There’s a lot of good content out there these days on the subjects that I care enough to write about here or on LinkedIn: AI and the practice of law, AI and insurance, ERISA litigation and exposures, insurance industry developments, and a number of other topics. I could have easily identified and included way more than five articles, posts, podcasts and the like for inclusion in this week’s Five Favorites for Friday, but as I have said before, both my workload and my preference for alliteration require that I continue to limit the list to five. And so without any more ado, here’s this week’s Five Favorites.

  1. Wondering what all the teeth gnashing is about with regard to the recent filings of class actions against plan sponsors and brokers concerning voluntary benefits that provide employees with additional coverage that fills in the gaps left by group health insurance? Nevin Adams tells you what those cases are all about in this article. My prediction? By the time these lawsuits and their inevitable offspring are done, either health insurance is no longer a plump and enticing target for the ERISA class action bar or else within ten years, just as occurred in response to 401(k) plan litigation, the structure of this entire area of benefits is fundamentally different than it is right now. Which one it will be tests my powers of prognostication, and here is why. The firm that filed these class actions not only knows what it is doing, but also doesn’t tend to waste its powder. Having filed these suits, the lawyers undoubtedly have the facts and legal theories to back up their claims. On the other hand and pushing back against this outcome is the skepticism we have been seeing for a while now by courts with regard to the latest theories and claims in ERISA class action litigation, which may continue in the future with the judicial response to these claims. If it does, I think you will see it in the handling by the courts of the safe harbor issues – but that’s a big topic all on its own, and too much to bite off here in a single paragraph addressing just one of the Five Favorites for this week. (If you are particularly interested in this precise point, though, I would love an excuse to discuss it in detail so feel free to reach out).
  2. I have been thinking a lot about the possibility that, despite the AI hype that it will replace lawyers or eliminate law firms, AI is more likely to do something still more radical and, for practicing lawyers, of potentially much more value: namely, free us from the mechanical, rote part of practice to instead act like the counselors, advisors, courtroom advocates, and the like that, on our best days, we are and aspire to be. I had been a little reluctant to actually sit down and put pen to paper on the topic, since in many ways this is what patent lawyer Robert Plotkin suggested in an article months ago, back when everyone was still noodling over the “first thing we do, let’s kill all the lawyers” subtext around AI deployment. Now, though, I am even more reluctant to write on the subject, as Eric Dodson Greenberg, the executive vice president, general counsel, and corporate secretary of Cox Media Group, just said the same thing, in this article. I highly recommend it and, I have to be honest, am not sure I would have said it any better if I had in fact sat down to write on this subject.
  3. I really like markets, of all types. I even wrote an article on LinkedIn comparing private equity investments in 401(k) plans to my local farmstand and market. But, as a practicing lawyer, the kind of markets I am really interested in are business and financial markets of all kinds and the impact on clients and lawyers of changes in them. For instance, I have written many times on the fact that deteriorating labor markets inevitably lead to an increase in disability, pension and other ERISA litigation. But one of the most fascinating markets to me is the one for insurance coverage, or more accurately, the multiple markets for different types of insurance, which can vary depending on the particular form of coverage for which one is in the market (pun intended – sorry about that). I have seen hard markets, soft markets and everything in between with regard to different types of insurance over the years I have been a coverage lawyer, and the differing factors that affect the type of market at any given time are complex and fascinating. You can see all of that in play here, in this blog post, on the current nature of the insurance market for cyber coverages. I confess the article is a little dated by the standards of the Five Favorites post, but it’s new to me and does a great job of explaining how insurance markets operate.
  4. For those of you keeping track at home, the next move in the effort to add private equity investments into 401(k) plans belongs to the Department of Labor and the instructions to it to issue regulatory guidance on the issue. Here’s the latest development on that, which suggests the regulatory process for its issuance is moving along apace. Color me basically nonplussed no matter what it says (hate to prejudge, but . . .) Why is that? Because I don’t think it is possible, after Loper and years of litigation over various ERISA safe harbors, for the DOL to conclusively regulate away the potential liability and class action litigation risks for plan sponsors and fiduciaries buried within the effort to add these investments to plans.
  5. A thousand times this. Legendary investor Charlie Munger once said “show me the incentives and I will show you the behavior.” Retired federal court judge Mark Bennett argues very persuasively in this LinkedIn post that the Federal Rules of Civil Procedure have created a perverse incentive structure that has led to unintended results that are harming the practice of law, courts and clients. I could write a law review article on this subject and I cannot possibly address all the subtleties of this issue here, in one paragraph. But there is no quarreling with his point that the rules and their implementation are at the heart of a system that overemphasizes unnecessary discovery and with it increased costs to clients. I suspect I speak for many experienced courtroom advocates when I say just give me all the documents, a way to make sure I was given everything relevant, an accurate itemization of damages, a legitimate list of witnesses and their subjects of knowledge, and a finite and preset number of depositions, then let’s set a trial date. (Okay, to be fair, maybe I would still like the opportunity to write and file a summary judgment brief before going to trial, in cases that actually might be served by a summary judgment motion).

