Wow – what an embarrassment of riches this week. Partly because of developments in AI and the law, partly because of regulatory and litigation developments in ERISA and partly because the insurance world never stops spinning, there is a metaphorical feast of articles and the like that I could discuss in this week’s edition of my Five Favorites for Friday series. (For any of you who may be new to the series, you can find its origin story here.)

My five favorites for this week:

  1. In honor of the Super Bowl this weekend, I had no choice but to open with a story about the NFL’s disability plan for injured – usually chronically – retired football players. I have been writing about the NFL’s disability benefit plan, CTE and disabled retired players since the case of retired Steeler Mike Webster turned the tables on the NFL’s ability to keep the issue far on the backburner and effectively out of sight. I wrote multiple posts on the case and its aftermath, starting with this one in 2006. In response, over time and under pressure, the NFL built out a new disability plan, one that appears to have been pretty successful both in increasing the availability of benefits and in prevailing against court challenges. The lastest win for the NFL in this regard is this rejection of a class action attack on the program. This article does a nice job with explaining that decision.
  2. I know what they’re afraid of. This article discusses a large sample survey by Allianz of the concerns that are keeping corporate officers up at night, with far and away the leading concerns being AI and cyber risks. What is driving that is almost certainly the novelty and with it the lack of predictability of the exposure and the unsettled nature of insurance coverage for that exposure. I recently argued a data breach case at the First Circuit and have been working with cyber policies for pushing fifteen years now. Unlike most other corporate and D&O exposures that companies face, this remains, to a large extent, uncharted waters. These worries will recede as a touchpoint for corporate pain once, as with employment, securities, antitrust or other risks, the scope of the liability and the management of it (including the extent of insurance) becomes both more consistent and more normalized.
  3. Speaking of things that corporate officers should be afraid of, employers should be very concerned by the opening of a new ERISA class action litigation front involving what are known in the field as voluntary benefits. At a minimum, given the potential scale of this liability and the talents of the firm bringing the suits, employers and their lawyers should understand what it’s all about. This article by my friend Joe Faucher does an excellent job of explaining it.
  4. AI hype has held for over a year now that lawyers will go the way of the dodo, replaced by AI. I have written frequently on the idea that this assertion ignores what lawyering really is and confuses it with the workflows that occur as part of lawyering. It is, however, generally my view that AI tools will become a commonplace for lawyering and that the successful lawyers of the future will be the ones who can turn them into force multipliers. One of the problems with the hype machine with AI for lawyers, though, is that it obfuscates what adoption will really look like and how it will affect law firms and lawyering (an issue I got out ahead of nearly three years ago in this post). Economists who study technological and other change think they know, however – it will be a J cure, with a drop off in productivity while the tools are incorporated followed by a boom in productivity from their adoption, as discussed here. Anyone want to hazard a guess, in light of this, as to why we read so many stories of large law firms investing early in creating, acquiring and adopting AI tools? The return may be poor for now, but the smart money is on those firms that invest early in the bottom part of the J curve so that they can reap the rewards of the upside afterwards.
  5. It can be a heck of a lot easier to set up a retirement plan for employees (especially defined contribution plans) than it can be to terminate one. I have worked with clients on both ends of that lifecycle, and the end game is much more complicated, both strategically and technically. This is a great post on the some of the key issues in putting a pension plan out of a plan sponsor’s misery. Fair warning – it’s real ERISA geek stuff, but I liked it.

I continue to push through the last few in my countdown of my Top Ten posts on this blog in 2025, having now reached the number three post. Number three is actually one of my favorites. It raises the question of when, exactly, AI claims processing is proper and when, instead, it will prove to be nothing more than a lawsuit magnet.

As I discussed in the post, the dividing line seems to be between claims that simply require the mechanical application of fixed rules to precise facts, and claims that require judgment calls as to the relationship between a particular fact pattern and the plan or policy terms at issue.

Anyway, I can’t say I am surprised that an AI centered post ended up in the top three. If anything, I am surprised it didn’t land higher, but when I unveil the top two posts, you will see why it didn’t.

So, in any event, here is the third most popular post on this blog in 2025, “Claims Processing by AI? Here Come the Lawsuits.”

This is the latest in a series of posts, always published on Friday, discussing five articles, topics, videos, podcasts, blog posts and the like that crossed my desk during the week just ended. Some weeks, the post has a consistent theme, such as last week when it turned out to be essentially “all ERISA, all the time.” Not so this week, as the topics wander (with great purpose, remembering that all who wander are not lost), from AI to private equity to regulations to ERISA class action litigation to what we can learn from The Princess Bride about the proposal to use 401(k) assets to buy houses.

