The problem with a positive control system is that he's being watched, intensively. So how do you reset that env variable without someone seeing you do it and thus discovering the server? Once they know the servers, they just need to take them out and the deadman's switch is neutralized.
If he had a way to do one-way broadcasts, like over the radio, where any snoopers could not discover the receivers then it would make more sense to do a positive control system. But there really isn't a mechanism for that on the internet. Even if he posted to usenet, given enough time, a sufficiently motivated nation-state adversary could probably trace through enough usenet servers to figure out what clients were looking for those reset messages.