Charles Barry says his life of crime began in 1984 when he lost his job at a printing press and his partner’s public benefits were suddenly yanked.
“The rent is due. There was no food in the house,” he recalled. “Welfare cut her off. I’m not working. What am I supposed to do?”
He went to 14th Street and began “messing with the turnstiles” in the subways — the start of decades of ripping off tourists.
What became Barry’s main scam is relatively simple: He gummed up the electronic MetroCard vending machines and raced in to assist flummoxed riders while wearing a vest that made him look like an MTA staffer. He then either stole the loaded MetroCard or used the tourist’s credit card information to buy another card after they left.
Barry, 57, has been arrested approximately 160 times for the scams, mostly conducted around Times Square. He’s currently facing a series of charges in Manhattan that could put him back behind bars for more than a decade, records show.
His story touches on several fronts — drug addiction, homelessness and a lack of job skills and opportunities — that criminal justice reformers say lead to repeated trouble with the law, if not addressed.
None of those underlying issues were ever effectively tackled in Barry’s repeated contact with the police and criminal courts, records show.
“The system definitely failed him,” said Ebette Fortune, his Legal Aid Society lawyer.
‘I Can’t Be Stopped’
Barry says that his life of crime was largely used to bankroll a cocaine addiction he’s struggled with for decades.
“No one has ever stopped to say, what’s going on with Mr. Barry? Why did he keep getting arrested?” said Brett Taylor, senior advisor for the Center for Court Innovation, which operates multiple alternate programs for people in the criminal justice system.
He’s been held up as the poster child for everything wrong with the bail reform that went into effect on Jan. 1 and was pared back a bit in April. His mugshot ran on the front page of the Daily News with the headline “Menace 2 Society.”
“Bail reform, it’s lit!” the newspaper quoted him saying. “It’s the Democrats! The Democrats know me and the Republicans fear me. You can’t touch me! I can’t be stopped!”
By all accounts, his prior time behind bars, which included six stints in prisons upstate totaling 16 years, did nothing to stop him from returning to crime.
“It’s easy to say that doesn’t work. The harder thing is, what does work?” said Michael Jacobson, who served as city Department of Correction commissioner and head of the Probation Department during the Giuliani administration.
Rehab and job training programs are pricey — but so is the cost of incarceration, criminal justice reformers point out. A conservative estimate of the taxpayer bill of Barry’s time behind state bars adds up to approximately $1.1 million.
Some believe cases like Barry’s highlight the need to overhaul the criminal justice system.
In Scandinavia and Germany, countries held by reformers as the gold standard, people with mental health issues or drug problems are automatically diverted from the criminal system into an entirely separate mental health track.
“I think there’s actually a bigger issue, that his case sharpens, which is the question at the moment, which is, what is the criminal justice system good for?” asked Liz Glazer, who recently stepped down as head of the Mayor’s Office of Criminal Justice.
“When do we use the criminal justice system? And when do we use a civilian system?” she asked.
‘Batman and Joker’
New York City has “this very well developed law enforcement muscle” with a 24-hour police service in every neighborhood, Glazer noted. People are trained to call 911 when they see something awry and that typically kicks the criminal system into gear, she said.
“But I think what we have started to learn is that a civilian approach in the first instance may seem more effective,” she added. “But to do that we need to be as disciplined and comprehensive in knitting together our civilian resources as we are in having a police service.”
Over the years, Barry has become so well known to cops he talks about it in comic book terms, referring to his repeated run-ins as “Batman and Joker.”
All told, 220 people served 10 or more stints in city jails from January 2017 to June 2020, according to the Mayor’s Office of Criminal Justice. Of those cases, 78% (2,087) were for 30 days or fewer and 40% (1,043) were for a week or less, MOCJ said.
As for Barry, whose nickname is “Midtown” for where he hangs out, he also believes he has been targeted by cops, most recently by those against bail reform.
“The reason why I was in the Daily News wasn’t for my criminal endeavors. It was because I was the poster child for bail reform,” he said. “They don’t want bail reform.”
The city contracts with several program providers who target so-called “frequent flyer” defendants like Barry.
They include the nonprofit Center for Alternative Sentencing and Employment Services’ newSTART programs, described as “short-term alternatives to incarceration” that include treatment, job workshops and community service. Participants had an average 26 previous misdemeanor convictions.
The Center for Court Innovation also runs a series of programs for people with repeated misdemeanor offenses.
According to Barry, the Doe Fund has been his current salvation, hooking him up with cleaning work in Manhattan and housing in a hotel in east Midtown.
He says he’s finally turning his life around after he hit rock bottom on the front page of the Daily News on Feb. 13. For the first time since his teen years he hasn’t been arrested in months and is drug free, Barry said.
But he insists that no program or service could have reached him earlier.
