The loss of readership is a bigger annoyance for him, because it means a loss of influence.
I changed that a bit because that is Bezo’s biggest problem. His hard core readership are already true believers (fanatics) so the paper is preaching to the choir hence changing nobody’s mind. So as a propaganda tool that is trying to convert folks to the leftist mind-set, it is a failure. And while the losses are small fraction of Bezo’s fortune I suspect that the FedGov has a way to offset those losses somewhat. I would not be surprised if a substantial number of hard-copy subscriptions are to FedGov offices and their personnel.
Thus, Tucker Carson, Joe Rogan, Alex Jones, and hundreds of smaller podcasters have audiences that Fox, CNN, and the old three TV networks envy. Elon Musk has broken the iron curtain imposed after 2017 by Big Tech. Additionally, numerous smaller sites like Rumble have bypassed the old guard tech platforms.
The powers that be have lost their formerly dominant mind control, so their rhetoric to their followers is ramping up to Goebbels like levels. Their attacks on Trump are only serving to strengthen him. If he dies or is imprisoned, the conservative base will reject Nikki Haley or Ron DeSantis, who are within the Overton Window and are well funded by the Bush wing of the GOP.