Trekking Toward The Truth – A Journey With Others Over The Road Less Traveled

Originally dedicated to the vagaries of matters involving Whitey Bulger and the FBI but now expanded into more general topics.

TTTT - Trekking Toward The Truth – A Journey With Others Over The Road Less Traveled

Re-Examining Whitey Bulger: The Early Years: Whitey’s Change Of Heart: Part Eight

South Boston
In Olden Days
(click to enlarge)

I noted yesterday the so-called war between the Killeen and Mullen gangs started in July, 1969. Using the word war to describe this conflict seems to be greatly exaggerating what occurred. It was more what we’d call a small gang fight with a few guns thrown in. It seems there were less than a dozen active participants on each side. One newspaper article stated the Boston police said the Mullen gang had 60 members but if true, which seems unlikely. I’d suggest it had less active participants in the shootings than the number of days in a week.

Another strange aspect of this fight is the territory in which it took place, South Boston. Southie is divided into three small sections: City Point, the area  generally to the east of Dorchester Street which is about 1/2 mile wide and one mile in length and includes the beaches and water front; the Lower End, to the west of Dorchester Street an area of 1/2 mile by 1/2 mile bordering the railroad tracks and the South End; and the third is around Andrew Square including the Old Colony and Old Harbor Village projects which is even of a less area than the Lower End.  These are densely populated postage stamp-size areas and it is hard to see how the combatants were not constantly bumping into each other. It seems clear that they all knew each other, at least by sight.

Sometime between July and November 1969, Billy O’Sullivan and Whitey ran into Buddy Roache, a Mullen, in a Southie bar room or had a sit down meeting with him at a lounge, depending on whose version is believed. O’ Sullivan and Roache got into a heated argument which resulted in O’Sullivan taking out his .22 caliber and shooting Roache in the shoulder. The bullet came out through Roache’s spine and he ended up being paralyzed for life.

On Tuesday, November 18, 1969, Donald McGonagle, who had nothing to do with the Mullen gang, was driving his brother Paulie’s car on Broadway. Being mistaken for Paulie, the Mullens’ leader, he was murdered. The fanciful Kevin Weeks who was 13-years-old at the time said Whitey was the hit man. But then again Kevin has to have Whitey doing lots of evil deeds. That is how he got his wonderful deal with the feds.

Little credence can be accorded to Weeks’s story. It is unlikely Whitey was packing a gun at this point. Further, the killer was probably Billy O’Sullivan. Paulie McGonagle and the rest of the Mullens believed O’Sullivan killed Donald. O’Sullivan is the person they planned to retaliate against.

It would take over a year for Paulie to gain his revenge.  On March 28, 1971, Paulie and two others Mullens confronted O’Sullivan as he entered his home at 300 Savin Hill Avenue around midnight. He fled down the street in the direction of the Woods. They chased after him. He tripped and fell. They caught up to him as he lay on the ground. Homicide detectives said he died from bullets in the head and chest fired at point blank range.

It was a little over a month later when FBI agent Condon directed his memo to Hoover suggesting Whitey was in fear of his life. He well should have been since O’Sullivan’s murder left him as the only one in the Killeen gang who the Mullens held in high respect because of his reputation.

Twelve days after the first memo to Hoover, Agent Condon wrote a follow up. He said Whitey would be “a very valuable source of information relative to the organized criminal activities in South Boston.” On June 6, 1971 Condon said Whitey told him that the murder of Billy O’Sullivan was a problem for him and “feels he will be murdered if he lets his guard down.”

Then around July 10, 1971, he writes Whitey told him, “there has been no change in the South Boston gang war situation since his last contact. . . . the young group under the direction of Paul McGonagle and Pat Nee are still attempting to “eliminate” Donald Killeen and his associate James Whitey Bulger.”  Condon emphasized that Whitey felt if he did not make a move (actively defend himself) he and Donald would be killed.

Condon, who was experienced with handling informants felt that Whitey was being less than forthright and putting distance between them. He concluded: “Contact with this informant on this occasion was not overly productive and it is felt that he stills has some inhibitions about providing information . . . if his productivity does not increase, consideration will be given to closing him out.”  Whitey had a change of heart.

The murder of O’Sullivan had caused Whitey to panic. He went to the FBI seeking help. Meanwhile he must have figured that with his life under such direct threat there was no succor with the FBI. Only by stepping up his game could he survive. He decided to fight fire with fire, literally.

He was now going to fight back and that meant moving away from the FBI.  On September 10, 1971, two months after noting Whitey was backing off, less than four months after opening him, Condon closed him out saying, “Contacts with captioned individual have been unproductive.  Accordingly, this matter is being closed.”  

If Nee is correct, Whitey actively moved against the Mullens. He had lined up some gunmen to help him. Nee went in hiding in a Charlestown project. Whitey tracked him down. He had a bead on him but backed down because a young girl was there. Two other times Whitey and his cohorts came shooting at him and the other Mullens according to Nee.

Considering the limited space in which these combatants roamed and the hiatus between episodes it seems no one’s heart was really in the fight. The best I can figure is the total dead in this battle that has been ongoing for two and a half years was one combatant, Billy O’Sullivan of the Killeens, and one innocent victim (or if you consider this dust-up a war, one piece of collateral damage), Donald McGonagle, the brother of a Mullen. Less than a half-dozen had been wounded, some badly.

The one notable change that came from it happened to Whitey. Prior to these episodes there is no showing he carried a weapon. He was probably still in fear of having his parole violated. Now having felt his life was in danger, he has begun to carry to protect himself. Not only carry, he is now actively shooting at other people. At age 42 Whitey has yet to kill anyone but that is not for lack of trying.  

Re-Examining Whitey Bulger: The Early Years: Start of the Killeen Mullen War: Part Seven

The Bride Over
Fort Point Channel

I had to go back to Ralph Ranalli’s book Deadly Alliance which I recommended in the early days of this blog to refresh my recollection about an FBI report.  Ranalli wrote one of the earliest of the Bulger books which he put together after attending the hearing held by Judge Wolf in late 1997 and 1998.  It is a general overview by a good writer that is off the mark in several important areas. Since I started a more in-depth study of these matter and gained a greater insight, Ranalli pretty much puts out the black and white government and media mindset that everything relating to Bulger is evil, although he does suggest the FBI is no slacker when it comes to doing evil deeds.

It is little wonder because many of his sources are media people, prosecutors and their investigators. Ranalli lists his five most helpful sources. First is the FBI agent Robert Fitzpatrick who broke his solemn duty of protecting an informant’s identity by divulging to the media that Bulger was an informant.  He wrote an inane book full of inaccuracies. He clearly demonstrated he hated all things Bulger. His description of a meeting with Billy Bulger would border on the hilarious if it wasn’t written by a person who at the time was an Assistant Agent in Charge of the Boston FBI office which makes it tragic. The other four most helpful sources were two investigators of the Roger Wheeler homicide in Tulsa, Oklahoma, and two attorneys for the gangsters, Tony Cardinale, who represented Frank Salemme, and Ken Fishman, who represented Steve Flemmi, the latter two with obvious anti-Bulger biases.

My foray back into it was to again read memos from FBI Agent Dennis Condon which went to FBI Director J. Edgar Hoover. The first was in mid-May 1971. Hoover would die within a year on May 1, 1972. Condon told of a meeting with Whitey saying he was “employed by Suffolk County, Mass. in maintenance department.” Whitey had suggested to Condon he thought his life was in danger.

I mentioned earlier Whitey had left his janitor’s job with Suffolk after working less than a year back in 1967 or 1968. Condon reports him as being employed in it as of 1971. We do know he was kept on the payroll but not being paid up until 1978 when he was removed by John E. Powers. This resulted in a little brouhaha between two Southie pols, Powers and Billy Bulger.

My take on this is that Whitey left the job in 1968 but stayed on the payroll without being paid because he needed to report a legitimate occupation to the federal parole people.  I have a hard time believing he showed up for work up until 1971. By that time he was fully employed in the South Boston rackets by Donald Killeen.

The first part of Whitey’s early year ended when he left the courthouse job. The second part involved the so-called Killeen/Mullen war (K/M) over the South Boston rackets. This war has achieved legendary status in Southie even though it paled in comparison to the earlier Irish War between the McLean/McLaughlin gangs where it is estimated 50 were killed.

On the Killeen side were the Killeen brothers, Donald, Kenneth and Edward, Whitey, Jack Curran and Billy O’Sullivan; on the Mullen side were Dennis (Buddy) Roache, Pat Nee, Jimmy Lydon, Francis (Buddy) Leonard, Tommy King, Mickey Dwyer and its leader Paulie McGonagle. The Mullen gang was named after the place where they hung out: John Joseph Mullen Square at O and East Second Street, South Boston. (Books on Whitey call the gang Mullin, misspelling the name. One book by Carr doesn’t even know the name of the gang calling it the McGonagles.)

The K/M war which was brewing for a while broke out in 1969. Some suggest it started when Pat Nee’s brother Peter Nee was gunned down in April, 1969. But that had nothing to do with it. Peter’s death resulted from a beer induced argument among a handful of Southie guys in the Coachman bar on East Broadway.  A couple of them left angry and one, Kevin Dailey, returned and used a small .22 caliber to murder Peter and wound Bobby McGonagle. Because Peter was the brother of Pat Nee, and Bobby of Paulie McGongle, people inferred the killings were part of the K/M war rather than the booze. Pat Nee would hunt down Kevin Daily and seriously wound him on November 10, 1969.

The K/M shooting war began in July 1969 when Kenny Killeen shot Mickey Dwyer in the arm and bit off a piece of his nose at the Transit Café near Broadway in Southie. The Mullens went looking for Kenny seeking to get revenge. The die had been cast.  Whitey would be active in this war as we will see tomorrow.

The End of The Year Is Nigh Upon Us: A Few Disparate Thoughts About Things Other Than Whitey

I am anxiously awaiting the decision on Motel Caswell.  That case is pending in the Federal District Court of Massachusetts under the name United States v. 434 Main Street, Tewksbury, Massachusetts. It is the case where the federal government is trying to steal a motel from a guy who has had it in the family since the 1950s on the grounds there has been one drug deal in that hotel over each of the last twelve years. Russ Caswell knew nothing about the drug dealings or that the town had a problem with him. The town of Tewskbury and the DEA conspired together to take it from him. The town can get 80% of its value which is estimated around 1.5 million and buy new police cars or even get one of those armored SWAT vehicles. Russ in his 60s who was working his butt off trying to make ends meet will lose his livelihood and retirement.  I wrote about this before here.

The Annie Dookhan saga continues with felons being released from prison and the prosecutors, investigators, courts, and defenders demanding more money to do their jobs. It has sort of faded into the background other than seeing the AG has indicted Annie Dookhan for 17 counts of obstruction of justice and ten other charges including perjury.  Her lawyer complained her 6 pm curfew was interfering with her social life so it was extended until 10:00 p.m. Annie’s thoughtless, selfish and stupid actions are going to cost that tax payer well into the hundred of millions of dollars. The case is scheduled for a conference in February.

This is a difficult case to handle as a prosecutor. Annie will not want to go to trial so she’ll be looking to wrap it up with a plea. How do you decide what is an appropriate punishment so you can begin plea negotiations?  The AG will probably have to ask for the maximum amount of jail time which would be something like eight to ten years; defense counsel won’t be able to go along with that especially since his client is worried about her social life which will really take a beating if she’s sent to prison. I’m glad I don’t have to decide on it. I’d feel I was punishing stupidity and naiveté. No one is being deterred by anything done to Annie because no one could quite conceive of the same inane plan again.

Speaking of the AG, she’s going to have to decide quickly about the Tim Cahill matter  I’m sure if Cahill’s lawyers are on the ball they’re going to be pushing for a speedy trial. I don’t know how the jury split in its decision. I’m sure the AG knows that by now. If there were more than six for an acquittal, then she’d best throw in the towel. The case smells too political for a clean-cut victory. My advice, for what it is worth, let it go. Five weeks of trial spent on a minor felony that probably should never have been made into a crime is enough punishment for anyone.

While waiting for Whitey to get up to bat in June, we’ll probably be treated to the case against three probation officers John J. O’Brien, Elizabeth V. Taveres, and William H. Burke, III.  According to the Globe U.S. Attorney Carmen Ortiz said: this ““is just one step’’ in the ongoing investigation into a criminal justice agency that allegedly was run like a criminal enterprise.”  These people who were charged with racketeering “gave jobs to friends and allies of legislators” in order to  “to aggrandize power to themselves” and to increase the agency’s budget, among other things.” They weren’t doing anything for themselves. They put no money in their pockets or any of their friends in jobs. They were simply not alienating legislators in order to  get more money for their probation department so it could operate more efficiently and perhaps give people raises.

Using the rationale under which these guys were indicted, every department head looking to do a better job and hiring more people and paying the a decent pay is aggrandizing power to himself or herself. No wonder we had the Annie Dookhan scandal. Her department head, “The Buck Stops With Me” Auerbach, who quickly cut and ran when he realized the extent of the scandal, was trimming the staff fearful of being accused by the feds of “aggrandizing power to himself.”

The probation officers were engaging in patronage which happens to be the life blood of a democracy but under  US Attorney Ortiz it has become racketeering. I don’t see how she can stand with a straight face and say no one on her staff got a job because of a connection. It would seem to me that if these probation officers were engaged in racketeering then all the judges and legislators who put the arm on them to get their friends jobs should be indicted along with them.


Re-Examining Whitey Bulger: The Early Years Before Springing Back Into Crime: Part Six

Spring In The
Salt Water Marsh

The year Whitey gets out of prison in 1965 saw the end of the so-called Irish Gang war sometimes called the Boston gang war. Legend has it that it began on Labor Day weekend at Salisbury Beach in 1961. Like the Trojan War, it was all over a woman.

It was a brutal affair of mindless street killings where dozens of gangsters were gunned down on the streets of Boston and surrounding communities. It involved a Charlestown group of hoodlums headed by the McLaughlin brothers and a Somerville group of like-minded individuals headed by Buddy McLean. Each group had other local area gangsters join in the shooting from time to time. The North End (Boston’s mafia group) closely watched the battle but mainly sat on the side lines happy that its competition appeared to be decimating itself.

The cops seemed singularly ineffective in enforcing the law, although it was believed one or two were quite helpful to one side or the other.  Again legend has it that FBI Agent Paul Rico set up one hit. He then let the person who did the hit live in his cellar until the heat died down.

Well known characters as Frankie Salemme worked on the side of the Somerville gang while also free lancing for the Raymond L.S. Patriarca, the head (Salemme called him a “king”) of the Patriarca Mafia Family in New England. He’d eventually become a king’s man and a king in the Mafia.  John “Murderman” Martorano and Stevie Flemmi also got caught up in this free-for-all.

The gang war died when it lacked sufficient combatants. Most of the men involved were dead and few targets remained. All the McLaughlin brothers were murdered so their gang disappeared. Buddy McLean was gunned down so the leadership of the Somerville group fell upon Howie Winter.  Howie would buy a garage in Somerville called Marshall Motors which was located on Winter Hill. His gang would be reconstituted from the survivors and would be named after that Somerville location.

Whitey missed all the fun. He can’t take the rap for any of the murders during that time. He returned to South Boston which he’d have called Southie. He’d find that for the most part it had little to do with the Irish gang wars even though it is the most Irish section of the city. In Boston criminal lore there seems to have been Southie,the North End, and everyone else.

Whitey having got out with 11 years of his 20 year sentence still hanging over his head meant he was on parole and had to come up with a legitimate occupation. Word has it that he began to work construction which a lot of  gangsters do after serving time because of the unavailability of other opportunities. His years in prison had smartened him up and made him more disciplined and hardened. The opportunity he took in prison to read about crime and combat made him smart to the way of successful gangsters.

Outwardly it looks like he is going straight but he was probably beginning to develop an association with the guys who were running the rackets in Southie, the Killeen brothers. He wouldn’t have been that heavily involved but would have made enough money from his legitimate work and Killeen enterprises to allow him to delve into the pleasure of female companionship.

I suggest the idea that he was a gay hustler or child molester are all false creations by people who see in Whitey parts of themselves. All Whitey’s gangster buddies, even those who came to hate Whitey believing he had ratted them out for many years, reject those allegations. He listed his address as 41 Logan Way in the Old Harbor Village where his mother lived. Sometime in 1967 or 1968 his brother Billy found him a job at the Suffolk County courthouse sweeping floors.

By the way, I happen to know a person who at that time worked with Whitey. I think of that because his birthday is today. He had served as a Marine Corps officer for three years and was attending law school full-time days. He was working nights to make ends meet having a wife and two kids. It was a tough grind.

His memory is that Whitey worked at the courthouse slightly less than a year. He said he and Whitey (he calls him Jimmy) were “a two-man team sweeping the 7th and 8th floors where the DA’s offices were.” 

He goes on to say they “got along very well.  I liked him. He was a good worker and I was sorry to lose him as a partner and co-worker. He told me that the two things he did in prison were to lift weights so he could fight off any physical attacks, and to read books.  I thought he was quite intelligent and well-read, but also a bit scary.  I wouldn’t want him as an enemy.  He was strong as hell, very muscular in a wiry way, and, in my opinion, he was a genuine tough guy.   I was glad we got along so well.”   

I’ve provided a first-hand account of a person with unimpeachable credentials who worked with Whitey. He went on to be a highly successful lawyer. The person remembers it as being in 1967. He saw him again once in 1968 when he was in Southie with his wife and kids. He never met him again.

One author who has Whitey engaged in sordid sexual activities said he had a no-show job. He’s just plainly wrong yet many believe him. I guess that’s how false legends are created.

Other than a brother trying to help his brother go straight, no one who knew  Whitey would think he’d be happy being courthouse custodian all his life. It shows you the power Billy had back in the late ‘60s which was practically nothing if the best thing he could do for Whitey was to get him a job sweeping floors where he had to actually show up. Yet some people in the media suggesting that when Whitey was in prison in 1956 he and Billy were bossing around Father Drinan, a law school dean.


Re-Examining Whitey Bulger: The Four Seasons: Early Years, Learning Years, Boss Years, Gathering Years: Part Five

Dorchester Heights
South Boston

The Thirty Years of Whitey Bulger’s life I’ve broken into four parts. I’m doing this for the purpose of trying to determine for myself if Whitey is the worst of the worst criminals or has been given that identity by people who have ulterior motives in elevating him to a status far beyond what he deserves. The Early Years (1965-1972) and The Learning Years (1973-1977) that I spoke about yesterday ended when Howie Winter went off to prison. Then followed the Boss Years (1978-1988) and the Gathering Years (1989-1995)

The Boss Years as I indicated were made possible by his connection to the FBI. Whitey had been opened as an FBI informant on May 13, 1971 by Agent Dennis Condon. This was during the Killeen/Mullins gang war.  Billy O’Sullivan and Whitey were the two big gunmen in the Killeen gang. O’Sullivan, the father of six kids, was gunned down around midnight by three of the Mullins in Savin Hill on March 28, 1971.  This was allegedly in retribution for O’Sullivan having killed Donald McGonagle in November of 1969. Whitey was also thought to have been with O’Sullivan when McGonagle was killed.

I’d surmise that when Whitey saw his fellow enforcer for the Killeens had gone  down, he figured it was time for him to seek out some additional protection.  He probably sought out Condon to feel him out. Later when the danger passed or he felt more in control, he walked away from him. Four months later Condon closed him out. Also closed out, but still carried as an informant by Condon and his partner Agent Paul Rico was Stevie Flemmi who was hiding up in Montreal.

During this time both Rico and Condon were looking ahead to getting out of the FBI business so they needed to pass Stevie on to another agent. There were none in Boston who they figured would be a good fit for Stevie. In New York they knew there was a young agent from South Boston who they thought might fit the bill. They had to figure out how to bring him back to Boston.

Working with Stevie they set up Frankie Salemme who was living in New York City and who like Stevie was on the lam for indictments against him for killing one of the Bennet brothers and blowing up lawyer John Fitzgerald’s automobile. Connolly “bumped into him” walking down Third Avenue and arrested him. In 1973 Salemme was returned to Boston and Connolly came back a short time later.

