Police Chief Joseph Bennett surveys the scene at the 2023 Boston Marathon. PHOTO/JOHN CARDILLO

Hopkinton Police Chief Joseph Bennett announced Friday in a press release that he will retire June 30.

Bennett’s retirement caps 35 years of police service, nearly all of which he spent in Hopkinton.

His law enforcement journey began in 1991 when he became a part-time officer and dispatcher at the Sutton Police Department. He later served as a reserve officer and dispatcher for the Southborough Police Department.

Bennett joined the HPD in July 1993. He rose through the ranks, serving as patrol officer, detective, sergeant, lieutenant and deputy chief. In April 2020, he was appointed chief during the early stage of the pandemic.

Over the course of his career, Bennett managed several aspects of the department, including overseeing professional standards, training, internal affairs, firearms licensing and the operation of the public safety communications center. He also served as the department’s public information officer, grant administrator and crime prevention coordinator.

Earlier in his career, Bennett supervised the detective division and school resource officer program and helped advance community policing initiatives. He also helped secure more than $1 million in grant funding that supported training, equipment purchases and expanded patrol resources.

Recent controversies mar HPD’s reputation

The HPD’s reputation under Bennett’s leadership has not been without blemish. His deputy chief, John “Jay” Porter, was convicted of three counts of child rape in June 2025 and is serving a seven-year prison sentence. Porter was a school resource officer when the acts occurred two decades before.

The survivor later reported the incidents to former HPD Sgt. Tim Brennan. Brennan replaced Porter in the SRO role when Porter was promoted to detective, which is how Brennan met the accuser. They maintained a relationship over the years, and the survivor told Brennan what happened between her and Porter in 2015.

An independent investigation concluded that Brennan should have reported what he knew to his superior officers.

After an explosive Loudermill hearing in January 2024, Brennan was terminated the following month. Dozens of residents rallied on Brennan’s behalf, calling for his reinstatement. They said Brennan made the right decision by not revealing what he knew to protect the survivor’s safety and confidentiality until she was ready to come forward. They received a moral victory at Special Town Meeting in May 2024, when a citizens’ petition to direct the Select Board to reappoint Brennan passed by an overwhelming margin. Since the Select Board does not have that authority, the vote was not enforceable.

More recently, the HPD was criticized by a group of area residents who formed Demand the Truth Hopkinton. They pointed out at several Select Board meetings that town did not perform required Criminal Offender Record Information (CORI) checks on applicants for common victualer licenses in the past.

They highlighted the case of Petros “Peter” Sismanis, the disgraced former owner of the now-closed Hillers Pizza restaurant, as an egregious example. Sismanis was found guilty of indecent assault and battery on a person over 14 years of age and two counts of witness intimidation in June 2025. He is being held at an Immigration and Customs Enforcement detention center in California and faces possible deportation.

Sismanis had a prior conviction for sexual assault. He pled guilty to charges in 1998 for assaulting a female employee at his prior Hopkinton business, Jelly Doughnuts. That conviction resulted in him being placed on the sex offender registry.

The Select Board recently implemented a Sex Offender Registry Information (SORI) check as part of the CV renewal process. Town Meeting members will vote on May 2 as to whether to implement a civil fingerprinting process for CV applicants. 

Officials thank Bennett for service

In the press release, Town Manager Elaine Lazarus thanked Bennett for his many years of dedicated service to Hopkinton.

“Over the past 30 years, Hopkinton has experienced significant growth in both population and business activity. Chief Bennett helped ensure the Police Department evolved with the town while continuing to serve the community effectively,” stated Lazarus. “His leadership will be greatly missed, and I wish Chief Bennett the best of luck in his retirement.”

Select Board Chair Joe Clark added that Bennett’s career represents a strong example of leadership and dedication within the department.

“Chief Bennett’s career is a great example of what it means to grow within a department and serve a community over the long term,” said Clark. “From patrol officer to chief, he has played an important role in the department’s development and has helped so many residents in the community along the way. On behalf of the Select Board and the community, we thank him for his service.”

“It has been a privilege to spend my career working with such dedicated professionals and serving the residents of Hopkinton,” stated Bennett. “I’m grateful for the support of the community and for the many colleagues and mentors who helped shape my career.”