As far as I can tell, the FBI looked into a report that Cheek had owned a boarding house where two unidentified Cuban males had rented rooms. One reportedly made regular calls to Havana. This taking place in 1958 or 1959. In a WC memo between staffers Bert Griffin and Leon Hubert they suggested checking a theory that Cheek had been involved with Ruby in gun running to Cuba (the two Cuban males were possibly involved in this operation) and that Oswald had somehow found out about it (from Roberts?). And that this needed to be investigated. I guess this is what Willens was referring to. There are several memos between Rankin and Griffin/Hubert on this idea.
Whew. How one goes from owning a rental property where two Cubans had rented a room (apparently this was not known to Cheek; she owned the property but rented it to someone who then rented rooms to the Cubans) to running guns with Ruby to Earlene Roberts to Oswald discovering this is...well, I guess if you're imaginative enough you can see a possibility. Maybe I'm missing more details but that's some wild speculation.
The FBI report is here: https://www.maryferrell.org/showDoc.html?docId=95674#relPageId=76&search=Bertha_Cheek
The Griffin/Hubert theory is discussed here: https://www.maryferrell.org/showDoc.html?docId=217852#relPageId=98&search=Bertha_Cheek
Thanks Steve! That’s helpful, and it is making better sense to me now.
Wild speculation indeed! However, it does appear that both Ruby and Cheek had somewhat similar styles of entrepreneurship. Neither one appeared to be very good at it, or had many scruples when it came to how they made money. And, I think that I can see why they made contact with each other for business purposes. And I think that I can see why suspicions and a theory by Hubert/Griffin came about.
But suspicions and a theory are just that. Here is another snip from “History Will Prove Us Right” by Howard Willens that I think says a lot:
“My second problem was their definition of the assignment. They wanted to answer three questions: Why did Ruby kill Oswald? Was Ruby associated with the assassin of President Kennedy? Did Ruby have any confederates in the murder of Oswald? But in their memo, Hubert and Griffin said that “although the evidence gathered so far does not clearly show a conspiratorial link between Ruby and Oswald, or between Ruby and others, the evidence also does not clearly exclude the possibilities [emphasis added] that (a) Ruby was indirectly linked through others to Oswald; (b) Ruby killed Oswald, because of fear; or (c) Ruby killed Oswald at the suggestion of others.”
I had no objections to the questions posed, but their view that the evidence in the commission’s possession had to “clearly exclude” any and all possibilities struck me then and now as unreasonable and unachievable. I said so. Ironically, the next time I saw something like this “clearly exclude” standard was in the final report of the House Select Committee in 1979, which used the equally unacceptable phrase “evidence does not preclude,” in its misguided denunciation of our work.“I think that way too many people fall into the same trap. They simply don’t realize that [another snip from Willens’ book, page 357]:
The commission’s investigation pursued a “ground up” approach that focused on the background, associations, and activities of Oswald and Ruby to unearth clues of possible conspiracies.
You need evidence—not speculation—before concluding that a conspiracy existed. One can speculate about the “possibility” of a conspiracy directed by one of the many groups that had reason to dislike the president’s (or his brother’s) policies or programs. If such a conspiracy existed, however, it eventually had to manifest itself in some manner through contacts with Oswald or Ruby relating to their actions in November 1963.
Also, many people fail to understand that [another snip from Willens’ book, page 380]:
The commission’s lawyers who came from the private sector were instinctively more inclined to distrust—rather than trust—the federal government. They would not have acquiesced in an indefensible commission investigation and report and would have gone public with their disagreement if that became necessary. As the only assistant counsel who was on a government payroll, I served as a representative of the Justice Department and Robert Kennedy with only a single mission—to assist the commission in conducting a far-reaching and intensive investigation of the facts and in writing a report that would accurately reflect that investigation. We were none of us perfect, but it would have been difficult to deceive us individually, and impossible to do so as a group.