The Gilligan Tapes: Ireland's Most Notorious Crime Boss in his own words

By Jason O'Toole

John Gilligan is no altar boy, by his own admission. One of Ireland’s most infamous criminals and drug lords, and widely believed in the court of public opinion to have ordered the cold-blooded murder of journalist Veronica Guerin, he remains a defiant figure.

In this remarkable book – the first of its kind – journalist Jason O’Toole distills hours of sensational face-to-face, no-holdsbarred interviews with the feared criminal into a fast-paced and jaw-dropping account of the Irish gangland scene.

And Gilligan doesn’t mince his words. ‘I didn’t believe in God, but I know I’m going to hell.’Starting out as a petty thief in Dublin, Gilligan rose to the status of crime lord earning £10 million from drugs within his first two years. He mixed with serious criminals such as Martin ‘the General’ Cahill, Gerry ‘The Monk’ Hutch, Patrick 'Dutchy' Holland and John Traynor. He was deeply involved with money laundering, miraculously survived an assassination attempt, and it is said he has millions stashed away at a secret location.

O’Toole demands answers from Gilligan for all the hard questions; some of his responses will make readers shiver. Gilligan knew that laying all his cards on the table could mean signing his own death warrant. But he has done it here. And with a cast of all the country’s deadliest underworld figures, this exposé is nothing short of explosive.

• Language: English
• Publisher: Merrion Press
• Release date: Sep 4, 2023
• ISBN: 9781785374685

Jason O'Toole

Born in Dublin, Jason O’Toole has worked as a journalist, columnist, editor and publisher. He was Senior Editor of Hot Press for six years, and his journalism has also appeared in the Irish Daily Mail, The Sunday Times, Irish Independent, La Repubblica, Playboy and Empire. O’Toole is the author of nine books, including The Path to Power: Brian Cowen (2008), Memory Man (with Jimmy Magee, 2012) and the bestselling Crime Ink (2009), an anthology of his in-depth interviews with Ireland’s most notorious criminals.

Book preview

INTRODUCTION

JACKIE KENNEDY WAS STILL WEARING her bloodstained Chanel dress on the emergency flight back to Washington, as Lyndon B. Johnson was sworn into office mid-air. She resisted all requests from the presidential aides to change her clothes. ‘Let them see what they’ve done,’ the First Lady famously whispered.

Emotive words. But the concealed bloodshed was even more haunting when we in the Irish Republic had our very own ‘Where were you when JFK was killed?’ moment on 26 June 1996. The heinous murder crime scene at the Naas Road traffic lights will live on in our collective memories: ticker tape wrapped around Veronica Guerin’s red Opel Calibra car with the windows shrouded. It left little to the imagination.

The wheels of justice don’t necessarily turn slowly – occasionally they’ll come to a screeching halt. There’s never been closure in either of these two assassinations, because the mysterious gunmen were not properly identified and charged. It’s impossible to maintain that justice was served in Veronica Guerin’s cruel death when the only culprit convicted was the motorcyclist, Brian Meehan, who ferried the unidentified pillion passenger with a concealed Magnum on that fateful afternoon.

There were echoes of the iconic photograph of Lee Harvey Oswald getting arrested for the JFK murder when the drug baron John Gilligan, dressed in a jumpsuit, was frogmarched off the plane following his extradition back to Ireland to face trial for allegedly ordering the assassination. The diminutive figure had emerged from the shadows to become Ireland’s answer to O.J. ‘absolutely, 100 per cent not guilty’ Simpson when he was unexpectedly acquitted of the murder. He was guilty as sin in the court of public opinion, but guilt by association was not enough to convict him.

As Judge O’Donovan pointed out in the murder trial: ‘While this court has grave suspicions that John Gilligan was complicit in the murder of the late Veronica Guerin, the court has not been persuaded beyond all reasonable doubt by the evidence which has been adduced by the prosecution that that is so and, therefore, the court is required by law to acquit the accused on that charge.’

It’s unusual for such shadowy figures to put their heads above the parapet – even if acquitted. But Gilligan has always maintained his innocence and didn’t want to shuffle off this mortal coil without telling his side of the story. He wanted to settle old scores in the process.

Soon after his release from prison in October 2013, Gilligan mulled over the idea of doing a book. He approached me first, but I soon went cold on the idea when he was reluctant to detail his drug empire while the legal battle with the Criminal Assets Bureau (CAB) was still ongoing. Mob bosses are hubristic beasts at the best of times, but the cagey Gilligan was not complacent enough to write a book like Simpson’s If I Did It: Confessions of the Killer.

