Nantucket Police Chief Bill Pittman Retires: The Exit Interview

Jason Graziadei •

When Nantucket Chief of Police Bill Pittman first arrived on the island to start his new job, the police department was located in an aging brick building on South Water Street. An old mailbox served as the department’s evidence receptacle, and there was no locker room for the female officers.

Much has changed in the ensuing 19 years with Pittman at the helm of the department. As he prepares to turn in his badge this week after reaching the state’s mandatory retirement age of 65, Pittman sat down with the Current to reflect on his nearly two decades as the island’s top cop and shared his plans for the future.

Nantucket Police Chief Bill Pittman | Photo by Joshua Simpson

“I've had a pretty good career,” Pittman said. “Forty-one years and the last 19 have been great here on Nantucket. I've made a lot of friends. We've made a lot of progress together here, this team at the department. And so I will miss that. But at the same time, the department's ready for some new energy. I'm not going to say it's getting stagnant, but we've implemented a lot of things, and I'm sure there's a lot more we can do. We'll get some new leadership, and they'll have an opportunity to continue where we left off. But I don't feel as if somebody has to come in here and rebuild anything.”

Since Pittman took over as chief in 2004, he’s presided over some significant changes for the department, including the construction of the new police station on Fairgrounds Road completed in 2011, a complete reorganization of the department’s “summer special” program, and the implementation of dashboard and body cameras. He helped NPD navigate through the COVID-19 pandemic and oversaw the department’s response to a series of high-profile cases and situations, including the murder of Beth Lochtefeld, the arrest of serial rapist David Matterson, a crackdown on Fourth of July beach parties, and the controversial African Meeting House hate crime in 2018.

But for Pittman, his legacy - and the thing he is most proud of - is the officers and command staff of the department, nearly all of whom he helped to recruit, hire, and promote. Indeed, with the exception of Deputy Chief Charles Gibson (who was in that position before Pittman’s arrival), all of NPD’s current leadership positions were filled with Pittman’s blessing.

“I'm really proud of what they've done and how they have taken control of the things they're given responsibility for,” Pittman said. “The town manager (Libby Gibson) gave me a free hand for dealing with the management of this department. She allowed me to groom the employees to give them the skills they needed, and then bring up the ones who have demonstrated the ability. I would say that's probably the most lasting legacy this department will have - that, and the building - from my tenure here. Because I can walk out the door tomorrow, and unless somebody tells them to do something different, they are going to keep doing what they're doing.”

Pittman, who came from the Springfield, Ill. Police Department to Nantucket back in the fall of 2004, raised two children on the island who went through the Nantucket Public Schools during his tenure. His wife Nancy Pittman has been a longtime senior executive at Nantucket Cottage Hospital, and the family owns a home off South Shore Road. But when he first took the job nearly two decades ago, none of that was part of his plan.

“When I started here 19 years ago, my intention was to work three years,” Pittman said. “And then really, I wanted to go to a bigger department. But by the time that three years had rolled around, my wife was firmly ensconced in Nantucket. My kids were firmly here. And if I would have gotten another job somewhere else, I probably would have been going by myself.”

And so unlike many other town department heads who have come and gone in the blink of an eye over the years, Pittman decided to stay. It was not a decision he regrets, but being the police chief of Nantucket was far different from his previous positions. And having such a high-profile job in a small community took some getting used to.

“You've heard of being in the fishbowl, well this is certainly a fishbowl here,” Pittman said. “There certainly is no shortage of people in the community who are taking shots at you and second-guessing what you're doing. Some members of the community will try to bait you to come out and say something, to take a position on something that really wasn’t my role as police chief to take a position on… So in Springfield, you go to the grocery store and you don't know anybody, right? And here you go to the grocery store and there's three or four people wanting to remind you about something and ask you about something or tell you about something.”

Over the past month, with his mandatory retirement date looming, Pittman has prepared to pass the torch to incoming Nantucket police chief Jody Kasper, who was hired by the town in October and is leaving her post as police chief in Northampton, MA. After introducing Kasper at a recent Select Board meeting and a gathering of the Cape Cod Police Chiefs Association, Pittman said he’s spent several hours with her to help bring her up to speed, give her the lay of the land, and offer some advice. What might that be?

“I think the best piece of advice is to get to know your staff and get to know the community before you start making too many changes,” Pittman said. "Because you'll realize the department is there's room for growth. There's room for improvement, there always is. But you're going to realize that the department is something from which you can build on rather than something that needs to be rebuilt.

