Whitey’s Handler John Connolly – His Early Life Up To College

Connolly was  born on August 1, 1940.   Billy Bulger born February 2, 1934.  He’s six and a half years older than Connolly.   Whitey Bulger born September 3, 1929.  He’s about 11 years older than Connolly.

These dates are important to flesh out Connolly’s connection to the Bulgers in his early years.

If you lived in the Old Harbor Village in the years that Connolly and the Bulger brothers did, you’d know each age group was sated with playmates.   Families with four, six or even eight children were not uncommon.  When you walked out your door you had tons of friends your own age to play with.  It would be extremely unlikely for someone from one age group to know another even a couple of years older or younger except through siblings.

When Connolly turned eight years old, Billy was off to high school and Whitey was off to the Air Force.  Billy spent the next four years studying hard.  According to a Boston Globe article on him, Billy was given the nickname “Beam” because the light in the room where he studied remained on late into the evening on school nights.  Whitey would have left the area as part of his service to our country.

Connolly and his family moved out of Old Harbor Village in 1952 to City Point, another section of Southie.  That year Billy graduated from high school and Whitey was discharged from the Army.  It is unlikely Connolly knew the Bulger brothers while he lived in Old Harbor despite stories otherwise.  If he knew them it was only in passing, he certainly had no relationship with them.

Connolly’s father was known as Galway John because his forebears came from Galway in Ireland.   He worked for Gillette for fifty years.  Speaker McCormick in a letter referred to him as “a lifelong personal friend”.

Connolly went to Columbus High School in Boston’s North End.  It was a Catholic High School staffed by Franciscan priests.  He graduated in 1958 and went off to Boston College (BC).  As a Jesuit college BC was pretty good at taking kids from Catholic high schools in those times before Doug Flutie came along.

It’s rumored that Billy helped get him into BC.  That’s pretty far fetched.  Billy was starting BC Law school.  He was in no position to  help anyone other than himself.  Whitey was out of town residing in the United States Penitentiary Atlanta.  Connolly had enough pull through his family or school connections, if he needed any, without implicating the Bulgers.


  1. How much time did it take u to post “Whitey Bulger,
    John Connolly, Billy Bulger – The Early Years | The Trial of Whitey Bulger”?
    It has got a lot of excellent information and
    facts. Thanks ,Mary

    • Mary:
      I have no way of estimating the time. I am still working on it. I’ve found some of my original ideas were in error and that there are so many facets to this story I keep running into another one. I think my biggest surprise is how much false information has been put out and how it has taken a life of its own that to challenge it is difficult. Thanks for your nice words.