Gilligan had much more pressing concerns when he was shot six times the following March. The book idea went out the window.

He clearly knew where all the bodies were buried, so to speak, when it came to Ireland’s volcanic gangland history. However, it appeared that the old man would go to his own cold grave without shedding any further light on his turbulent life and heinous crimes.

Then, in more recent times, Gilligan once again warmed to the idea of going on record. It had finally dawned on him that there was not much time left in his own sand clock. He attempted to write a memoir at first, but quickly abandoned the idea. He might have been able to steal a work of art, but he was never going to write one. He’d be the first to admit it.

One morning in April 2022, I fired up my laptop and noticed an email from my old employer, Hot Press magazine, with the subject heading: ‘Voice Mail from John Gilligan!’ It arrived in my inbox without the exclamation mark, but my overactive imagination added in a few expletives, too. Why would one of Ireland’s most notorious criminals suddenly want to reach out to me?

We hadn’t spoken in almost a decade. Our paths first crossed when I conducted an interview with him for the magazine at Portlaoise Prison in 2008. It had been arranged by the convicted fraudster Giovanni Di Stefano, who was granted early release from jail in England in April 2023. He received a fourteen-year prison sentence for fraud, theft and money laundering in 2014. The British judge ordered an additional eight-and-a-half-years be later added to the sentence if he refused to compensate his victims to the tune of £1.4 million. Di Stefano gave the judge a proverbial two-finger salute and refused in colourful language.

It was a dramatic fall for this Walter Mitty chancer. Di Stefano had hoodwinked the world into believing he was a qualified legal eagle. He revelled in his moniker, The Devil’s Advocate, which was bestowed upon him because he’d represented the bad, the ugly, and the downright evil. He’d even appeared on CNN to discuss his ‘clients’ Saddam Hussein and Slobodan Milošević. He’d also claimed to represent serial killer Dr Harold Shipman, which was subsequently denied by his actual legal representative. Other clients he boasted about representing included British gangster John Palmer, disgraced businessman Nicholas van Hoogstraten, the Great Train Robbery gang member Ronald Biggs, and mass murderer Jeremy Bamber.

Di Stefano duped the Irish establishment too when he appeared on The Late Late Show to discuss his representation of Paddy Holland and other notorious local criminals. He even claimed Gilligan was one of them. ‘He never represented me,’ Gilligan later told me. But he acknowledged that they did meet in Portlaoise Prison.

Di Stefano was nothing more than a modern-day version of the con artist Frank Abagnale Jr, the fake doctor, airline pilot and solicitor. He was portrayed by Leonardo DiCaprio in Steven Spielberg’s Catch Me If You Can. However, Di Stefano was still the best contact to ask when I first sought interviews with Gilligan and Holland in the late noughties.

I had a date with The Devil’s Advocate in late 2007. I jetted out to Rome on Hot Press magazine’s dime to interview him. The then 52-year-old Di Stefano ran his international law practice, Studio Legale Internazionale, from his plush apartment in an affluent part of central Rome. He was in the headlines at the time for supposedly ‘representing’ Chemical Ali in Iraq and the serial liar and fantasist Ian Strachan, the now deceased blackmailer of a minor British Royal Family member.

‘I am generally very weary of journalists because, like hookers, they generally only want something and give very little. It’s really a question of supply and demand. But Jason, you seem somewhat different,’ Di Stefano told me in a funny hybrid Cockney-Italian accent, which felt almost put on for show. He was a British citizen but was born in southern Italy and raised by his parents in England.

‘Why am I different?’ I asked.

‘I pay a lot of attention to my dog, Rufus,’ the affable character replied somewhat cryptically, as he stroked his dog’s stomach. ‘You see, young children and animals have no prejudices in life. They have no axes to grind, and they are, to coin a phrase, mentally, socially and philosophically innocent, so I pay a lot of attention to the conduct of my young son and my dog to outsiders.’

‘Your dog!’

‘Let me give you an example. You never see a miserable dog in a happy family, and you never see a happy, joyful dog in an unhappy family. An animal or young child is like a kind of thermometer measuring ‘the intruder’. Now, Rufus nearly always barks at almost everything. First, he barks, then he sizes up the person, and then decides what action, if any, he will take. When you came in, no bark from Rufus. No aggression. No warning. Rufus just lay near my feet or near your feet, Jason. Since Rufus approved of you, there was no reason why I could not be more open than usual.’