“Bottom line is it’s not about the system helping you sooner,” he said. “It’s about you. You have to make a conscious decision to stop.”
“I could have been greater years ago,” he added, noting he’s had “his hand in transit money for 37 years.”
‘Dying for Help’
Academics and service providers say people with scores of arrests are the ones in most need of help, even if they don’t see it.
“This is absolutely a guy who can be helped, he’s dying for help,” said Adam Brown, assistant professor at the Silberman School of Social Work at Hunter College.
Research shows that people with addiction issues are also battling depression, anxiety or some other intense mental health disorder.
“I’ve worked with people with addiction for many years,” said Brown, a forensic social worker.
“And I can tell you that I’ve never worked with anybody with an addiction, who doesn’t have a comorbid psychiatric diagnosis,” he added, noting that it isn’t always something as severe as schizophrenia.
People with addiction could be battling depression, anxiety, OCD, post traumatic stress disorder, or a bipolar disorder, Brown said.
“These are things that you see quite commonly in people who have substance abuse dependency, whether it’s alcohol, heroin or cocaine,” he said.
Still, Barry was never offered some kind of intensive or long-term drug treatment, according to his lawyer.
“I don’t think he had many opportunities to help him get on his feet like the opportunity he has now,” Fortune said.
“My experience is that often when someone has continued to be arrested for a crime...that there’s a sense of giving up on the person,” said Courtney Bryan, the executive director for the Center for Court Innovation.
In those cases, the repeat offender is rarely given a broad assessment to identify underlying factors that cause the bad behavior, she added.
‘Dignity and Humanity’
Barry’s long term recovery faces an uphill battle.
He earns $15 an hour, minimum wage, for his street cleaning job with the Doe Fund, which touts providing “paid transitional work, housing, educational opportunities, counseling and career training to people with histories of homelessness, incarceration, and substance abuse.”
The pay is a steep drop from the $200 to $300 Barry says he could make in a few hours running MetroCard scams underground. A large portion of that money, he said, went to buying drugs.
Meanwhile, his hotel fee is part of a program the de Blasio administration is seeking reimbursement from the Federal Emergency Management Agency.
New York City, and the rest of the country, doesn’t have nearly enough programs in place for people with jail or prison histories, said Thomas Safian, co-founder and executive director of Refoundry, which provides people out of prison with job skills and mentorship.
Manual labor is not a fit for everybody coming home from incarceration, he said.
“We have to develop better ways to assess and amplify what skills and talents they do have in order to place them in living wage jobs that are upwardly mobile,” he said. “And that brings with them a sense of dignity and humanity.”
Programs that include six to eight weeks of work training typically lead to low-paying jobs that “employers don’t invest in,” he added. Those programs are also more likely to get government support because they are able to churn out more people, he said.
Barry is part of the Doe Fund’s Ready, Willing & Able nine-to-12 month residential re-entry program for men leaving jail or a homeless shelter. Since 1990, the Doe Fund says it’s has helped 28,000 people obtain some kind of employment. Of the men who graduate the program, 82% retain employment for at least 3 months. The number drops to 67% after six months, according to the fund.
‘Belongs Behind Bars’
Some in law enforcement don’t think repeat offenders like Barry can turnaround their lives without being locked up.
“After 160 arrests, Mr. Barry belongs behind bars — period,” said Michael Palladino, former head of the Detectives Endowment Association who retired earlier this year after more than 40 years with the NYPD.
“The question is not how the system has failed Mr. Barry, the question is how the system keeps failing the innocent law-abiding New Yorker,” added Palladino, now the president of the National Police Defense Foundation. “It’s time the good governor should admit his mistake and amend the law.”
Barry is now facing more time away just as things are finally starting to go his way, according to his lawyer.
He’s currently charged with multiple thefts, including allegedly stealing $50 out of a woman’s hand near Times Square on Jan. 19. He’s also charged with selling someone a bogus $32 MetroCard at the Bryant Park subway station on Feb. 18, according to the criminal complaint.
At Barry’s arraignment for the various offenses earlier this year, the prosecutors sought to have him held on bail. Judges in each case rejected those arguments.
“The easiest thing to do is to keep arresting him a million times even though it costs a fortune but it obviously does nothing with or without bail reform,” said Jacobson.
His lawyer hopes some plea arrangement can be worked out so Barry can continue his recovery.
He’s got an unlikely ally: a New York City victims’ rights group.
“Our system is not set up really to be rehabilitative or to reintegrate people,” said Azaleea Carlea, director of legal services for the New York City Alliance Against Sexual Assault, which advocates and runs programs for sexual assault victims.
“It’s more of a reactive adversarial system where a lot of the goals are punitive and adversarial,” she added. “We need more community based approaches and more programs that get to the root of why people engage in violent behavior and offenses.”