§28: Re-Examining Whitey Bulger: The Learning Years: John Connolly’s FBI Journey

The Prosecutor’s Galley – All Pulling Together To
Get Whitey

I would suggest the most logical way to examine the question of how Whitey learned Stevie Flemmi was an FBI informant is to look at it from the point of view of the FBI and more particularly the Rico/Condon team who were handling Stevie and John Connolly, who would become his handler.

First a few words about John Connolly and the Bulgers. Connolly was six and a half years younger than Billy Bulger and 11 years younger than Whitey. Connolly lived in the Old Harbor Village housing project where the Bulgers lived until he was 12 years old. I also lived there at that time.

When Connolly moved out Billy would have been 18 1/2-years-old and Whitey 23. The age difference between them makes them knowing of each other, never mind friendly, as so remote as to lean heavily on the impossible. The project teemed with youngsters in those days and friendships beyond a narrow age range or court-yard  or school level were non-existent.

John Connolly entered the Jesuit Boston College in 1958 after graduating from a Catholic high school in Boston. In those days above average students in the Catholic high schools were the farm team for BC continually filling its classes. The idea that Billy, who was in law school, had anything to do with Connolly getting into BC makes no sense. Connolly would have gotten in with his Catholic high school diploma and a recommendation from one or two of his high school priests.

I’d suggest Billy first knew of Connolly as one of the younger kids who hung around L Street. Billy was the head life guard there. I’m told that Connolly was one of the younger life guards. Whether he was or not, the chance of them knowing each other around that time from the summers when all are out playing on the beaches and sitting around Castle Island are pretty good. Did Billy inspire Connolly to go to BC?  I have no way of knowing. If they knew each other he may have inspired him but not so much as many others such as his parents, his teachers and contemporaries who were also going off to college.

I should mention L Street was a huge bathhouse with athletic facilities located on Carson Beach that was frequented by every aspect of society from the very good to the very bad, the cop to the crook, the priest to the sinner, the prize-fighter to the pacifist. It was the home to city folk, especially in the summer. It had a little widespread fame for the L Street brownies. Overall it was a motley assembly that liked to hang around there, play hand ball, work-out, run the Strandway and lie in the sun. All were welcome and all types came. Kids gawked at wise-guys like Frankie Salemme with reputations. It would have been common knowledge who was who.

Connolly graduated in 1962, spent some time in Suffolk law school, and  ended up teaching school. He got into the FBI because his father knew the Speaker of the House of Representative who wrote a letter to J.Edgar Hoover on his behalf. Bulger, despite what you may have heard elsewhere, did not have the same influence as the Speaker. He was  one of 240 members of the Massachusetts House of Representatives and not in a leadership position. He would not have nearly enough influence to cause Director Hoover to who was in his 44th year leading the FBI to do any particular favors.

Writers have greatly over stated Billy’s influence at the time in order to hint at some questionable relationship between him and Connolly as if Billy was grooming Connolly to be Whitey’s handler down the road. So much of the inferring of early sinister connections between Billy, Connolly and Whitey is just so much rot yet it shows the mindset of people intent on presenting a false picture.

The start of Connolly’s FBI career was somewhat unusual. He joined in the fall of 1968 and was trained in Washington, DC.  He joined at the height of the Vietnam War when the need for warm bodies to keep up our force of over five hundred thousand troops in that Southeast Asian country was at its greatest. The government earlier that year change the draft exemption for teachers. I’ve suggested that was what motivated him to join.

He was assigned to Baltimore in 1969, to San Francisco in 1971, to New York City in 1972, and to Boston in 1973.  My understanding was that FBI agents stayed in their assignments for three or so years before moving on. I may be wrong. Even so, he seemed to have moved frequently and was back in his hometown a lot sooner than one would expect. Boston was a choice office and he had to have jumped over others to get here. The FBI was undergoing a great upheaval after J. Edgar Hoover died on May 1, 1972, so Connolly could have taken advantage of that.

I think it more likely that Speaker John McCormack from South Boston, his father’s friend, could have been helpful in moving him around. He was Speaker from January 3, 1963 to January 3, 1971. Even after he left DC he still had powerful connections and helping a constituent change FBI offices would not require much heavy lifting.