I wasn’t going to argue with such outlandish logic. I later had to stop myself from sniggering when Di Stefano produced his certificate for the New York State Bar without any prompting. It looked just about as convincing as a teenager’s forged sick note for school.

I merely nodded my head and handed the obvious fake copy back to him. My main goal here had been to cajole him into getting me access to his two most famous Irish ‘clients’. Afterwards, as we both walked out of his apartment complex on that warm early summer day, I asked if he could arrange an interview with Gilligan.

‘Leave it with me. I’ll see what I can do,’ said this small and bald rogue, as he threw a suitcase into the boot of his BMW.

Di Stefano declared he had to catch a late flight to Baghdad to meet with Chemical Ali and Tariq Aziz. As he dashed off at breakneck speed, I wondered if he was merely going around the block a few times until I’d left.

I doubted that I would ever hear from Di Stefano again, but some months later I received an unexpected call from him.

‘Would you like to meet my client John Gilligan for an interview?’ His voice crackled down the phone. He said he was making a long distance call from Baghdad. In light of this con artist’s future jail sentence, it is entirely plausible that he was buzzing me from the comfort of his home and crunching newspaper for special effects.

‘This interview is my idea. John Gilligan says he’s doing this against his better judgement, but he also says you can ask any question and he’ll give you an honest answer – or a no comment if he won’t answer it. That’s the deal. But he won’t tell you a lie,’ Di Stefano told me.

A few days later, I was sitting eyeball-to-eyeball with Gilligan at the visitors’ centre in Portlaoise Prison. I was unable to bring in even a pen and paper for the visit, but soon I started receiving late night phone calls from Gilligan, repeating what he’d told me that day we’d met.

The subsequent 13,000-word interview ran over two parts in Hot Press. There was praise and hysteria in equal measure. It resulted in the then Minister for Justice, Dermot Ahern, ordering an investigation into how I managed to obtain a prison visit with the country’s most infamous inmate. According to the prison authorities, new airport-style security measures have been implemented as a result, but they were already in place when I visited Gilligan in Portlaoise. The magazine itself was banned from prisons.

I next interviewed Gilligan when he called me a few weeks after his prison release in 2013. I printed some of our extensive conversations in a 2,000-word piece in the Irish Daily Mail. But our paths hadn’t crossed in the ensuing eight long years, and I had felt it was not likely to occur in this lifetime – until Gilligan left that voice message.

I was in two minds about calling him back, but after a few hours I purposely picked up a new burner phone to call him. For obvious reasons, I shuddered at the prospect of Gilligan having my personal phone number. Like Gilligan, I too was now residing in Spain, and the last thing I wanted was for the local authorities to see my number flashing up on the screen of a well-known drug dealer. They could’ve erroneously branded me as an underworld associate.

Gilligan picked up on the fourth ring. He sounded surprised at the Spanish code +34 popping up on his screen, and cackled with laughter down the phone when he learned that I was also over there. The man dubbed ‘evil personified’ made his best efforts to come across as charm personified. Once the obligatory small talk was out of the way, he got down to brass tacks. Even before Gilligan launched into his sales pitch, I’d already read between the lines and sensed he wanted me to do a book on him. He’d singled me out because I was the only journalist with whom he had spoken at length on the record in the past twenty-five years and hadn’t ‘twisted’ his words.

‘I’m running out of time. I’ve nothing to lose,’ Gilligan told me.

It was undoubtedly a journalistic scoop, but he could sense my hesitancy and gave me a week to mull it over. I spent the next few days asking myself: Was it really an offer I couldn’t refuse? I lead a relatively quiet life these days and was unsure if I wanted to weather another media storm.

There has always been a peculiar propensity in some quarters in Ireland to shoot the messenger, or rather, the interviewer. In 2006, RTÉ bosses refused Pat Kenny permission to interview Paddy Holland on The Late Late Show. In 1997 the television host was allowed to conduct a pre-recorded radio interview with Holland, but even that never aired when the management at RTÉ felt it could prejudice any future court trials.