We are now on the sixth most popular post in my annual top ten countdown of blog and LinkedIn posts from the year just gone by. You can find the rules of the contest here.

The post that finished sixth asks the seemingly eternal question of “What Do You Do on Appeal With a $90 Million Bad Faith Judgment?” Although they were not originally written as a two-part series of posts, it is a follow up to the issues addressed in the seventh most popular post of 2025, which I discussed here. In the first post, which finished seventh in the countdown, I discussed the issues raised by a $90 million bad faith verdict. In the second post, which is the one that finished sixth, I discussed the question faced by the defendant insurer in that case, which is whether to take an appeal through to conclusion on that case.

You can find the post that finished sixth in the countdown, here.

This post continues the countdown of my top ten posts of 2025. I was aiming to finish the countdown by the first of the year, but the road to heck is paved with good intentions and all that. I will now settle for finishing the countdown before the last week of the month if I can. (If memory serves, I was way later than that finishing last year’s countdown of my top ten posts from 2024). For those of you new to the countdown, you can find the ground rules here.

There are 90 million reasons to read the seventh and sixth most popular posts on my blog or LinkedIn in 2025, namely the $90 million in bad faith damages entered against Liberty Mutual, which is discussed in both posts. Today I cover the seventh most popular post from 2025, which was titled “What’s a Nuclear Verdict When Doubled for Insurer Bad Faith?” It’s the story and lessons of a massive bad faith verdict, and of the fact that it was massive because it came on top of a nuclear verdict in the underlying tort action itself. The sixth most popular, which I will cover the next time, discusses additional issues raised by the same judgment.

You can find the seventh most popular post here. Hope you enjoy it.

And their off! The old racing call seems like a good fit for the first week of a new business year, as everything and everyone that was put to the side for the last two weeks of December comes racing back onto the desktop.

And so it has been as well with articles, blog posts, videos, podcasts and the like this week, as everyone fires up the old content generator again.

For anyone new to this series of posts, here’s a rundown. My “Five Favorites for Friday” blog post is a weekly series – published, unsurprisingly given the title, every Friday – reviewing five articles, videos, podcasts or the like that caught my eye during the preceding week and that I want to discuss and share.

And with that, here is this week’s fabulous fivesome:

  1. Insurance is morphing away from being simply payment for a covered loss and to a form of partnership, in many instances, between insurer and insured to both first avoid and mitigate loss, and then to reimburse for it if needed. This will be no surprise to many in the industry, but I think for others, they may not have noticed how much of this has occurred, simply because it has taken place over the course of a number of years. If you haven’t been paying attention along the way, it can seem, to steal an old phrase, like the changes occurred slowly, then all at once, but in reality, it has been a long and gradual process, but one that now seems to have hit the proverbial tipping point. I could tell a host of stories about this, such as what EPLI coverage has changed into since I worked as a coverage lawyer on its first rollouts, or the extent to which the scope of both coverage and insurer control has changed in fiduciary liability policies from the time I first defended a case under one until today. This short article from Sompo on the risk mitigation and prevention aspects of cyber policies illustrates the point nicely. With climate change and tech risks becoming ever more central to the insurance environment, this type of faux or quasi partnership between insured and insurer either is already or will be the wave of the future.
  2. AI in claims handling is a fascinating issue on a number of levels. First off, there is no question that some aspects of claims handling are ripe for AI intervention regardless of the type of coverage at issue, and that some forms of coverage – first party in particular – are well suited to its widespread adoption. On that last point, for instance, there is no reason, beyond the challenges of the software, that AI can’t determine whether a cracked car window claim is covered, apply the deductible and approve – or reject – a particular vendor. The issue is going to be more in third party coverages and similar areas where reasonable people can disagree on coverage or settlement decisions made by an insurer. I have written about this in the context of claims handling statutes and bad faith claims more than once, such as here. This Fenwick & West piece, and this Lion Specialty post, among many others, make clear that insurance regulators plan to tackle this directly and publicly. Barring federal preemption, I don’t think there is any doubt that state regulators and legislators are going to assert control over this issue and dictate some of the key terms of use of AI in insurance, at least in claims and in policyholder facing aspects of the industry.
  3. “In 2025, more than 1,700 class lawsuits were settled for a total of $79 billion—nearly double the amount from the prior year.” That’s the click bait data point from Forbes’ review of the past year in class action litigation. The article goes on, though, to talk about some of the substantive issues for companies and industries arising from this class action boom. After over a decade of vigorous class action litigation over 401(k) plan fees and expenses, one issue that is often overlooked when the discussion just shifts to the amounts at issue is the extent to which that litigation campaign and history has reshaped so much of industry practice in this area. It’s the single best example of the private attorney general model of corporate regulation that we have ever seen, in my view. Now those same lawyers are coming for health and similar benefits. Buckle up.
  4. In an article in Above the Law, lawyer turned tech journalist Stephen Embry discussed the open question of what the future, in the face of AI, looks like for lawyers in light of a new AI native law firm that, apparently, will basically do securities compliance work solely through AI tools. This gets us to the root problem when people talk about AI replacing lawyers or being able to practice law, which is that it depends on how you define lawyering. Taking ten rules of compliance and twenty examples of violations each, and then running trading or similar actions against them to determine whether compliance is met, is perfect for AI – it is simply applying a fixed body of rules to a set of circumstances. If that is your definition of lawyering, then certainly AI can do it. Likewise, if you define lawyering as just crafting slightly different versions of documents created for similar transactions a thousand times before, then certainly AI can project out the differentiation and spit out the document. But that represents the commodifiable portions of the practice of law, the types of almost rote training work assigned to associates and young partners to build their foundational knowledge and skills. Most experienced lawyers, if pressed to speak bluntly, wouldn’t even consider most of that to really constitute lawyering – they would instead consider lawyering to be the judgment calls, the advice, the new approaches to new problems, and the like that clients actually pay for (rather than the documentation, which just comes along with it). That’s the Rubicon that AI still has to cross before there can be any serious discussion of AI either practicing law or replacing lawyers, rather than just being another technological innovation that commodifies certain aspects of the practice, although admittedly in very dramatic and more extensive ways then we have seen in the past with other techological advances. (If the differential between lawyering and AI driven work product interests you, follow me on LinkedIn for more on this topic – I seem to be posting more and more on the question of how much of what AI does is really what we mean by lawyering, as opposed to just elements of the work of a lawyer).
  5. I have written extensively on my views about nuclear verdicts, developed through decades of studying large verdicts for purposes of both advising insurers on how to resolve or avoid them as well as for purposes of litigating the bad faith and coverage actions they inevitably generate. Central to my views and writings on this subject is the rejection of the idea that nuclear verdicts are something unpredictable, attributable to the bad faith tactics of plaintiffs’ lawyers or to the biases of jurors, and are a surprise outcome in a given case. My view is that they are instead generated by predictable circumstances and fact patterns that reappear time and again across overly large and nuclear verdicts, meaning that insurers have the ability to avoid nuclear verdicts by learning to identify the claims that are likely to trigger them in time to settle before or during trial. After all, a too high settlement is still magnitudes less than a nuclear verdict. So I was extremely pleased to come across this detailed article explaining how nuclear verdicts are not arbitrary but instead attributable to predictable differences in the exploitation of information, and calling on insurers to match the plaintiffs’ bar in this regard. Nuclear verdicts aren’t a mystical thing – they are a predictable outcome of repeating patterns, and it is on insurers and their defense counsel to learn to identify (and settle) the risky cases before they can turn into nuclear verdicts.

