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O’Brien rise and reign defined by tenacity

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By Thomas Farragher
Globe Staff / May 24, 2010

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Just before he took over as the state’s chief administrative judge, Robert A. Mulligan began meeting with the court system’s department heads, chummy meet-and-greet sessions that gave the incoming boss a chance to get to know his top lieutenants.

But when the judge shook hands with Probation Commissioner John J. O’Brien during that summer of 2003, the encounter was icy.

O’Brien was still fuming about a district court judge’s 2002 decision to hold him in contempt of court, an embarrassing episode in which he found himself confined to a Brighton court’s prisoner dock after a dispute with the judge over drug testing procedures.

Mulligan thought the probation chief wanted an apology, but O’Brien had something else in mind.

“His demand was $300,000,’’ Mulligan said.

O’Brien’s surprise push to be compensated for what his pending lawsuit said was emotional distress, post-traumatic stress, and the damage that his reputation had sustained took Mulligan aback.

“It cast him in a different light,’’ Mulligan said of O’Brien.

The contempt-of-court dust-up offers a window into the insular, sharp-elbowed world of the state’s probation commissioner, the man who, as the Globe’s Spotlight Team reported yesterday, presides over an agency whose payroll is thick with patronage hires, whose sloppy financial controls make it vulnerable to employee theft, and where political contributions by employees often appear tied to career advancement.

Jack O’Brien does not want to talk about much of this. He declined the Globe’s request to discuss his career, his management philosophy, and a growing chorus of criticism about his department.

If he is by choice mostly silent, others are willing to fill out the picture. O’Brien is, by all accounts, a man of force and ambition and not inconsiderable achievement, a man who takes things personally and knows how to keep score.

This year, when Governor Deval Patrick sought to take control of O’Brien’s empire, proposing to move the probation agency from the judiciary into the executive branch, O’Brien let it be known that he considered the initiative a wounding personal affront. And he began to battle back.

Those who have watched O’Brien, 53, across the years — from his upbringing in a large family to his unremarkable but formative Boston College gridiron career to his methodical rise through Suffolk County’s Probation Department — would have expected no less.

“O’Brien is one of these guys [for whom] everything is personal,’’ said Robert F. Kumor Jr., the recently retired first justice of the Springfield District Court. “It’s like his own power fight.’’

O’Brien’s ambition and his appreciation for power and turf may have had its roots in Dorchester, where he was one of six siblings who grew up in one of that neighborhood’s Catholic parishes. He was a sprinter on the track team and a guard for Catholic Memorial’s basketball squad. By the time he arrived at The Heights in the mid-1970s as a football wide receiver, his older brother Joe was a year ahead of him and the team’s quarterback. The college’s media guide spoke optimistically about a “Joe-to-Jack pass completion [that] could make the BC aerial attack a family affair.’’

But that did not happen. O’Brien would have just three receptions in a winless senior season, but the alliances he forged in the old neighborhood and at BC would prove more enduring and more valuable than ephemeral football glory at Chestnut Hill.

Thomas M. Finneran, who had watched the O’Briens grow up from his home in St. Gregory’s Parish in Dorchester, would later become speaker of the Massachusetts House. John J. Irwin Jr., who cherished his affiliation with Boston College, where he earned his undergraduate and law degrees, would later become the state’s chief judge for administration and management, essentially running the trial court system to which the Probation Department belonged.

O’Brien had caught their notice early and cultivated relationships with them. They, in turn, would become the chief architects of his probation career.

“My association with him professionally would have been that Judge Irwin thinks a lot of Jack and is bringing him along or coaching him or schooling him or creating opportunities for him,’’ Finneran said in a recent interview.

If those sterling connections were key to O’Brien’s rise, he also paid his dues.

Two years after earning a sociology degree from BC in 1979, O’Brien was among 18 probation officers working at the Suffolk Superior Court building in Pemberton Square, where he would make lasting professional allegiances and earn a reputation as a stalwart co-worker who knew how to leaven the drudgery of courthouse routine.

“He was a real stand-up guy,’’ said Kathy L. Tate, an assistant chief probation officer at Suffolk Superior who worked with O’Brien through the 1980s. “He was one of those who would help me out if the job duties got too heavy. He was willing to step in and help out a colleague.’’

Tate, whose opinion of O’Brien would later sour, also remembers him and a group of other probation officers, some of whom he would later take with him into the probation commissioner’s front office, playing cards at lunchtime, part of a clique to which she did not belong.

