Or he didn't look closely enough into what was happening. He might not have been very capable, just lucky. "Should have known" is not an answer to (potential) incompetence or stupidity.
Given his funds went bankrupt, he probably did not know.
The law seems to take a dim view of sophisticated investors who pretty clearly could have trivially found something fishy and instead chose not to look. Deliberate ignorance apparently gets clawbacks.
Given his funds went bankrupt, he probably did not know.