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A Homeless Man Has Spent 800 Days At Rikers After Stealing Cold Medicine. Now His Prison Sentence May Be Beginning.

Blind in one eye and at risk of losing vision in the other, 58-year-old Reginald Randolph is now on the verge of being sent to state prison to serve out a maximum of four years.

Randolph and his family in 1997.
Courtesy of Legal Aid Society.

A Homeless Man Has Spent 800 Days At Rikers After Stealing Cold Medicine. Now His Prison Sentence May Be Beginning.

Blind in one eye and at risk of losing vision in the other, 58-year-old Reginald Randolph is now on the verge of being sent to state prison to serve out a maximum of four years.


This story was published in partnership with New York Focus.

After failing out of drug court, Reginald Randolph, 58, was sentenced in August to two to four years in state prison for taking dozens of boxes of cold medicine from two Duane Reade stores in 2018.

“[Shoplifting] was just to support my addiction and to deal with my homelessness, deal with my poverty,” Randolph told New York Focus and The Appeal in a phone call from the Rikers Island jail complex in New York City.

Blind in one eye and at risk of losing vision in the other, Randolph is now awaiting a transfer from Rikers to a New York state prison.

“We’re not treated as humans in here,” he said, referring to Rikers.

Randolph says he goes without meals for three or four days and has lost about 40 pounds. At a recent dinner, a mouse was found in a pan of potatoes. For the 50 people in his unit, there are three working toilets, but they occasionally back up while someone is using them. There’s one working shower.

A spokesperson for the New York City Department of Correction told New York Focus and The Appeal in a statement: “We are committed to a safe environment in our jails where every person in custody is fed healthy food and has access to functioning facilities and to services.”

The agency also said Randolph’s housing area was inspected and all showers and toilets are operable; food is provided regularly; and they were not able to substantiate a rodent complaint like the one described. The agency’s denials conflict with widespread reports of inhumane and dangerous conditions at Rikers from elected officials, incarcerated people and their family members, the federal monitor overseeing the city’s jails, and public defenders.

In September, the Legal Aid Society, which represents Randolph, submitted a clemency petition to the Executive Clemency Bureau, which conducts a preliminary review of applications before sending them to the governor. Legal Aid is requesting that Governor Kathy Hochul grant Randolph emergency clemency and a full sentence commutation so he can be immediately released to the supportive housing program that Legal Aid has already obtained for him.

A spokesperson for the Manhattan district attorney’s office told The Appeal that assistant DA Megan Joy, counsel for collateral consequences, sent an email on Oct. 15 to Joshua Norkin, the governor’s assistant counsel for housing and civil rights which says: “Under the conditions presented by defense counsel (that defendant has a place in supportive housing and will go to the supportive housing), we do not oppose a commutation of his sentence.”

The governor’s office told New York Focus and The Appeal that they cannot comment on pending clemencies.

Randolph’s case is one of many examples of New York’s continued criminalization of mental illness, substance use disorders, and poverty. As of Oct. 15, almost half of the more than 5,500 people incarcerated in the city’s jails received mental health services, according to city data.

“Clients like Reggie have been failed by nearly every system they have touched since birth— from health care to education, housing, mental health, courts, and beyond,” Legal Aid attorney Jeffrey Berman, a member of Randolph’s legal team, told New York Focus and The Appeal in a statement. “There is an opportunity to right a wrong here, and to release Reggie from the shackles of this system so he can take a step forward in his journey of healing and recovery.”

Homeless, sick, and trapped in the system

Randolph’s biography is replete with trauma, untreated mental illness, and institutional failures, according to Legal Aid’s filings—details familiar among those trapped in the legal system.

Randolph’s stepfather regularly beat him, his mother, and his siblings. Randolph left school after the eighth grade and was first arrested when he was 16 years old. By 19, he was using cocaine, LSD, and PCP.

