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.