In 1960 Billy Bulger got married and decided to try politics. He ran for a vacant seat that opened in his Southie district in the Massachusetts House of Representative. He won. He got reelected to four more terms before running for the vacant senate seat from his district in 1970. Connolly lived in and hung Billy’s district. He was a life guard at the L Street bathhouse. He taught for a while at Southie High. It was probably during the time Billy was in the House that Connolly got to know him. It is likely he would have worked in his campaign doing things as holding political signs especially when Billy had little opposition There relationship would not have been that close. Billy was not a hang around type guy. When he wasn’t at work he was home with Mary who by 1968 when Connolly went off with the FBI had seven kids eight years old or under.
Connolly graduated from Boston College in 1962. He entered Suffolk Law School but dropped out. He then taught in the Boston Public School system.
JFK a Boston boy had been elected in 1960. The country still had a draft but those with connections seemed to be able to avoid serving. By 1962 names like Laos, Thailand and especially Vietnam were appearing more and more in our newspapers. JFK had dipped the country’s toe into Vietnam. That may have been a Catholic vs Communist thing. Ngo Dihn Diem was Catholic and firmly anti-Communist which would have appealed to JFK’s father, Joe.
Diem was assassinated on November 2, 1963 when JFK okayed an Army coup. JFK was assassinated on November 22, 1963. LBJ, with his phony Silver Star which he always wore on his lapel that was given to him by General Douglas McArthur for his heroism (he sat in an air plane that was in a combat zone) decided to plunge the country totally into Vietnam.
Why all that is important is that it changed Connolly’s life. At the end of January, 1968, the Tet Offensive took place. During the week February 11 – 17, 1968, 543 Americans were killed in action and over 2,500 wounded. At the end of March LBJ announced he was increasing the number of authorized troops in Vietnam to 549,500. In 1968 the highest troop level of 536.100 of the Vietnam War was achieved.
The country needed more and more men to fill the ranks. Draft boards were running short of their quotas and those whose connections kept them out of the service were now at risk.
I assume Connolly had no physical reasons why he did not serve in the armed forces. It was a mystery to me how he could have avoided the draft. Then I came across a February 17, 1968, article in the Milwaukee Journal stating that the administration was curtailing occupational draft deferments including those for teachers. Then it fell into place. Connolly was on the chopping block and could expect a call up within a matter of months.
On August 1, 1968, Connolly’s 28th birthday, Speaker McCormick wrote a personal letter to J. Edgar Hoover recommending Connolly’s appointment to the FBI which took place in October 1968. Connolly avoided having to serve in the military. FBI agents were not required to serve.
Unlike many who join the FBI because they have a deep desire to become and agent, Connolly expressed no such motivation. It’s not an auspicious start to come to the dance because you wanted to avoid going to another one.
Up to this time, there is no objective reason to believe Connolly had any close relationship with either Billy, who was one of 240 representative, or Whitey Bulger, who had got out of prison three years earlier and was slipping back into his old habits. Neither man had the clout to get him into the FBI.