I’d love to know if he’s just artless and arrogant; or if whoever is advising this scheme is working on the theory(quite possibly correct) that displays of vulnerable characteristics tend to sway the judgement of psychologically normal observers even if they don’t, if asked outright to think about it, believe them; in a way analogous to the fact that humans are atrocious at probability, even the ones who can run the numbers if they stop and think about it first.
If this is an attempt to actually succeed at overt deception it is starting off from the “oh, what a surprisingly rapid decline from previous rude good health; how very convenient…” back foot; and isn’t being adhered to nearly rigorously enough(whether out of incompetence, arrogance, or sheer force of habit); and overall doesn’t seem terribly likely to fly.
However, if the sort of people who don’t smile and go for the throat when faced with apparent vulnerability respond to it with some degree of pity regardless of the success of the deception at a fairly abstract level, because you are aiming for an affect hit, there may be no reason to bother maintaining the charade except in the immediate term.
Unless, of course, you are also concerned about people responding negatively to suspected deceptive signals, which seem like the sort of thing that might also have emotional salience, even if subconscious, so it’s potentially further considerations all the way down.
All that said, I hope that moral clarity prevails regardless of his little display. Even if it were 100% true; we know how he treats those vulnerable to him, why should his apparent frailty stay our hand?