  1. William M. Connolly

    Matt: I’ll check the yearbooks. But I have a personal recollection of seing John at BC and cousin Jim remembers sitting beside him in 1965. So, I’ll stand corrected if I’m wrong. Maybe he was taking graduate courses! As far as the draft, I lived through those years and remember that if you got to age 27 you were home free. I’ve researched the Selective Service regulations/policies during those years and am convinced the draft eligible were from 18.5 to 26; everyone signed up for the draft at 18. My point is that based on all the information I’ve researched, Connolly was 27 to 28 years old in 1968 and was no longer eligible for the draft.
    There were plenty of warm bodies between 18 and 23 in 1968, as the baby boomers born in 1945-46 were turning 18 in 1963.
    I was baptized at St. Monica’s and had my first communion at St. Williams, but I worked two summers in Old Harbor and Old Colony when I was about 16-17. I remember Jim worked at L-Street.
    I thought I got the date 1950 from Black Mass.
    Rest assured: I don’t have all the answers; I’ve got more questions than answers. It’s good that we all keep an open mind on all these things.

    • Bill:
      Check the year books. No one can be blamed for not remembering things correctly from the forty years ago. Isn’t that why we have a statue of limitations that recognizes memories do not improve as years pass. Yesterday I went to a restaurant I had been to last year. I swore the entrance was off one street and not the other. I was wrong. A person with me swore that there were certain things in the salad bar that she remembered from last year that the restaurant staff said were never part of it. She was wrong. That was only a year ago.
      You base your memory of the Vietnam draft that if you reached age 27 you would be safe. Maybe that was the case but maybe in 1968 as you saw the war heating up and seeing the generals asking for more bodies you wouldn’t feel that safe. What’s that saying, “better safe than sorry.”
      The problem with the Whitey case is relatively simple. People are pretending they remember things from 30 plus years ago as if they happened last week and those with these great memories have been induced to remember “correctly” and given great benefits when they do.
      As far as agent Connolly is concerned, as you know I’ve never been a big fan of his. But I do agree totally he should not be in prison and it has reached the stage where his imprisonment if considered fairly would be considered outrageous. I will say though that he has not helped himself with his out-of-court comments to the newspaper people who will then write them down and put them in a false context. I understand his frustration at still being unjustly punished but the newspapers will never help him and he should stop giving them fodder to use against him. His remedy has to come in the courtroom and you know what, he’s not pursuing that avenue.

  2. William M. Connolly

    I wrote in the last sentence, “before the draft”; I meant “before the lottery”. The first year the lottery was instituted (69?) everyone from age 18 to 26 was eligible for it.
    Another wrinkle in the draft back then as I remember it was that if you got a deferment (let’s say a 2S deferment for college) once you graduated college, you went to the front of the list before those who received no deferment. All local draft boards were told to draft people starting with the oldest (26) down to the youngest (18.5) until they had filled their quotas.
    I know guys who were immediately drafted when they took a semester off from college. I know many guys who were immediately drafted after graduating from college. The only guys over 26 I know who were drafted were physicians.

    • Bill:
      In 1968 things were hot, teachers were in the mix, whether Connolly decided to join the FBI to avoid the draft only he knows. You’re looking back and explaining things from the perspective of what happened. In 1968 no one knew that was going to be the height of our involvement. The military wanted more and more bodies to send off to war as it always does.
      Let me refer you to an article dated February 28, 1968 that says the chairman of the joint chief of staffs reported: “To meet the new enemy threat and regain the initiative, according to Wheeler, Westmoreland would need more men: “The add-on requested totals 206,756 spaces for a new proposed ceiling of 721,756.
      As I pointed out the draft rules were changed in 1968 to make teachers eligible and we were scouring the land looking for warm bodied. Connolly had lost his deferment and was single. Everyone was worried. I had already done my three years in the Marines and thought if things kept up I’d be called back. During that summer I got a certified letter from the Department of the Navy that I chased all over town to find because of my sense of desperation that I was going to be called back up.
      If, as you say, Connolly had served in the Army he need not have worried. If he hadn’t then at that time he had good cause. Don’t fall into the trap of not putting yourself in the shoes of the people as things happen. A lot of good guys didn’t want to go off to Vietnam to end up with their names on the wall. If Connolly took the FBI as a way out that was his choice and many would say it was a smart choice. After all, the guys who fled to Canada were eventually pardoned and achieved somewhat of a heroic status in our topsy turvy America where history is often interpreted looking back and deciding what feels politically correct. I would say though that a lot of guys from Southie picked the other way.

