The story was that he had gone to Cuba after Castro had taken over. According to a web page, Ruby went in August of 1959. Castro had assumed power on Jan 1, 1959.
For a brief period the U.S. media successfully hid the fact that Castro was setting up a Communist state. I have no idea whether this was common knowledge by August of that year. It is quite possible that Ruby did not have a clue. It also seems rather early for intrigue against the U.S. to be coming from Cuba.
“For a brief period the U.S. media successfully hid the fact that Castro was setting up a Communist state.”
Bear in mind that Castro flirted with both sides, and our government really, really hoped (”crossing my fingers”) he’d tip our way. Just like they hoped Mao wasn’t such a bad guy. And that the Soviet Union would hold free elections in its satellite states.
Oh, and the media is, in my opinion, oftener stupid than sly.