He’s been diagnosed with chronic obstructive pulmonary disease (COPD), polysubstance use disorder, schizoaffective disorder, and asthma. Homeless for more than two decades, he has primarily received mental health care when he has been locked up or at emergency rooms.

By the time he was arrested for stealing cold medicine in 2018, he’d been convicted of more than 50 misdemeanors and a handful of felonies, the most recent in 2005 for attempted robbery and sale of a controlled substance.

Although the DA’s office had the discretion to charge Randolph with a misdemeanor (or not pursue charges at all), they chose to bump up the charge to a felony—two counts of third-degree burglary—because Randolph had a “no trespass” order that banned him from Duane Reade. (Manhattan DA nominee Alvin Bragg, who most likely will be elected, wrote in his Day One memo that “ordinary shoplifting cases should not be charged as burglaries.” Bragg, a Democrat, was not available for comment.)

His bail was set at $15,000, although the DA’s office had asked for $20,000. Unable to pay, he stayed on Rikers Island. (The current version of New York’s bail reform law, which went into effect last year , allows judges to set cash bail for nonviolent offenses in limited circumstances.)

More than a year after Randolph’s arrest, he was accepted into Manhattan Drug Court. In August 2019, he was released from Rikers to an inpatient treatment program. If he didn’t complete the program, but was not arrested on a new charge he would be incarcerated for two to four years, according to the plea agreement he signed with the drug court. If he was arrested again, he faced up to 14 years.

Randolph left the treatment program after three days. “It was too much,” he said. “It was too much coming at me.”

Over the next two years, Randolph picked up more shoplifting charges and tried a second court-ordered treatment program. He left that one after almost four weeks.

“​​It was another residential program, it was basically mental health slash drug treatment,” said Randolph. “We only go out for one-hour walk a day. … It was really intense.”

Randolph’s experiences in drug court are not unique. The DA’s office told New York Focus and The Appeal that between Jan. 1, 2019 and Oct. 28, 2021, 404 people in Manhattan’s felony drug court had their cases resolved. Of those, about 47 percent graduated and over 50 percent failed out of drug court.

Court-ordered treatment programs are often highly regimented, emphasizing obedience and entry into the low-wage workforce, according to Kerwin Kaye, an associate professor of sociology at Wesleyan University and the author of the book “Enforcing Freedom: Drug Courts, Therapeutic Communities, and the Intimacies of the State.”

“Think of it like boot camp,” said Kaye. “There’s a lot of discipline and there’s a lot of rules to follow.”

Drug court—often hailed as a more compassionate alternative to the ’90s-era war on drugs—too often acts as a speed bump before prison, said Kaye.

For drug court participants in Manhattan, minor infractions can result in a range of punishments. For missed appointments, “rule breaking at program,” or arriving late to drug court two times, a judge can order participants to write essays and letters, or take away “program privileges,” according to the Manhattan Drug Court handbook. Repeated violations of these rules can result in jail time, reads the clip-art illustrated handbook.

“The [drug] court is still using prison as a threat in order to coerce people to do what they want them to do,” said Kaye. “It’s not really ending the war on drugs … It’s modifying the way that the war on drugs is waged.”


“Deterrence and retribution”

After he left the second treatment program, Randolph’s chances with drug court had run out.

In August, he went before Criminal Court Judge Cori Weston—herself a former public defender—to be sentenced on the charges from 2018. Before Weston’s appointment to the bench in 2016, she she was an attorney with Legal Aid for seven years and with the New York County Defender Services for almost 20 years. New York County Defender Services, which represents indigent clients in criminal cases, has publicly criticized the Manhattan DA’s practice of charging people who shoplift with burglary.

When Randolph attended the sentencing hearing, he was on crutches. He had fallen in the shower, he told New York Focus and The Appeal, “due to my vision situation.”

Weston sentenced Randolph to two to four years in prison. For each count there was a mandatory surcharge of $375, which Weston deferred until Randolph is released from prison.