Are you old enough to remember Soviet figure skating judges in the Winter Olympics? They used to be accused all the time of putting their thumb on the scale, lowering the allegedly “objective” scoring for American skaters so as to get the results they wanted. If you recall, I reserved the same right this year in counting down the top ten posts on this blog and by me on LinkedIn in 2025.

Today’s post in the Top Ten, which comes in at number eight in the countdown, is the first instance in which I have lowered a post from where it would otherwise rank on sheer number of readers based on subjective, Soviet thumb on the scale judging.

Why? Well, it’s a great post, in my opinion – it has video, it has internet mob currency, it has McDonald’s in it, it has AI, it has insurance bad faith, it is visually appealing (if I say so myself) and it makes a good point. And, judging from the number of readers, it is an objectively very good post.

But it has a relatively high flash to substance ratio (by the standards of lawyers and legal thought, at least; we are not exactly in TikTok influencer territory here) and I am, by nature, more of a substance over flash lawyer.

So I dropped it a couple of notches in the countdown for these reasons, but to be fair, I really like it nonetheless.

And so, here is my eighth most popular post on this blog or on LinkedIn in 2025, which asked what internet backlash against a very funny but AI driven McDonald’s ad can teach us about insurers relying on AI in claims handling.

It’s the first Friday of the Year of the Horse, making it time for the first Five Favorites for Friday post of the year. As a reminder, every Friday, I do an entry in this series, each of which covers five topics, posts, articles, podcasts or videos that caught my attention over the preceding week but which I didn’t have time to post about in any depth on either this blog or LinkedIn. For those of you who may just be joining this series with the start of the New Year, you can find the first entry, and more information about the series, here.

A tremendous amount of interesting information crossed my desk this past week, but I narrowed what I wanted to talk about today down to the following five. So let’s get to it.

  1. They say that a fish doesn’t know it lives in water, meaning that we often don’t recognize the details or unusual aspects of the environments that are native to us. I thought of this when I read this article about the growing scope, use of and industry capacity for captive insurance. Probably because the Harvard medical institutions used a captive insurer structure when I started out and I did coverage and bad faith work for their excess insurers, I spent large amounts of my time in the first decade or so of my career working on captive insurance issues. It even involved working with the captives, the insured entities, reinsurers and others to resolve what we would now call nuclear verdicts against the insured entities, as well as being the junior associate on some fascinating coverage and bad faith disputes related to the actions of captives. Like the fish in water, captive insurance was just the environment I was in, and I thought it was a commonplace structure across the industry. It literally wasn’t until I read this article on its expanding use in the industry that it occurred to me that captive insurance is actually a little bit of an unusual beast within the industry as a whole.
  2. Nevin Adams wrote a great end of the year review of ERISA and retirement plan developments in 2025. It’s the kind of article I would have loved to have written, but that a practicing ERISA lawyer just could not possibly find the time to write at the end of the year, given plan amendment and other end of the year deadlines. I agree with Nevin’s conclusions and view, though, that for a year in which there was no significant statutory activity, it was a ridiculously challenging year for retirement plans from an operational and execution perspective.
  3. I am going to say out loud what most clients and potential clients or target audiences already know – most law firm newsletters and similar content are useless pablum. A few are really good and I read them. What makes them different? They either tell me in depth how to solve a particular knotty problem in my field or they use hard won expertise to provide some guidance about the near term future. In the latter category, I like this Haynes Boone newsletter’s article addressing the halting progress towards developing a consensus on how policy language should be read in regards to cyber claims. History is littered with decades of coverage litigation caused by the uncertain fit of particular policy language to widespread risks, such as pollution, and whether that will occur as well with cyber losses in the future is a key issue to study and plan for.
  4. I have written numerous posts and articles cautioning plan sponsors, fiduciaries and their lawyers about rushing head first into adding alternative investments to the 401(k) plans they oversee.  This particular post here is the keystone of my thinking on this issue, and I have written numerous other articles, blog posts and LinkedIn posts to the same effect or on narrower aspects of this issue.  This series of podcasts points out a broader point as to why plan fiduciaries and their counsel should play it safe and stay on the green on this issue – there is just way too much uncertainty on way too many issues concerning the economy for it to make sense for plan sponsors or fiduciaries to play hero ball or to get ahead of their skis right now on any issues where they don’t have to do so right now.  And adding alternative investments to 401(k) plans is one of those issues.
  5. I have written a great deal on the two faces of ESOPs.  When done – and run – in good faith, they are the embodiment of the best of capitalism, a win-win for both employers and employees. But their design and operation are open to manipulation and, with it, litigation, to the detriment initially of the employees and eventually, through the costs and potential liabilities of litigation, employers and company founders.  This write up by Kantor and Kantor of a case – Botterio – alleging misconduct in operating a plan illustrates my point.

