Lennie Patrick Chicago Outfit Enforcer

Lennie Patrick Flips

Gary and Cam discuss an Outfit gangster named Lennie Patrick with Chicago mob historian and attorney Paul Whitcombe. Paul and Camillus Robinson are associated with John Touhy and the Killers Kings and Clowns You Tube Mob channel and the Mafia Facebook group, Killers Kings and Clowns. In 1992, Paul was a law clerk for the trial Judge Patrick Alesia when 78-year-old Lennie Patrick testified against the Outfit’s chief political fixer and then boss Sam “Wings” Carlisi and several others. He traded off what would have been a life sentence for racketeering and extortion for a 2-year sentence and is testimony in this famous trial. Besides the discussion about Lenny Patrick in general, Paul tells great stories about events during the trial like his small talk with spectator Antoinette Giancana and the time the defense lawyers presented a theory that Lenny Patrick was the actual killer of JFK and they claimed he shot from the “grassy knoll.” Paul tells about how he was given the entire unredacted JFK murder file to review for any mentions of Lenny Patrick. Plus, he had to review a Cuban documentary film about the assassination for any evidence that Patrick was the killer.

Lennie Patrick and the Outfit

Patrick grew up in the Jewish section of Lincoln Park on the Near Northside during Prohibition. At age 15, Patrick quit school and started a life of crome. An Outfit capo named Joey Glimco noticed him when he started gambling at dice games at the Chicago taxi driverā€™s union. Like most young mobsters, Patrick graduated to armed robbery. In 1932 it is suspected he murdered his first man. He got into a fight with a gambler named Herman Glick and Glick knocked Patrick out. Patrick returned a week later and shot the man in his head. Patrick and his stick-up crew started robbing banks when the police caught them. An Indiana court sentenced him to 10 years in about 1933-34. He left prison in 1940 and returned to Chicago. He was a trusted and seasoned gangster by then. He was noticed by Outfit up and comers like Paul Ricca, Sam Giancana, and Milwaukee Phil Alderisio. He got involved with an Outfit gambler named Dave Yaras. The Italian dominated Outfit granted Patrick control of all book-making in the Jewish neighborhoods. It was during these years that he met the man he would eventually turn on, Outfit political fixer Gus Alex. over his first few years as an Outfit bookie, he would murder West Side book-maker Harry Krotish, a rival gangster named Edward Murphy, a man named David Zatz, and Milton Glickman. When he went into the witness program Patrick claimed he murdered a man who scammed him out of $165,000 for a phony sportsbook. Patrick “made his bones” and was a tough and respected Chicago Outfit mobster.

The Patrick crew

Lennie Patrick was probably making over $800,000 a year from his sportsbook. He was a lucky gambler and liked to gamble like most of the mob bosses in Chicago. it is claimed he once won a huge amount of money gy taking the Jets over the Colts in the 1969 Super Bowl. He must have seen something in Joe Nameth. He and his crew also extorted local business by starting fires or planting bombs. He claimed he and Dave Yaras extorted $300,000 from Allen Dorfman. These activities were all under the direction of the Outfit and he was a non-Italian who had his own crew on the Northside of Chicago. The FBI watched him meet with all the upper echelon Outfit Capos and boss at different times and appeared to be the equal of any other capo.

Ā Lennie Patrick was a mean vicious gangster

Patrick showed no mercy and had few scruples. it is said that one time he offered a young kid some money for helping to push him out of the snow. When the kid refused the money, he decided the family must be wealthy. Thereupon, he extorted thousands of dollars from the kid’s father who owned a neighborhood pizza joint. In another example, Patrick’s own brother, Michael owed him $250,000. When the brother was unable to pay, Patrick threatened the brother’s son-in-law. He admitted to extortion a large sum from his common-law wife’s nephew. Once, the son of a pizza chain owner stopped to help push Patrickā€™s car in the snow. Lenny tried to give the kid a few bucks, but he refused to take it. In return, Lenny chose to extort the family-owned pizza chain. Honor?

Gus Alex

At age 78 in 1992, Patrick agreed to testify against the Outfit’s political fixer Gus Alex and the Outfit boss Sam ā€œWingsā€ Carlisi. Patrick had maintained such a low profile that when he agreed to come over and talk, the FBI did to even have a photo of him. They had to review old surveillance photos of him with known Outfit members to prove he was important and had the knowledge he claimed

Show Notes by Gary Jenkins

Ā Support the Podcast

Hit me up on Venmo for a cup of coffee or a shot and a beer @ganglandwire

To go to the store or make a donation Click Here.


To rent Brothers against Brothers, the documentary, click here.Ā 

To rent Gangland Wire, the documentary,Ā click here

To subscribe on iTunesĀ click here, please give me a review and help others find the podcast

Listen on Pandora

5 thoughts on “Lennie Patrick Chicago Outfit Enforcer”

    1. Have they ever done a book on Lenny Patrick? Boy that would be a great read. All the history that guy had of the doings of the Outfit.

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Scroll to Top