It seemed like we had moved with the times when Gerry ‘The Monk’ Hutch was permitted TV airtime by the national broadcaster on Prime Time in 2008, and we don’t know how many his gang killed. ‘The Hutch organised crime gang is in the frame for at least nine murders,’ according to the Irish Mirror in May 2023. For years The Monk was erroneously perceived as a Robin Hood criminal and it was rarely mentioned in the press that his gang members imported drugs into the country.

I would imagine Irish TV stations would still jump at the chance to interview The Monk even now, and gory documentaries like Serial Killer with Piers Morgan are a big hit in Ireland. But John Gilligan is a different kettle of fish, it seems. I was a little taken aback when a prominent politician who introduced me to the producer that agreed to help turn The Gilligan Tapes into a documentary forewarned me: ‘They always shoot the messenger. Sour grapes, and all that. Be prepared.’ I don’t necessarily agree. Why should there be a big media storm when the self-confessed double killer Malcolm Macarthur conducted interviews for a book earlier this year without much, if any, controversy?

The Irish public might have an insatiable thirst for true crime, but they rarely get to hear both sides of the story, as they often do in England. There have been numerous crime memoirs published over there, such as the ones by Charlie Richardson and ‘Mad’ Frankie Fraser.

It’s peculiar that no book has ever been published by a prominent Irish gangster. But it’s not from a lack of trying. Christopher ‘Bronco’ Dunne wrote a memoir titled Wildfire in his formative years, in which the iconoclastic criminal attacked the Christian Brothers for their handling of the reform schools, but was unable to find a publisher at the time, which was understandable because Ireland was still under the dark cloak of the Catholic Church.

What excuse would Bronco be met with now if he tried in vain to shop it around town? There would undoubtedly be more than one. I’d be astonished if any major Irish publisher would print John Gilligan’s autobiography if he had written one, but their British counterparts would be falling over themselves if he happened to be from there.

Ireland is much more conservative than we like to pretend, with such self-imposed censorship. We’re light years behind our American counterparts when it comes to their liberal libel laws. The late Cormac McCarthy, who borrowed one of his most famous book titles from W.B. Yeats’s poem ‘Sailing to Byzantium’, would be bewildered by how Ireland is no place for old criminals longing to tell their stories.

As Anne Harris, former deputy editor of the Sunday Independent, once said, in a different context, everybody should be entitled to tell their side of the story. That paper’s current editor, Alan English, clearly agreed with this sentiment because, when he was in charge of the Limerick Leader, he bravely interviewed Wayne Dundon in 2010. Here was a bloodthirsty crime boss whose gang was linked to the murders of several innocent individuals, including Roy Collins and Shane Geoghegan. The provocative headline on the inside two-page spread read: ‘Why should I be sorry for Steve Collins [Ray Collins’ father]? says Dundon.’

As headlines go, this one certainly didn’t mince its words, but it also didn’t glorify crime. Nor does this book. Sure, the main objective of my interviews with Gilligan was to get as much information as possible directly from the horse’s mouth, but I also warmed to the idea because there would be great value in the exercise if it included obvious moral lessons for younger readers.

According to one of Britain’s best-known crime correspondents, Duncan Campbell, there has always been an appetite for criminals’ gory memoirs, but the ‘most successful are those that include self-reflection’. Similar sentiments were echoed by the Glaswegian hardman-turned-artist Jimmy Boyle, who wrote his autobiography, A Sense of Freedom, at Barlinnie Prison in 1997. Could Gilligan be on the same page as them?

Boyle articulated very well why such books are valuable exercises when he noted: ‘In writing the book in a manner that expresses all the hatred and rage that I felt at the time … I have been told that I lose the sympathy of the reader and that this isn’t wise for someone who is still owned by the state and dependent on the authorities for a parole date … The book is a genuine attempt to warn young people that there is nothing glamorous about getting involved in crime and violence.’

As I mulled over Gilligan’s offer to be interviewed, it also hit me that the Irish public would be curious to hear him in his own words, not just on the page, but also on camera. It had been a real ‘water cooler moment’ when The Monk appeared on RTÉ’s Prime Time in 2008.

Yet, apart from the aforementioned interview with The Monk, I couldn’t recall any other major Irish criminal willingly captured on film – excluding Martin ‘The General’ Cahill’s childish striptease down to a pair of Mickey Mouse boxing shorts outside the Four Courts. For that matter, I couldn’t even recall any English-speaking mafia boss in modern times who had spoken on camera at length for a major documentary. It would be a bit of history in the making, which was enough motivation for me.