Continuing with the countdown of the top ten most popular blog posts, LinkedIn posts and articles I published this year, we come to the ninth most popular, an article on LinkedIn from the summer which asked the question of “How is Private Equity Like a Coffee Frappe?”

In addition to explaining that frappe is New England speak for milkshake, the article also addressed how sponsors and fiduciaries of 401(k) plans should respond to the political and marketing pressure to add private equity investments to those plans. The underlying theme was that, just like a frappe for a middle- aged lawyer, private equity investments in plans aren’t good for plan fiduciaries, but nonetheless we are all likely to give in to the allure of each. While I have no advice on how to avoid the harms of downing a frappe, I have plenty of advice on how plan fiduciaries can reduce the harm from falling for the allure of private equity investments. And I discussed that advice in the article, which was the ninth most popular blog post, LinkedIn post or article I published in 2024.

Last year, I did a top ten countdown of the ten most popular posts on this blog in 2024, inspired by how radio DJs in my youth would count down the top 100 songs of the year to close out the year. It was a lot of fun and people seemed to enjoy it, so I am doing it again this year.

However, this year, I am changing the rules of the contest a little bit. First, the pool of competitors has been expanded from just blog posts to also include LinkedIn posts and articles, so that the countdown is now of my top ten blog posts, LinkedIn posts and articles on LinkedIn in 2025.

Second, last year’s countdown was solely based on numbers – in other words, the most popular post finished at number one in the countdown, the second most popular post finished at number two in the countdown, and so on down the line. This year, a more subjective element is being added to the judging as well, sort of like the way Soviet judges would put their thumbs on the scale in ice skating or gymnastics judging in the old days, even though the results were supposedly objective and mathematical. So in effect, standings in the countdown will be based on two elements – the first strictly numerical in terms of readers, the second subjective, in terms of quality or interest value, in the eyes of the judges (i.e., me).

So without further ado or introduction, let’s get right to the countdown. Here is the tenth most popular blog post, LinkedIn post or article on LinkedIn for 2025, which was my blog post titled “Best Practices for ERISA Plan Sponsors and Fiduciaries in a Changing World: Handling Vendor Contracts.” As the title suggests, it was part of my series covering the need for ERISA plan sponsors and fiduciaries to modernize their practices, and covered the art of negotiating and interpreting vendor contracts in the ERISA space.

You can find my Tenth Most Popular post of 2025 here.

Boxing Day is my favorite post-holiday holiday, similar in many ways but better than the day after Thanksgiving, because the latter has, over the years, been overtaken by pressure to either shop or get started on end of the year rushes for work. Boxing Day, at least for me, suffers from none of that.

Boxing Day this year falls on the very last Friday of the year, making it also the last scheduled date for publication in 2025 of my Five Favorites for Friday series, in which I typically discuss five topics, articles, issues, podcasts or videos that I didn’t previously get a chance to blog about or discuss in a LinkedIn post.