It was then arranged that the witness who could tie Stevie into the bombing and murder would get out of town for a while. Stevie was told to come back in May 1974. He did and rejoined his old buddies the Martorano brothers who were then with Howie at Winter Hill. He’d find a new member there, Whitey Bulger.

Within six months all the charges against Stevie were dismissed and he was passed on to Connolly.  A little over a year later, Stevie would have convinced Whitey that he too could get on the gravy trail by becoming an FBI informant. On September 18, 1975, Whitey signed on with Connolly.

Much of this was going on outside of public view. It’s difficult to know how much the other members of Winter Hill resented the growing friendship between Stevie and Whitey. They acted as if they were  totally oblivious that they were teamed up with the FBI even though Martorano alleged Whitey told him Connolly was going to feed him inside information. It didn’t seem to bother them that of the seven leaders of Winter Hill who were equally involved in the Race Fix matter only five of them were indicted. It doesn’t say much for their collective mentality.

The Boss Years were made possible by the FBI and it was during that time that the FBI worked closely to ensure that Whitey and Stevie were well protected and also that the most egregious murders were committed, those beyond the pale of normal gangster-on-gangster type killings. When I examine those years more closely I’ll be able to better judge the validity of Whitey’s reputation.

The Gathering Years are the years when Whitey having sown his evil sits back and gathers in the results of his efforts. He’s made most of his money. He’s moving it around in varying locations in the U.S. and Canada. He seems to have gotten out of the murder business.  It was appropriate he’d have stopped doing the active murders after all he’s gone through six decades of living and is into his seventh. Moreover, it wasn’t necessary for him to do any heavy lifting.  He had his right hand man Kevin Weeks available for the strong-arm stuff.

These were also the years when Whitey lost his FBI protection, John Connolly retired in late 1990; DEA had pretty much destroyed his drug operations in South Boston; Whitey won a share of the state lottery; the Boston Globe had pretty much indicated he was an FBI informant; Stevie Flemmi started hanging around more with Frank Salemme who had been released from Walpole prison after serving 16 years, and Fred Wyshak was starting to do his probe into his past activities.

I don’t expect I’ll find much to enhance his reputation in the Gathering Years, but it remains to be seen.

Re-Examining Whitey Bulger: The Thirty Years, 1965 to 1995, Separated Into Segments: Part Four

I’m reviewing Whitey’s life to determine if his reputation as the most evil of criminals is justified rather than being erroneously posited to us by people who need us to accept it as true. I’ve run through his time up to getting released from prison in 1965 and suggested the next 30 years are the times within which he has made his reputation.  Prior to 1965 the worst that could be said of him was he robbed a handful of banks, was caught, and did nine years, some of it hard time, before he got out in ‘65.

As of January 1995 Whitey was a man on the lam for 16 years unconnected with the Boston scene. He traveled over parts of the U.S. finally settling in Santa Monica, California.  He lived in a multi-apartment building with his female friend, Catherine Greig, in a third floor walk up with the covered windows that blocked prying eyes from looking in and the inhabitants from seeing out. They lived with little contact with others in a hermit-like existence, hardly one step up from being confined in a cell with conjugal visits.

He was imprisoned by the money hidden in the walls ever fearful of its loss to criminals like himself limiting his ability to make forays from his hole-up. The pillow he put his head on never gave a decent night’s sleep. He depended on an arsenal of guns including military-type weapons that he would never use to maintain what he thought was his freedom.  Now he probably sleeps better at night in the Plymouth County jail than he did in Santa Monica where he allegedly stayed up at night peeking out the window at threatening spectres.

I divided these years from 1965 to 1995 into four segments because certain factors exist that make them somewhat easy to segregate out although there may be a small amount of overlapping.  The four periods are in sum: The Early Years, 1965 to 1972, 8 years; The Learning Years, 1973 to 1977, 5 years; The Boss Years, 1978 to 1988, 11 years; and The Gathering Years, 1989 to 1994, 6 years.  All the murders charged in the indictment occurred in the learning years 11 murders, and the boss years, 8 murders.

The Early Years period is the time he got out of jail up until the time he became involved with the Winter Hill gang. These seem to be years of figuring out what he will eventually do with his life.  He’s on parole so he has to watch his step. He’s out of prison at age 36 and has yet to have murdered anyone unlike Martorano, Flemmi, Salemme, Nee, and some of the Mafia people who were veteran murderers by his age. Whitey may have begun his first murders around the time he turned 40 in 1969 when he became involved in the Southie Killeen/Mullen gang wars.

The Learning Years from the time White joined Winter Hill in 1972 up through 1977, a period of about four to five years when he’s an understudy. During this period it was clear that there was one boss of Winter Hill and that was Howie Winter. Howie who took over from Buddy McClean had two close associates, Joe McDonald and Jimmy Simms. Next to associate with them were the Martorano brothers, Murderman John and Jimmy. Whitey was somewhat down the line.

Eleven of the murders alleged in the indictment against Whitey occurred during this time of the learning years when Whitey was somewhat down the command level of the group.  Howie, who was in charge, and who was in 2012 charged with extortion has never been charged with any of these murders. The first, Michael Milano, occurred in 1973  and the last Richard Castucci happened in 1976.

