The 'prison preppers' giving advice to high-profile inmates like Harvey Weinstein

Steve Dagworthy had never received so much as a school detention when, in 2009, he was escorted into HMP Chelmsford to begin a six-year sentence for fraud. Until then, the 44-year-old had lived a quiet, middle-class existence with his wife and two children in Essex, where he worked as a financial broker.

But he ended up in prison, an environment he knew only from television.

Dagworthy was staggered by just how little his lawyers had prepared him for life behind bars. He was a stranger to what his fellow inmates called “cell etiquette”, for example, like the rule that whoever arrives first in a cell gets the bottom, “senior” bunk. And he was appalled to witness bloody knife fights among his fellow inmates, some of whom planted ‘shivs’ in the handles of toothbrushes.

Upon his release in 2012, Dagworthy founded Prison Consultants, the UK’s first jail time advice service, which teaches wealthy clients how to adapt to life inside.

The bizarre (and expanding) world of these “prison preppers” was highlighted this week by Harvey Weinstein, who hired his own prison consultant shortly before his conviction on Monday for third-degree rape, for which he faces up to 25 years in prison. For thousands of dollars, experts say, the unnamed consultant will most likely explain to Weinstein how to survive life in the slammer as an ultra-recognisable sex offender, going into everything from how to deal with his fellow inmates to how to fill his long, empty days.

It is a lesson that the Hollywood mogul may have taken from Bernie Madoff, the disgraced financier who reportedly hired his own consultant to help him adjust to his 150-year federal prison sentence.

And it is a service for which Weinstein will be grateful: when he leaves the hospital prison ward to which he was rushed after suffering heart palpitations following his conviction, the 67-year-old will be held at Rikers Island, a notorious New York jail which housed Tupac, Sid Vicious and Mark Chapman, the man who killed John Lennon. Rikers has been plagued by overcrowding, gang brutality and allegations of human rights violations, and conditions are so brutal that in 2017 mayor Bill de Blasio vowed to shut it down within a decade.

Dagworthy tells his British clients that their first six months inside will be dominated by fear and bewilderment. “The prison van might as well have been a spaceship, because it put me into a whole new world. I liken it to arriving in North Korea. The sights, smells, sounds, the language the other prisoners speak was all alien to me. Most middle-class prisoners will come across as slightly different to the rest. They’re not of the villainous nature, they probably speak slightly differently, they probably don’t understand the language.”

Then, about six months in, clients will reach their “realisation point – when the adrenaline stops pumping. You’ve realised this is your home now and then the enormity hits you, and the stress you put on your family. That’s a massive low point. It took me about two weeks to get through. It happens with everybody. I get calls from concerned relatives.”

He advises his clients to find something to fill their day, but to keep away from jobs that might put them in an awkward position. If you work in the kitchen, for example, you might be asked to provide extra food to certain inmates. “As soon as you get involved in that, then you’re known, and you succumb to the professional prisoners who are there to try and get something from you or bully you.”

But what of American prisons, such as the one in which Weinstein will eventually find himself? David Parker*, who spent 12 years incarcerated in the US federal system and now also works as a prison consultant, says Weinstein’s experience will depend massively on where he is held after sentencing. High-security institutions such as Rikers are “violent and dangerous”, but Weinstein may eventually be moved to a medium-security facility, which, in Parker’s experience “wasn’t that bad”.

In order to survive – and even thrive – he says Weinstein will need to show respect to his fellow inmates. The old adage that you should “find the biggest guy you can and punch him” – as demonstrated by Edward Norton’s character in American History X (1998), who gets into a brawl to prepare for his spell inside – is “horrible advice”, Parker says. Your relationship with fellow inmates is far more important than your relationship with guards, whom you should keep at arm’s length in case you are seen to be currying favour.

“When I went in, I kept looking to the guards for guidance on what you do and when you do it, and quickly found out that that was absolutely the wrong thing to do,” Parker remembers.

“A mistake I made was being too friendly with too many people. You eventually fall into a routine where you’ll associate with people who look like you, you’ll eat at certain tables in the hall. The advice I give my clients is look for someone who looks like you and get them to teach you the ropes.”

Weinstein’s own situation will be complicated, of course, by the fact that he is now one of the most widely known sex offenders in history. It is likely that Weinstein will be placed in protective custody, Parker thinks, to stop him meeting the same fate as James ‘Whitey’ Bulger, the organised crime boss who was beaten to death in his West Virginia cell in October 2018. But this may be no good thing: while shielding him from violent inmates, protective custody usually means less freedom, too.

Although Parker would not recommend it, some ultra-wealthy clients like Weinstein decide to bribe other inmates, either by buying objects such as radios and MP3 players at the prison commissary, or by arranging payments to be made outside prison: “There are probably going to be people around,” says Parker, “think of them as groupies. They want to be a wealthy person’s friend.”

In British prisons, Dagworthy advises strongly against any display of wealth, warning that gangs have been known to threaten wealthy inmates with violence unless their families, on the outside, pay up.

But there is no harm, he thinks, in a well-connected inmate like Weinstein using their education to help others, like Andy Dufresne in The Shawshank Redemption (1994), a former accountant who thrives by doling out financial advice. “There’s high levels of illiteracy in prison – they’re getting letters from family or lawyers, and they can’t reply. Anyone who’s able to read and write is always useful.”

Ultimately, Parker says, Weinstein might not have such a terrible time in prison as he expects: “It’s typical for people who are sentenced to long terms in prison to despair. But what eventually happens is that your former life falls away. So it’s not ‘what am I missing – my girlfriend, my family?’ Instead, it’s: ‘On Tuesdays I play the sports league’, or ‘on Thursdays I go watch a movie in the library’.

"You develop a different life in there. The first six months are really hard. The last six months are also really hard. But the 10 years in between, they’re really not that bad.”

*Some names have been changed

Read more: Inside Rikers Island, the brutal jail where Harvey Weinstein will await his sentence