Kevin Cullen

Conflicted interest

It was with considerable reluctance and more than a tinge of regret that Dennis Saylor recused himself as judge in the federal trial of Jack O’Brien, former state probation chief, and two of O’Brien’s aides.

A relentless, full court press by defense attorneys got Saylor to tap out, even as he insisted that remaining on the case did not present an actual conflict, just the possible appearance of one.

That just about sums up the case against Jackie O’Brien, doesn’t it? Was he actually corrupt in doling out jobs to the politically connected, or does it just appear that way?


Saylor provided a 20-page explanation of why he stepped aside, and it reads as if he felt more bullied than persuaded to see the light. In the end, it came down to the list of potential defense witnesses, which is approximately as long as “War and Peace.”

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It reads like the invitation list to a “time” at the late, lamented Anthony’s Pier 4: House Speaker Bob DeLeo, Senate President Therese Murray, Mayor Marty Walsh, Attorney General Martha Coakley, not to mention half the congressional delegation.

If you’re keeping score at home, the list, still growing, contains 179 names, including 96 former or current judges, 64 former or current legislators, and 19 former or current law enforcement officials, many of whom recommended candidates for probation jobs.

Saylor’s eyebrows hit the ceiling when he read the list. “It is hard to imagine that any judge in this district does not have a ‘material connection’ to multiple individuals on that list,” he wrote. “It is also highly doubtful that all 179 individuals actually would testify. And it is likewise doubtful that all 179 individuals actually have testimony that is relevant and admissible.”

The defense had initially tried to get Saylor to recuse himself because he was a former law partner of Paul Ware, the special investigator appointed after the Globe Spotlight Team exposed a Probation Department beholden to corrupt manipulation. After Saylor refused, saying he wasn’t friendly with Ware and hadn’t seen him in years, the defense seized on Saylor’s friendship with federal judge Timothy Hillman, one of the many potential witnesses on that Santa-size list.


Saylor doesn’t believe defense lawyers when they say they only recently became aware of that friendship, as he and Hillman were the only judges assigned to the federal courthouse in Worcester for years. Saylor said the defense could have raised the Hillman issue two years ago. He could barely conceal his contempt for the false claim by John Amabile, lawyer for O’Brien aide William Burke, that Hillman had recommended his own daughter for a job.

Saylor suggested he could have denied the recusal motion based on a technicality, because the defense didn’t file it in a timely fashion. But he couldn’t ignore defense claims that Hillman had recommended more than 20 people for probation jobs. Any attempt by Saylor to limit lines of questioning would open him to charges he was trying to shield Hillman.

Besides, Saylor ruefully concluded, if he didn’t recuse himself over Hillman, the defense would just move on to someone else on that list. There are two other federal judges he is friendly with who recommended a single applicant.

Which raises this question: Wouldn’t a list of judges and pols who never recommended anyone for a job at Probation be much shorter than the current defense witness list?

So Jackie O’Brien’s trial will be pushed back. When it finally starts, Assistant US Attorney Fred Wyshak, who spent the summer prosecuting Whitey Bulger, will try to convince a jury that O’Brien did more than hire the favored constituents of politicians who controlled his purse strings, that O’Brien used a fraudulent system to ensure unqualified people got those jobs.


Just for the record, let’s stipulate that Whitey Bulger’s brother Billy practiced patronage on a scale that makes O’Brien and everybody else look like amateurs. They don’t call the MBTA Mr. Bulger’s Transit Authority for nothin’.

Kevin Cullen is a Globe columnist. He can be reached at Follow him on Twitter @GlobeCullen.