So here goes nothing, as the saying goes:

  1. This is an interesting little post on an insurance product offering increased limits and coverage on AI and agent risks. I like it solely because it illustrates a particular point. There is a lot of discussion out there about the scope of coverage for these types of risks, about increased efforts to exclude them under certain policies, and related or similar issues. As this post shows though, there is also a counter narrative of insurers increasing coverage limits and scope for this type of risk. That’s the great thing about insurance – there is generally always a real market with real competition at play over the availability, nature and scope of various types of coverage. While this is particularly true during the early days of a particular novel risk or new type of coverage, it typically continues over time, with market and competitive forces driving further development of any particular form of coverage, its terms, and the like. As I have mentioned before, EPLI policies and fiduciary liability policies, for example, have evolved substantially in the decades I have been involved with them as either a coverage lawyer or as a defense lawyer for clients covered under them. Adam Smith would think well of the modern market for insurance. The market’s response to AI risks is more proof of that.
  2. I don’t believe people really think that a new regulation or substantive guidance from the Department of Labor will fully shield plan sponsors and fiduciaries against litigation and liability risks stemming from adding private equity investments into 401(k) plans. Provide them with more litigation defenses? Sure. Dissuade the class action bar from coming after them where the case is a close call? Definitely. But preclude litigation or eliminate all potential liability where a plan has a big loss from including those investments or in cases where the plan fiduciary didn’t have (or rely on someone who had) a sophisticated understanding of that investment? Absolutely not. And if they tried to write a regulation broad enough to do that? It would be sufficiently contradictory to the actual language of the statute that it would never survive a Loper challenge, if the new Loper standards are applied objectively. Anyway, you can read what is currently known – as opposed to my predictions – about the upcoming regulations in this article, which provides a nice overview of the subject.
  3. One of the most famous lines in movie history has to be the line from The Princess Bride, that “you keep using that word [but] I do not think it means what you think it means.” I keep thinking about that line these days with regard to all sorts of proposals to reorient 401(k) plans away from their fundamental purpose, which was to encourage and protect long term retirement savings. Some of their best features – tax deferral and employer matching – are tied directly to this purpose or directly promote it. Lately, it seems like a lot of people are forgetting this point and viewing 401(k)s as simply some other type of savings account or treasure chest to be accessed for all sorts of purposes, such as most recently buying houses. At what point does the 401(k) cease having any discernable purpose that warrants its tax favored treatment if it just becomes another savings or investment instrument for all sorts of uses? At the end of the day, I think many of these proposals come from people who keep saying 401(k) but, as in The Princess Bride, don’t necessarily really understand what that word means.
  4. This is a great article summing up the state of ERISA litigation at the end of 2025 and making some predictions as to key issues that will be on the radar screen in 2026. There are two particular things I like about it from a meta or 30,000 foot perspective, even though neither is expressly mentioned in the article. First, it reflects the extent to which two competing themes in ERISA litigation, particularly class action litigation, can be true at the same time – in this instance that ERISA class action litigation, potential plan sponsor exposure and new theories of liability are expanding but, at the same time, courts are in other ways narrowing those risks and exposures. Remember this when you read stories and posts bemoaning only the risks to plan fiduciaries from novel liability theories and the like, without any reference to the countervailing story line. Second, it reflects the extent to which not only class action plaintiffs lawyers – with their novel theories and copycat suits – are pushing the envelope, but also the extent to which judges are constantly revisiting issues in this area of the law, thereby changing the landscape (for instance, see the discussion in the article about jury trials in ERISA cases). This constant give and take is what makes it fun to practice in this area of the law.
  5. Insurers and claims administrators don’t have to be right when they decide a claim for benefits under ERISA to prevail in litigation (in most cases, anyway, as this is only true if the benefit plan at issue contains certain magic language, but almost all such plans contain that language nowadays). Their decisions as to whether to grant, or instead deny, benefits just have to be reasonable. As I like to explain it, they are held to a horseshoes standard – they don’t have to hit the post, they just have to get reasonably close and, if so, their decision on a benefit claim stands. At the same time, as a necessary check on this power, they are expected to properly investigate the claim for benefits and communicate accurately with the participant seeking benefits during the processing of a claim for benefits. The expectation that insurers and claims administrators will conduct themselves that way with regard to a claim for benefits has come to be thought of as a procedural obligation on their part in deciding benefit claims. Courts have slowly over time developed a body of case law holding that a denial of benefits that rests on procedural flaws in the investigation and communication by the insurer or claim administrator – regardless of the substantive accuracy or lack thereof of the benefit denial – should be overturned. This issue, which has been slowly developing over the years, at different rates in different circuits, is well discussed in this article addressing a new Sixth Circuit decision taking this approach.

