R.I.P. James DiPaola

People who knew Jim DiPaola say he was a nice guy, very gregarious. It’s hard to succeed in politics if you’re not. Others say he cared about other people, was loyal to his employees and committed to providing the social services needed by prisoners if they are to reenter and adjust to life outside. But he committed suicide last week, just after Thanksgiving, in the wake of media reports that were less than flattering.

An allegedly disgruntled former employee was reported to have said he had used campaign contributions for personal purposes and that he had had an employee drive him home in a government vehicle when he had too much to drink. The Boston Globe had called him on a scheme to double dip, retiring temporarily from his sheriff’s post to collect his pension while also collecting a pension from earlier stints of public service. It was legal but too cute by half. In a slow news week, the gambit and his reaction to it dominated the headlines. He decided to leave politics, concluding that he didn’t want, as reporter Sean Murphy had warned, that story to be his legacy.

But his suicide doesn’t compute. He came out ahead of the pension story when he decided against the ploy, saying that while it was legal, it wasn’t right. And the use of campaign finances for personal purposes? Not right, but penny ante stuff. If true, it most probably would have resulted in a fine and a slap on the wrist. As for having a staff person drive him home after having had a few drinks, should he have driven alone having imbibed? As I said, I didn’t know DiPaola, and I don’t have information about what he did or didn’t do. I have no idea whether there was another shoe to drop. But none of what’s come out seems to explain suicide as a response.

DiPaola’s friends are stupefied. They have no answers. Political consultant Michael Goldman, who worked with DiPaola for many years and was his friend, has written a piece that appears in the Salem News. Unless I learn otherwise, Michael’s column tells me all I need to know about Sheriff Jim DiPaola. I reprint it here, with Michael’s permission.

Sometimes the Dragon Wins


Nobody had a bigger laugh, or a bigger heart, than did Jimmy DiPaola.


For years, when I would introduce him at political events, I’d always tell the same story.


It was about a day 14 years ago, shortly after he was officially sworn in as Middlesex County sheriff, and we had made our way back to the office he would occupy for the next decade on the 17th floor of the county courthouse in Cambridge.


The previous sheriff, an interim appointee selected a year earlier by former Gov. Bill Weld, and whom Jim had defeated in what was described by the media as a “huge upset,” was gone, as was his entire staff.


Gone, too, was just about everything else that had been in the office, including pens, pencils and even paper clips. All that remained, it seemed, was a single desk and chair.


Jim made his way over to the desk and started opening its drawers, only to discover that they, too, had been cleaned out. Then he opened the very top drawer, took out a single piece of paper, read it, and let out a classic Jim DiPaola roar of laughter.


Someone had left a cartoon as a greeting for the new sheriff. It depicted a knight in shining armor lying on the ground looking up at a smiling dragon holding his sword.


The caption read: “Sometimes the dragon wins.”


“I guess they think I’m the dragon,” the still-laughing sheriff said.


The truth is Jim was never the dragon. If anything, for 14 years, Jim was a dragon-slayer. Nobody did more to take on the many “dragons” who resisted his big vision of what the sheriff’s office could and should be.


His e-mail address was simply, “thesheriff@…” The message on his cell phone bellowed, “It’s the sheriff! Leave a message!” His personal notes were always signed, “Your friend, the Sheriff.”


It was never “Sheriff DiPaola,” It was always just, “the Sheriff.”


The fact is, it would be too easy for me to simply repeat stories already reported in other media outlets about just how special a person Sheriff Jim DiPaola really was.


His success at turning the Billerica County Jail from the facility with the highest rate of recidivism in the commonwealth, to the jail with the lowest rate of prisoner re-incarceration, is a documented fact. The training programs he implemented for jail personnel are now the models of professionalism used by virtually every other sheriff in the state.


His culinary program; the Youth Academy; his acquisition of a state-of-the-art mobile communication vehicle using federal grant money; his post-Katrina trip to Louisiana, where he was the first outsider to bring food, water and hope to hundreds of traumatized victims of the hurricane; his inmate education, addiction and violence prevention programs; and, most important, his success at never overspending his budget in any of the 14 years he ran the system, are a huge part of the reason he easily won re-election less than a month ago.


But there was one thing more. There was Jim himself.


Serving as sheriff in the 23rd biggest county in the entire country, the reality was that there was virtually no place you could travel with him where someone didn’t recognize him, and then choose to come over to shake his hand to thank him for some private kindness he had done on their or another person’s behalf.


From downtown Lowell to distant Marlborough; from liberal Cambridge to conservative Dracut; from the town of Acton to his beloved hometown of Malden, it didn’t matter. Someone had met him at some political event, or at one of the thousands of parades he attended, or through some veterans group he’d supported.


Jim would always smile and, to my astonishment, tell me who the person was, where they lived, and how he’d met them. His memory was a steel trap; his love of the business of politics contagious.


This has obviously been a sad week for me, as it has been a sad week for the hundreds who called James DiPaola friend. Sadly, I have no answers for what he did.


He adored his wife, beamed with pride when he spoke of his daughters, and never tired of sharing pictures of his beloved grandchildren. In the end, the simple answer may just be that sometimes the dreaded dragon does win.


Rest easy my friend, the Sheriff, rest easy.

Please let me know your thoughts in the comments section below.

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