 2017 WL 5593777, at *7. We discern no clear error. 

The short of it is that the district court was confronted 

with a welter of evidence — evidence that lent itself to differing 

interpretations. In such circumstances, the applicable standard 

of review requires that we defer to the district court's "fact-

 7 In this instance, the finding of reasonableness was 

bolstered by a trial report that Attorney Kenney submitted to 

Sedgwick the next day. In it, he estimated the verdict potential 

for the wrongful death and conscious pain and suffering claims, as 

an aggregate, to be between $300,000 and $500,000 (which presumably 

would be split between the two defendants). 
- 22 - 

intensive findings, absent clear error." Reliance Steel, 880 F.2d 

at 576 (quoting Irons v. FBI, 811 F.2d 681, 684 (1st Cir. 1987)). 

We conclude that clear error is clearly absent and that deference 

to the district court's findings is manifestly appropriate.8 

This conclusion does not end our odyssey. The plaintiff 

makes two further arguments, which he characterizes as matters of 

law, evoking de novo review. It remains for us to deal with those 

arguments. 

To begin, the plaintiff submits that the district court 

imposed an additional (and improper) burden on him with respect to 

his derivative rights under Chapter 93A section 9. Specifically, 

he contends that the district court erred in requiring him to prove 

that some unfair or deceptive act on Sedgwick's part caused him to 

suffer a loss. In support, he points to the district court's 

statement, in its conclusions of law, that the plaintiff "has not 

shown that Sedgwick's actions constitute an unfair practice." 

Calandro II, 2017 WL 5593777, at *7. 

 8 The district court also found that Sedgwick's post-verdict 

conduct did not violate Chapter 176D. See Calandro II, 2017 WL 

5593777, at *8. On appeal, the plaintiff denigrates this finding, 

but he makes no developed argument that the court below committed 

clear error in this respect. Consequently, we deem any such 

argument waived. See United States v. Zannino, 895 F.2d 1, 17 

(1st Cir. 1990) (explaining that "issues averted to in a 

perfunctory manner unaccompanied by some effort at developed 

argumentation, are deemed waived"). 
- 23 - 

Whatever the district court may have meant by its 

conclusion that Sedgwick had not committed an "unfair practice," 

it plainly did not make any adjudication of the plaintiff's rights 

under Chapter 93A section 9. "Everything depends on context," 

Rivera-Velázquez v. Hartford Steam Boiler Inspection & Ins. Co., 

750 F.3d 1, 5 (1st Cir. 2014), and the context in which this phrase 

appears in the district court's rescript undermines the 

plaintiff's contention. We explain briefly. 

The plaintiff's complaint sets out causes of action 

under Chapter 176D alone. Under the claims as pleaded, Chapter 

93A section 9 comes into play only derivatively, that is, as a 

remedial vehicle for a Chapter 176D violation. Cf. McDermott, 775 

F.3d at 117 (noting that "Massachusetts courts have recognized" 

that a violation of Chapter 176D "automatically give[s] rise to 

liability under Chapter 93A"). The district court, therefore, was 

never tasked to make an independent adjudication of a Chapter 93A 

claim: relief under Chapter 93A section 9 was material only if — 

and to the extent that — a violation of Chapter 176D was found. 

Here, the district court supportably concluded that 

there was no Chapter 176D violation. See Calandro II, 2017 WL 

5593777, at *7. In the absence of an antecedent finding that a 

Chapter 176D violation had transpired, no derivative liability 

could exist under Chapter 93A section 9. See McDermott, 775 F.3d 

at 117. Since the district court never reached the issue of the 
- 24 - 

plaintiff's right to recover through the medium of Chapter 93A 

section 9, it necessarily follows that the court's use of the 

phrase "unfair practice" cannot conceivably signal the imposition 

of an improper burden. 

The plaintiff's remaining argument is no more 

persuasive. He insists that the district court erred as a matter 

of law by assessing whether liability was reasonably clear 

according to a subjective standard rather than an objective 

standard. The premise on which this argument rests is sound: 

under Chapter 176D, the question of whether liability is reasonably 

clear such that an insurer would be bound to make a reasonable 

settlement offer is an objective inquiry. See Demeo v. State Farm 

Mut. Auto. Ins. Co., 649 N.E.2d 803, 804 (Mass. App. Ct. 1995). 

In such an inquiry, liability is reasonably clear if the factfinder 

determines that "a reasonable person, with knowledge of the 

relevant facts and law, would probably have concluded, for good 

reason, that the insurer was liable to the plaintiff." Id. 

Here, however, the conclusion that the plaintiff would 

have us draw is not borne out by the record. Although the district 

court did not say in haec verba that it was employing an objective 

standard, actions sometimes speak louder than words. This is such 

a case. 

The record makes manifest that the district court 

consulted objective evidence and assessed the clarity of Radius's 
- 25 - 

liability under the appropriate standard. In finding that 

liability was not reasonably clear on the wrongful death claim, 

the court relied on investigation reports, status reports, 

credible testimony from Attorney Kenney about Radius's liability, 

and the state court's verdict form. Fairly read, the court's 

finding makes it plain that the court was employing an objective 

standard. 

We need go no further.9 Inasmuch as the plaintiff has 

not shown that the district court either misapplied applicable law 

or clearly erred in finding the facts, his appeal fails. 

Affirmed. 

 9 Because we discern neither clear error in the district 

court's factual findings nor any error of law, we need not consider 

Sedgwick's alternative defense under the "safe harbor" provision 

of Chapter 93A section 9. See Calandro I, 264 F. Supp. 3d at 323 

(discussing this provision's limiting effect on recovery amount).