Tuesday, May 19, 2026

Invitation to my Tuesday June 2, 2026 webinar, Untangling Coverage: A Practical Guide to Your First Insurance Dispute

On June 2, 2026, from 4 to 6 PM, I will be presenting a webinar sponsored by the Social Law Library in partnership with The Insurance Library, “Untangling Coverage: A Practical Guide to Your First Insurance Dispute.” Insurance coverage disputes can feel like a maze even for seasoned practitioners, and for attorneys stepping into their first coverage matter the learning curve can be steep.

This focused, highly practical webinar is geared towards attorneys and summer associates, but is appropriate for anyone who wants to develop a deeper understanding of insurance coverage law.   I will offer a clear, usable roadmap for navigating your first coverage dispute, from making sure you are working with the correct insurance policy to understanding the obligations and pressure points of the insurer, the policyholder, and the claimant, to moving the matter toward resolution.

What You’ll Learn:

  • How to identify and verify the applicable insurance policy;
  • Notice requirements: occurrence vs. claims-made policies;
  • Analyzing coverage: triggers, exclusions, and exceptions;
  • Duties of the insurer and the policyholder;
  • Claims under Mass. Gen. Laws chs. 93A and 176D;
  • Reservation of rights letters; and
  • Declaratory judgment actions
The program runs from 4:00 p.m. to 6:00 p.m. and is priced at $25,

Featuring Panelist Nina Kallen

The session is led by Nina Kallen, a respected Massachusetts attorney known for her deep experience in insurance coverage and bad‑faith litigation. Nina’s practice has long focused on helping insurers, policyholders, and other lawyers navigate the complexities of policy language, statutory obligations, and the strategic decisions that shape coverage outcomes. 

You can sign up here: https://www.socialaw.com/about/library-calendar/2026/june-2026/untangling-coverage-a-practical-guide-to-your-first-insurance-dispute/

Monday, April 13, 2026

I'm presenting at a webinar on Reservations of Rights: Ethical Rules, Conflicts, Right to Independent Counsel on Wednesday, April 22, 2026 at 1 PM; discount codes available

Ethics of Insurance Defense Under a Reservation of Rights: Ethical Rules, Conflicts, Right to Independent Counsel

This CLE webinar will discuss how policyholders, insurers, and panel counsel determine whether a reservation of rights (ROR) creates a disqualifying conflict of interest for panel counsel at various stages of the case, and the possible consequences if a conflict exists. We will offer guidance and best practices for insurers, policyholders, panel counsel, and independent counsel. The program will discuss roles in the tripartite relationship, defense counsel's ethical obligation if a conflict arises, and examples of disqualifying conflicts in various jurisdictions.

Description

When an insurer agrees to defend its policyholder under a reservation of its right to later litigate or deny coverage, a particularly delicate and dynamic tripartite relationship is created. Everyone involved in this relationship needs to be aware of conflicts and potential conflicts of interest, and sometimes determine how to use them to their advantage.

What constitutes a conflict within the context of the tripartite relationship is often hotly contested. The case law continues to develop and no less than 50 American jurisdictions have issued rulings on these important issues.

An insurer's reservation of rights will necessitate panel counsel to evaluate many ethical duties: undivided loyalty (Rule 1.7), disclosure (Rule 1.4), confidentiality (Rule 1.6), and limitations on compensation from insurers (Rule 1.8). At the same time, policyholders need to make a determination of whether the convenience and known competence of panel counsel is outweighed by the advantages of independent counsel.

Listen as this esteemed panel examines the scope of the appointed defense counsel's ethical obligations, discusses the insured's right to independent counsel, reviews emerging issues in independent counsel litigation, and offers best practices for policyholders and insurers. 

You can sign up here.  https://www.barbri.com/course/professional-development/CLE/ethics-of-insurance-defense-under-ror-model-rule-17-conflict_2026-04-22

Feel free to use and share this code for 50 percent off tuition:

Kallen 05mVRIAYACV2

If this program remains cost-prohibitive for you even at 50 percent off, please reach out to me.  I have a limited number of free tuition spots, first-come, first-served.  

