I have a different opinion. I think that he has bought some bitcoin long ago and hodling. Of course, not for the tech, not for the freedom, instead, purely as investment. I see no other reason he spends this much time keeping an eye on everything that happens with bitcoin (and some more).
Of course, he may not admit that. That's a different story.
Not really impossible(knowing that bitcoin really fits his ideology, only except that he's a huge boomer that thinks digital stuff doesn't have value), but I wouldn't bet on it. We can easily assume that him trashing on Bitcoin left and right is just a huge marketing ploy for his gold business(SchiffGold). And his marketing stunt sure worked(and is still working).