Before he was sentenced, Randolph’s legal team filed a motion asking the court to reduce his charges or dismiss the indictment entirely, citing his deteriorating health and mental illness. The Manhattan DA’s office opposed the motion, and Weston denied it.

“Dismissal of the charges could adversely impact the safety and welfare of the community, and would undermine the public’s confidence in the criminal justice system,” Weston wrote in her ruling.

The purpose of imposing Randolph’s sentence, she wrote, was “deterrence and retribution.”

Continued incarceration will have potentially catastrophic consequences for Randolph, according to two medical experts who reviewed his records. He needs consistent, timely medical care to have any hope of preserving his vision, they wrote in letters attached to his clemency petition. But in prisons and jails, medical care for incarcerated patients is routinely denied, delayed, or inadequate.

In a letter submitted with Randolph’s clemency petition, Dr. Alexander Bardey, a former director of mental health services at Rikers Island, wrote that Randolph’s “best hope of keeping what is left of his remaining vision would be for him to be removed from a carceral setting and reside in a supportive residence.” Bardey warned that Randolph is also at risk of potentially fatal complications if he were to contract COVID-19.
“In an environment like Rikers Island or a DOCCS facility, the risk of a sudden, catastrophic outcome is increasingly likely for Mr. Randolph,” he wrote, referring to the Department of Corrections and Community Supervision.


A life in the governor’s hands

Sentenced more than three months ago, Randolph hasn’t been transferred to state prison; the reason for the delay is unclear, said Berman, the Legal Aid attorney. And although he’s been eligible for parole since July 18, he has not yet gone before the parole board. Since his arrest in 2018, Randolph has spent more than 800 days at Rikers Island.

But Legal Aid and Randolph’s supporters are not requesting an expeditious release on parole.

If Randolph is granted parole, he’d likely be sent to a shelter, according to Legal Aid. In 2019, Legal Aid and other groups sued the Department of Corrections and Community Supervision for holding people with mental illness past their release dates. After the suit was filed, DOCCS started to parole people with mental illness to homeless shelters and psychiatric institutions, instead of housing with supportive services. Legal Aid amended the complaint to challenge this practice as well. Last month, the court denied DOCCS’s request to have the class action suit dismissed.

His team at Legal Aid — Berman, along with co-counsel Yvonne Nix and mitigation specialist Afeisha Julien — wants Randolph immediately released so he can move into The Redemption Center’s transitional supportive housing program. Randolph will stay there until he moves into long-term housing with wraparound services, according to Berman.

If Randolph is released he’ll receive additional support from the Bridge Back to Life Center, which will provide intensive outpatient mental health and substance dependence treatment, as well as medication management services, the organization’s CEO wrote in a letter to the Executive Clemency Bureau. Medical care for his eyes will continue at Bellevue Hospital, according to Berman.

“We have the opportunity to get him in a transitional housing program with supportive services,” said Mark Graham, executive director of The Redemption Center. “We’re going to ensure that he’s fed, has a place to sleep. … Parole is not going to do that.”

If Graham could speak with the governor, he would tell her: “When we hear the term and the concept of travesty of justice, we’re looking at it in Reginald’s case.”

The governor’s decision on Randolph’s clemency petition could determine whether he continues a cycle of homelessness and incarceration, or whether he can finally attain the kind of stability and support that he’s been denied for almost 60 years.

Randolph said that if he is released, he plans to participate in treatment programs, take his medications, and “live a normal productive life.”

“I’ll be able to do that cause I won’t have too much poverty to deal with,” he said. “My attorney has me connected with The Redemption Center. I have living quarters there. … I’ve never had that stability in my life. And I would appreciate the opportunity to be able to have that.”


Editor’s Note: This story has been corrected to reflect the fact that Randolph’s attorneys filed their motion to reduce his charges or dismiss the indictment before Randolph was sentenced, not after, as the story originally stated. We regret the error.

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