In 2003, 17-year-old Omar Paisley spent three days in a Florida jail cell moaning in agony. Prison staff said he was faking his illness and told him to suck it up. Then he died.

This year and last, the deaths of numerous African-Americans at the hands or in the custody of prison officials and police—including Michael Brown, Freddie Gray, Walter Scott, Tamir Rice, and, most recently, Sandra Bland — have drawn renewed (and belated) national media attention to the state of the criminal justice system. And that, in turn, has made candidates’ stances and records on criminal justice policy a factor in the 2016 presidential race.

It’s a particularly sensitive topic for Jeb Bush, who as governor faced two situations that mirror the deaths of Gray and Bland, both of whom died while in police custody. When Bush was governor of Florida, two teenagers died preventable deaths while in juvenile detention centers. And Bush’s approach to their cases casts some light on how he might look at criminal justice issues if he becomes president.

Paisley’s death could have been averted, and it took a long time. The African-American teenager was put in the 226-bed Miami-Dade Regional Juvenile Detention Center “for cutting another youth with a soda can,” the AP reported, and he filled out a form on June 7—one day after going to the jail—saying he was ill.

“My stomach hurts really bad,” he wrote. “I don't know what to do. I cand [sic] sleep.”

Some of the staff at the facility, according to a Feb. 27, 2004, USA Today story, didn’t take him seriously.

“Ain’t nothing wrong with his ass,” said one nurse.

And supervisor Jack Harrington told Paisley to “suck it up and walk around.”

But you can’t suck up appendicitis. The paper reported that a guard later found the teen lying in his cell covered in feces and urine, sweating profusely and clutching his stomach. Nurse Dianne Demeritte refused to enter the cell, saying she didn’t “want to take his [mess] home to my kid.” (The Palm Beach Post noted that two of his cellmates had to change his sheets and clean up his vomit.)

Demeritte made the sick teen, who could barely walk, walk out of his filthy cell and sit on a chair in the hallway. She concluded that there was “nothing wrong with his ass.” Then, according to USA Today, she filled out paperwork to have him moved to a hospital, left him sitting on the chair, and went on a break. Guards found him passed out and didn’t perform CPR because their first aid kid didn’t contain the necessary equipment.

That’s how Omar Paisley died.

Bush’s communications director, Jill Bratina, sent that USA Today story to the governor and others a few hours after it was published, according to emails made searchable by the Florida Center for Investigative Reporting.

Paisley’s death became national news, and, in one email, Bush promised a constituent it was just an isolated incident.

Bill King of Pensacola emailed the governor to voice his outrage about Paisley’s roommates being forced to clean his vomit from their cell.

“The lives of those kids are as much if not more important than any employee working there as they are not there by choice as the employees are, they are there by design and they have no say over their own lives,” King wrote.

“All of these children are important and should not be placed into any dangerous or unhealthy situations,” he added.

Bush concurred, and emailed King back to say so.

“The interim Secretary [of Juvenile Justice] is cleaning up the mess,” the governor replied. “Thankfully, this is not a problem that is systemic statewide. I appreciate your writing.”

And his assistant general counsel, Wendy Berger, emailed another concerned constituent, Lynda Morse, to promise the governor would do everything he could to ensure that no more incarcerated teens would have to suffer Paisley’s fate.

“Like many throughout this State, Governor Bush was saddened and outraged over the death of this child,” Berger wrote. “Please know that those responsible will be held accountable. Governor Bush has full confidence in Interim Secretary [C. George] Denman’s ability to implement needed reforms. His hope is that the changes made in the Department will prevent anything like this from ever happening again.”

Those hopes were misplaced. Some leaders at the Department of Juvenile Justice stepped down in the wake of Paisley’s death, and the department implemented a new policy allowing any staffer or volunteer to call 911 without first having to get permission.

But there was scant accountability for the adults responsible for Paisley’s death. The two nurses were indicted on murder charges, according to the Palm Beach Post, but neither got jail time. Prison Legal News reported that the prosecutors dropped charges against one of them and that the other nurse—the one who forced Paisley to leave his cell and then insisted that nothing was wrong with him—just gave up her nurse’s license and spent one year on probation. Several prison employees were fired, and Paisley’s mother got a $1.45 million settlement from the Department of Juvenile Justice. In the meantime, nonviolent drug offenders in Florida faced stiff prison sentences.

Less than three years after Paisley’s death, 14-year-old Martin Lee Anderson—also African-American—died in custody at the Bay County Boot Camp detention center in Panama City, Fla. Anderson landed there because he and a few of his cousins took his grandmother’s car joy-riding and then crashed it, according the book The Boys of the Dark: A Story of Betrayal and Redemption in the Deep South, by Robin Gaby Fisher, Michael O’McCarthy and Robert W. Straley.

