Sure, we kid each other mercilessly, but that's not the same. We don't kid a man whose wife just died in a car accident, or whose child was just murdered. We don't try to tell him how he was partly responsible. We rally to his side, and support him. From an American point of view, that is how friends behave. Nothing else is acceptable.
Above is one of the long form style of posts he's best known for. I wonder what his take on Trump was, given the above. As with most of us, he started in a sort of tech-commentary phase, which then shifted as 9/11 occurred. He found an audience in fellow warbloggers, and adjusted his positions to lie in congruence with them as their popularity grew (we all tend to lean into our best audiences). His most recognized style was the rambling long form, sewing up disparate bits and historio-strategic trivia into a narrative (boy, the use of 'Jacksonian' takes me back). You could dub him a sort of Tom Clancy of warbloggers - often so long, you skimmed his posts to get to the meat.
As with most of the original blogger generation, I never cared much for the warblogger niche. Going back to read their archives shows how quickly a closed loop can become divorced from reality. Den Beste was someone I read infrequently, but I could not help but read him from time to time. I mark his passing as an archetypal blogger of the past. RIP.