Long Bay, 14 kilometres south of the Sydney CBD, is a walled citadel of workshops, offices, warehouses, officers' accommodation and car parks, an outer ring of the ordinary world that surrounds the sadness of jails at its core. There are 1284 prisoners and 304 custodial staff, not including auxiliary professionals such as teachers, drug and alcohol workers and psychologists. Like the city it serves, the prison is an architectural hodgepodge of proud old buildings and more humble, modern extensions. Its centrepiece is a partly sandstone Federation Gothic entrance block. The site – although not the yards or cells – has million-dollar views across Botany Bay, and developers are seagulling around the property in anticipation of its eventual sale when a projected new prison is built in the city's south-west. I meet Aboud in his office, where he greets me with a happy barrage of handshakes, smiles and sometimes startling conversation. He talks about infamous prisoners as if they were wayward family members. "I've known Roger [Rogerson] for years," he says. "I put him in the old-age unit so he can't pick on anyone. And the whole unit's confined, so we can actually watch what he's doing. I believe he's still got influence with organised crime." Rogerson's accomplice-turned-nemesis Neddy Smith is in the prison too, a hard man turned to jelly, depleted by Parkinson's disease. He's at Long Bay Hospital and totally dependent on nursing staff. He and Rogerson "don't cross paths", says Aboud. Although Aboud started on The Job at Long Bay, he went on to work in prisons all over NSW and only returned to Long Bay as general manager in 2015. In his last role, he was governor at Silverwater Women's Correctional Centre, in Sydney's west. There he encountered Harriet Wran (daughter of the late former NSW premier Neville Wran), who served time for her role in the murder of a drug dealer. ("We couldn't really put her anywhere because people could extort money from her. We ended up putting her in the Mum Shirl Unit, where we put female inmates who cannot be managed in mainstream. We placed her there, under a protection order basically, and we ended up ensuring her welfare was maintained."

He also oversaw Lindt Cafe siege gunman Man Haron Monis' partner Amirah Droudis, who was charged with (and later convicted of) murdering Monis' ex-wife. ("This was very challenging, because they wanted me as the governor to communicate with her directly about the burying of [Monis'] body and the funeral service … In the end, they buried him in an undisclosed location.") Aboud chats about incarceration in the casually fatalistic way that doctors discuss death: they might prefer it didn't have to happen, but it's a fact of life. He cannonballs through the corridor of the administration building, greeting every officer in his path with a grin. On the whiteboard schedule, I notice, he is rostered as "God". It's all the what-ifs: what if I said the wrong thing, would that steak knife have gone into the officer's throat? Because she had it really dug into her throat. An officer would have been killed on my watch. That's what really scared me. Aboud takes me to his car and drives me slowly around the outer areas of the complex. Inmates in the green overalls of trustees work by the side of the path. One man carries a pickaxe, like a neutered threat. We cruise Area Three, a minimum-security "workers' jail". Knots of drab-faced, pale-skinned men appear to be on a break. They sit in unsmiling groups. "A lot of them are sex offenders," says Aboud. "They work in the buy-ups area." Prisoners with sufficient funds can "buy up" discretionary items such as Diet Coke, Heinz Tomato Soup, M&Ms, thongs and "culturally friendly meals" such as butter chicken.