Wednesday, January 21, 2026

Massachusetts Superior Court issues giant 93A judgment against insurer for ignoring the facts of the underlying case

Every few years, a decision comes down against an insurance company for breach of Mass. Gen. Laws ch. 93A that makes the plaintiffs' personal injury bar chortle with glee and insurance defense attorneys wipe their brow and say, thank goodness that wasn't my case.  The recent Massachusetts Superior Court decision in Peerless Insurance Co. v. Rooney is one of those, with a judgment against the insurance company of $90,771,612.00 plus attorney's fees.  But although this case seems like a crazy 93A verdict, the yikes factor here is really the underlyling judgment of $45.49 million including prejudgment interest.  Finding that she had no choice under ch. 93A, the judge ordered that the insurer pay double that judgment for its bad faith.  If the underlying judgment had been $100,000, would anyone take note of the $200,000 ch. 93A judgment?  The analysis would be exactly the same.  

The accident, and factual development during the underlying lawsuit

A consortium of contractors called JV entered into a contract to repair the Longfellow Bridge.  John Rooney worked as a mason for United Stone, JV's masonry subcontractor.  He was injured on the job on May 9, 2014, resulting in nine surgeries including cervical discectomies and cervical fusions.  He sued JV in 2015, alleging various negligence counts.  

Peerless Insurance Company issued a primary policy to JV. Liberty Mutual Fire Insurance Company and Ohio Casualty Insurance Company issued umbrella policies.  The court refers to the insurers together as "Liberty." 

Very early in the case Liberty understood that Rooney's injuries were causally related to the accident.  As to liability, Liberty's independent investigator wrote that Rooney had fallen off a plank that he himself had placed ("the single plank theory").  Liberty first concluded based on this information that there was only a 25 percent chance that Rooney would prevail at trial.  

Facts developed during discovery that showed that this initial assessment was incorrect.  There was no support for the single plank theory.  Rooney had fallen through a wide gap in scaffolding.  JV was responsible for safety at the job site.  It was supposed to inspect the scaffolding daily but failed to do so.  Rooney had complained prior to the accident of the unsafe conditions.

These facts were never conveyed from the lower level adjuster at Liberty to senior management.  As a result, Liberty continued to overestimate JV's chances of success at trial and to undervalue the claim.  

The jury awarded Rooney $26.6 million.  Judgment with interest entered in the amount of $45.49 million.  

Post-trial settlement offer and 93A demand letters

A month later, on September 15, 2021, Liberty offered in settlement the aggregate policy limits of $19.5 million.

On April 8, 2022 and June 27, 2024, Rooney sent 93A demand letters to Liberty.  Liberty did not make an offer of settlement.  

The 93A lawsuit

Liberty filed a lawsuit seeking a declaration that it had not violated Mass. Gen. Laws ch. 93A.  Rooney counterclaimed. 

Failure to make a reasonable investigation 

Rather than jumping straight to whether Liberty failed to effectual prompt, fair, and equitable settlement of a claim in which liability had become reasonably clear, the court first looked at a different section of Mass. Gen. Laws ch. 176D, requiring an insurer to conduct a prompt and reasonable investigation.  The court noted that this requires an insurer to "take basic steps toward obtaining an independent or neutral assessment of potential fault."  An insurer is not permitted to "cherry-pick facts favorable to it or disregard unfavorable evidence, and, instead, has to assess the evidence objectively."  Liability arises when, if an adequate investigation had been conducted, liability would have been reasonably clear.  

The court held that Liberty failed to make a reasonable investigation.  

Failure to make an offer of settlement when liability was reasonably clear

The court held that when liability is reasonably clear, an insurer must make an offer of settlement even if there are disputes as to comparative fault or the extent of damages.  Liability can be reasonably clear well before a verdict or judgment resolves every contested issue.  An insurer cannot turn a "blind eye" and fail to credit or give appropriate weight to readily available information related to liability while relying on defense counsel's trial strategy and assessment of trial risk.  The insurer is obligated to conduct a neutral assessment of liability separate from defense counsel's litigation strategy.  