According to Pat Nee, Howie had not even heard of Whitey in 1972 when outside interests were trying to establish a Southie gang war truce. Whitey didn’t walk into that group of murderers with much status despite what we are told now.  It was probably not until 1974 when Stevie Flemmi returned from his years on the run and Whitey teamed up with him that he slowly accrued power.

Howie ran the operation through 1977. Howie was indicted for extortion by prosecutors in the Middlesex DA’s office under the oversight of our new Secretary of State, John Kerry. He and Sal Sperlinga went to trial for trying to force pin ball machines, of all things, into some bar rooms through threats and intimidation. Howie was convicted and got 18-20 years in prison. That left room at the top.

Although Whitey was not in line for the big job of boss, the race fixing case in 1979 would cause Joe McDonald, Jimmy Sims, and John Murderman Martorano to flee town. Jimmy Martorano who was also indicted in that case was already in prison for extortion.

The whole Winter Hill Gang could have been put out of existence had both Whitey Bulger and Stevie Flemmi been indicted in the race fixing case. Whitey with his record would have been convicted and gone back to prison for what I have called his boss years. However that was not to be.

FBI Supervisor Agent John Morris and FBI Agent John Connolly went to AUSA Jeremiah O’Sullivan and asked him to keep them out of the indictment. They told him these vicious gang leaders were FBI informants. O’Sullivan would later say he didn’t keep them out because they asked but the facts seem irrefutable that he did accommodate Morris and Connolly.

Whitey and Stevie Flemmi’s ascension to the leadership of the Winter Hill Gang can be directly attributed to the FBI and US Attorneys office.


A Time For Family And Friends: A Wish, A Thought and A Thanks

Merry Christmas to those who celebrate the birth of Christ; Happy Holidays to Everyone and Best Wishes for the New Years.

When the  country was established one of the greatest ideas of the Founding Fathers was the way to deal with the issue of religion. It was the recognition that you have to stay out of a person’s thought process. I should be able to believe X and practice the doctrines of X as long as they don’t impede the ability of others who believe and follow the practices of Y and Z.  However, there are some things that you are not allowed to do no matter what you believe which may endanger the public health and welfare of all.  These founders recognized they could not have created a country if one religion was going to dominate over others.

I do have to think that one thing they could never have foreseen is that the nine justices on the highest court of the land would be members of religions that were not present at the founding. These are my thoughts around Christmas where many celebrate the holiday and many others don’t and we have the constant Christmas wars with some wanting more displays of it and others finding offense in the displays. Fortunately it is played out in non violent ways and is quickly forgotten a day or two after Christmas except for the ongoing court battles.

Whitey’s spending his second Christmas in his later years in jail. An article in the Globe today talks about the police concentrating their efforts to crack down on the drug dealing in South Boston. It still thrives despite Whitey’s absence from the scene. Drug dealing and addiction is one of those things that rears its ugly head and survives no matter who is around.  We’ve seen that in our war against drugs where one leader of a drug cartel is taken down and within 24 hours there is a new leader. I suggest blaming Whitey for the drugs in South Boston, which existed before his rise to power and still continue today 18 years after he left the scene, is another one of those media created fictions that enhance Whitey’s status.

Blogging will be light for a couple of days.  Thanks to all who have read and participated in the blog. 2013 should be an interesting year.  When I pick up I’ll start in 1965 and try to break down the next 30 years into some segments.

Re-Examining Whitey Bulger: A Look At His Early Criminal Life And Those Times: Part 3

If I Had The Wings
Of An Angel

How bad is Whitey?

When he’s arrested for the three bank robberies, the Boston Globe on March 5, 1956, noted Bulger first came to the attention of authorities in 1948 when he was arrested in Southie for an attempted criminal assault. What happened after that is pretty easy to understand if you knew how things operated back in those days. I happen to know this because my father was chief probation officer in Dorchester. Things like this couldn’t happen now because of all the formalities we’ve introduced into our system.

When a kid like Whitey was brought into the court either the clerk or chief probation officer would pull him aside and say, “look sonny, you got a choice, jail or the service.” They’d give the kid a few days to make up his mind. If the kid opted for the service they’d destroy his criminal record. My father told us on many occasions that these men came back and to thank him for what he did. They were able to get on jobs where a criminal record would have disqualified them.

Whitey went off to the Air Force where he served four years. For restless youth living on the cusp of a criminal life the service was a growing up time with its discipline, the structure teaching responsibility, and the chance to work and play with other Americans. That is the true melting pot where the ingredients have to blend and the sharp edges of prejudices are toned down. Most came out with a different attitude and went on to college and a law-abiding life. Then there were the Whiteys.

Again the Globe has an article on July 1, 1953 telling about the Boston cops looking for guys doing tailgate jobs. A couple of detectives watch a car following a beer truck. When the beer truck pulls up at the corner of Mass Ave and Boylston Street the driver gets out and enters the store. The car pulls up behind the truck. Its two occupants jump out and start opening its rear gate planning to hoist a few cases of beer and the cops grab them. In their car they find the loot from a truck that had cigarettes stolen from it the day before.