In honor of Boxing Day falling on the last Friday of the year, I am changing the rules for this weekly post and publishing a slightly revised version of my weekly Five Favorites for Friday post. This one consists of five of my favorite items covered in this series over the past year. Think of it as Five Favorites from Past Five Favorites for Friday, or something like that.

Here goes:

  1. Nuclear verdicts are, in my opinion (which is based on decades of studying them for purposes of resolving and, where necessary, trying the insurance bad faith and coverage claims that arise from them), driven by a number of identifiable factors, including changing views of jurors of the world around them. Employers and insurers need to think carefully about what a recent nuclear verdict, including an award of $10 million in punitive damages, in an employment discrimination action, tells us about how jurors are viewing workplace dynamics. For what it’s worth, I predicted the expansion of nuclear verdicts from the personal injury environment to the employment context years before it happened, in this post. This is the next big frontier for nuclear verdicts.
  2. UBS economists do not like the looks of the labor market. This is your periodic reminder from those of us who litigated ERISA breach of fiduciary duty and other claims during and after the Great Recession that, when job prospects weaken, employees and former employees start to look very carefully and very skeptically at the performance of retirement, 401(k) and other plans. We have already, in my own practice, been seeing the smarter money, which holds deferred comp benefits, looking carefully at those types of plans, as I discussed here.
  3. Stephen Embry’s article on advanced AI weaponry for plaintiffs’ personal injury lawyers points out that the development could be a game changer for both the plaintiffs’ bar and the defense bar. I have written before, however, on my concern in the ERISA space with regard to what an AI powered plaintiffs’ class action bar suggests for ERISA plan sponsors, fiduciaries and their insurers – namely, the ability of more such shops to litigate more such cases, including against smaller plans that previously wouldn’t have justified the expense of suit, with the same or less investment and staffing. Other than the class action defense bar, more class action ERISA suits is the last thing that anyone on the defense side of the “v”or their insurers need. Whether it’s number of suits, settlement amounts, defense costs, or any other rubric, the trendlines in this area are already worrisome for plan sponsors and their insurers. The continued rollout of AI isn’t going to help.
  4. You know what I think is particularly scary if you are an insured or an insurer? The need and interest of insurers to write exclusions for AI to include in coverages. As this article points out, there is a significant issue of how to word the exclusions to exclude what is meant to be excluded, and no more or less. This isn’t going to be as easy as it sounds. When policy language is well drafted, there is limited dispute later over whether certain types of claims are covered. We saw this, for example, in the business interruption coverage cases arising out of the pandemic, where most denials of coverage were upheld based on language that was well drafted to handle the risk, even though the ability to foresee the scope of the pandemic and the resulting business losses at the time the policies were issued or when the language was drafted was limited. On the other hand, for those old enough to recall it (and, if you aren’t, you may find it valuable to read up on the history of it), there were decades of massive coverage litigation concerning exactly what types and extent of asbestos related exposure was precluded by the wording of different exclusions. For me personally, I spent a good amount of time in 1987, as a paralegal fresh out of college, reading insurance industry periodicals in the Library of Congress seeking extrinsic evidence for use in arguing what meaning should be attributed to certain wording in the exclusions at issue. How underwriters and coverage lawyers define AI and choose language for use in capturing this latest exposure in policies and their exclusions is going to decide whether coverage for AI liabilities ends up over time playing out more like coverage for business interruption after the pandemic, or instead more like coverage for asbestos losses, or perhaps more likely, somewhere in between those two polar extremes.
  5. $90 million is a lot of money. Even the judge who awarded it as bad faith and Chapter 93A damages against Liberty Mutual because she found unreasonable claims handling and believed the case law to leave her with no discretion in this regard, thought it was a disproportionate award. On the flip side for Liberty Mutual and other insurers who are presumably looking at the ruling in horror, if there was ever a decision perfectly written to allow an appeals court to revisit various aspects of bad faith law in the Commonwealth and rein in some of its most debatable aspects, this is the one. And I don’t mean that in a negative way with regard to the opinion itself – the decision is an excellent analysis and presentation of the totality of a complex area of law and of decades of case law (the judge actually goes so far back that she cites a decision from the first Chapter 93A case I ever tried, back in 1995). Instead, I mean that the Court’s scholarly treatment of the issues presents the perfect trial court decision for testing the appropriate scope of recovery in such cases. I discussed the opinion here.