Liability can be reasonably clear even if there are other potential tortfeasors or the possibility of comparative negligence.  

When liability is reasonably clear, an insurer must extend a reasonable settlement offer, even if the plaintiff would not accept that offer.  

The court held that the standard for whether liability is reasonably clear is not whether "no reasonable insurer would have failed to settle," as articulated in Hartford Casualty Ins. Co. v. New Hampshire Ins. Co., 417 Mass. 115 (1994).  Rather, the standard is set forth in Demeo v. State Farm Mut. Auto. Ins. Co., 38 Mass. App. Ct. 855 (1995) as "whether a reasonable person, with knowledge of the relevant facts and law, would probably have concluded, for good reason, that the insured was liable to the plaintiff."  The court held, however, that the two standards are essentially the same.  Under the Hartford test, once liability is reasonably clear, "no reasonable insurer, acting in good faith, would fail to make a prompt, fair, and equitable offer of settlement.  No reasonable insurer would knowingly violate chapter 176D (and face the risk of significant punitive damages) by perpetrating litigation where there is no legitimate dispute  to the insured's fault or the scope of the claimant's injury."  

Based on that standard, Liberty failed to make an offer of settlement after liability was reasonably clear.  JV's liability became obvious during discovery.  Although there was a comparative negligence defense, defense counsel never advised Liberty that a jury would likely find Rooney more than 51 percent liable for the accident.  

Failure to adopt and implement reasonable standards for the investigation of claims

The judge rejected Rooney's claim that Liberty had failed to adopt and implement reasonable standards for the investigation of claims.  She held that Liberty trained its claims professionals and had written protocols and procedures.  The failure in this case was the adjusters', but it did not stem from a lack of protocols and procedures.  

Liberty's violation of ch. 93A was willful and knowing

The court held that it "cannot conclude otherwise" than that Liberty’s conduct was willful or knowing.  "Liberty deliberately closed its eyes to known and available information, in order to hold fast to its premature, yet somehow cast in concrete, theory of the case."

The court held that the question was not "whether, on the roll of the dice, a defense verdict was possible.  . . .  The question does not depend on trial counsel's assessment of the potential jury verdict.  If the possibility of a defense verdict -- whether forty percent or twenty-five percent-- was alone sufficient to avoid making a reasonable offer of settlement when liability was reasonable clear, no insurer would settle. Ever.  Jury trials are, by definition, unpredictable."

93A damages

I wrote here a few weeks ago about Gretzky v. AmGuard, 2025 WL 3140762 (D. Mass. 2025) (unpublished), in which the United States District Court for the District of Massachusetts held that single damages under ch. 93A is lost interest, not the amount of the underlying verdict.  I wrote that in that case the measure of damages seemed to be based on the timing of the 93A demand letter, which was sent after the insurer had paid its policy limits after the verdict.

The court in Rooney seems to disagree.  The court held that single damages under ch. 93A is always lost interest, but that where damages are multiplied because the violation was willful or knowing, the damages to be multiplied is the underlying judgment.  Although the court does not provide a complete analysis, its method could actually result in a larger award.  Liberty should be liable for the trial verdict up to the policy limit as actual damages, lost interest as 93A single damages, and double the entire trial verdict as 93A damages.   

The judge ruled that, given the size of the underlying judgment, an award of double damages resulted in a "grossly excessive punitive damages award . . . far in excess of the goals the statute is designed to achieve."  However, the statute and controlling precedent offer no discretion.  She issued an award of $90,971,612 plus attorney's fees.  

What happens next 

Entry of judgment has been stayed pending a determination of attorney's fees, which means that the clock for Peerless to file an appeal has not yet begun to run.  

Takeaways

There are number of important points in this 68 page decision, but from the point of view of an insurance litigator I'll focus on the relationship between the insurer and insurance defense counsel.

The decision carefully outlines what happened in each step of the underlying litigation, including communications between insurance defense counsel and the insurer.  At one point, insurance defense counsel asked his supervisor if the insurer was reviewing his reports, because it continued to rely on old analyses.  The decision also states at various points that the insurer should not rely only on communications from defense counsel, who may be biased in favor of the client, and that the insurer should instruct defense counsel to provide more information.  

