As abuse allegations in a rural jail piled up, criminal inquiries dragged on or went nowhere. No one scrutinized how the sheriff ran his jail.

By Ilyssa Daly and Jerry Mitchell

Part I

Ilyssa Daly examines the power of sheriff’s offices in Mississippi as part of The Times’s Local Investigations Fellowship. Jerry Mitchell is an investigative reporter who has examined civil rights-era cold murder cases in the state for more than 30 years.

Terry Grassaree was dogged for years by questions about how he did his job as a law enforcement officer in Macon, Miss., a tiny, rural town near the state’s eastern border.

There were allegations of rape inside the jail that Mr. Grassaree supervised, and lawsuits claiming that he covered up the episodes. At least five people, including one of his fellow deputies, accused him of beating others or choking them with a police baton.

Mr. Grassaree survived it all, rising in the ranks of the Noxubee County Sheriff’s office, from a deputy mopping floors, to chief deputy, to the elected position of sheriff, making him one of the most powerful figures in town.

The Noxubee County Courthouse is reflected in the window of an abandoned shop in Macon in February. 

(Photo: Rory Doyle for The New York Times)

Now, more than three years after losing an election and retiring, and 16 years after a woman first claimed that Mr. Grassaree pressured her to lie about being raped, the former sheriff faces criminal charges.

A federal indictment filed in October accuses him of committing bribery in 2019, near the end of his eight-year tenure as sheriff, and of lying to federal agents when they questioned him about whether he requested sexually explicit photographs and videos from a female inmate. Mr. Grassaree has denied the charges and pleaded not guilty.

But an investigation by The New York Times and the Mississippi Center for Investigative Reporting at Mississippi Today reveals that allegations of wrongdoing against Mr. Grassaree have been far more wide-ranging and serious than those federal charges suggest. The investigation included a review of nearly two decades of lawsuit depositions and a previously undisclosed report by the Mississippi Bureau of Investigation.

At a minimum, the documents detail gross mismanagement at the Noxubee County jail that repeatedly put female inmates in harm’s way. At worst, they tell the story of a sheriff who operated with impunity, even as he was accused of abusing the people in his custody, turning a blind eye to women who were raped and trying to cover it up when caught.

Over nearly two decades, as allegations mounted and Noxubee County’s insurance company paid to settle lawsuits against Mr. Grassaree, state prosecutors brought no charges against him or others accused of abuses in the jail. A federal investigation dragged on for years, and led to charges last fall, a few weeks after reporters started asking authorities about the case.

Even now, no higher authority has reviewed how Mr. Grassaree ran the jail or whether his policies endangered women, because in Mississippi, as in many states, rural sheriffs are left largely to police themselves and their jails.

In 2006, after Mr. Grassaree and his staff left jail cell keys hanging openly on a wall, male inmates opened the doors to the cell of two women inmates and raped them, according to statements the women gave to state investigators. One of the women said Mr. Grassaree pressured her to sign a false statement to cover up the crimes, according to the state police report that has never been made public.

About a year later, in a lawsuit, four people who had been arrested gave sworn statements accusing Mr. Grassaree of violence. Two of the people said he choked or beat them while they were in his custody. A third said he pinned her against a wall and threatened to let a male inmate rape her.

Photos of sheriffs, including Mr. Grassaree, top center, in the Noxubee County Sheriff’s Department in Macon, Miss. Despite being a mostly Black county, every sheriff in Noxubee County was white until 1988. (Photo: Rory Doyle for The New York Times)

In 2019, a jailed woman told investigators that she had been coerced into having sex with two deputies who offered her a cellphone in exchange for her compliance. Instead of punishing the deputies, she claimed in a lawsuit against the county, Mr. Grassaree demanded that she send him explicit pictures and videos of herself. The federal indictment also accuses Mr. Grassaree of using his cellphone to facilitate a bribe, which experts say could have been the perks the woman says she received.

All told, at least eight men – including four deputies and Mr. Grassaree himself – have been accused of sex abuse by women inmates who were being held in the Noxubee County jail while Mr. Grassaree was in charge.

At least eight men – including four deputies and former Sheriff Terry Grassaree – have been accused of sexual abuse by women being held in the Noxubee County jail while Mr. Grassaree was in charge. (Photo: Rory Doyle for The New York Times

Over the years, the accusations of rape and other misconduct at the jail have been investigated separately by the F.B.I., the Department of Justice and the Mississippi Bureau of Investigation. No rape or assault charges have been filed.

Mr. Grassaree has denied all of the allegations against him and has faced no disciplinary action. His lawyer declined to comment further.

Holding people accountable for rapes and assaults behind bars is difficult under the best of circumstances. There is little to protect incarcerated victims and witnesses from retaliation for speaking up. When they do come forward, they are often dismissed as not credible, especially if the person accused is a law enforcement officer.

What happened inside the Noxubee jail, and how the authorities responded, is a case study in how those difficulties can be even harder to surmount in rural places, where jails are the exclusive domain of a county sheriff who operates largely without oversight.

No state agency oversees Mississippi’s county jails, and no state regulator has the authority to fine a sheriff for endangering people in custody or for failing to train the staff who operate the jail. In 2017, state lawmakers stopped providing funds for jail inspections by the Mississippi Department of Health, removing even the basic requirement that the facilities meet food safety and cleanliness requirements.

