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St. Petersburg man was one of first in Florida sentenced under ‘two strikes’ law

He has seen people who commit homicides, including a man who killed his brother, get released from prison while he serves a life sentence for a robbery in which no one was injured.
Carolyn Youngblood holds photos of her son, Dorian Mackeroy, inside of her St. Petersburg home. He is serving a life sentence in Hardee Correctional Institution.  Mackeroy was designated a prison releasee reoffender after committing a robbery in 1997. He has been in prison for 23 years.
Carolyn Youngblood holds photos of her son, Dorian Mackeroy, inside of her St. Petersburg home. He is serving a life sentence in Hardee Correctional Institution. Mackeroy was designated a prison releasee reoffender after committing a robbery in 1997. He has been in prison for 23 years. [ BOYZELL HOSEY | Times ]
Published Nov. 11
Updated Nov. 13

This article was published in partnership with The Marshall Project, a nonprofit news organization covering the U.S. criminal justice system.

Dorian Mackeroy’s days begin early — 4:30 a.m. — on a bunk bed in an open dormitory. They start with a walk, past stacks of razor-wire coils to a chow hall.

His days press on after the sun blankets a small courtyard that lies beyond the steel doors of Hardee Correctional Institution, about 45 miles southeast of Tampa. In the Florida heat, he trims grass, prunes Indian hawthorn shrubs, nurtures hibiscus and jasmine and Mexican heather flowers beneath a set of towering palms. On lunch breaks, he reads newspapers or law books.

His days end back on the bunk, where he scratches out letters to academics, lawmakers, lawyers, judges — anyone who might listen.

He writes of regrets and grief and injustice. He writes of the crime he committed — a St. Petersburg armed robbery that still haunts its victim. Piled onto his past troubles, it was enough for the state of Florida to decide Mackeroy deserved to be locked up for life.

Mackeroy, 46, is one of 2,134 Florida prisoners serving life sentences without parole as “prison releasee reoffenders.”

Dorian Mackeroy is serving a life sentence in Hardee Correctional Institution. Mackeroy was designated a prison releasee reoffender after committing a robbery in 1997.
Dorian Mackeroy is serving a life sentence in Hardee Correctional Institution. Mackeroy was designated a prison releasee reoffender after committing a robbery in 1997. [ MARTHA ASENCIO-RHINE | Times ]

The designation denotes a law unique to Florida that gives prosecutors the power to increase sentences if a person commits a new crime within three years of release from prison. The law, sometimes referred to as a “two-strikes” rule, took effect in 1997, amid an era of policies that made punishment the foremost goal of Florida’s criminal justice system.

Related: In Florida, two strikes and you’re in prison forever

So Mackeroy, who did not end anyone’s life, is serving the same sentence as those who have.

The state abolished parole in 1983; and the law makes no exceptions for people who committed their first crime as a young adult, or in Mackeroy’s case, as a youth. Even Florida judges cannot reduce a sentence like Mackeroy’s — what a prosecutor seeks, he or she gets, if a jury convicts.

The two-strike punishment has been disproportionately applied to Black men, an analysis of state data by The Marshall Project and the Tampa Bay Times found. Among all prisoners serving life in Florida, 54 percent are Black; but among those serving life with enhancements like two strikes, 74 percent are Black.

In some counties, the racial disparities regarding sentence enhancements are glaring, the analysis found: In Leon County, home to the state capital of Tallahassee, among people serving life sentences for crimes committed within three years of release from prison, 96 of 107 are Black. In Pinellas County, where Mackeroy grew up, 75 percent of prisoners serving life with two-strikes sentences are Black.

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Imprisoned for 23 years, Mackeroy was among the first to receive a life sentence under the new law.

Lawyerless, he files his own court papers challenging his sentence. He asks for mercy.

So much trouble he couldn’t get out

In a photo on a kitchen wall of a small St. Petersburg home, Mackeroy sits beside a Christmas tree, clad in prison-issued blue.

This is the home of Carolyn Youngblood, Mackeroy’s mother, who remembers struggling to raise three sons while sometimes working three jobs, who remembers her oldest helping care for his brothers, who remembers a gifted football player and track athlete.

Much of Mackeroy’s childhood happened in Childs Park, a neighborhood west of Interstate 275, not far from Tropicana Field. Most residents are Black, and many live below the poverty line. It’s a place from which many young people struggle to escape.

“I could tell him stuff that he should be doing,” Youngblood says of her son. “But he needed a male figure to show him what to do.”

Carolyn Youngblood holds photos of her son Dorian Mackeroy inside of her St. Petersburg home. Mackeroy is serving a life sentence in Hardee Correctional Institution in Florida. He grew up in St. Petersburg.
Carolyn Youngblood holds photos of her son Dorian Mackeroy inside of her St. Petersburg home. Mackeroy is serving a life sentence in Hardee Correctional Institution in Florida. He grew up in St. Petersburg. [ BOYZELL HOSEY | Times ]

His father worked for the city. Alvin Mackeroy met Youngblood when they were teenagers. They split up when their oldest son was about 7. Dorian Mackeroy’s father wasn’t a consistent presence.

Guidance came from his peers. They drank and smoked weed and sometimes fought.

In his early teens, he racked up a string of arrests. Things like running out of the store without paying. Or breaking into cars. Or carrying a concealed weapon.

His mother warned him: If he kept hanging around the wrong people, he might get into so much trouble he couldn’t get out.

At 16, he was accused with three other teens of robbing a man in a park near the University of South Florida’s St. Petersburg campus. Years later, Mackeroy recalls that they were looking for a car to steal to go joyriding. He says he only stood by as an older friend decided to rob the man. A police report states the victim identified Mackeroy as one of those who confronted him. The man said the group beat him. One of the teens jabbed the man with a screwdriver.

