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….


New York City and the Today Show

More from my travels on the east coast and my continuing coverage of the Whitey Bulger trial….

Welcome back.  The Whitey Bulger trial has cost U.S. taxpayers millions of dollars for court appointed lawyers, extra security and much more. A detailed accounting of these costs is sure to be included in a new book that Howie Carr is writing about the case. As I mentioned last week, Howie is a big radio personality in New England and I met him on several occasions while I was attending the trial. Steve Davis (whose sister was murdered by the Winter Hill gang) is working on a documentary about the gang which should reveal more about their organization as well. I am keeping in contact with both Steve and Howie and should be bringing you another related story hopefully next week.

In the meantime there is an ongoing dispute surrounding the distribution of $822,000 that was discovered in the walls of Whitey’s Santa Monica apartment. The families of several of his victims have obtained judgments against him and others are now filing suits. Whitey himself has just been convicted of racketeering and 11 counts of murder and is facing life in prison when he is sentenced in November.


The Original Buffalo Dale with Steve Davis outside the federal courthouse in Boston. Steve has his own story to tell about the Winter Hill Gang in his forthcoming book.
The Original Buffalo Dale with Steve Davis outside the federal courthouse in Boston. Steve has his own story to tell about the Winter Hill Gang in his forthcoming book.

My time in Boston was far too brief but I had other business in New York City. It started with a 30 minute Metro North train ride to Grand Central Station, and then it was a six block walk to the Today Show set on Rockefeller Plaza. Tickets to participate in the audience are free but no political activism or advertising is allowed. When I attended last Thursday morning there were at least a dozen people protesting the prison at Guantanamo Bay as well as others whose causes I couldn’t determine. The plain clothes security people meandering through the crowd acted quickly with the assistance of New York City police they removed all the protestors from the set.


A cowboy lost among the 8.25 million people who live in NYC, I was no problem for these bad boys. Here’s a few interesting facts about this particular piece of earth that I learned on Wikipedia:


  • The total area of NYC is 304 square miles and change as compared to Oklahoma with 69,898 square miles and 3.8 million residents


  • The city is made up of 5 boroughs, Manhattan, the Bronx, Brooklyn, Queens and Staten Island.


  • New York was settled by the Dutch in 1624 and came under English control in 1664.


  • It was the capital of the United States from 1785 to 1790.


  • It is the largest city in the United States and one of the most ethnically diverse places in the world: over 80 different languages are spoken here.


This was not my first trip to NYC and it won’t be my last.  It also was not the first time I took the opportunity to visit Strawberry Fields in Central Park. This is a 2.5 acre area of the park that has been designed as a tribute to the late Beatle John Lennon.



Strawberry Fields was established with a 1 million dollar gift from Lennon’s widow Yoko Ono. Today over 120 countries contribute to the plantings and maintenance of the area. At the center of the area is a beautiful mosaic medallion with the word “Imagine” in the middle referring to Lennon’s song about his hopes for peace among people everywhere. On this day as every day dozens of people were taking pictures there. A single guitar player was playing Beatles’ songs and the site that has been designated as a garden of peace was just that.


A few tips for travel to the city: Don’t drive your car into town. Parking is tough to find and extremely expensive. Cabs are good for short distances and the double Decker sight seeing buses are great. It is usually free to attend any of the TV shows but expect lines to get in. If the weather is good the Today Show is fun because you can be seen out on the plaza. Matt, Al and Savannah were very nice, shaking hands and having their photo taken with everyone. You can find food everywhere in New York, from street vendors to swank restaurants. With the diversity of the population any cuisine you can think of is represented. According to my daughter and traveling partner the shopping is amazing which may be the worst thing that happens to you in the city…


I also want to mention how friendly and helpful I find New Yorkers, despite their reputation.  Even a scout, tracker, translator and interpreter can get turned around.

Do you want to be careful? Yes, but on average, given the size of the population, your chances of meeting a kind person are better than good. This really is a uniquely beautiful part of our country.