As Finneran was chairing the House Ways and Means Committee with an eye on the speaker’s chair, O’Brien was on the move, too. He would become executive director of the Office of Community Corrections, supervising a network of treatment and education programs for offenders across the state, and he was a key Irwin ally as legislative liaison for the Administrative Office of the Trial Court.

That meant, Finneran said, that when Irwin showed up on Beacon Hill, O’Brien was his shadow. And the strategic importance of O’Brien’s friendship with Finneran almost certainly was not lost on Irwin, whose trial court budget was controlled by legislative leaders.

“He was always in the company of Judge Irwin, and Judge Irwin was carrying the ball on behalf of the judicial branch,’’ Finneran recalled. Someone who “used to be a neighborhood kid became part of Judge Irwin’s administrative team.’’

An insurgent Finneran was elected speaker in 1996, outflanking then-majority leader Richard A. Voke by collecting the support of every House Republican. When longtime Probation Commissioner Donald Cochran retired a year later, O’Brien was tapped to succeed him, a much lower-profile but equally surprising turn of events.

The consensus insiders’ choice was Ronald P. Corbett Jr., a longtime and respected probation professional with sterling credentials. He was a deputy probation commissioner and a Harvard graduate. He held a doctorate in education and was a former president of the National Association of Probation Executives. The year the commissioner’s job opened up, the national association named Corbett its probation executive of the year.

But O’Brien had something more important: Irwin’s unwavering support and Finneran’s friendship.

“Everyone was scratching their head because Ron Corbett was eminently qualified,’’ recalled R. Peter Anderson, a retired district court judge.

Anderson said he had never heard of Jack O’Brien before. “I was just shocked that somebody who was so qualified was overlooked,’’ he said.

But on Jan. 1, 1998, O’Brien had completed his climb to the top of the Probation Department. Soon, with Finneran’s support, he would remake it in his own image, an agency that he and his allies say is rigorously run and tightly controlled but which critics assail as a bureaucratic island unto itself, opaque, poorly managed, and answerable to no one.

Dan Winslow, a former judge and legal counsel to Governor Mitt Romney, said he first met O’Brien just after he became commissioner, when Winslow was the presiding justice in Wrentham District Court.

Winslow, who is now running for a seat in the Legislature, said he was frustrated by his limited options when dealing with repeat drunken-driving offenders. When Winslow proposed using an ignition interlock device that would prevent anyone with measurable alcohol on their breath from driving, he said, O’Brien accompanied him to a potential vendor’s shop in Rhode Island.

“He was new to the job at the time,’’ Winslow recalled. “He was very responsible and approachable and no-nonsense. What I liked about Jack O’Brien at the time was that he was a straight shooter. If he thought something was a lousy idea, without deference to the robe, he’d tell you what he thought.’’

Finneran says too much is made of how his relationship with O’Brien fueled the younger man’s rise. “At the State House, people would think Finneran and O’Brien are joined at the hip,’’ Finneran said. “Overstated to the nth degree.’’

The former speaker said they were neighborhood acquaintances. They played on opposing teams in the same local softball league. They trained together for the Boston Marathon, when Finneran’s wife would host pasta parties before the race and would ferry the runners in her van to the starting line on race day.

“But we don’t go out socially,’’ Finneran said.

But he acknowledged that in 2001 when the Legislature stripped judges of the authority to hire probation officers and gave it to O’Brien, a seminal moment in his tenure as commissioner, Finneran helped shepherd that legislation, which consolidated O’Brien’s power.

Finneran said he was motivated to make the change in part after watching the trial court squander millions of dollars on a new computer system that he described as a debacle for which no one could be held accountable. He wanted someone in charge.

“He’ll stand up and take responsibility,’’ Finneran said, explaining his move to dramatically strengthen O’Brien’s hand. “I do think he was probably more politically attentive than a judge would have been.’’

Indeed, many judicial critics of the Probation Department’s hiring and promotion system under O’Brien say he is politically attentive in the extreme. As the Globe reported yesterday, O’Brien’s agency has hired or promoted at least 250 friends, relatives, and financial backers of politicians and top court officials.