Whitey age 23 and Dick Kelly, 30, of Roxbury are arrested. Whitey’s hardly had time to change out of his uniform than he’s back committing crimes. He manages to avoid arrest until 1956 for the Hammond, Indiana and Pawtucket, Rhode Island bank robberies. Later he is charged with one he did in Melrose, MA.

The Globe reported on January 7, 1956, the FBI announced it was looking for him for the Indiana robbery. It noted he is sometimes called Sonny or Whitey. Of interest, “Two women acted as lookouts in the escape car, according to the FBI. They are about 20 years old.” 

I note that because the FBI had the option to charge those women with involvement in the robbery. When Whitey was arrested on March 4 the FBI agents suggested to him that if he quickly confessed to the robberies and told his girl to cooperate with the agents that they’d give her a pass. She did. She was never charged. Whitey took the hit and it came fast.

Whitey is arrested on March 4th. He’s held in $50,000 bail on the 5th.  A hearing was then scheduled for the 19th.  The next we hear is that on May 5, 1956, Billy O’Brien. 30, of Dorchester is arrested up in Vermont. He pulled the Melrose robbery along with Whitey.

No doubt none of these guys got their Miranda rights. Miranda didn’t come in until ten years later. I doubt they had lawyers. Back in those days for guys who confessed it was a quick shuffle off to the can.

Look at the time line. On June 21, three and a half months after he was arrested Whitey pleads guilty to the three robberies. He gets 20 years. Billy O’Brien a month and a half after being arrested is off for eight years to prison. Justice then was like it should be, sure and swift. Whitey’s 20 years gives lie to all those who suggest he was some type of informant.

Whitey did nine of his twenty years in prison. Not much to tell about there. He had a hard time adjusting being suddenly dropped among some of the worst people our nation has produced. He fought the system and lost every time in his early years. He finally settled in to doing his time. May have gotten some years knocked off for being an LSD guinea pig. But mostly did hard time, Alcatraz wasn’t known for its amenities.

For all the influence that the media would have us believe he was supposed to have among so many powerful people, it certainly didn’t help him out much during these years. He was just another con biding his time. When so many in America adulate these gangster’s lives they should open their eyes to the less than glamorous life of being locked-up. Prison is prison. It’s best avoided.

Whitey gets out of prison in 1965.  Thirty years later he’d flee when the feds indict him for racketeering.  (to be continued)


Re-Examining Whitey Bulger: Are We Being Snookered By Others? Part 2

North Of
Carson Beach

The little lie about Whitey being an informant adds to the picture of his evilness. Not content with fabricating this conclusion, the media then reached out for another gangster to tell him Whitey informed against him back in the Fifties.  The method of doing this was eye-opening.

But what tipped the scale was the scurrilous attack on Father Drinan, the Dean of Boston College Law School, who Whitey reached out to in the first few months after starting his 20 year prison sentence. Then the media contacted past associates of Father Drinan and suggested he was somehow in league with Whitey duping these naïve people into expressing horror that Father Drinan had so acted. All of this press hysteria spreading and cementing a belief in Whitey’s evilness and the suggestion that it was aided and abetted by members of the Catholic clergy showed its ability to turn a piece of straw into a castle when it came to Whitey.

I began to sense something with the whole Whitey story is not right. The over-the-top attack on Whitey was made clear when Dick Lehr who posits himself as Whitey’s biographer absurdly opined that the Bulger  brothers (Billy was then in college) were making a “beachhead” with Father Drinan. When a simple act of a young man reaching out to a priest for help is turned into a conspiracy to set up an evil empire, I had to stop and ask whether I was being snookered.

Maybe it wasn’t the light tapping of a far off drum but a big bass drum banging boldly on my brain that made me stop. I began to think that if these people could make such serious errors out of so simple situations what have they done in the past with their writings. There is almost total unanimity that Whitey Bulger is Public Enemy Number 1. He was put on the FBI’s Top Ten Criminals next to Osama bin Laden. How did he ever get to deserve this notoriety to climb so high?

I never stopped to ask this. It was only when I saw this extremely biased reporting that I have to question my basis for believing he is so infamous. Up to now I’ve just accepted it. I figured J.W. Carney was giving it a good shot but we all know his client is Mr. Evil but even if so, being magnanimous, I’d suggest he deserved his day in court and a fair trial, if one is possible. One of the persons who wrote a comment to me suggested Whitey should be taken out and shot. I understood where she was coming from and hardly winced at her suggestion. I’ve been there myself having accepted this common theme: Whitey is the worst of the worst.

Don’t get me wrong, I’m far from suggesting Whitey is Mr. Clean. I do happen to believe in the idea of birds of a feather and all those old saws, you know, you are judged by the company you keep. Whitey sure dwelled with a hellish group and as sure as the day is long one must accept that so many murders were committed by his associates that he must have been involved in some of them. But that doesn’t make him a genius among criminals. Rather, just another low life, exactly like the people the prosecutors are now utilizing as witnesses and who have, unlike Whitey, bragged about their exploits in books and on television.