From a practical standpoint, that's an instruction that goes both ways.  Insurance defense counsel has an obligation to make sure that an insurer is receiving the message they are sending.  The rules of tripartite relationship (sorry for jargon -- this term means that insurance defense panel counsel fully represents both the insurer and the insured) means that insurance defense counsel does not dictate settlement strategy and needs to be careful not to back the insurer into a corner.  But if you're insurance defense counsel and you've sent a written report to an adjuster that you're concerned is not being read, it's time to pick up the phone.  

Wednesday, January 14, 2026

Update: webinar is being rescheduled. I'm moderating a webinar on insurance policy interpretation on Tuesday, January 22, 2026 at 1 PM; discount codes available

Update:  One of the other panelists had an emergency, so this webinar is being rescheduled.  


This is a full description of the webinar: 

Insurance Policy Interpretation: Recurring Issues, Ambiguities, Exclusions, Plain Meaning, Burdens of Proof, and More

This CLE webinar will discuss the interpretation of some of the most fiercely and frequently litigated words and phrases in insurance policies in the context of coverage disputes. The program will review the rules for construing insurance policies with respect to ambiguities, exclusions, plain meaning, burdens of proof, and more, and then consider whether these rules are evolving to produce unexpected coverage decisions that are changing insurance law. The speakers will offer both insurer and policyholder perspectives. 

Description 

Resolving coverage disputes and interpreting policies requires applying both traditional principles of contract interpretation and unique insurance-related rules of construction about ambiguities, exclusions, reasonable expectations, unconscionable advantage, illusory coverage, duty of utmost good faith, and much more. Notwithstanding that many policies have standard language and phraseology, policyholders, courts, and insurers often have difficulty ascertaining a policy's plain meaning in a given factual or procedural context, leading to seemingly inconsistent outcomes and unpredictability. 

Insurance policies are long, complex, and labyrinthine documents that may not have been precisely drafted for a variety of reasons. Coverage can turn on the meaning of a single word or phrase, perhaps located paragraphs or pages away from the main provision. Some words and phrases get debated and interpreted over and over: arising out of, because of, connected or related to, accident, any, an, of, and for are just a few examples. As courts tweak or modify interpreting policies, the law can evolve about what is or is not covered under particular language. 

Listen as this accomplished panel of insurance coverage attorneys reviews the rules for policy interpretation, discusses frequently litigated issues in the policy language, and offers insights into whether the law is evolving with respect to these often-disputed provisions.

You can sign up here.   https://www.barbri.com/course/professional-development/cle/insurance-policy-interpretation-recurring-issues-ambiguities_2026-01-13   

Feel free to use and share this code for 50 percent off tuition:

Kallen 7MORfIAOACV2

If this program remains cost-prohibitive for you even at 50 percent off, please reach out to me.  I have a limited number of free tuition spots, first-come, first-served.  

 

 

Friday, December 12, 2025

Massachusetts Lawyers: Want to Build a Career Litigating Insurance Bad Faith and Coverage Issues? Hit Me Up.

I’m in the fortunate position of having an embarrassment of riches right now: my insurance coverage and bad-faith caseload is full to overflowing. I’m having to turn down good cases from good clients simply to ensure that the clients I already serve receive the attention they deserve.

Which is to say: I’m looking for help. Maybe from you.

If you’re a Massachusetts attorney who’s interested in building—or further building—a litigation specialty where:

  • you can genuinely help people,

  • you can do real justice,

  • the work is plentiful, and

  • the issues are intellectually engaging,

you may want to come on board with me.

Here’s what my ideal collaborator looks like (but please reach out even if you don’t check every box):

  • You have excellent legal research and writing skills.

  • You’re already set up in solo practice. For the time being, I’m looking for a contract-basis relationship, not an associate role (and the amount of work will vary based on my caseload and your availability) - though that could evolve. You should have access to Westlaw or Lexis, malpractice insurance, a secure computer setup, a conflict-check system, etc.