After Kumor, the former Springfield chief justice, joined with another jurist to ask the Supreme Judicial Court to return control over probation hiring to judges, he bumped into O’Brien at a sporting event at the University of Massachusetts Amherst. Kumor recalled that the commissioner made it clear that he took the judge’s legal challenge personally. He was not interested in the underlying legal niceties about separation of powers, Kumor said.

“He’s not a very sophisticated player, as much as he thinks he is,’’ said Kumor, who stepped down from the bench last year after being diagnosed with amyotrophic lateral sclerosis, also known as Lou Gehrig’s disease. “He had gotten checked, and all he knew how to do was to check back. . . . He’s either got thin skin, or unless he’s got his hockey pads on, he can’t take a hit.’’

As it turns out, it wasn’t much of a hit. O’Brien’s appointment powers have remained unchecked.

If the challenge from Kumor irked O’Brien, his contempt-of-court showdown in Judge Anderson’s Brighton courtroom in the spring of 2002 infuriated him.

And in the boiling back-and-forth that ensued, O’Brien made clear that he would brook no challenge to his control of his department.

Anderson had ordered urine testing for several probationers convicted of various drug offenses. He ordered the Office of Community Corrections, run by the Probation Department, to conduct the random testing at least once a week beginning in January 2002. O’Brien’s office, citing financial constraints, said it could perform only more limited testing, twice a month.

That led to a series of increasingly contentious courtroom hearings.

During an April 19, 2002, hearing, Anderson made it clear that his patience with O’Brien had worn thin.

“Let me . . . tell you how I see it,’’ Anderson said, according to a court transcript. “I see this as the commissioner interfering with my orders.’’

Anderson said that if O’Brien had shown any willingness to cooperate, he would not be facing the contempt-of-court order Anderson was now weighing.

“I have never in my 11 years as a judge ever had any other court official respond in the manner in which the commissioner has responded,’’ Anderson said, according to the transcript. “It is a shocking and very sad state of affairs.’’

Six days later in Brighton District Court, it was clear the two sides could not find common ground. Anderson said he had issued a lawful order O’Brien must obey. O’Brien, represented by James Arguin, an assistant attorney general, said he would run the Probation Department, not Anderson.

Arguin conceded that if he wished, O’Brien could comply with the court order and have the drug testing done, as the judge had ordered, by the Office of Community Corrections.

“He does not believe your honor has the lawful authority to tell him how to allocate his resources,’’ Arguin said.

Anderson had had enough.

“Today, when I put to him directly this opportunity to comply, he has refused again,’’ the judge said, before motioning to a court officer. “And pursuant to all the evidence before me, I find that he is in contempt of this court. Mr. Crowley, I ask you to put the commissioner into custody.’’

In an interview, Anderson said he took no pleasure in ordering the probation commissioner into the courtroom’s dock. “But I had never seen anything of this level of mendacity,’’ he said.

A lawsuit O’Brien later brought against Anderson was dismissed. But the commissioner sued the trial court, too.

Mulligan rebuffed O’Brien’s demand for a $300,000 settlement, but the probation chief did receive $20,000 to settle the case, a payment that continues to mystify Anderson, who wonders about the trial court’s motive.

“He had no law on his side,’’ Anderson said. “I never got any sense of why they made that decision.’’

O’Brien isn’t talking.

He declined the Globe’s request for an in-person interview for this report. He would not be photographed or tape-recorded.

When asked why he would not answer personal questions, his spokeswoman intercepted the question for her boss.

“He’s not interested in profiles,’’ she said.

O’Brien began his 13th year as probation commissioner in January, the same month the governor proposed to take control of his department. To say the Legislature, where O’Brien’s network thrives, has greeted the proposed change dismissively is an understatement.

O’Brien did not even bother to show up for a hearing on the proposal before the Judiciary Committee, at which not a single legislator asked a question.

The day before, when the Joint Ways and Means Committee examined the measure at an otherwise sleepy hearing in Sturbridge, the lawmaker chairing the session seemed to go out of his way to make sure that the governor was not mounting a personal attack on O’Brien.

“Are there some pejorative connotations relative to the Probation Department?’’ wondered Senator Stephen M. Brewer, the committee’s vice chairman.

The budget debate is far from over. But the governor’s attempt to overhaul O’Brien’s department has foundered in the House. Patrick’s plan never made it out of committee.

The Globe Spotlight Team would like to hear from readers with tips about the state’s Probation Department. The telephone number is 617-929-3208. Confidential messages can also be left at 617-929-7483. The e-mail address is