I have been thinking more and more about the tactical questions raised by the recent $90 million bad faith judgment under Massachusetts Chapter 93A against Liberty Mutual, which I discussed here. By sheer good timing, it was issued just as I was leaving to attend a major insurance coverage conference and also just before a number of end of the year meetings and lunches with clients. The decision generated plenty of discussion.

I don’t represent any of the parties and, as I have said before, I don’t have a bias against the statutory enforcement under Massachusetts law of reasonable claims handling practices. Having studied and litigated the issues for decades, including in relation to nuclear verdicts and runaway juries, I believe that the standards governing multiple damages in this scenario are due for rethinking. Maybe that rethinking ends up with the standards exactly where they are now, and if so, that is fine. But too much of the current regime governing this type of claim, and in particular multiple damages awards, has essentially been driven by simple extension of prior precedents, or by the phenomenon whereby bad facts drive an outcome, or both. I think it may be time for the courts to step back and look at the body of law as a whole, and ask whether the legal standards still work correctly and actually fairly address the harm at issue. In fact, I think that’s effectively the same question posed by the trial judge who entered the judgment, who raised the question in her opinion as to whether the $90 million award aligned with the harm but noted that the case law required that outcome.

Judges sometimes write opinions that read like treatises, covering the history of a particular area of the law in depth and synthesizing inherent conflicts or ambiguities already present in the case law. Judge Woodlock, on the federal District Court bench in Massachusetts, did it on the scope and nature of equitable relief under ERISA in a long decision in one of my cases, discussed here in this article. The judge did that here as well, this time for Chapter 93A and multiple damages law in Massachusetts. She thoroughly discussed the historical development of the case law, citing three or four of the decisions in my own cases over the years and even going so far back that she cited the opinion in the first Chapter 93A case I tried, back in 1995.

I don’t know if it was the judge’s intent, but the depth and breadth of the opinion makes it a natural vehicle for asking the Massachusetts appellate courts to revisit the key legal issues that led, here, to a massive multiple damages award, under circumstances where an award of half as much (or less) would have still fully served the remedial and deterrent purposes of the applicable statutes.

It’s a lot to ask, given the amount of the judgment and the interest that accrues on a judgment in Massachusetts, but the insurer here should think long and hard about not settling this action and instead prosecuting an appeal for the exact purpose of advancing the case law under circumstances where additional clarity could be obtained on some of the central issues in bad faith law in Massachusetts.

In my discussions with interested and knowledgable observers, many have pointed towards the ratio of the multiple damages award to the original possible settlement ranges in the underlying tort case as a likely target for appeal and as the basis for a reversal. If I were the insurer, though, I would argue that only as the fallback option for the court on appeal.

Where would I focus an appeal instead? On the standards of when and under what circumstances a violation of the claims handling obligations imposed by Massachusetts law can support the findings necessary to trigger a multiple damages award. Over the years, Massachusetts courts have often addressed these standards with amorphous characterizations and phrasings, or else in very fact specific rulings. As a result, an appellate court could easily clarify these standards, without overruling prior decisions, on the facts of this action, by finding that the claims handling in this action may have violated the relevant statutes but was not sufficient to satisfy the standards for multiple damages. In so doing, the court could establish a clear baseline – namely, the facts of this action – for violations that only warrant single damages, and for what baseline has to be soundly cleared to trigger multiple damages.

Because in my reading of the $90 million bad faith verdict, the issue is only secondarily the amount and how that was driven by the statutory rules governing multiple damages awards in Massachusetts bad faith actions, and instead the primary issue is the bar, which is not high enough, for triggering such an award in the first place.