I’ve been told how bad he is but I have not really examined the evidence to support the propaganda I have been fed. I’ve seen how it is in the interest of some to build up his reputation like a house of cards with one story building on another. I recognized I am fully capable of making my own determination as to how bad he really is. I have to stop and ask what is the basis am I using to make him so infamous? What did he do to deserve this great infamy? What is our evidence that Whitey is a mythical figure rather larger than life when he may be just a run of the mill cold-blooded killer.

I am going to try to jettison all the prior beliefs I have had pounded in my head by the media and story tellers about Whitey. The media’s false take on what happened in 1956 enlightened me. It demands that I go back to see what I can learn of Whitey’s criminal life after he served his time on the Rock and was released from Lewisburg federal prison in 1965.

I need to put it in context of the gangsters with whom he was involved. I have to understand it in relation to what was happening in those times. In doing this I want to see what other people knew or should have known about Whitey at the time. For instance I have suggested that FBI agent John Connolly had to know he was murdering people. I have to find out what basis and sources I have used to conclude that. Are they reliable or trustworthy in light of what I now know?

Many have suggested Billy Bulger should have known his brother was a murderer. I have to examine whether that is true. I have to ask who knew and when did they know Whitey was murdering people. How widespread was that belief. What about the gangsters he hung around with? What was believed about them back at that time?

It is important to see how Whitey fit into all the murders in relation to his fellow gangsters. I believed him Father Evil because people needing to make him larger than life for their own gain told me he was that.  It is time for me to examine the matter with a more prosecutorial eye as if I were preparing the case for trial.  I’ll then see where this  music takes me.

(continued tomorrow)

The Start Of A Re-Examination Of Whitey Bulger: What Is The Source Of Our Belief He Is Ichiban Criminal?

I know this will sound odds from a guy who has a site called “” Obviously, I selected that name because I knew of the great interest in the master criminal Whitey Bulger, the Professor Moriarty of our time, throughout my country if not internationally. I bought into the idea that Whitey was this unique criminal, the Napoleon of crime, who was the genius of all things bad and despicable. I would have been very happy to leave it that way had I not become more involved in this matter.

As I dug into these things about Whitey certain items I discovered forced me to reconsider many of my previously held beliefs. More and more I began to wonder whether I have been sold a pig in a poke. Have I and a multitude of others been led on a merry chase down the wrong road because it became in the best interest of some to to divert our attention from the truth of the matter? Am I moving with the herd in a stampede in a headlong plunge into a deep canyon of ignorance and convenience?

These little voices of dissent that arise from some of the corners of the Whitey story seem not to be heard by most others. Why is it I am having some doubts and slowing down when all others seem to be of one mind rushing ahead? What should I do? Go along or question my assumptions by reexamining them. It reminds me of what Henry David Thoreau said many years ago: “If a man loses pace with his companions, perhaps it is because he hears a different drummer. Let him step to the music which he hears, however measured, or far away.

The tune that I’ve been faintly hearing tells me I’ve been neglecting the motive evidence. As a prosecutor I knew that motive was not a necessary element of any crime but having done many arson cases I knew that without it I had no chance of winning. The motive into making one’s citizens believe that another group is less than human by blackening it in such a manner that its citizens are repulsed by its existence is to prepare the people to war against or commit genocidal acts against that group.

I was being asked by this tapping if there is a motive in making Whitey into something he is not. Who benefits by making Whitey numero uno, or as we used to say in Japan, ichiban among American criminals. Before I went on with the mob, I wanted to examine this.

One group is making a good deal of money off of vilifying Whitey and Billy Bulger by writing books. The more infamous he becomes, the more they sell their wares. There is profit to them in depicting Whitey as bad to the core. If he is merely just another hoodlum, who cares about him or his life?

Another group is the vicious gangsters who have been getting good deals because they, like the book writers, are trading off of Whitey. These men get more than money, they get the gift of freedom. It is in their interests to push Whitey up to the top of the criminal ladder.

Obviously the prosecution team has made deals with these devils so it serves its interest to keep Whitey as the Beelzebub of our age. The families of the victims benefit. When one gangster is murdered by another little care. When it is the Devil himself doing the killing the perception of the killing changes. Especially when it’s done in league with a federal agency such as the FBI.

The FBI benefits by him being the master criminal who outwitted them rather than having us look at its system of operation. Best have eyes on Whitey and not on its internal workings which if exposed would cry out for change. Then the courts following the clamor of the public have all bought into this picture of Whitey as evil incarnate.

What if they are all pitching the wrong story for their own ends or because they got hoodwinked and can’t admit it?

I’ve been caused to pause in my thinking which made me attuned to the taps of that far off drummer because of the articles I recently read in the media which were written over the summer. They took a couple of  simple actions by Whitey and twisted them into something quite macabre. These happened in 1956 when he was arrested for armed robbery and first sent to prison.

His arrest occurred because he and another were ratted out by a fellow robber. In order to save his girlfriend from going to jail, Whitey admitted his participation in the robberies and told his girl to cooperate with the FBI.

Howie Carr (who has made a six figures spouting falsehoods such as maligning Whitey as a male prostitute cruising the Combat Zone without a shred of evidence) along with others in the media gleefully wrote that Whitey’s action in confessing made him an informant for the FBI as far back as 1956. I knew nothing could be further from the truth.  Why this little lie?

(continued tomorrow)