Your analysis seems to fit the old saying that the rich can only be eccentric. More accurately, I would say few other than the rich can be worthy of the wasted time on analysis (beyond the simple categories).

Since I believe that even the "eccentric" are unconscious rational actors, to a point, I would still like to know why people don't believe his goal is to diversify away from his holdings without ruining their value. If he sold a lot of stock his companies would be doomed, unless he can justify it with a complex expenditure with unexpected problems. Then he can ditch the unwanted investment and fail to put the money back in his one basket.