Updated Sept. 5 at 3:09 p.m.

During a meet-and-greet campaign stop at Providence House Assisted Living in Brighton, Sandy Zamor Calixte introduced a group of residents to her campaign for Suffolk County sheriff — and her plan to unseat incumbent Steve Tompkins, her longtime colleague and former boss.

“There are only two Democrats in the race,” Zamor Calixte said. “Whoever takes it on September 6, takes it. Does anyone have any questions?”

Two residents cautiously raised their hands to ask variations of the same question: what does the Suffolk sheriff actually do?

“I know nothing about the sheriff’s office,” resident Ann Kennedy, 85, said. “I mean I've heard of it, but I don’t know what it’s comprised of, and I have no idea what the responsibilities are.”

Kennedy isn’t alone: 83% of Massachusetts voters don’t know who their county sheriff is, according to a Beacon Research poll from April, and 41% of those surveyed didn’t know that the county sheriff is an elected position.

If voters are already confused about what the sheriff does, this election cycle presents a new layer of complexity: Tompkins says he has been faced with frustrating limitations during his nine years in the position, and Zamor Calixte says he’s not pushing hard enough to overcome those barriers.

Tompkins started working at the sheriff’s department in 2002, Zamor Calixte began in 2006. Both candidates were born in New York City: Zamor Calixte in Brooklyn, and Tompkins in Harlem. They both believe in creating change from inside what they describe as a flawed system, and they share a lot of the same goals. Both have worked on programs to reduce recidivism, help people reenter society following incarceration and provide opportunities for at-risk youth, aspects of the job that go beyond the official “care, custody and control” mandate of the office.

The sheriff oversees people sentenced to less than 2.5 years at the Suffolk County House of Correction and pre-trial detainees at the Nashua Street Jail. Anything else a sheriff does is technically outside the job description, Tompkins said.

“The sheriffs in the commonwealth are basically the jailers,” Tompkins said. “It's incumbent upon us to take care of the people that are with us while they are with us. All the additional things that we do are not a part of our mandate. We do it anyway, because we have to help people.”

Sandy Zamor Calixte speaks with a resident at Providence Assisted Living in Brighton about her campaign for Suffolk County Sheriff, August 22, 2022.
Tori Bedford GBH News

Zamor Calixte says Tompkins has mishandled challenges presented in recent years, namely a crisis of homelessness and crime at near the intersection of Massachusetts Avenue and Melnea Cass Boulevard — Mass. and Cass — and a series of deaths of people under his jurisdiction in the past year.

Six people have died while incarcerated at Suffolk County facilities since July of last year: Pre-trial detainee Ashley Emma, 35, was found hanging by her bedsheet in a medical unit in July. Charail Premdas, 33, died following a “what appeared to be a seizure” on December 5 of last year. Carl “Chuck” Robouin, 47, was found unconscious in his cell in the medical unit in September 2021. Three people died in July 2021, two on the same day. Rashonn Wilson, 31, died at a hospital on July 12 after he “fell ill” while he was detained. On July 28, Edward “Jay” Isberg, 42, was found unresponsive in his cell in the medical unit, and 35-year-old Ayesha Johnson was found unresponsive in a holding cell at the Nashua Street Jail while waiting to go to a treatment program. Because Johnson had been civilly committed, Tompkins says he couldn’t legally place her in a medical unit.

“I think it's asinine and backwards for that to be the case — anybody that comes into a facility like ours should have a physical so that we do know what's going on with them — but the law says we can't,” Tompkins said. “Our hands are tied.”

After 16 years of employment at the sheriff’s department, Zamor Calixte says the recent series of deaths — and Tompkins’ response — was her final tipping point. In January, Zamor Calixte left her position leading the department’s Communications and External Affairs Division and launched a campaign to unseat her former boss.

Sandy Zamor Calixte and Suffolk County Sheriff Steve Tompkins at a debate about Mass. and Cass in Roxbury, Wednesday, July 20, 2022.
Tori Bedford GBH News

“It just isn’t acceptable,” Zamor Calixte said. “Someone that has been [civilly committed] and has substance use disorder shouldn't have to be sent to the sheriff's department and wait to go to their treatment facility, they should go straight there. He says that we’re mandated to do it — just because you're mandated to do something, if it's not working, then you have to advocate for that change.”

Tompkins was asked about the deaths at a debate in July and accused of lying by members of the audience.

“The four people that passed away last summer, frankly, should not have been there, and it's just a confluence of incidences that they died on our watch,” Tompkins said. “It wasn't like we did anything untoward to help them along that path of expiring. ... They would have passed wherever they were.”

The deaths are currently under investigation, and HIPAA laws prevent Tompkins from revealing details, even to family members demanding information. “That’s not just a limitation of my role, that’s a federal regulation,” Tompkins said. He says he recommends that loved ones appeal to the court in order to access “more information than I could provide” from a medical examiner.

“All of the sheriffs are essentially the Uber drivers for the courts,” Tompkins said. “When people leave court, they are brought to a facility like mine and they're waiting for a ride. [Ayesha Johnson] was not going to stay with us. [She] was waiting for a ride to go elsewhere and unfortunately expired when she was with us.”