Till next time I’ll see ya down the road….




Whitey Bulger Boston Trial-2013

I have been traveling and have not been able to post anything while I was on the road. Hope you enjoy this update to the Whitey Bulger story- a verdict is expected soon.

Welcome back. Although the closing arguments of Whitey Bulger’s trial, which I attended, concluded Monday, today I’m in New York City following another unsolved murder case.

Throughout the Bulger trial I met and visited with dozens of victims, lawyers and special FBI agents and investigators assigned to the case so this week I’m bringing you my impressions of the proceedings.

The FBI called it “Operation Lobster” and much of the work was done by the C-3 unit which is the organized crime squad of the Boston FBI. During the days I spent sitting in the courtroom (via TV in an adjacent room) agents like Joseph Kelly and Robert Fitzpatrick told stories about the corrupt FBI agents and Boston policemen who were on Whitey’s payroll. Murder, extortion and drug dealing were all mentioned, along with kidnapping and money laundering. The Winter Hill gang which Whitey ran from the late ‘60s until he eluded capture and went on the lamb in 1994, ran the Boston crime scene.

photo with Whitey's lawyer-fixed

In the recently released book “The Rifleman” by author Howie Carr, Whitey’s longtime partner in crime, Steve “the Rifleman” Flemmi describes how he and many other members of the Winter Hill Gang killed and disposed of more than 50 people. Their murder victims weren’t just fellow criminals; anyone who stood in their way would get wacked. People were shot, strangled and even bombed. Gang members went as far as pulling people’s teeth out to torture them before death and prevent their identification.

The gang stopped at nothing to control their territory. A brave man, Carr himself had been threatened numerous times before the publication of his books about the Winter Hill Gang including “The Brothers Bulger.”

On the stand the special agents also told about the informants they developed to infiltrate the gang. The informants were given secret code names such as P1 and P2 to protect them but because of corrupt cops many of the informants were killed anyway. Agent John Connolly, now spending 40 years in a Florida prison, set up many of these victims to meet their deaths.

Steve Davis, whose sister Debra was Flemmi’s longtime girlfriend, told me several stories about Whitey that will be included in a documentary that is coming out soon about the gang. Debra was choked to death by Whitey and Flemmi and her younger sister Michelle was raped by Flemmi. Michelle was a minor at the time and later committed suicide.

Steve was in the courtroom everyday during the trial and he and I visited several times. I am working on a piece about everything Steve and his family have been through which should be done soon and you won’t want to miss it.

I also had the chance to speak with Whitey’s lawyer, J.W. Carney, Jr. whom I met in the parking lot of the federal courthouse where the trial was being held. The question on everyone’s mind was whether or not Whitey would take the stand. Carney told me it would be Whitey’s decision alone and by now the whole world knows he decided not to testify.

On Friday, which was the last day of testimony, Carney called John Martorano to the stand. Martorano is another associate of Whitey’s who had previously been convicted of 20 other murders. He testified that Flemmi told him he had choked Debra Davis although in previous testimony Flemmi had said that Whitey strangled her in front of him.

Other witnesses testified about the boatloads of marijuana that the gang had brought into Boston, receiving a million dollars for each load. Their trafficking in cocaine reportedly brought Whitey himself $10,000 a week.

Another dramatic piece of testimony was expected from former Bulger associate Patrick Nee who could have revealed additional details about the gang’s murderous activities. Because Nee had his own problems with the law, U.S. District Court Judge Denise J. Casper ruled that he could the Fifth Amendment to avoid incriminating himself during cross examination by Assistant U.S. Attorney Fred Wyshak and he did.

Following Monday’s closing arguments dozen’s of reporters await the jury’s ruling which as of today has not yet been announced. Next week more on Whitey and my mission to New York.  Till then I’ll see ya down the road…

P.S. I have just learned that my friend Rubyane Burkhart Surritte’s recipe for Blue Ribbon Pecan Pie is featured in this month’s issue of Saveur Magazine. Check it out!