scorecardresearch Skip to main content
Thomas Farragher

The spectacular collapse of Jack O’Brien

Jack O’Brien never believed he had done anything wrong, let alone criminal. Why would he?

For years, from his office atop Beacon Hill, O’Brien’s power was absolute. His orders were carried out reflexively.

You did what Jack said. Or else.

The doors to the most powerful suites at the State House always swung open for Probation Commissioner O’Brien. He arrived bearing gifts. And he never failed to deliver.

He routinely rigged hiring and promotional interviews. He handed out treasured state jobs (oh, those pensions!) like chocolates in a box.

He made sure that House Speaker Robert A. DeLeo’s godson got a plum chief probation officer job. When the wife of one powerful politician applied for an electronic monitoring position, the other candidates were doomed.


By one account, he sometimes handed out jobs to politicians who weren’t even looking for them, an effort to assure that DeLeo would win the speakership in 2009, an effort that an angry DeLeo has called pure fiction.

But there’s little doubt that the hiring system was a farce. The process was phony. The candidates were preselected.

The system was rotten, and, for years, it was simply how the Massachusetts probation system operated.

Trial Court superiors who should have interceded, shrugged in resignation instead. O’Brien’s top lieutenants, men and women not without skill, far from blowing the whistle, took willful part in the fraudulent scheme.

And now, with the federal jury’s verdict in Judge William G. Young’s courtroom, the spectacular collapse of Jack O’Brien’s pugnacious public service career is complete.

His defense, simply put, was this: Hey, everybody does it. It’s called patronage. You take care of me. I’ll take care of you. A crime, you say? Come on. It’s a Commonwealth custom.

But this clearly hard-working jury, after weeks of testimony and a parade of 60 witnesses, did not buy it.


Perhaps they didn’t buy it because damning testimony showed that O’Brien did more than help powerful people get jobs for their friends and relatives. He virtually commandeered an entire state agency, 2,000 strong, converting it into his personal plaything.

This was patronage on steroids. And it was criminal.

“Fraud and bribery are not business as usual in the state of Massachusetts,’’ Assistant US Attorney Karin Bell told the jury, words ringing in their ears as they began deliberations.

She called O’Brien’s claims that he hired and promoted candidates based on merit “a bald-faced, outright lie.’’

If O’Brien’s ruinous downfall, played out across the last four years, was swift, his rise to power in the Probation Department was steady and sure.

And, tellingly, it was rooted in friendships and connections.

He played football at Boston College and caught the eye of John J. Irwin Jr., a devoted BC alumnus, who would later become the state’s chief judge for administration and management, which ran the state trial court system to which the probation agency belonged.

O’Brien grew up in Dorchester, not too far from Thomas M. Finneran, who would later become the speaker of the Massachusetts House.

Irwin and Finneran were the twin architects of his probation career, which began at Suffolk Superior Court. O’Brien was a probation officer there and was later tapped to lead the Office of Community Corrections, where he supervised a constellation of education and treatment programs across Massachusetts.

When Finneran was chairman of the House Ways and Means Committee and Irwin would lobby him for Trial Court funding, O’Brien accompanied the judge, who was not unaware that the Dorchester roots O’Brien shared with Finneran could not hurt.


Soon enough, Finneran was House speaker and O’Brien was tapped to become the commissioner of the probation agency where he quickly gained a reputation as an insular leader whose skin was thin and whose elbows were sharp.

In 2001, Finneran engineered legislation that stripped judges of the power to appoint probation officers. And when he handed that authority over to his old neighborhood friend and jogging partner, O’Brien’s consolidation of power was complete.

Perhaps O’Brien’s most corrosive relationship, replayed through volcanic trial testimony, was the one he suffered with Robert A. Mulligan, a successor to Irwin as the chief administrative judge and O’Brien’s putative boss.

When the Spotlight Team was investigating O’Brien’s agency in 2010, Mulligan told me about his icy first encounter with O’Brien in summer 2003.

O’Brien was still bristling over a district court judge’s decision the year before to hold him in contempt of court, an embarrassing episode in which O’Brien was briefly confined to a Brighton court’s prisoner dock because he had balked at a judge’s order about drug testing procedures.

Jack was not used to being treated like that. He filed a lawsuit, claiming, among other things, post-traumatic stress. And now he was out for compensation. “His demand was $300,000,’’ Mulligan recalled.
It was a stunning, audacious demand.


“Meetings we had were tense and difficult,’’ Mulligan testified at the trial. “It seemed everything between us became a contest.’’

O’Brien contended that everything he did was approved by Mulligan. Indeed, trial testimony showed that in some instances Mulligan himself was not above using jobs as favors.

Mulligan was lampooned by defense lawyers as O’Brien’s “do as I say, not as I do’’ supervisor.

In the months the Globe Spotlight Team spent examining O’Brien’s tenure at the Probation Department in 2010, he repeatedly refused to meet with me. He declined to be photographed. He finally agreed to a single 30-minute interview.

I wanted to do it in person. No, he said, over the phone.

And over the course of that phone call it became clear why O’Brien did not want to meet face to face. The probation chief was clearly reading from a script, filibustering with facts and boiler-plate statistics, some of which were clearly cooked. And he declined any questions of substance. No personal questions at all, please.

No, Jack O’Brien really didn’t want to talk to me. And, exercising his constitutional right, he didn’t want to talk to Assistant US Attorney Fred M. Wyshak Jr. or the federal jury either.

Through it all, Jack maintained that he did nothing wrong. He was just doing what everybody did. “I don’t know what anybody means by [a] rogue agency,’’ O’Brien told a reporter when he was suspended in May 2010, the day after the Spotlight Team series began.

When we were kids and my siblings and I trotted out the but-all-my-friends-are-doing-it defense, my mother, hands on hips, would point to the towering rusted railroad trestle over the Nashua River in the near distance beyond our back yard. “If all your friends jumped off High Bridge, would you?” she demanded.


That seemed to be the message from the federal jury on the fifth floor in Judge Young’s courtroom.

Perhaps that message began to sink in as Jack O’Brien, now a newly minted felon, stood solemnly before a packed federal courtroom.

Just because all your friends were doing it, commissioner, didn’t make it right.

In fact, the jury said, it was a broad criminal enterprise.

Thomas Farragher is a Globe columnist. He can be reached at