"A lot of the sex offenders – I'm not stereotyping – are professional people," says Aboud. "They're ex- maybe white-collar, ex-clergy, possibly." Long Bay inmates package buy-up items for almost every prison in NSW. "Since the Royal Commission [into Institutional Responses to Child Sex Abuse], we've had more priests come into jail. And we find they usually have the temperament for this role. Aboud's parents ran a fish shop in western Sydney's Parramatta, where Aboud was raised. He says his family is long-established in the Lebanese-Australian community. There have been Abouds in government and the judiciary, including magistrate Robert Aboud. "But then, we also had prisoners back in the late '80s," he says. "When I joined The Job, I was asked to leave. Because Rule 10 back then was you had to declare all the prisoners you know." Aboud continually recognised members of his own community: " 'Oh no! Another one!' " Aboud's start on The Job coincided with a provocative time for NSW Corrective Services, characterised by sudden searches, property confiscations and riots. "We raided the cells," says Aboud, "emptied them out. I had a cousin in jail, Stephen Aboud. I opened up the cell door and said, 'Steve, how're you going?' And he went off. He said, 'What're you doing?' I said, 'I work here.' He said, 'You're a dog.' " But Stephen was outnumbered in the family. Not only was his uncle Robert a magistrate, but his brother Michael was a police officer, and his brother Jeff worked in the prison service, too. During Aboud's first stint at Long Bay, the jail was home to gangsters such as Abe Saffron, Arthur Loveday and Bruce "Snapper" Cornwall. "And they were hardened," says Aboud. "Not like we've got now. Back in the '70s and '80s, prisoners were prisoners. You knew where you stood with them; they knew where they stood with officers. These days they're either mentally ill – drug-induced – and they have no regard for other prisoners, or they have no regard for prison warders. We've also got gangs. Back then, we never really had the gangs."

Aboud parks outside the gates of Area One, the maximum-security jail. Before we go inside, Aboud says, "When I first picked up my deputy's rank, I was involved in a hostage siege in Silverwater prison." I tell him I'm sure that's going to happen to me today. "Well, don't worry," he says, "you've got a negotiator." He returns to his story. "This particular day, I was actually planning to go home at 3 o'clock. I was off to the footy to watch Parramatta. I was taking my son, Dom, who was 10 at the time, and my nephews and my brother." The governor told him to go to the Mum Shirl Unit and speak to Roxanne Holmes, a prisoner who had been refused parole. Holmes had asked to talk to a case officer and, when the officer arrived, Holmes had "grabbed her by the throat and put a knife to her", says Aboud. "So I sat down and negotiated for maybe about 45 minutes, and the steak knife was just at this officer's throat and in the end I made no promises, I just said, 'No one's gonna hurt you. We're gonna take you straight to segregation, and that's where you'll be placed. And you'll be charged.' I was honest with everything I told her. At the end of 45 minutes, because she's mentally ill, I was buggered." Holmes surrendered, "all three of us sat down and we had a glass of milk," says Aboud. "Instead of barrelling her."

After typing up a report, he didn't get home until 11pm, but his wife had taped the football game, so he watched it with Dom in his pyjamas, with a plate of sandwiches. Aboud was awarded a citation for bravery and for managing the incident without violence, and was invited to attend the Corrective Services Academy. "I was comfortable talking to Roxanne Holmes," he says, "but it's all the what-ifs: what if I said the wrong thing, would that steak knife have gone into the officer's throat? Because she had it really dug into her throat. An officer would have been killed on my watch. That's what really scared me." Between Area One's entrance block and the maximum-security yards are a series of bolted and locked fences and gates. An armed officer – the first I have seen – signs me in and Aboud guides me through the maze. Somewhat surprisingly, we pass a couple of people going the other way. A Catholic priest (identified as "the Padré") says to Aboud, "I wanted to come to see you the other day, just to remind you that I'm on the scene." A few metres later, we come upon a smiling woman who says she is feeling "wonderful". "It's a beautiful day!" she declares. "It's good to be positive. I'm a psychologist. I have to be this way." The maximum-security wings are arranged around "the Circle", where an Immediate Action Team of prison officers gathers to steer the inmates through a muster from the yards. The prisoners are sullen, unsmiling. The yards remind me of the playgrounds at my state school in England, but with boxing equipment. Aboud says there are fights "maybe twice a week sometimes, or you could go two to three weeks where nothing happens" – which is also like my school.

