This article was last modified on December 23, 2015.

Barney Grogan, Whitey Bulger’s Man in Chicago

Note: In 1929, there was another Barney Grogan, who was involved in West Side vice and politics with Mike Heitler. It is unknown at this time if he was related to “our” Grogan or connected in any way.

Bernard Joseph (Barney) Grogan, known as “Dirty Shirt”, was born in November 1929. He was a star athlete at St. Patrick Academy on the old Near West Side, where he set a record by returning a punt 103 yards for a touchdown.

Grogan was convicted of bank robbery in April 1956. Barney’s brother was John B. Grogan, a judge in Chicago. While in Alcatraz, he became friends with a man who would become one of the country’s most notorious mobsters: James “Whitey” Bulger. (Some sources say that Grogan was born John Joseph O’Brien, but changed his name in prison to “protect” his brother. This is not correct.)

Grogan, who once busted out of a Tennessee jail in the middle of his trial, only to be caught a couple miles away drinking beer in a saloon, is credited with plotting Bulger’s escape from the U.S. in 1994. According to author Howie Carr in “The Brothers Bulger”, Whitey hid out with Grogan in Chicago in 1994 — and Grogan was working for a mob-controlled union at the time.

Grogan died in October 2004, before he was able to tell investigators anything more (assuming he would have, which is doubtful).

Also try another article under Organized Crime
or another one of the writings of Gavin.

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