It’s probably become obvious over the years to anyone that reads this blog regularly, that I love contracts. It was my favorite class during first year of law school (everyone else preferred torts, with its car crashes and the like) and one of the reasons I have spent decades litigating insurance coverage disputes is they are really just glorified contract disputes with their own specialized associated body of rules. Even my business litigation practice is often very contract based at heart, such as disputes over deals and transactions that have gone south, which at the end of the day rest on contracts at their foundation. My ERISA practice has much the same flavor – although it is heavily dependent upon understanding and being able to weaponize a whole host of related matters, such as the rules governing prohibited transactions or the law of fiduciary liability, at heart all cases start from one of the most complicated contracts known to American lawyers, the ERISA governed plan.

I have always enjoyed – partly as a result – the art of reducing a really complicated settlement to a written agreement. Not the kind where it just says the plaintiff gets paid and releases all defendants and their insurers from anything and everything, but the kind with lots of contingencies, moving parts, parties and carve outs. ERISA is a natural area for this, but so too are some of the multi-party, large dollar coverage exposures that I have resolved.

One of the issues with that type of drafting, however, is that there is always a question of what to leave in and what to leave out (to quote – or possibly misquote – an old Bob Seger song). I have litigated a number of cases over the scope of settlement agreements (always in the context of me litigating agreements written by others), including in both ERISA and insurance disputes, and the question of interpretation of unclear language becomes a little bit like asking about the number of angels on a head of a pin, meaning it’s really open to debate. Sometimes, the court’s approach to addressing that problem is to simply treat the document literally and declare that, if it wasn’t expressly stated in the agreement, then that is the end of the story, no matter what the parties intended. It can often be hard to get courts to go past that initial approach, which can be very frustrating for parties who know that neither they, nor the other side, actually meant the interpretation adopted by the court using that rubric.

So I thought this new decision out of the Massachusetts trial court was terrific, holding that a settlement agreement could be reformed to correct a drafting mistake where the extrinsic evidence was sufficient to demonstrate that a term was only omitted for that reason. The devil, of course, in these scenarios is always in the details, as to whether there is enough evidence to persuade a court that this type of an error occurred, but these types of holdings are few and far enough between to warrant filing this one away for future use in a case.

You can find a Massachusetts Lawyers Weekly article on the decision here, although I suspect it’s behind a paywall.

I am continuing with the countdown of my top ten most popular blog or LinkedIn posts of 2025, and we have now made it all the way to number four. For those of you new to the countdown, you can find the rules of the contest here.

The fourth most popular post of 2025 is one I am very fond of, because it draws on my experience litigating a range of cases in a variety of areas over the past thirty years. In it, I discuss how my past life as a patent and IP litigator (which was at least a third of my practice running up to the Wall Street collapse in 2008, at which time ERISA class action defense and related litigation arising out of the downturn swallowed up every spare minute I had) can help us figure out the way forward for defanging the boom in ERISA class action litigation.

With that introduction, the fourth most popular post on my blog in 2025 was this one: “Déjà vu All Over Again! What Patent Trolls Can Teach Us About Tackling Problems in the ERISA Class Action Industry.“

This week’s Five Favorites is very ERISA heavy. Sometimes that’s just the way the world spins, as there is a lot going on with retirement plans and ERISA litigation, even at the Supreme Court. A lot of it touches on some of my favorite topics, such as the role of the jury trial in ERISA litigation, or on the most important topics in ERISA at this point, such as allowing private equity investments into 401(k) plans. So here goes this week’s entry in this series of posts, and I hope you enjoy it:

