G-men interviewed Chicago mobster Jimmy "the Monk" Allegretti only a week after the November 22, 1963 assassination of President John F. Kennedy in order to determine whether he had any connections to Jack Ruby who on November 24 had killed supposed assassin Lee Harvey Oswald according to the recently released FBI file on Allegretti.
Allegretti was the Rush Street crew boss who ran the vice rackets -- gay bars, strip clubs, whore houses, gambling dens -- from the mid-1940s to the mid-1960s on the Near North Side for Chicago Outfit underboss Ross Prio, and in the FBI interview he denied knowing Ruby although with typical wise guy attitude "indicated that he was not sure whether he would be willing to discuss him if he would have any information concerning this man."
An FBI memorandum dated December 17, 1963 by Special Agent August C. Kempff summarizes this interview with Allegretti as follows:
On November 29, 1963, JAMES ALLEGRETTI was contacted in Room 1177 of Wesley Memorial Hospital by SAs AUGUST C. KEMPFF and [name redacted]. ALLEGRETTI was contacted for the purpose of inquiring as to any knowledge he may have had concerning JACK LEON RUBY and RUBY's previous residence in the Chicago area. On entering Room 1177 ALLEGRETTI was observed in the company of four male persons three of whom were unidentified and the other was [name redacted] is a lieutenant of ALLEGRETTI's and formerly operated the lounge in the Devonshire Hotel and has alleged to be a collector and payoff man for ALLEGRETTI's gambling activities. One of the unknown persons at the time of the Agents entry to the room was observed counting out money to ALLEGRETTI from a sizable roll of bills. As the Agents entered the room and were recognized by ALLEGRETTI this man discontinued counting money and both ALLEGRETTI and the unknown individual put the money there were handling out of view.
ALLEGRETTI stated that he did not know JACK RUBY and indicated that he was not sure whether he would be willing to discuss him if he would have any information concerning this man.
According to this same report the FBI also suspected gay bar operator Nate Zuckerman as an Allegretti associate, and interviewed either him or an employee – the name is redacted – at the Front Page Lounge at Rush and Grand Streets who similarly disclaimed knowing Ruby:
[Name redacted] was characterized by [informant] as an employee of JIMMY ALLEGRETTI who has been an associate of his over many years. [Name redacted] was said to be the bartender in the downstairs “gay” bar of the Front Page Lounge, located at Rush and Grand Streets, Chicago.
[Name redacted] was contacted concerning any knowledge he may have concerning JACK LEON RUBY and stated he did not know RUBY. [Name redacted] stated that although he would ordinarily not furnish any information to the Federal Bureau of Investigation in the case of JACK RUBY he would be willing to help if he were able.
Two years earlier, an FBI informant alleged that he saw Allegretti at a nightclub with the owner of Jay Potato Chips who supposedly was grousing over the Kennedy Administration crackdown against the mob. A December 19, 1961 memo by Special Agent Edward J. Nehls states the following:
[Informant] advised in August, 1961 that he observed JAMES ALLEGRETTI at the Shh club in company with a Mr. Jay, owner of Jay Potato Chips. Mr. Jay appeared to be very well acquainted with ALLEGRETTI and was voicing around that the Kennedy Administration is unduely harassing the so-called hoodlums.
The then-owner of Jay Potato Chips actually was Leonard Japp, Sr. -- the brand previously was Japp's Potato Chips -- who allegedly got his start by delivering nuts and pretzels to Al Capone's speakeasies in 1927, and it's unclear whether the informant was referring to Mr. Japp.
The FBI interview with Allegretti confirms that it was interested in a possible mob connection to the Kennedy assassination from the very beginning. Indeed, the feds perhaps were right about their instincts. The evidence compiled over the years suggests that in the mid-1940s Ruby did work in Chicago for a seedy joint or two which may have been associated with Allegretti according to some investigators.
Further reading that may be of interest: