Whitey Bulger’s Winterhill Gang

I hope to bring you more on this case in November when I plan to be back in Boston at Whitey’s sentencing. It looks like the end of the trail for the last of the Winter Hill Gang.

Welcome back.  The Irish Mob wars of 1966 in Boston were dangerous if you were a gangster but there was also opportunity for advancement. When the founder of the Winter Hill Gang, Billy McLean was killed, James “Whitey” Bulger stepped in. This week I am bringing you a brief profile of Whitey’s top hench men who helped him keep an iron grip on the crime scene in Boston for over 20 years.

As I wrote last week, Stephen “the rifleman” Flemmi was one of the men who was closest to Whitey and together they murdered many people including Flemmi’s own stepdaughter (who he was secretly dating) and another longtime girlfriend. Flemmi was eventually convicted of ten murders and has been implicated in 10 others. In partnership with Whitey, he was involved in extortion, drug dealing and just about any other crime the gang came up with. Eventually he became an informant and today he is being held at an undisclosed federal prison. He is 79 years old.

In his youth John Martorano appeared to have a bright future as an athlete and a student. He grew up in the Boston area and was a devout Catholic, even serving as an alter boy. In high school he was a standout football player and played along side future CBS News television journalist Ed Bradley. Bradley called Martorano, “the milkman” because he said he always delivered. Although Martorano was offered several college athletic scholarships, after high school he became involved with the Winter Hill Gang and worked as a hit man. Martorano was convicted on twenty murders but he served only 5 years in prison after agreeing to cooperate with federal prosecutors. Today he is 72 and a free man.

Although you have probably never heard of him, Kevin Weeks was a key witness against the corrupt FBI Special Agent who helped Whitey, John Connolly. Weeks was a tough kid when he was growing up and he worked as a bouncer at the gang owned “Triple O” bar where Whitey, Flemmi and Mortorrano hung out. He quit college in 1976 to become part of the gang’s extortion ring, shaking down drug dealers. In his memoir “Brutal, Life in Whitey Bulger’s Winter Hill Gang” Weeks recalled that this was lucrative work and he didn’t mind it even though things could get bloody. Although he was also involved in many gang murders Weeks managed to spend just a short time in prison by turning state’s evidence and he is now at work on another book.

Catherine Greig had been one of Whitey’s girlfriends since 1977 and she was arrested with him in 2011. According to a longtime Bartlesville police officer Grieg’s was also once arrested in Bartlesville! After pleading guilty to harboring a fugitive, conspiracy and identity theft, Grieg was sentenced to time in a low security facility and she is scheduled to be released on June 10, 2018.

Greig had attended the Forsyth School for Dental Hygiene and when she got involved with Whitey she provided the pliers he used to torture some of victims. He often pulled peoples teeth before they died to get information and make it t difficult to identify them.

At one point in his “career’ Whitey lived in a Boston condo with a view of three  of his private cemeteries where he had buried bodies, many without fingers or teeth and many without heads.

Of course there were many more gangsters involved in this case as well as over a dozen corrupt Boston cops and FBI agents. If you want to learn more about the gang look for Steve Davis’ new book called “Impact Statement” which is scheduled to be released on September 22nd. Steve is the brother of Deborah  Davis who was murdered by Whitey and Flemmi and he tells a true story of some of Boston’s darkest days.

And now from the bad to the good. Sunday’s big party and fly-in at Will Roger’s Dog Iron Ranch drew record crowds. As many of you know Will is one of my heroes and apparently hundreds of others haven’t forgotten him either. Most of the Rogers clan was there and as a special treat Will’s great great grandson flew in from California. Although he is still in high school, he is the first Rogers descendant to land a plane at this event. I think Will would have been happy to see everyone enjoying the beautiful weather, fine food and great entertainment. If you haven’t been to the Dog Iron lately you need to visit. The ranch and the museum in Claremore offer fascinating information about one of Oklahoma’s most interesting and beloved men.

Next week a report from “the world’s richest cow sale” and its right here in Oklahoma.

Till then I’ll see ya down the road….


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