Tompkins has created vocational programs to help incarcerated people reenter society and redirect at-risk youth away from criminal behavior. He has established partnerships with neighborhood organizations, civic associations and municipal agencies, advocating for increased funding for mental health programs and reducing the cost of prison phone calls, all things Zamor Calixte agrees with.

“I think aspiration is good. I think idealism is really good because that could be the foundation for some really good things to happen,” Tompkins said. “But you have to keep in mind what the taxpayers pay us to do. Everything that my opponent is talking about, I taught her how to do. That's a fact, whether she wants to agree to that or not.”

Zamor Calixte sees things differently. When Tompkins was appointed sheriff in 2013, she says she began to feel a disconnect: ideas she pitched were consistently rejected, including proposals housing solutions for formerly incarcerated people and people experiencing homelessness.

“My views just no longer aligned — I was at the table, but I wasn’t being heard,” she said. “I would make recommendations and propose things, and I was told no. No reason was given to say no, I was just told no. I think some of those limitations are there because he just doesn't want to put in the work.”

A special court created to arrest and process people with outstanding warrants at Mass. and Cass. — held at the Suffolk County House of Correction with authorization from Tompkins — was shut down after just nine days due to “low case volume,” following complaints about the lack of medical services for people in custody and confusion about the legal process. Tompkins’ proposal last year to use a former ICE detention facility to house people with criminal warrants at Mass. and Cass faced backlash and accusations of criminalizing poverty, and was never picked up by city officials.

A man in a blazer laughs with a small group of supporters around him, standing in a restaurant with low-hanging pendant lights
Suffolk County Sheriff Steve Tompkins at a campaign event in Charlestown, August 26, 2022.
Tori Bedford GBH News

“When that was shunted to the side, you didn’t hear a word from me, and you didn't hear a word from my administration, because that's not our charge,” Tompkins said. “That is something that we wanted to do to help. ... We have some challenges unlike challenges in other areas of employment, but we're big men and women, and we've chosen to do this work. Even with the frustrations that may come with it, our job is to find ways to make it work better.”

With nearly $118,000 in cash on hand, Tompkins’ campaign coffers eclipse Zamor Calixte’s roughly $30,000. Though Zamor Calixte has the support of the Massachusetts Women’s Political Caucus (MWPC) and Elect Black Women PAC, Tompkins' list of endorsements includes blue-chip supporters like Mayor Michelle Wu, a majority of Boston elected officials, Correction Officers Local 419 and leaders from major labor unions around the city.

Zamor Calixte says she's not fazed by Tompkins' long list of big-name support. "Endorsements don't win campaigns," she said. "Meeting people and getting people to the polls, that's what gets you your win. We've been running a strong grassroots campaign from the beginning ... and I don't think anyone can predict where this race is going."

As part of her campaign announcement, Zamor Calixte pledged to refuse donations from department employees or current contractors affiliated with the sheriff's office, promising "a campaign that models integrity by not taking money that presents a clear conflict of interest."

A report released in January from government watchdog organizations Common Cause and Sheriffs for Trusting Communities detailed $319,002 in “ethically conflicted” campaign donations to the Suffolk County Sheriff's Office between 2010 and 2021. In 2016, a Fox 25 News investigation found that more than one third of donations to Tompkins' 2016 re-election campaign came from his employees. In interviews with Fox 25, employees described a "pay to play" culture where employees were pressured to contribute, an allegation Tompkins described as "utter nonsense" in an interview with the station. “All I ask from my labor force is to come to work and put in a good day's work for a good day's pay,” Tompkins told Fox 25 reporters. “You don't have to contribute to my campaign. You don't have to hold a sign for my campaign. You don't have to do anything for my campaign.”

Tompkins was raised in Harlem by a single mother who struggled with substance use issues, leading him to become, in his words, “parentified” at a young age. When former Suffolk Sheriff Andrea Cabral tried to recruit Tompkins to work in the communications division of her office, he rejected the offer twice, not being comfortable with “getting a paycheck in a jail... it just didn’t resonate with me.” Eventually Cabral, his friend and former Boston College classmate, convinced him to join the department, leading to a job that he now describes as “my destiny.”

Tompkins recognizes that he occupies a position of power within a flawed system where he faces constant “frustrations and pitfalls,” one that he says he still believes he can change.

“The criminal justice system isn't broken,” Tompkins said. “It was built to be punishing and punitive. We have to look at ways in which we can circumvent that, how we get around that.”

Zamor Calixte, born in Brooklyn, raised in Cranston, R.I., and educated in Boston, is described by her parents as “strong-headed,” a quality passed down from her mother and her mother’s mother before her.

“I never take no for an answer, no matter what anyone says, and Sandy learned that from me,” Zamor Calixte’s mother Margareth said, accompanying her daughter at a campaign stop. “If you can imagine it, you can find a way to make it possible.”

Both candidates agree that the mandate for the sheriff is “care, custody and control,” but they differ on what that initiative means for the future of the role and what a county sheriff can — and should — be able to do.

Update: This article has been clarified to include cash on hand for both candidates from this year only excluding campaign donations from previous years, and to clarify Sheriff Tompkins' involvement in the Suffolk County trial court at Mass. and Cass.