A video showed seven guards at the boot-camp detention center kicking, kneeing, and hitting the 14-year-old because he wouldn’t run around a track, according to WCTV.

“A medical examiner originally said the teenager died of Sickle Cell trait, but after Anderson’s body was exhumed, a second autopsy revealed he did not die of natural causes,” reported WCTV.

Bush appointed the special prosecutor who ordered the second autopsy that found Anderson didn’t die of natural causes. That autopsy “determined that by blocking Martin’s mouth and forcing him to inhale ammonia fumes—an effort, the guards said, to revive him—they had caused his vocal cords to spasm and block his airway,” The New York Times reported.

Anderson’s family got a $5 million settlement from the state. An all-white jury acquitted the guards who beat and kneed him on video, Time reported.

Later, Bush signed legislation eliminating juvenile detention boot camps in the state. The New York Times noted that previously, Bush was “a strong supporter” of the boot camps. And during his failed 1994 gubernatorial campaign, he told theSun-Sentinel that he wanted to “reform our juvenile-justice system by emphasizing punishment over therapy for juvenile offenders.”

The teens’ deaths may have changed his view.

“Throughout Gov. Bush’s tenure, he worked to reform the juvenile justice system in Florida to improve services, help young offenders turn their lives around and give them the tools needed to be successful in the future,” Bush aide Kristy Campbell said via email.

Campbell noted that the juvenile crime rate dropped by 18 percent during Bush’s tenure in office and that the rate of juveniles entering the adult system went down by more than 40 percent.

“In the tragic cases of Omar Paisley and Martin Lee Anderson, Governor Bush took immediate action to hold those individuals involved in these deaths accountable and to provide additional funding to increase staff and services at juvenile justice facilities,” she added.

The 911 reforms Bush’s Department of Juvenile Justice implemented after Paisley’s death don’t seem to have outlasted his time in office with complete success. On July 10, 2011, four and a half years after Bush’s departure, another teen, 18-year-old Eric Perez, died in a manner that CBS Miami called “hauntingly similar” to Paisley’s. It also recalled Anderson’s death: Guards at the West Palm Beach juvenile detention center where Perez was held roughhoused with him, picking him up and dropping him, before he retreated, hallucinated, passed out, and died.

One guard said Perez was faking his illness and decided that sending him to a hospital wasn’t worth the paperwork, CBS Miami reported.

“[Superintendent Anthony] Flowers insisted he never ‘prohibited or discouraged’ staff from calling 911,” the station reported. “But officers on the scene said they were told the superintendent had ordered staff not to call for help.”

“Though administrators had pledged years earlier to ‘treat every child as if he was your own,’ detention staff had, once again, neglected a youth to death,” the station continued.

And another guard, Floyd Powell, said his superiors specifically told him not to dial 911—even though he feared, correctly, that the worst would happen. He told the Palm Beach Post that he was later fired for sharing that detail with investigators.

Cathy Purvis Lively, the attorney who represented Powell during that time, told The Daily Beast that systemic problems set up Perez’s death.

“The overwhelming concern was staffing,” she said.

Calling 911 meant sending a prison staffer to the hospital along with Perez, and endemic overcrowding and understaffing meant supervisors often hesitated to make the call.

“There were multiple problems,” she said. “At the time, I was representing someone who was essentially the scapegoat, the low guy on the totem pole.”

“He was the one trying to seek intervention,” she added.

Perez’s death wasn’t unforeshadowed. Dale Dobuler took over the Miami-Dade Regional Juvenile Detention Center after Paisley’s death and watched the rollout of the reforms from Bush’s Department of Juvenile Justice. He quit because he didn’t think he could keep the detainees under his watch safe, as “many of the protections put in place after Omar’s death already had begun to erode,” according to the Palm Beach Post.

I asked Dobuler if he stands by those comments in retrospect.

“I stand by my comments,” he said in an email. “They were accurate when I made them and remain accurate now—though I obviously now have less insight into the current state of affairs with DJJ. The fact is, in the aftermath of the Paisley tragedy, DJJ was able to put significant resources in place to address some of the systemic issues at Miami (and other detention centers). With time (and less public attention and media scrutiny), those resources were taken away bit by bit as a result of funding concerns. At the time I left in 2008, I was very concerned that no matter how much of a leadership effort I made locally, it was only a matter of time before another tragedy took place that I would not be able to prevent.”

The failures of Florida’s prison system weren’t unique to Bush’s governorship, as Perez’s death shows. In October 2007, Time detailed a lengthy history of horrific abuse in the state’s prisons that predated Bush. And those kinds of abuses also happen around the country.

After the acquittal of the prison guards who watched Anderson die, his parents’ attorney, Benjamin Crump, summed up the verdict this way:

“You kill a dog, you go to jail,” he said, according to The New York Times. “You kill a little black boy, and nothing happens.”