Aboud went to Parramatta Marist High School at Westmead, whose old boys include an archbishop, generals and judges. However, while middle-class boys were educated in the school's classrooms, some of the poorest students were raped in St Vincent's Boys' Home on the school grounds. In 1993, Aboud's former school principal, John Aloysius Littler – whose religious name was Brother Nestor – was convicted of abusing a boy at the home. Littler was on a good behaviour bond when he fled to the US, where he remained connected with the Marist Brothers. He was taken back to Australia under police escort to face 30 more charges of offences against children, but suffered the standard clerical problems of ill-health and amnesia and eventually was granted a permanent stay on the charges. But the elderly brother spent some time at Berrima Correctional Centre, in the NSW Southern Highlands, in 1996, and Aboud saw him in the yard. "I went after him," says Aboud. "I said, 'Are you Brother Nestor?' He was on his walking frame. And he said to me, 'I have not been called that for nearly 20 years.' " Aboud stresses he is a "big supporter" of the Marist Brothers, but says, "It made me feel sad for what the boys went through at the boys' home. I was angry, I was upset. It did make me cranky that he was exiled overseas. And there were two blokes I really felt sorry for: two Aboriginal boys I went to school with, who died in jail. My parents used to pick them up on a Friday or Saturday afternoon, take them back to our place. We used to look after them. And I saw one of them when I was at Parklea and he hung himself a couple of years later."

Aboud leads me into one of the wings. The inmates look through us, as if they can only see walls. One prisoner is cutting another's hair, or at least shaving his head. They all look as if they don't care what happens, today or any other day. Aboud took over at Long Bay three weeks into the new prison smoking ban. The inmates were angry and, says Aboud, the authorities were worried about the possibility of losing control at both Long Bay and Goulburn correctional centres. But Aboud put a team together and they managed to implement the policy with nicotine replacement therapy and without riots. "Staff and inmates don't smoke cigarettes," says Aboud, "but inmates get the nicotine replacement patch and soak it in water, get the tea leaves, soak it in that, dry it out and smoke it." A prisoner in Melbourne died smoking tea and patches, he adds. Too much nicotine went to his brain. "Tobacco is a new dimension for Corrections," says Aboud. There has always been a problem with drug smuggling in jails but now, "We've found our drugs have decreased and our tobacco has increased for trafficking." He recently stood down a prison officer caught trafficking at Long Bay. "It sours the whole system," he says, "because the public perception is officers are traffickers." At midday, Aboud takes me out of maximum security and leads me to the prison cafeteria for lunch. The cafe is staffed by prisoners and used mainly by prison officers. The inmates are muscular young men, some of them bearded, wearing black T-shirts and tattoos. They look like every other Sydney barista.

Over lunch – an old-school hamburger with beetroot – I realise what kind of a man Aboud might really be. Amid all the misery and hopelessness, he still sees the possibility of redemption. He desperately wants to give the best inmates another chance. He has a home a long drive away in the north-western suburb of Kellyville, a wife who is also a prison officer (they met at the Corrective Services Academy), and three children, but he spends much of his spare time trying to help the men he keeps locked up. Acura Niuqila (with trophy) celebrates with Tribal Warriors CEO Shane Phillips, Pat Aboud and correctional officer Peter Shiraz after helping Redfern All Blacks win a grand final against Coogee Randwick. Credit:Corrective Services As part of the Clean Slate Without Prejudice program, prisoners are allowed to leave the jail three times a week for boxing training in inner-city Redfern. The scheme originated with Redfern police, whose commander Luke Freudenstein grew urgently tired of seeing the same faces pulled in for every robbery, in a nation that often seems prepared to hopelessly tolerate the fact that Indigenous people are far more likely than other inmates to end up back in prison. At first, Clean Slate targeted local at-risk youth for early-morning boxing sessions where police officers hold the pads. Freudenstein built the program with Shane Phillips, an Aboriginal elder and CEO of the Tribal Warrior organisation, and other community leaders. Last year, Freudenstein set out to extend the boxing sessions to prison inmates with connections in the Redfern community. When he raised the idea with Corrective Services, the response was "certainly a lot more positive than what I thought it would be", says Freudenstein. "Obviously, Corrections are the ones who would suffer most if something were to happen. You've got to look at the public perception. You've got to look at the risk of [prisoners] being out. And Pat was pretty progressive with it. He's taken to the program as I don't know how many others would."

