Gerard M. O’Neill’s new book, Rogues and Redeemers: When Politics Was King in Irish Boston, tells two interesting anecdotes that were fateful for Kevin White, Thomas Menino, and our city. O’Neill is the former head of the Boston Globe’s Spotlight Investigative Team who, with Dick Lehr, reported and wrote Black Mass, the chilling account of the horrible acts of mob boss James Whitey Bulger and the FBI agents who protected him.

The 1975 mayoral election was a titanic battle between Dorchester/Mattapan State Sen. Joe Timilty and the incumbent, Kevin White, who was at the time under a cloud of suspicion, namely, an ongoing investigation trying to determine if his administration was pressuring city workers to donate to his campaign. Meanwhile, the city was seething over the busing that was being implemented citywide that fall in what was called Phase 2 of the desegregation campaign. White was getting blamed by white working class residents for not stopping busing, even though Federal Judge W. Arthur Garrity was the one making it happen, and by some in the black community for not doing enough to protect their children from violence they were facing from anti-busing protesters.

In the book, O’Neill praises Timilty for not trying to ride the anti-busing tide to win the election. Timilty had made clear his opposition to the court order, but he did not call for active resistance, obstruction, or violence.

Just days before the election, on Halloween, then Boston Police Commissioner Robert diGrazia held a press conference and said Timilty was being influenced by certain deposed cops, the insinuation being that they were corrupt. DiGrazia also said that those backing Timilty would not allow him to reappoint DiGrazia, so his reforms within the police department would come to an end. DiGrazia was at the time the most popular figure in Boston, so his charges were very important elements in a close-fought campaign. There were those who felt that the commissioner had stopped Timilty’s momentum in the race, which White won, 52 percent to 48 percent.

While working on the book, O’Neill interviewed the now-retired DiGrazia, who said he relied on information for his ’75 press conference charges from another police official and now he feels the information may not have been true. O’Neill writes that DiGrazia answered the question “Was it fair?” this way: “In retrospect, probably not.” … he “fell in line” with City Hall. …”I think what happened was they knew that if I said something, people trusted me. And so, yeah, I was foolish to trust them.” So the question here is: “What if these charges had never been aired by DiGrazia? Would Timilty then have beaten White?

In the 1970s, Tom Menino was an aide to Sen. Timilty and heavily involved in his 1971, 1975, and 1979 campaigns for mayor before he took up his own cause and was elected Hyde Park district city councillor in 1983.  In 1992, Mayor Ray Flynn, then at the beginning of his third term, seemed less and less interested in being mayor while spending a great deal of time working on Bill Clinton’s presidential campaign. Flynn wanted a cabinet job, but ended up being appointed Ambassador to the Vatican.

O’Neill writes that Flynn notified then City Councillor Tom Menino that he might be moving on with Clinton, meaning that if he left, the person sitting in the Council president’s chair would become acting mayor. With Flynn’s support, Menino won the presidency in a 7-6 vote, with Roxbury City Councillor Anthony Crayton casting the tie breaking vote.

Flynn didn’t officially leave office until early July, so Menino had time to prepare for what he’d do when he moved to the mayor’s office for the few months before the September primary election. In his first week, he announced a freeze in water and sewer rates and a new teen job program. He finished first in the primary and won the final election decisively over then-Dorchester state Rep. Jim Brett. Many people felt at the time that if Menino had run for mayor in September as a councilor, and not as acting mayor, he would have been a serious candidate but maybe less likely to have won. Another “What if” for our city as Mayor Menino is now in his fifth term and maybe considering another run.

Rogues and Redeemers has interesting chapters on busing/desegregation and other colorful Boston political figures like John “Honey Fitz” Fitzgerald, who was President John Kennedy’s grandfather, James Michael Curley, “the Rascal King,” the legendary ward boss Martin Lomasney, and Mayor John B. Hynes, John F. Collins, and others. Gerard O’Neill has presented us with a detailed look into our political history, and in the process given those “what ifs” for our consideration.

Lew Finfer is a Dorchester resident.