I don’t doubt your estimate of his understanding; but he’s arguably laboring under the additional burden of being such weak material.
The best conditions for humor to be incisive are when there’s a target that has more internal structure than it’s aware of. It doesn’t need to be well-formed internal structure(indeed, the humor usually works better, or at least more readily, if it’s internally contradictory, hypocritical, or turns out to be either monstrous or nonsensical on closer inspection); but there needs to be something for the keener observer(or the speaker themselves taking a moment for self-awareness) to tease out.
If you are just bad at satire you are in the position of an amateur attempting an illuminating pathological dissection with shaky hands and a blunt penknife. If you are bad to satire you’re a dish of jello: you could throw Andreas Vesalius at the problem and there would be no cuts that expose anything that wasn’t already visible and already dull.