Like Aboud, Freudenstein gives up his own time to attend the training, which forms a central part of Clean Slate's broader effort to provide mentoring and find jobs and housing for the mentees. Freudenstein now gets up at 3.30am to drive across town and pick up inmates from Long Bay at 5.15am. Reoffending rates are down in Redfern, and Freudenstein says the program works because the youth see that their elders respect the police, and that the police care about the youth – and "if they see that we care, it's amazing what they'll do". The inmates absorb the positivity of training with happy, healthy, hard-working people, he says: "They're not gonna get that inside." And the mentored inmates become mentors themselves. "Very, very covertly, they influence the young kids not to make the same mistakes," says Freudenstein. "They quietly tell the kids, 'If you keep going down that road then you'll end up where I am, and I'm wasting my life. If I'm in jail for three years, I might as well be dead for three years.' " Selected Long Bay inmates are also invited to take part in a Tribal Warrior scheme that allows them to earn their coxswain's certificate on sailboats. Recently, several prisoners were permitted to take a boat about 80 nautical miles south from Sydney Harbour to Jervis Bay, to pick up another boat. "And they brought it back!" says Aboud. Long Bay inmate Acura “Junior” Niuqila before a Redfern All Blacks rugby league match. Aboud accompanies him to every game. Credit:Peter Rae

Perhaps the star of Clean Slate is Acura "Junior" Niuqila, who is in Long Bay for armed robbery conspiracy. Shane Phillips requested Niuqila be given time to play rugby league for Redfern All Blacks. Initially, Aboud said, "You're joking. You'll get me shot." However, it was eventually agreed that Niuqila could be allowed out as long as Aboud would supervise him. Niuqila now trains and plays with the All Blacks and Aboud attends every game. "We've got a great team," says Aboud, with all the partisan pride of a football dad. He loves football, but he isn't involved for the sport. "I'm doing what I'm paid to do," he says, "which is to reduce recidivism in the community." Not every inmate who begins Clean Slate has a success story. Stanley Ceissman first attracted public notice as a boy jumping on the roof of a police car during the 2004 Redfern riots, and had spent most of his adult life in jail. He did not complete the program but he was released from custody with a home and a job, and now he's back under maximum security at Silverwater. "He's just a young kid, got a lot going for him," says Aboud. "I took him out to the footy one night. His sister saw me. She said, 'Mr Aboud, thanks, it really means so much to my family. Look, all Stan knows is jail. We're going to help him, but don't hold your breath.' It's very sad." It seems incredible that, after all his years in The Job, Aboud still worries enough about a single case to be visibly angry with Ceissman, yet remains sufficiently empathic to see the man's life as a catastrophe outside his own making.

"I think he truly cares," says Jeremy Wright, acting mentor co-ordinator at Tribal Warrior. "Pat's in a really true partnership and shares the values with Luke and Shane. They are all committed to either keeping young Aboriginal community members out of jail, or making sure they're in jail for as short a time as possible, and – when they get out again – making sure that they stay out of jail." But some inmates – particularly some women – prefer to stay in jail, says Aboud: "It's structured, it's orchestrated, it's simple. They've got status in prison, where in the world they've got nothing. They get paid to work. They've got camaraderie. They know who the officers are. They get free medical. It's tragic, but that's their life." The prison population is ageing, and includes an increasing number of women with "mental health issues due to domestic violence and being sexually abused", says Aboud. "Through domestic violence, they've turned to drugs. Society has a lot of work to do on that, in my view." Loading But what does it mean when a safe and affluent society like Australia locks up women – and men – who have been driven to despair by abuse? Should they ever have been imprisoned at all? "I can't really say," says Aboud.

"That's up to the courts to make that determination. We get who we get, and we've got to manage who we get. But for me to say, 'No, they shouldn't be [imprisoned]', would be wrong. For me to say, 'They should be', it'd be wrong. At the end of the day, we face what society is, and we manage it the best way we possibly can." In the end, there's a limit to the problems that can be solved by a few good men.