BY GREG O’BRIEN
SPECIAL TO THE BIR
A local superman of sorts, James W. Dolan has pursued truth, justice, and the American Way for most his adult life. But there’s a little of a Tom Cruise character in him, and, for that matter, in all of us, defined in the compelling courtroom moment in the classic movie A Few Good Men when Jack Nicholson as the crusty Col. Nathan R. Jessep turned to Cruise in the role of prosecutor Lieutenant JG Daniel Kaffee, and barked, “You can’t handle the truth!”

Maybe none of us can, at least when defined on our own terms, concedes Dolan, former First Justice of the Dorchester District Court. “It’s the enduring pursuit of truth and justice that distinguishes an individual in life,” he observed in a recent interview at his unassuming Dorchester law office that overlooks the clatter of the Red Line and houses Dolan Connly, a full-service firm featuring this veteran judge, gifted mediator, and diligent arbitrator.
“How does one account for the fundamental flaw in human nature that makes us incapable of perfection?” he wrote 11 years ago in a Boston Globe commentary upon his retirement after 26 years as a Dorchester District Court judge and acting First Justice of the Lynn, West Roxbury, Roxbury, and New Bedford district courts. “It has been said that capitalism and democracy are not visions of man’s perfection but of his imperfections. That is why they work. The same can be said of our system of justice. It acknowledges what is self-evident—humanity is flawed. Despite our meticulously crafted and carefully balanced efforts to adapt a justice system to the human condition, we must recognize its weaknesses. We struggle with our limited capacity to find the truth and do justice. The pursuit of truth and justice is not a sporting event or a board game despite the existence of winners and losers. The system works best when the right person wins, and it fails when the wrong person loses.”
The journey for Dolan began back in grammar school in Dorchester where he attended St. Mark’s, St. Matthews’s, and St. Gregory’s as the family moved to different parishes. Sister Rose Paula caught his attention in the third grade at St. Mark’s with her comments about fundamental unfairness and the lack of accountability in life. “There, but the grace of God, go I,” she taught, forever stressing “a final day of reckoning before God.”
The self-effacing Dolan, whose glib nature often conceals an introspective man, has been preparing ever since.
Asked what’s most important to him now in life, he replies without hesitation, “Dying gracefully!”
Now you’re getting the point.
A father of five, grandfather of nine, and the dutiful husband for 49 years of Joan (Sullivan), the Milton resident views the life around him – and in years past, the drama of the courtroom – far more importantly than his own. “I remember my days at the courthouse and looking up at the rows of framed black and white photos of retired Dorchester District Court judges, sepia in tone, and thinking that I never wanted to be remembered as that,” he says. “Most judges, I suppose, would love to have their pictures hanging in a courthouse. I had no interest in it. You do your job and move on.”
Dolan’s job, as he saw it, was to take a “transformational view” in the courtroom. “It is an incredible privilege to be a judge,” he says of his years on the bench, adjudicating mostly criminal cases, many of them tragic. “To have a job where you go in every day and try to identify truth, which isn’t easy. That’s your job—try to do justice to the extent one can within the limitations of imperfection. That’s a privilege to see life played out every day, real life, and you have the opportunity to reach out and touch it, affecting someone, and hopefully for the good.”
Dolan had reached the callow age of 33 when he was first appointed to the court on Washington Street after a successful tenure at the State House as Legislative Counsel to the Massachusetts Bar Association, and he wasn’t sure if he was up to the task. Briefly on the job, he spoke with seasoned Justice Paul King about his youthful hesitation. King looked at him and instantly replied, “Beats practicing law!”
Dolan was sold. The rest is judicial history.
But there was a time when Dolan thought he might want to be a physician, following in the footsteps of his late father, the venerable Dr. Ralph Dolan, a Dorchester general practitioner for 50 years, the old school type with a black bag who made house calls. The judge’s grandfather was the founder of Dolan’s Funeral Home operation in Fields Corner, now located in Lower Mills and East Milton and run by his cousins Craig and Paul Dolan.