“And now the good thing about Chief Kasper is she's not a new chief,” Pittman continued. “She's been a chief for a number of years now. And so she doesn't need to learn the job. But she just needs to learn about the fishbowl of Nantucket, the community. And she seems very, very ready to understand that dynamic. And we've had that conversation about how everybody knows you, everybody sees you, everybody wants to talk to you.”

In the fall of 2004, just weeks after Pittman had started in his new role as Nantucket police chief, the island was shocked by the stabbing death of Elizabeth “Beth” Lochtefeld, which at the time was the first murder on the island in more than 20 years. Many of his officers at the time had never been part of a homicide investigation. But Pittman had, of course, so the initial response was both imparting his experience from Springfield and learning about how NPD interacted with the Massachusetts State Police and the Cape & Island’s District Attorney’s Office to respond to such cases.

“What I remember about it was that it wasn't really that startling for me,” Pittman said. “It was kind of another day at the office from when I was in Springfield, for sure. We used to deal with quite a few homicides in a year. But what I didn't have at that point was a good understanding of how the DA’s office and the state police managed homicide investigations. And because that's not the way it was in the rest of the world, it's kind of a Nantucket or Massachusetts thing. And so, initially, my people were kind of shocked. It's not something that's happened in 20-some years. But I just kicked in and said well, we need to do this, do that, you get this done, find out about this, etc. In the meantime, they're like, well, the ‘CPAC unit’ is coming. I said ‘Who's CPAC?’ And they told me, and I said ‘When are they gonna get here?’ Well, the next boat’s at such-and-such time. So in the past, they would have just all stood there and froze things. As it turned out, we identified the suspect, we had an APB out, and all that stuff before the State Police even got here. And so it was a learning experience for me and the community, and fortunately, I think the officers started understanding that I actually might know what I'm doing. Before that, I was just a guy from Illinois. And so I think that helped me get ingratiated with the officers.”

Another one of Pittman’s initial moves to reconfigure the police department was adding sergeants. When he first arrived, Pittman found there was not always a sergeant or supervisor on duty at all times which, he said, “scared me the most.” So he slowly started adding sergeant positions to augment the department’s existing command staff, and promoting others to high-ranking positions as they opened up. And so now, Pittman said, the department’s leadership team had become a high-functioning group that he could rely upon in difficult situations and with younger, inexperienced officers.

“I won’t say that everybody up here (in NPD administration) is buddy-buddy, okay, but it’s truly a team of rivals so to speak,” Pittman said. “That led to me being able to get multiple positions and views on things and then make decisions which I think were better decisions.”

Recruiting and retaining officers was a challenge when he arrived on Nantucket, and remains a difficult puzzle even as he prepares to leave the department nearly 20 years later. But Pittman emphasized that he is proud of the fact that nearly one-third of the patrol force now consists of female officers.

“It's become the norm rather than the exception,” Pittman remarked. “In the next few years, there'll be some transitions and some people will be ready to retire, and I fully expect some of those female officers to move up into some of those new roles. And they're certainly capable.”

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Pittman, right, promoting Nantucket Police Department detective Jackie Hollis to the rank of sergeant in Nov. 2022. Photo by David Creed

Looking back at some of the most significant moments of his law enforcement career on Nantucket, Pittman noted that one of the department’s darkest moments - when full-time and summer officers confronted a group of black teenagers on Broad Street in 2007 leading to an altercation in which they were later found to have used excessive force - ultimately led to one his most sweeping reforms. In a 300-page report, the department acknowledged the faults in its response to the situation, and Pittman disbanded the so-called “summer special” police program in which college-aged recruits were given police powers for the summer. Pittman then implemented the “community service officer” program - still in place today - which still allowed the department to hire seasonal officers, but removed their police powers. Today, the CSOs are the eyes and ears of the department, responding to calls for parking issues, noise complaints, and minor motor vehicle accidents - but cannot make arrests.

“And it was something that should have been done years ago,” Pittman recalled. “ I actually remember when I first heard who they (summer specials) are and what authority they had. And I thought, ‘Who thought that was a great idea?’ So, in 2008, when I made that change, it took me a few years to get to that point, but the Broad Street incident demonstrated exactly why it needed to happen.”