“They are closed-off institutions, and the people held inside them are unpopular and politically powerless,” said David Fathi, director of the American Civil Liberties Union National Prison Project. “That makes them ripe for neglect and abuse that is entirely foreseeable.”

Scott Colom, the elected district attorney for Noxubee County, took office in 2016 and was not involved in the investigation of the 2006 rape allegations.

After learning of the more recent allegations against Mr. Grassaree and his deputies, Mr. Colom said, he notified federal authorities and worked with them on an investigation. Although he believed the evidence against Mr. Grassaree in the case was “clear and strong,” Mr. Colom said he knew it would be tough to seat an impartial jury in Noxubee County. He has twice been forced to cancel criminal trials because there were too few potential jurors available, he said, and neither of those cases involved a public official.

Darren J. LaMarca, U.S. Attorney for the Southern District of Mississippi, declined to comment on the case and so did others responsible for investigating the alleged abuses in the Noxubee County jail.

Mr. Grassaree spoke briefly in an interview about his professional history, but would not answer detailed questions about the 2006 rape cases or the more recent allegations related to his federal charges.

Mary Taylor, a retired dispatcher who worked full time at the jail from 1988 to 2017, said in a phone interview that in her years at the jail she never witnessed any sexual abuse.

She said she wasn’t working on the day the two women said the rapes took place in 2006, but that she doesn’t believe their version of events.

“My belief? They weren’t raped,” Ms. Taylor said. “They did that to get out of jail.”

She maintained that it’s “impossible for one man to rape a woman, unless she’s not moving, unless it’s a Bill Cosby thing.”

“They could have yelled out and told somebody,” she said. “You can’t rape the unwilling.”

Building a Tough Reputation

When Terry Grassaree was born in Macon in 1962, the idea that he could one day be sheriff seemed far-fetched.

In Macon, which briefly served as Mississippi’s capital during the Civil War, only white men worked as law enforcement officers in those days. The county had a long history of violence against African Americans, including the massacre of 13 Black Mississippians at a church, gunned down by nightriders on a single August night in 1871. The sheriff at the time arrested no one.

In this 2000 photo, Terry Grassaree kneels on the neck of Teronto Calhoun after charging the 20-year-old with resisting arrest. (Photo: Scott Boyd/The Macon Beacon)

Though the county’s population is mostly Black, every sheriff elected in Noxubee County was white until 1988, when Albert Walker became the first Black man to hold the office. Mr. Grassaree, his handpicked successor, was the second.

Mr. Grassaree started his law enforcement career as a police officer in Macon and in nearby Brooksville, and sold insurance on the side to help make ends meet. Sheriff Walker hired him as a county deputy in 1992 and put him to work mopping floors, among other duties, at the county jail. Mr. Grassaree was also a deputy coroner, paid $85 for each body he handled.

He worked his way up to chief deputy, and took on running the jail.

Mr. Grassaree, known to keep order by issuing physical threats, said in an interview last year that he drew inspiration from the professional wrestler “Stone Cold” Steve Austin.

“Even while they were whipping him, he was still the toughest guy on the mat,” Mr. Grassaree said. “He’s like, ‘Is that all you’ve got?’ No matter how long a man whips you, he will get tired. He might think he’s winning. The only thing you’ve got to do is hold out.”

This idea, he said, became the foundation for how he behaved when he put on his uniform.

Early in his career, he beefed his 6-foot-2 frame up to 230 pounds, and people started calling him “Big Dog.” Not many people crossed him after that, he said.

His reputation for being aggressive spread across town. In a 2006 letter to the editor in the local paper, a mother complained that Mr. Grassaree had threatened her 16-year-old son. The boy, she wrote, had fought with Mr. Grassaree’s son at school.

The editor of the same newspaper, The Macon Beacon, arrived to cover an arrest near a nightclub in 2000 and snapped a picture of Mr. Grassaree kneeling on a man’s neck. The photo made the front page.

People who passed through the jail describe being attacked by Mr. Grassaree when he thought they were causing trouble. Four people gave sworn statements about such attacks as part of a 2005 lawsuit against Mr. Grassaree and Noxubee County filed by former deputy Kendrick Slaughter. In the lawsuit, Mr. Slaughter claimed that Mr. Grassaree tried to bribe him not to run for City Council, and then hauled him to jail for talking to the F.B.I. about the alleged bribe.

Noxubee County’s insurance company settled the suit for an undisclosed amount.

The four sworn statements accuse Mr. Grassaree of a number of violent acts, which he has denied committing. One man wrote that while he was handcuffed in a courtroom in 2002, Mr. Grassaree beat him until a judge came off the bench to rescue him.

Another man said in his sworn statement that Mr. Grassaree choked him with his nightstick and warned him to follow his orders. The man said Mr. Grassaree told him, “I’ll shoot you in the head! I’m the Big Dog! I’m Number One! This my jail!”

A 19-year-old woman said Mr. Grassaree hit her twice with his nightstick and threw her against a wall after accusing her of stealing potato chips from a man held in jail. Mr. Grassaree “spread my legs apart with his foot,” she said in her deposition.

Then, she said, he told her that he ought to let the inmate rape her.