But that's neither here nor there, because my issue in this case isn't that Levison was on the wrong side of a controversy with DOJ.
My issue is that Levison never should have been running this particular service. Like many other short-sighted developers, Levison built a site that made expansive claims about its security capabilities which anyone familiar with the actual technology could see were preposterous.
The framing of the "debate", such as it is, about Lavabit seems to take as a given that DOJ or NSA can compromise secure messaging services, and that our only reasonable response is outrage directed at the USG (or "Five Eyes" or whoever) in the hopes of effecting policy changes. No. It is more than possible to build services that thwart the kinds of orders Levison received. It's not even difficult to do that. Levison could have built a service that would not have provided him the capability of furnishing the FBI with Snowden metadata.
Levison didn't not build that system because that was hard to execute technically. I think he did it because it was hard to execute as a business. Users want communications tools that work like the ones they already have, and, in particular, they want tools that interoperate with Internet email. Like virtually everyone on HN, Levison probably understands that such a tool is virtually impossible to implement as a web application. But Levison also knows that building native applications is expensive, and getting users to install things is more expensive still.
So instead of building something that protected his users, he appears to have built something that didn't, and then pretended that it did. He may have "gotten away with it" so long as the court orders he apparently quietly complied with didn't pertain to the highest-profile target on the Internet. But once that happened, the game was up.
If all of that's true, I'm not sure from where I'm supposed to find sympathy for people who play those kinds of games with people's secrets.