Though I would argue that the explanation requiring the fewest assumptions is not that Ma was being calculating and strategic, but that he just got cocky and said something dumb in the moment. He let all the global feting of his rise from schoolteacher to China's richest man go to his head, made an all-too-human mistake, and said something inadvisable.
He may even have been trying to defend the CCP in that moment, trying to communicate to US audiences that the CCP doesn't need to be feared because it's not scary, and thus he himself didn't fear it. But Xi and the powers that be interpreted it differently, and disappeared him. Which is always a risk in that system, but not in liberal democracies.
See also, Twitter is was not worth $44 billion in 2022.
Missing option (4). If you have billions, sacrificing a lot of wealth and power to do something you want is just another valid option.
See also, sacrificing 20% of your net worth to support "freedom of speech" is a reasonable choice, especially if you are left with an objective fortune.
FWIW I know it’s his right to do this as he owns the platform but it is relevant in the context of “but Elon didn’t do X”
1. Jack Ma knows things you don't, and those things made mouthing off seem worthwhile to him. Still, he miscalculated, but not out of sheer cluelessness.
2. You, HN commenter, understand Chinese politics and power better than Jack Ma, a prominent Chinese billionaire. He is clueless.
Doesn't 2 seem a little arrogant to you?