  3. Johnny Depp? Who will play Martorano? One of the Dorchester Wahlbergs?


  4. William M. Connolly

    Double check your facts on this: First, John Connolly was at BC when I was there, from 63-67. Second, John was in the same year as our cousin Jim who graduated in 1965. Jim confirms they were in many classes together. That would mean he entered BC in 1961. Third, John was born in December 1940 (wasn’t he?) and his family moved out of the projects in 1950. So unless they moved out late in December, John would have been 9 when they moved out. Whitey joined the Air Force in 1948 and served for four years. The Black Mass stories about John and Whitey interacting in the summer of 1948 are bogus on several accounts: John is still seven years old; Whitey is in the service; Whitey is over 11 years older as you said; Black Mass says John Connolly “tagged along” with Whitey going to Mass and with Billy going from Mass at St. Monica’s. How many six or seven year olds “tag along” with eighteen year olds. Did Whitey even go to Church? I tried to nail the dates down on these things. I even wrote the Air Force asking for a copy of Whitey’s service record; apparently you have be next of kin to get this; from what I gathered Whitey joined up in April of 1948 and did basic training in Kansas, a sixteen month tour that would have him absent during the summer of 1948. None of this is set in concrete. When JOhn joined the FBI in 1968, he was twenty-seven, beyond the draft age. Draft eligible people were between 18.5 and 26. At 18, all males had to register for the draft.
    P.S. Even if John moved out of the projects in the summer of 1952, he would have been 11 years old; Whitey was still in the Air Force and would have been 22. Whitey did four years in the service. Add in the nine years Whitey was in prison, and add in the fact that when Whitey got out, John had just graduated from BC and was teaching for a few years—teachers were exempt from the draft—-then in 68 JOhn joins the FBI, gets married, gets stationed in New York, then you can reasonably conclude that John’s contacts with Whitey from the 1940s through the 1960s up until the time he recruited him were virtually non-existent; he probably had as many contacts as I did: none. Neither you nor I ever tagged along with Whitey to St. Monica’s. The 6.5 year difference between John and Billy also make the likelihood of any meaningful contact extrememly remote, until mid to late 1960s when John along with 100 hundred other young people probably did some volunteer work in Billy’s campaign. I remember many of the guys in Savin Hill in their early twenties used to help local politicians like Bob Quinn in their early runs for office.
    I always thought that John Connolly who graduated from Christopher Columbus in 1958 when he was 17 (most of us were 17 when we graduated from high school then) did two years in the Army and that was why he entered BC late in Jim’s class.
    So, these are all facts you could double check. I’m 100% certain what the draft elibible ages were then; there were exceptions for physicians who could basically be drafted at any time, and many were after they finished their medical school studies. Dick Cheney was draft deferred first because he was married; then secondly because he had children. By the time he was 27, he was too old to be drafted. At least, those are the facts as I know them.
    We’ve had this discussion about the Selective Service Administration before. The Selective Service’s enabling act allowed the SSA agency to draft anyone up untill the age of 34 or so during a national emergency. But like all agencies, the SSA issued regulations pursuant to its enabling statutes. The regulations in the mid- to late 1960s (before the draft) allowed local draft boards to draft males between the ages of 18.5 to 26 for the Vietnam War.

    • Bill:
      I had a source go to the BC yearbook for ’62 and saw that John Connolly was in that class. I don’t know if you ever go to BC but if you do my source told me that in the first building on the right off the Commonwealth Avenue entrance has copies of the old year books. You can check that out. Never heard Connolly was in the Army. Would be happy to reconsider all that if he were. I have no problem admitting my mistakes on this journey to learn the truth.
      I don’t know where you got the date 1950 that John moved out of the project, I’ve read it was when he was 12 years old. John was born in August 1940 – he’d bee a couple of months shy of 18 getting out of high school. Black Mass had Connolly tagging along with Billy and as a great friend of Billy’s. As you may hae known I lived in the projects during the time John Connolly and the Bulgers lived there. I didn’t know any of them although I and all my friends were afraid of a kid named Whitey who I’ve assume was Whitey Bulger although I never laid my eyes on him. All anyone knew were boys around their same age in their court, and if you don’t know what a court is then you won’t understand any of this growing up stuff I’m talking about.No doubt in my mind the Bulgers did not know Connolly in the projects. I didn’t know you made your First Communion at St. Monica’s. I know a guy named Jim who was a lifeguard at L Street who tells me that Billy and Connolly met during that time because they were both lifeguards, of course that was long after Connolly left the project. Even if they weren’t, Billy was a politician as you said and like with the local politician in Savin Hill Bob Quinn everyone knew him and he, as all good politicians do, knew all of us but we didn’t hang around with together. I have read that 1968 was a good time for the FBI to get recruits because Vietnam was waiting for so many.

  5. Where “FBI agents stayed in their assignments for three years or so before moving on”, why was agent Connolly allowed to stay working out of Boston for so long?