When Harvey Weinstein, Luigi Mangione and NXIVM cult leader Keith Raniere faced hard time, among the first people they called was Craig Rothfeld.
Rothfeld is the founder and owner of Inside Outside Ltd., a company that helps clients, including the aforementioned three, navigate the unnerving world of life behind bars.
With only about a half-dozen prison consulting firms in the United States, Rothfeld is part of a little-known niche industry spawned around the criminal justice system that caters to big-name and no-name clients, all with the same goal.
“I’m advocating for their human rights,” Rothfeld said.
Rothfeld said he knows firsthand the misery and anguish prisoners experience because he was once incarcerated himself. He served 18 months after he was indicted for various financial crimes and was released in 2017.
He said he started his company later that year to help others get through the challenges he faced.
“Somebody needs a CPAP machine. They can’t breathe or sleep without it. How do I arrange for that CPAP machine to be able to be brought into either a federal prison or a state prison with them?” Rothfeld said.
When someone hires him, Rothfeld gives the person a list of do’s and don’ts based on the 40 questions clients most often ask him, he said.
“Never sit on somebody else’s bed. … Do not go into their cell unless you’re invited. You do not join a conversation that you’re not a part of,” he said.
Rothfeld, whom Weinstein granted permission to talk about his experience behind bars, said Weinstein’s first questions before he was locked up were the same as those of other, nonfamous clients.
“How am I going to talk to my family? Where am I going? And where do you think I’m going, and how are we going to deal with all of my medical conditions and medical needs?” Rothfeld said.
Weinstein, who has chronic myeloid leukemia, or bone marrow cancer, is serving time at Rikers Island in New York City as he awaits sentencing stemming from a sexual assault conviction in June.
One of his attorneys, Jennifer Bonjean, said prison consultants are important advocates for people entering the system.
“As lawyers, we depend heavily on them to help our clients adjust to prison in all manner of ways, whether it’s to help resolve a medical concern, assist with a disciplinary issue or to advocate for a placement in a facility,” Bonjean said this week.
Arthur Aidala, Weinstein’s longtime criminal defense attorney, said he refers clients to Rothfeld because the “fear of the unknown” is overwhelming.
“Preparing to enter prison, and then crossing that threshold, is an experience whose horror is truly indescribable,” Aidala said this week. “For most people, it feels insurmountable.”
In the case of Raniere, who was sentenced to 120 years in federal prison in 2019 on sex trafficking and child pornography charges, Rothfeld’s first task was to get him out of solitary confinement, he said.
Raniere was confined to solitary in 2022 after he was allegedly assaulted by another inmate.
“If you spent 280 days in the SHU [Special Housing Unit] with no explanation whatsoever and you have feces on the floor and the walls, yeah, your human rights are being violated,” he said.
One of Raniere’s attorneys, Ronald Sullivan, said navigating the federal Bureau of Prisons requires knowledge of a “byzantine set of regulations, the understanding of which can make a tangible difference in time served.”
He said that regulations change frequently and that relationships with prison officials often determine how quickly or slowly requests are granted.
Rothfeld said conditions at Rikers Island and the Metropolitan Detention Center in New York City are “deplorable.”
“Some days you have cold water, and that’s it. Sometimes you don’t get to shower for the week,” he said. “The food is inedible. Quite often, there’s leaks coming from the ceiling. There’s broken lights in cells, there’s mice, there’s cockroaches. It is completely inhumane.”
Officials at Rikers Island, a jail that is operated by the city of New York, did not respond to a request for comment.
The federal Bureau of Prisons, which oversees the Metropolitan Detention Center in Brooklyn, said that it makes every effort to ensure inmates’ physical safety and health and that their treatment is humane. It also said the detention center provides nutritionally adequate meals.
Rothfeld said he charges a flat fee for his services but would not provide specifics. He said celebrity clients account for only about 2% of his business.
“I don’t cost what an attorney costs. I don’t cost six figures. I don’t cost what a brand-new, fancy sport car costs,” he said. “I work with families to meet them where they’re at.”
It is not publicly known whether Sean “Diddy” Combs, the former music mogul who is scheduled to be sentenced Friday, has hired a prison consultant. Prosecutors are seeking a sentence of 11 years and three months in federal prison after he was found guilty on two counts of transportation to engage in prostitution.
Combs has been held at the Metropolitan Detention Center for over a year.
Rothfeld said Combs can expect better conditions in a federal prison than at the detention center.
“He’ll be able to go outside,” he said. “There’ll be a yard of access to fresh air. He’ll be able to work out if he wants to work out. The second thing is the nature of his living quarters. In all probability, he will be in a dorm-like setting. Anything is nicer or better, relatively speaking, than the MDC.”
Rothfeld said he encourages his clients to become voracious readers.
“I always recommend that people read fantasy,” he said. “Speaking from personal experience, I read ‘Game of Thrones’ when I was in prison, and it got me outside of where I was.”
For the victims of the crimes his clients have committed, Rothfeld said he is not an arbiter of morality.
“It’s not my job to judge; it’s not my job to argue. It’s my job to advocate. And as I tell people, the punishment is prison,” he said. “I believe, no matter who you are, famous or not, most of my clients should have humane living conditions. Your civil rights should be honored when you’re incarcerated.”