“I wanted to be a doctor,” Dolan recalls, “But I just didn’t think I had the skill.”
Born on Gallivan Boulevard and schooled in street smarts at the hand of his mother, Mary Ward, a first generation Irishwoman from Sligo, Dolan, after graduating from Boston College High School and Boston College with a degree in English, took up the law. While his dad was easy going, “unflappable,” as he says, Dolan’s mother was a disciplinarian with a purpose that she instilled in her five children. There must be a mission in life, she counseled. By his own admission, Dolan as a youth was reaching for the handle on his life; he had an undistinguished career in sandlot sports and schoolwork early on.
“As in most Irish families, being the oldest, I was the target,” he recalls. “If anyone else did anything wrong, it was my bad example.”
So when it became time to choose a career, his pragmatic mother pointed him on a parallel track with his father. “Had I been good in math and science, I would have been a doctor,” Dolan says. “My dad was a guy you always wanted to please, and I think he would have been happy if I had gone into medicine.”
Left-brain, right-brain, the two aren’t easily transferable on the family tree, but Dolan was richly blessed with creative talents that his mother instinctively drew on. “My mother suggested that I go into law, noting that lawyers and judges were interested in truth and justice. I thought it was an appealing argument.”
After law school and working as an attorney with the Boston Legal Assistance Project, managing the South Boston office during President Johnson’s War on Poverty, Dolan became a State House lobbyist in 1970 for the Massachusetts Bar Association, rubbing shoulders with Beacon Hill’s political movers. When an opening developed five years later on the Dorchester District Court bench, Dolan, a Democrat and a compromise candidate at the time, was appointed to the bench by Republican Governor Frank Sargent.
Ultimately, Dolan settled in with the ease of a gavel. His years on the court shaped and refined him in ways he had never imagined would be the case. Looking back now at 72, he has become nostalgic about life and where society is heading these days. “We’ve made strides over the years in areas like civil rights and gay rights,” he says, “and we should be proud of that. But something has been lost in the process of progress. I have this theory that for everything we term today as progress, there’s an equal and opposite problem it creates— it’s a law of cultural physics, I suppose, action and reaction. We live at such a fast pace with cellphone, Facebook, Twitter and the like. Constant chatter, but often nothing of significance. There’s no time for silence, no time for reflection. We’re always in the moment, driven by the spin of the day.”
He pauses for a minute, then looks up at an observer as if he were about to make a comment, wise yet reflective of his age. His dad probably said the same thing, and it was just as true then. “I tend to think people of my generation were better grounded,” he says. “Life was a lot easier, simpler, and safer.”
Dolan today is grounded in his wife, his children (four daughters and a son), and his grandchildren. He’s blessed, he says, that they live nearby. Many years ago, in true Irish form after four daughters, he longed for a son. His wife told him that if he ran in the Boston Marathon, she’d conceive a boy. He did, and she did. Individuals of their word, it pretty much sums up close to a half century of marriage.
With family, friends, and colleagues still cheering him on, Dolan goes about his legal work with partner and son-in-law Greg Connly with the same focus and dispatch as demonstrated on the court. In a November 2000 letter, Margaret Marshall, then Chief Justice of the Massachusetts Supreme Judicial Court, wrote to Dolan, “You have been exemplary in serving so long and faithfully in some of the busiest courts. You have shown us all that efficiency in the management of the court’s business need not be at the expense of fairness to those who appear before you, or with whom you work every day.”
Dolan still ponders that day of reckoning with the Lord; it drives his existence. He points to a copy of the Globe commentary he wrote years ago that was headlined “Confessions Of A Judge.” The philosophy applies uniformly to him today.
Without belief in a day of reckoning, “it would be difficult to participate in the [legal] process,” he writes. “Without belief in ultimate ‘absolute justice,’ I would see myself simply as an instrument of life’s imperfections and its unfairness. For me it is a comforting belief and, yes, even a necessary one. Some might call it superstition, myth, or a crutch. I prefer to call it faith.”
Greg O’Brien is editor and president of Stony Brook Group, a publishing and political consulting company based in Brewster on Cape Cod.