The race for Hampshire County sheriff heats up with first of 3 debates before Sept. 6 primary

Daily Hampshire Gazette
Staff Writer

EASTHAMPTON — The job of Hampshire County sheriff is up for election in the fall, and at a candidate forum on Thursday night, the two Democrats challenging incumbent Patrick Cahillane criticized his record and their own experiences when they worked for his administration.

Cahillane defended his nearly six years in office and the programs that are offered to inmates, while explaining the legislative hurdles and budgetary realities that stand in the way of greater progress on issues like staffing shortages.

The three candidates — Cahillane, Yvonne Gittelson and Caitlin Sepeda — are running in the Democratic primary on Sept. 6. The winner will be the only candidate on the ballot in the Nov. 8 general election.

The Easthampton Democratic City Committee sponsored Thursday’s two-hour forum and chair Jackie Brousseau-Pereira was the moderator.

Gittelson, a Goshen resident for 30 years, is the state education department’s corrections program specialist, responsible for overseeing educational programming for the entire corrections system including jails, prisons and Department of Youth Services facilities. She served as the Hampshire County jail’s education coordinator from 2017-21 and ran Teacher’s Pet Dog Center in Goshen for 13 years after founding it in 2004.

“I’m a lifelong educator. I’m also an entrepreneur,” Gittelson said in her opening remarks. “I’ve got varied experiences that give me a vision for innovation and creative problem-solving. … I am a 100% successful competitive grant writer — not just entitlement grants — who brought hundreds of thousands of dollars into the Hampshire County jail.”

She said she voted for Cahillane in 2016, when he was first elected sheriff, but now, “I’m taking my vote back” and pushing for more education as the “only thing that has been proven to reduce recidivism.”

Sepeda, a Ware native and resident of South Hadley, is a registered nurse at the Berkshire County Jail and House of Correction in Pittsfield and held the same position in the Hampshire County jail in Northampton for almost 10 years until last October, working under Cahillane and his predecessor Robert Garvey.

“I sat on the Institutional Review Board for two years and I am well-versed in every aspect of the facility on the ground level,” Sepeda said. “I am the only staff member running right now. ... I continue to do that, the face-to-face work with justice-involved individuals” and other staff “carrying out all of the plans and procedures and policies of the facility.”

Cahillane is a Leeds resident who has worked at the jail for 35 years, holding numerous positions from correctional officer to deputy superintendent and special sheriff. He highlighted accomplishments like the Rocky Hill Re-entry Collaborative, a temporary home for up to 16 freed inmates with nowhere else to go.

“As your sheriff, I’m responsible for making tough calls that protect the lives and the safety of all individuals who interact with us,” Cahillane said. “This job requires a multidimensional skill set, which I have developed over many years with the department, 24 hours a day, 7 days a week and 365 days a year.”

Staffing, health, wellness

Asked about the biggest problems at the jail, the candidates agreed that staffing needs to be addressed, while Sepeda and Gittelson described a facility with low morale.

Sepeda said there has been a shift in the type of applicant over the past decade; whereas the area colleges and universities once produced a high number of eager young job seekers, those applicants are now “bypassing” the corrections field and finding other positions in law enforcement.

“The role of the corrections staff — and treatment staff and medical too, for that matter — is expanding every day. The hats that they’re required to wear grow heavier and multiply every day,” Sepeda said, adding that the situation is “blowing our overtime budget” and making conditions less safe.

The facility’s technology needs to advance, she said, to free up staff who now get bogged down in secretarial tasks like typing up reports on typewriters.

Cahillane said staffing is likely a challenge at every jail and police department in the state, and maybe the country; this year, the sheriff’s office has received more than 300 job applications and hired 15 qualified people. Under its most recent budget, the office spent almost $100,000 for IT upgrades, he said, “to prepare the staff for training and prepare the inmates for educational purposes.”

Gittelson said the security staff are the most overworked at the jail, since they are required under their contracts to work overtime.

“That’s a fast recipe for burnout,” she said. “It’s other staff, as well, that feel like they’re not heard, they’re not included, they’re not considered when it comes to major decisions” by the sheriff.

She said there is a need for more women in security roles since they can “bring down the level of tension very often,” and more people who “represent and look like those in custody,” who are largely white but less so than the county as a whole.

Cahillane pointed out that the jail was among the first in the state to offer medication-assisted treatment (MAT) to inmates with opioid-use disorders and was federally recognized as an opioid treatment program last year; Sepeda said she was “instrumental” in bringing those efforts to fruition and served as the medical liaison to the MAT program for several years.

During the COVID-19 pandemic, Sepeda said, she was “in the units” every day performing the most critical and dangerous medical tasks and, if she were sheriff at the time, she would have adhered more closely to federal guidance.

Before she could get her own vaccination, she said that she was required to administer vaccines to staff who were not on the front lines of the virus response. Cahillane, in fact, took the first dose that was delivered to the jail last year; at the time, he told the Gazette that the medical staff suggested it.

“If I were sheriff, I would have taken the last” dose, Sepeda said.

On the issue of education, Gittelson said the jail population is 70% pretrial detainees and 30% sentenced inmates, but only inmates serving six months or longer are entitled to educational programs under the law. She gave an example of a detainee that she said spent four years awaiting trial without the right to get his high school equivalency degree.

“Would I open up the pretrial side to all services? I sure would,” she said.

Although Cahillane said he did not know which detainee Gittelson was referencing, he speculated that the reason for depriving him of those services was related to staff safety or the potential for escape.

He said the average length of pretrial detention is about 27 days and the site’s modular building houses detainees who are cleared to attend classes and “any other program that they so choose.”

Sepeda said she would like to add more technical and vocational training in fields that tend to hire people despite a criminal record like manufacturing and construction. She also suggested getting “everyone in the facility” trained in first aid, CPR and use of an AED.


Brian Steele can be reached at This email address is being protected from spambots. You need JavaScript enabled to view it..