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Chief Bill Pittman attending the candlelight vigil organized by the Nantucket Justice League in June 2020. Photo by Kit Noble

That same year, the Nantucket police responded to the first of what would become a series of heinous rapes on the island in which women were bound in their homes by a man wearing a mask and assaulted for hours. It soon became clear as similar incidents occurred each fall that Nantucket was dealing with a serial rapist. But for nearly seven years, the suspect managed to elude investigators.

“I would say that was probably the most consequential case we had in my 20 years here,” Pittman said. As the incidents continued, Pittman and his detectives tried everything in their playbook to identify the suspect. He even brought in a retired detective he knew from Springfield, Ill. who was head of that department’s special victims unit. “He actually came out and sat down with our guys here and they just kind of went through stuff, numerous times, trying to find something we missed, some loose end.

“I dreaded October,” Pittman recalled. “We realized after a couple of years, it seemed to be happening in the fall.”

Then in 2015, investigators caught a break that ultimately led to an arrest. A suspect was identified following another attack on a victim - as the woman was able to fight her assailant off until a neighbor heard screams and yelled back, startling the attacker. The man fled the apartment but left behind several items used in the assault, including sexual enhancement pills. Those items ultimately aided Nantucket police in identifying the rapist as David Matterson, a native of Jamaica who had lived on Nantucket intermittently for nearly 10 years.

“That ultimately came down to some great detective work by Brett Morneau,” Pittman recalled. Matterson was ultimately sentenced to serve 20 years in prison.

While that may have been the most consequential case of Pittman’s career, the most controversial incident came in 2018 when Nantucket’s historic African Meeting House was defaced with racist graffiti. No one was arrested for the hate crime, leading to rampant speculation and accusations of a cover-up involving members of the police department. After Jeffrey Sayle, the brother-in-law of deputy police chief Charles Gibson, allegedly disclosed to Gibson the identity of the perpetrator on June 17, 2019, Pittman announced two days later at a Select Board meeting that the case was being turned over to the District Attorney. Pittman and the Select Board were later sued by island residents James Barros and Rose Marie Samuels, who claimed their civil rights had been violated during a Select Board meeting on March 11, 2020. The lawsuit claimed Barros and Samuels had their right to free speech abridged during the meeting in which both attempted to express their frustration with the lack of progress in the investigation into the defacing of the African Meeting House. While Pittman and the Select Board were later cleared by a judge, the case is under appeal.

“Obviously, it's still an active case because there's an appeal so I’ve got to be kind of judicious about what I say,” Pittman told the Current. “But one thing I would say, I never felt that it's a good idea to talk about ongoing criminal investigations at a public forum. As I've learned over the years, nothing good comes from that, you know? You don't solve the cases that way. So it would have been better had the Select Board not pushed for briefings because it's really not their role. But some community members wanted it. And then when we gave it to them, they realized, well, we can't say that to the public, because it's not substantiated. That was the problem with the whole case: there were all kinds of rumors. But there's no physical evidence.”

While a civil lawsuit later identified the alleged perpetrator as Dylan Ponce - who ultimately exercised his fifth amendment right not to testify in the case - to this day no one has been charged criminally. Pittman said the District Attorney’s Office maintains the case is open and there’s still a potential for prosecution.

“We chased after a lot of rabbits on that case and ran down a lot of leads on things that weren't factual,” Pittman added. “We spent a lot of time on it and there were a lot of investigative hours that went into that that case. And we had to turn it all over to the State Police and I, honestly, I don't even remember seeing them here. I know, they came once.”

Now just days away from his retirement, Pittman said he plans to keep his Nantucket property, but to spend the winter in Key West where his daughter Katherine is stationed with the U.S. Coast Guard, stay at his family’s property in western Kentucky during the spring, and return to the island for summers.

“What I want to do now is experience Nantucket from the other side of the fence,” Pittman said. “You know, without being burdened by ‘Oh I know about this road being closed or I know about this or that.’ About a year ago at this time, Nancy and I had a long talk and we just decided that, you know, 41 years is a long time what more am I going to do other than just make more money? I think it’s just time, and I'm still healthy and we’ve got a lot of things we want to do that my wife and I've dreamed about and kind of planned.

“Plus,” he added, “my wife’s got a honey-do list that’s a foot long.”

The town is welcoming the island community to say goodbye and have coffee with Chief Pittman this Thursday morning, Nov. 30th, from 9 a.m. to 10 a.m. in the community room at the public safety facility.

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