  1. I believe it is United States District Court Judge Young, in Massachusetts, who I have heard routinely say, in setting firm trial dates, that nothing concentrates the mind like an execution date – implying that nothing focuses lawyers and clients on settlement like the impending risk of a trial. Very few ERISA cases, particularly large exposure ERISA class actions, are actually tried, for various reasons, and there are even fewer jury trials in this context. However, jury trials have become a thing in ERISA class action litigation over the past couple of years, after a major one went resoundingly in favor of the defense. Since then, though, the risks for plan sponsors, plan fiduciaries and their insurers inherent in trying these types of cases to a jury have become manifest, with some bad results for defendants, at numbers that would make those concerned in the tort world with the rise of nuclear verdicts stop and count their blessings that a nuclear verdict is typically just ten million or more, and not the numbers coming in from the rare ERISA jury trial. Well, given this backdrop, it’s not surprising that the certainty of an ERISA class action jury trial concentrated the minds of the lawyers and clients in this Massachusetts ERISA class action against Liberty Mutual on settlement, which was reached this week, avoiding a jury trial over 401(k) performance issues.
  2. Look, I am not unsympathetic to the idea that the worst aspects of ERISA class action litigation need to be reined in. I am also not unsympathetic to the idea that the private attorney general model for regulating ERISA plans is a necessary adjunct to Department of Labor regulatory and investigatory tools for protecting plan participants. The issue to me isn’t the meritorious case or the serious effort by serious firms to target abuses and losses to plan participants through class action litigation. The issue is the drive by class action case that results in the quick $2 million settlement with the half million fee to the lawyers, in which the case is filed by firms just looking for a quick payday, in which the average plan participant sees little actual financial benefit from the settlement and the defendant or its insurer settles early just to avoid discovery costs. In my days as a patent litigator, we used to refer to these as strike suits, filed just to trigger a settlement rather than to actually vindicate a patent holder’s substantive rights. But as I have written elsewhere, the tools to control this already exist in the hands of courts and, if they are willing to press them aggressively, defense lawyers. They lie in the assertion of greater court control of discovery, use of tools to phase litigation to decide outcome determinative legal issues long before discovery or defense costs get out of hand, and the like. They even reside in the hands of corporate clients in challenging their lawyers over whether the traditional model of class action defense – motion to dismiss followed by massively expensive discovery followed by a summary judgment motion followed by large settlement payout when, predictably enough in many cases, the summary judgment motion doesn’t resolve the case -is really the right approach to a given case, or whether instead there is a better way to approach a particular ERISA class action case. And given that, combined with the law of unintended consequences, I am highly skeptical of these types of legislative efforts in response to particular court rulings or developments in ERISA class action litigation, which really just seem to be reactive rather than a thoughtful attempt at tackling a complex problem.
  3. Apropos of my point in the preceding item, the recent history of forfeiture class action litigation in ERISA reflects the extent to which the system already pushes back successfully against novel approaches to ERISA liability that seem more intended to create a market for class action lawyers to work in than to fix an actual problem with ERISA plans. This article on the recent defeat of another such case is a good illustration. I wrote a recent post on the three key underlying elements that need to exist to get a court to look favorably on new legal theories, and those elements are proving to be absent in the forfeiture cases.
  4. The Supreme Court is taking up another ERISA class action case, this one involving the use of private equity investments in 401(k) plans, although that is not technically the central issue of the appeal. I wrote about it here the other day. This is a thought provoking piece on the idea that the real issue in this case isn’t what the Supreme Court accepted cert about, but instead underlying issues that the eventual ruling may well bless.
  5. The Supreme Court’s decision to hear the latest action will dominate the ERISA news as well as current thinking on key issues in ERISA class action litigation during the months ahead. Its mere pendency will also impact the progression of and arguments in a variety of already pending actions. It’s also worth nothing that, again apropos of the topics discussed above, it is in many ways another action about pleading standards and what types of barriers to meritless ERISA class action cases already exist, without some sort of legislative effort to put particular rules in place. This is an excellent article to understand the history, status and nature of the case as it goes up to the Supreme Court. At a minimum, it has everything in it you need to carry on a conversation about it at the (now mythical or perhaps always apocryphal) water cooler.

I am determined to finish my countdown of my ten most popular posts of 2025 while we are still within sight of the beginning of the year – in other words, before the calendar flips over to February.

So with that said, I am taking a break from drafting a number of complaints that I am trying to get filed, as well as the great fun of drafting discovery, to write up this post about my fifth most popular post of 2025. The fifth most popular post on this blog in 2025 concerned the lessons for plan sponsors and fiduciaries about including private equity investments in plans that could be drawn from the Ninth Circuit’s decision in Intel.

It’s ironic, and not evidence of a rigged contest, that this post came up as the fifth most popular right now, because the latest news in ERISA land is that the Supreme Court has just accepted cert to hear the Intel case.

So without any more delay, here is the fifth most popular post on the blog from 2025: “What the Ninth Circuit’s Decision in Intel Tells Us About the Fiduciary Risks of Adding Private Equity Options to 401(k) Plans.”

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.