Some weeks are an embarrassment of riches. For the author of a running series like this one, this week was one of them. From insurance for AI risks to alts in 401(k) plans, there were enough excellent articles to fill several of these columns. But here are the five I picked this week.
- I started out as a paralegal working on the late stages of the never ending dispute over asbestos coverage and then was a junior associate working on environmental coverage disputes when I started practicing. I learned, as many did, that these types of long tail, long running exposures and liabilities continue as insurance coverage disputes for many, many years. Heck, even after the start of the twenty first century, we were still litigating various tributaries from the environmental coverage disputes, including in one of the cases in my own practice, as an example, what type of discharge was sufficient to fall within an absolute pollution exclusion. As late as around 2000 or so, in fact, I was trying a case in Superior Court in Massachusetts concerning to which year’s tower of coverage an environmental loss should be attributed – and that was a good fifteen or so years after I first touched an environmental coverage file. I bring this up because the interesting back story to the recent high profile plaintiffs’ victories against social media companies seeking recovery for social media addiction is that, like tobacco claims, there is an almost infinite number of similar suits in the queue behind them, with likely decades of insurance coverage fights over them still waiting to be fought. This blog post sheds some light on these issues.
- I have written multiple LinkedIn posts (see here and here) and a blog post on a new Chapter 93A decision out of the Massachusetts Appeals Court, which I believe advances the ball on three different issues in Chapter 93A law in the Commonwealth. One of the reasons those developments are important is because insurance and insurance bad faith law in the Commonwealth is overwhelmingly controlled by the manner in which obligations, duties and rights under Chapter 93A are interpreted. As I have discussed before, one of the interesting and important aspects of the new decision is the guidance it provides on how misrepresentation comes into play in this context. This point is focused on in this article on the decision in Massachusetts Lawyers Weekly.
- In my feeds, including on LinkedIn and in newsfeeds, stories about a boom in ERISA class action litigation continue to proliferate, and everything from pro-defense court rulings to Department of Labor action indicates that there is an ongoing pushback to that dynamic. It was interesting to see that this trendline didn’t spare the federal courts of New England, with twenty ERISA and securities class action filings in 2025, as this article explains. However, of some interest to me as a committed skeptic on the question of whether the boom in ERISA class action cases is really as egregious as is often said, the same study showed that the total number of class action filings in New England in 2025 was 604. Less than 20 ERISA class action filings out of 604 class action filings in a large region spanning multiple states during the course of an entire year may not really represent a gold rush of claim jumpers.
- I like this article on the trend towards carriers and corporate defendants retaining appellate counsel, independent of the trial team, to watch over cases while they work their way through the trial court and through trial. But I am also not totally sold on the idea and think it depends on the case and the trial team. If you have an experienced trial lawyer who is also an experienced appellate lawyer, I am not sure how much is gained by adding an appellate lawyer as some type of embedded observer. I have tried at least one case with separate appellate counsel from a specialist practice having been retained by the client to attend the trial – I am not sure that I or the client gained much from it. On the other hand, I have parachuted in as appellate counsel after judgment was entered and where experienced appellate counsel had not been part of the trial team. I can tell you that when I went to write the appeal brief and also when I went to prepare for argument, there were some issues I wished had been addressed at the trial court when the case was pending there, and which might very well have been addressed at that stage if separate appellate counsel had been present at that stage of the proceedings.
- So many things I could have chosen for the coveted number five spot in the batting order this week, many of them being very astute and very fast takes on the Department of Labor’s new proposed regulation on alternative assets in 401(k) plans. But that’s too obvious a choice for this slot and, moreover, there is way too much to say about it – I may have to write a separate, special edition of the five favorites solely covering articles, newsletters and blog posts on this issue. Instead, I like this article comparing the development of the AI insurance market to the prior development of the cyber insurance market. I like it for two reasons. First, it takes me back to one of my favorite stories, which is the time that I was giving a presentation on cyber insurance, by video broadcast, to thousands of claims staff at a major carrier, when the tech driving the PowerPoint deck crashed, which for you young ‘uns who don’t know what the work world was like before Zoom and Teams, was about every speaker’s worst nightmare. I solved it by immediately announcing that “Clarence Darrow used to give multi-day closings without a deck, so I can finish this presentation without one,” and then just kept plowing on, like an old-fashioned speech from before the days of tech. To be honest, I had that line in my back pocket, having used it in the past when tech crashed. Second, though, I like the article’s focus on what brokering and underwriting look like behind the scenes. There is some really good information there for anyone who deals with placing coverage or counseling insureds but doesn’t have a front row seat to how the sausage gets made.