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FBI Documents: Special Agents Asked Chicago Mobster Jimmy Allegretti About Jack Ruby A Week After The Kennedy Assassination

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:

NATE ZUCKERMAN

 [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:

Robert F. Kennedy Suspected Mafia Was Behind President's Assassination

Outfit Enforcer Faces Life On Gun Conviction

One-time mob enforcer Mario Rainone faces at least 15 years and perhaps life in prison after his conviction as a felon in possession of a weapon as reported by Annie Sweeney for the Chicago Tribune.  The 58-year-old Rainone already is serving a 7 1/2-year term for a home burglary, and previously did a 17-year term on a racketeering conviction as a tough guy for the Chicago Outfit's North Side crew involved with shaking down restaurants and bars.

Windy City Declares El Chapo Public Enemy No. 1

Not since Al Capone during Prohibition days had Chicago declared a Public Enemy No. 1.

However, yesterday the Chicago Crime Commission resurrected the notorious spot for Forbes-listed billionaire Joaquin "El Chapo" Guzman who heads the Sinaloa cartel "which supplies most of the narcotics sold in the city" as reported by Michael Tarm for the Associated Press:

What Al Capone was to beer and whiskey during Prohibition, Guzman is to narcotics," said Art Bilek, the commission's executive vice president. "Of the two, Guzman is by far the greater threat. ... And he has more power and financial capability than Capone ever dreamed of."

The Windy City is a major distribution hub for the Sinaloa cartel, and most of its product is delivered directly from Mexico by freight rail and semi trucks as reported by Frank Main for The Courier-News. 

Jack Riley, the special agent in charge of the DEA's field office in Chicago, IL, said last year that the local street gangs are proxies for the Mexican drug cartels in the battle for turf as reported by Armen Keteyian for CBS News:

Riley says Mexican cartels have a significant influence in Chicago's gang violence problem. "Let's take the gloves off on that," he said. "We know that the majority of the drugs here in Chicago, cartels are responsible for. We know that the majority of the murders are gang related. So it is very clear to see the connection and the role." As it stands now, at least three major Mexican cartels are battling over control of billions of dollars of marijuana, cocaine and -- increasingly -- heroin in this city.

Federal authorities in Chicago have an outstanding indictment against Guzman, and have offered a $5 million reward for information leading to his capture.  However, since Peña Nieto won Mexico's  Presidential election last July, some have predicted a capitulation to the cartels as then reported by Erin Carlyle for Forbes:  "the new government is likely to be a lot less confrontational with people like the world's most powerful druglord: billionaire Joaquin 'El Chapo' Guzman Loera."

Chicago More Violent Today Than Al Capone's Day

The gang violence that rips through Chicagoland today is more deadly than the turf wars among rival mobsters during the 1920s as reported by Chuck Goudie for WLS:

Let's compare two months: January 1929, leading up to the St. Valentine's Day Massacre, and last month, January 2013. Forty-two people were killed in Chicago last month, the most in January since 2002, and far worse than the city's most notorious crime era at the end of the Roaring Twenties. January 1929 there were 26 killings.

Mob Scion Convicted For Internet Scams

Anthony Boscarino has pled guilty to multiple fraud and money laundering counts in a Las Vegas federal court as reported by Kim Janssen for the Chicago Sun-Times:  "he stole more than $7 million and lived the high life thanks to a series of Internet scams that promised huge returns on phony investments in sports betting, a slot-machine gambling system, oil drilling and mortgage-backed securities, prosecutors say."

The scam artist is the son of Outfit mobster Angelo Boscarino who was whacked in the mid-1960s on the mistaken belief -- whoops! -- that he was cooperating with the feds.

Anthony's older brother Nick "gained notoriety in 2005 when he refused to answer questions before the Illinois Gaming Board about whether he secretly controlled a trust that owned stock in the proposed Emerald Casino in Rosemont" which was ultimately killed, and in an unrelated matter "was sentenced to three years in prison in 2005 for ripping the village off in an insurance scam" as reported by Steve Warmbir for the Chicago Sun-Times.

Outfit Mobster Was A Bum Father

Apparently recently deceased Outfit killer Frank Calabrese Sr. was a lousy dad according to his son Kurt as reported by Steve Warmbir for the Chicago Sun-Times:  "his father had haunted him his entire life, first when he was a child with routine beatings and belittlings, then later as an adult, with more of the same but with greater intensity, culminating in bullying him into a family business he wanted nothing to do with."

Further reading that may be of interest:

Frankie Breeze Passes Without Fanfare