  • You have at least two years of Massachusetts civil litigation experience and have had primary responsibility for cases. You can explain Superior Court Rule 9A without breaking a sweat. Insurance defense experience is a plus.

  • You have at least a general understanding of basic insurance coverage concepts: the difference between the duty to defend and the duty to indemnify, how to tell if a policy is complete, that sort of thing.

  • You’re familiar with Chapter 93A in the insurance context.

  • You’re not just looking to fill spare hours—you’re looking to build a long-term specialty.

  • You want to form a sustained professional relationship as you develop that specialty.

About my practice:
I represent policyholders, claimants, and insurers in coverage and bad-faith matters. On the policyholder and claimant side, I work with both consumers and businesses. My work includes everything from consultations to coverage opinions to full-scale litigation, in both first- and third-party contexts. I’ve been doing this for a long time, and - honestly - I’m still having fun.

What I offer:

  • Mentorship: I will teach you this practice area.

  • Introductions: I will connect you with people you should know as you build your practice.

  • Fair compensation for your billable work, based on your skills and experience.

  • Referrals: I will send you appropriate cases with fair referral fees, and I will advise you on them.

If this piques your interest, send me an email. Eventually I’ll need a résumé, a writing sample, and references, but you’re welcome to start with a brief note of interest. If you don’t hear back from me right away, it just means I’m very busy - not that I’m not interested. Please feel free to circle back.


Thursday, December 4, 2025

U.S. District Court holds that even after court judgment in underlying case, measure of 93A damages is lost interest -- and my advice to both sides for handling 93A claims

Victoria Gretzky was injured when she fell on a staircase at an apartment building owned by the Arrudas.  In September 2022 she sued the Arrudas, who were insured by AmGuard.  AmGuard made a number of settlement offers, each of which Gretzky declined.  She demanded the policy limit of $1 million, plus interest.

On the second day of trial the parties settled, with a consent judgment that Gretsky was entitled to $2,250,000 plus interest and costs, and she reserved her right to bring first and third party claims against AmGuard.  AmGuard paid its policy limit of $1 million.  

The 93A Demand and the Safe Harbor Provision Argument

Gretzky then sent a 93A demand letter to AmGuard.  In response, AmGuard offered $232,769, which represented prejudgment interest from the date the lawsuit was filed through the date of the accepted check.  Gretzky rejected the proffer and sued AmGuard for breach of ch. 93A.  

AmGuard filed a motion to limit the damages to the interest payment it had offered, arguing that the offer was reasonable and entitled it to the safe harbor provisions of ch. 93A.  Gretzky argued that prejudgment interest was the wrong measure of economic damages, and that damages for mental anguish and unnecessary prolongment of the litigation should have been included in the offer.  

Mass. Gen. Laws ch. 93A §9 provides that if a recipient of a 93A demand letter timely responds with a written settlement offer that is rejected, damages may be limited to the amount of the offer if the court finds that the relief tendered was reasonable in relation to the injury actually suffered.  This is called the safe harbor provision. 

AmGuard argued that "injury actually suffered" in the safe harbor provision is the loss of use of money (the interest) wrongfully withheld.   Gretzky argued that loss of use of money is not the correct standard when there is an actual judgment in the underlying tort case and the insurer committed a willful violation of ch. 93A.  

Court Agrees that Safe Harbor Provision Applies 

In Gretzky v. AmGuard2025 WL 3140762 (D. Mass. 2025) (unpublished),  the United States District Court for the District of Massachusetts sided with AmGuard.  The court held that that AmGuard's offer was to settle the 93A claim only, because the underlying tort action had already been settled.  It then turned to what the 93A loss was.  Prejudgment, AmGuard never had an obligation to settle for more than the $1 million policy limit.  So  Gretzky was deprived of use of the $1 million as a result of AmGuard's failure to timely settle.  Her damages were the interest accrued on that amount.  AmGuard's settlement offer was reasonable relative to the prejudgment injuries.  

Gretzky argued that, after the judgment, AmGuard was obligated to pay the prejudgment interest, and that since it wrongfully withheld that amount, it also owed interest on the interest.  The court held that failure to pay that interest over a two month period resulted in a de minimis $5000 in loss of use damages.  

The court rejected Gretzky's argument that she was entitled to damages for the emotional distress she suffered from loss of use of the funds, because she did not include a request for such damages in her 93A demand letter.  

What to make of this case

Damages under ch. 93A can be very confusing.  This decision is not a model of clarity, but the most important part of the decision is the court’s analysis of why the case is different from Rhodes v. AIG Domestic Claims, Inc., 461 Mass. 486 (2012).  In Rhodes, the SJC had held that single damages to be multiplied when an insurer willfully acted in bad faith was the underlying tort judgment. But in that case, after receiving a post-judgment 93A demand letter the insurer offered less than the tort judgment (and less than the policy limit) to settle both the underlying claim and the 93A claim.  That’s different than in Gretzky, where the insurer had already paid its policy limit before it received the post-judgment 93A demand letter.  The policy limit was the most that the plaintiff could be entitled to under the insurance policy itself. After receiving the 93A demand letter the insurer offered loss of use damages (interest) as 93A damages.  In other words, if the insurer had paid its policy limit at the beginning of the case, the plaintiff would have had use of the money earlier.  The court held that the insurer’s offer was reasonable, so under the safe harbor provisions of 93A the damages would not be multiplied.

My advice to someone who is contemplating bringing a ch. 93A claim against an insurer for bad faith settlement practices is that they should send the 93A demand letter as soon as liability and damages are reasonably clear, laying out in detail in the letter exactly why they are reasonably clear, supported by exhibits.  That provides the evidence they need down the road that the insurer failed to make a reasonable offer of settlement based on the information available to it.  The last paragraph of the Gretzky decision is telling here.  The court rejected a claim of emotional distress damages because those damages were not included in the 93A demand letter.

And of course, on the other side, I would advise any insurer receiving a 93A demand letter to take it seriously.  A large verdict does not retroactively prove that an insurer violated ch. 93A by not meeting the plaintiff’s settlement demand, but the insurer should be prepared to show why the information it had with respect to liability and damages did not justify the settlement sought.

Lawyer's Weekly quoted my comments about the case here.

 

Thursday, July 24, 2025

Suffolk Superior Court applies continuous trigger and pro rata allocation to asbestos coverage dispute


Timothy Ross was exposed to asbestos from 1965 to 1977 while employed by NEIC.  He developed symptoms related to the exposure in 2012, and died from mesothelioma in 2013.  

After Ross's death, his widow sued NEIC.  Liberty Mutual insured NEIC from 1973 to 1983.  It asserted that a continuous trigger and pro rata allocation theory applied.  Under a continuous trigger theory, coverage is triggered from the time of exposure to a hazardous substance to the time when physical harm from such exposure becomes manifest.  In pro rata allocation, in a long-tail loss the loss is allocated among all insurers who provided insurance during any time the loss was occurring, and the loss is frequently allocated to the insured for periods where it had no or insufficient insurance.  So Liberty Mutual was arguing that where it provided coverage for ten years out of 47 years of total exposure, it was liable for about a fifth of the total damages.

In Ross v. Liberty Mutual Insurance Co(behind a paywall) (Suffolk Superior Ct. May 14, 2025, Kazanjian, J.) a judge of the Suffolk Superior Court agreed with Liberty Mutual.  The court accepted expert testimony that damage from asbestos fibers is continuous—from initial exposure through latency, diagnosis, and death.  Relying on Boston Gas Co. v. Century Indem. Co., 454 Mass. 337 (2009) and New England Insulation Co. v. Liberty Mut. Ins. Co., 83 Mass. App. Ct. 631 (2013), the court held that coverage is triggered across all policy years during which injury occurred. It rejected Ross’s argument that injury was not continuous during the latency period and found that Liberty Mutual’s pro-rata allocation was consistent with Massachusetts law.

The court rejected Ross’s claim that Liberty Mutual owed post-judgment interest on the full judgment. It ruled that the insurer was responsible for interest only on the portion of the judgment that was allocable to its coverage periods.