Mackeroy spent 21 days in a juvenile lockup. Upon his release, his mother enrolled him in a Job Corps program in Gainesville.

While he was there, he missed a court date. He was arrested on a warrant for failure to appear and brought back to Pinellas County.

He later pleaded guilty in adult court to the robbery charge and accepted a four-year prison sentence.

“A lot of things I did were really dumb,” he says. “It wasn’t as much as I was a bad kid or I didn’t have the morals or values. I just didn’t know what they were at the time.”

Dorian Mackeroy’s high school diploma on display inside the home of his mother, Carolyn Youngblood in St. Petersburg. Mackeroy, is serving a life sentence in Hardee Correctional Institution.
Dorian Mackeroy’s high school diploma on display inside the home of his mother, Carolyn Youngblood in St. Petersburg. Mackeroy, is serving a life sentence in Hardee Correctional Institution. [ BOYZELL HOSEY | Times ]

When he came home in 1994, he moved in with a girlfriend. He got a job washing dishes at Denny’s, and another painting and remodeling houses.

He became a dad.

D’Shauna Wilson is the oldest of Mackeroy’s three daughters. She has memories of accompanying her father to baseball games in downtown St. Petersburg and watching planes rise over Tampa Bay from Albert Whitted Airport. She remembers her father getting her dressed in the mornings and styling her hair in pigtails.

‘The bite of the statute’

How did it go wrong? Mackeroy blames alcohol and, again, hanging out with the wrong people. In 1995, he was ordered back to jail for nine months for writing a forged check and violating probation.

He remembers one night in June 1997. He was 22. He remembers drinking. He remembers a friend egging him on in a kind of dare. He remembers taking a socket wrench and wrapping it in a bandana, so that the metal end looked like a gun barrel.

He remembers a woman in a car near a small eatery called Red’s Snak Shak.

She was alone in the dark, waiting for a friend who’d gone to get food.

He got into the driver’s seat.

She knew him. They’d gone to school together, she would later say in court. She would describe him telling her to “give me what you got” and pressing the cold metal against her temple.

She said his name.

He told her not to say it. He told her not to look at him.

“I’m not playing,” he said.

She gave him two diamond rings, a bracelet and a gold necklace. She said he threatened to shoot her before he left.

He was arrested the day before Christmas, 1997.

At trial, he took the witness stand and claimed he didn’t know the victim.

A jury took about 90 minutes to find him guilty.

He’d never heard of the two-strikes law. He says he didn’t learn about it until his lawyer explained it the day he was sentenced.

The victim told the judge she wanted the longest sentence possible.

“I’m still having problems after the fact,” she said.

The prosecutor read a litany of Mackeroy’s past troubles and said that because of those, the state required certain punishment.

“That is a life sentence.”

If he’d gotten in trouble just a month earlier, before the two-strikes law took effect, sentencing guidelines may have allowed his release after 11 years.

Judge Richard Luce made it final.

“It would appear then that really there are not any circumstances that can mitigate from the bite of the statute,” he said.

‘It doesn’t reduce crime’

The victim in the robbery case, whose name the Tampa Bay Times is withholding to protect her privacy, said recently that the memory of the crime still gives her anxiety and panic attacks.

“It doesn’t go away,” she said. She told a reporter not to call her again.

Thane Covert, the prosecutor who sent Mackeroy to prison, was appointed to the bench in 2005 by former Florida Gov. Jeb Bush. He served 15 years as a judge before retiring early this year.

He vaguely recalls Mackeroy’s case. When told of the circumstances, he said it sounded like a serious crime but declined to comment further.

Speaking in general, though, he said there were times when he as a judge would have liked to have more say.

“But the law is what the Legislature decides it to be,” he said. “I took an oath to follow the law.”

State Sen. Jeff Brandes, R-St. Petersburg, has twice introduced a bill that would roll it back. He’s not optimistic but feels he has to try to address what he sees as a law that’s arbitrarily designed.

And the truth is it doesn’t work,” Brandes said. “It doesn’t reduce crime.”

Related: How Florida’s ‘two-strikes’ law leads to life sentences

Alex Piquero, a criminologist and professor at the University of Miami, says data backs that up. He also noted that research has shown young people who commit crime have a tendency to grow out of it, or become less likely to commit crimes if they receive substance abuse and mental health treatment.

“What actually happens is you lock up people who shouldn’t be there for a very long time,” he said. “And it costs more money to incarcerate these people.”

Slow-motion death sentence

In 23 years, Mackeroy’s only disciplinary actions, as reflected in Department of Corrections records, were for “disrespecting officials” and “disobeying regulations.” Both occurred more than 15 years ago.

In prison, Mackeroy has seen his daughters become adults. He’s seen his mother cry when she has to leave her oldest son at the end of monthly visits. He’s endured the pain of learning his younger brother was murdered, and frustration and rage when the man who killed him got released in little more than eight years.

He files his papers. He writes of having completed classes in substance abuse, anger management, critical thinking and victim impact. In 2012, he wrote a “second-chance profile,” telling the judge that he knows what he did was wrong, how he doesn’t deny he deserved punishment. But not life.

“Every time I think about the situation, I feel remorse,” he says. “I feel embarrassed. I feel so much.”

He’s trusted enough that he’s been able to work as a barber and on the prison grounds crew. He dreams of working for a landscaping company.

Ask about his family, his children especially, and his eyes glisten.

“I feel so stupid that I left them—” He pauses as his voice rises. “Alone,” he says. “Alone in this world without a father figure.”

He fears losing his mother. He fears getting so old in prison that he can no longer think to fight his legal battle. He fears what amounts to a slow-motion death sentence.

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