I called Gilligan back and told him that I would be happy to write a book on him, not with him. There was a big difference. I wasn’t going to be his mouthpiece and I would not pull any punches in the book. Gilligan accepted that he would not be given an easy ride. It was a risky move on his behalf because he’d be hoisted by his own petard if the veracity of his version of events was shown up as lies.

I forewarned him that he wouldn’t be able to seek final approval of whatever I decided to print. He would have to buy a copy like everyone else. He understood and was still happy to conduct the series of interviews. When I said that I wanted to video record our interviews for a potential documentary, it was now his turn to ponder it all.

A book was one thing … but a tell-all documentary, Gilligan was probably thinking, was a different matter. For him, there was the criminal underworld’s unwritten code of silence. The omertà, as the Italian and American Mafia called their twisted version of honour among thieves. ‘I don’t want to be seen as a rat,’ he said.

Gilligan seemed reassured when I said that I was only interested in hearing about his backstory and version of events surrounding the murder on the Naas Road. He didn’t have to proffer views on any topic that didn’t personally concern him, such as the Hutch–Kinahan feud. I wasn’t asking him to do punditry.

Meanwhile, I felt the book would be best suited to the Q&A format. A straightforward biography would result in much fewer direct quotes on the page, which would be a defeat of the entire exercise: the main reason anybody would want to crack open this book would be to read Gilligan in his own words. My task as an interviewer was to be ‘curious, not judgemental’, to quote Walt Whitman, to coax him to open up as much as possible – leaving it to others to look for any holes in Gilligan’s words.

Fortunately, I was at ease with the Q&A style of journalism because I had done, on average, two such in-depth interviews a month for a total of six years with ‘The Hot Press Interview’. The magazine’s in-depth interview has long been considered an institution in itself, ever since Charles Haughey famously told John Waters in 1984: ‘I could instance a load of fuckers whose throats I’d cut, and push over the nearest cliff.’

The key to Q&A interviews is to ensure they flow almost as if they were first-person prose at times, or even a play. It’s a format that requires its own editing skills, which are almost second nature to me after conducting approximately 120 of them for Hot Press. It helped that Gilligan was a born raconteur.

There was precedent for a Q&A book on criminality. The famous British gangster John McVicar, played by The Who’s Roger Daltrey in a movie, did interviews for such a book with university lecturer Laurie Taylor. Entitled In the Underworld (1984), it was ‘written in dialogue format and offered a rare insight into organised crime in Britain’, according to his obituary in the Sunday Independent.

McVicar, once described in the British press as ‘public enemy No. 1’, would later embark on a relatively successful journalism career. It’s hard to imagine an Irish gangster, even if he could string a proper sentence together, sneaking into print, even on the letters pages. But Gilligan could definitely offer that same rare insight into the Irish underworld in an extended Q&A format.

However, Gilligan was apprehensive about implicating himself in various unsolved crimes. ‘Because now I’m a free man and I’m going straight,’ he claimed on our first day recording these interviews. ‘The police and the media would say, Make sure you charge him with them admissions that he’s making now. So I’ll be as honest as possible, but don’t want to incriminate myself. I’m not going to tell a lie. But I can’t answer every question on criminality. I can answer every question [on a crime] that I was before the court on, when found guilty or acquitted. So, when you ask me questions about that, I will not be lying. There’s no double jeopardy from that period … if I done anything wrong and I got found not guilty, I could say to you, Yes, I did, I did it. So I’m not afraid to admit anything I did, because nothing can happen to me.’

In the end, I would present to Gilligan every serious allegation made against him in countless newspaper clippings and the half dozen books written on Veronica Guerin and him.

We agreed to start recording interviews for five days straight in early May 2022. I told him that my goal was to record at least twenty hours on tape. I assumed, incorrectly, that the book could be turned around quickly enough. Some nine months later, I was still meeting with Gilligan in an effort to probe deeper and deeper for both book and documentary. I wanted to get under the skin of this complex character, who comes across like a mixture between The General and Robert De Niro’s character in Heat, and, in the process, help shine a light on Ireland’s underworld in a way that has never been done before.

In total, we would meet on five different occasions for twenty-odd days of extensive face-to-face interviews, recording approximately thirty-five hours on film, plus many more hours of phone conversations. There are more than fifty hours of tapes there. I transcribed some 250,000 words of direct quotes; enough to fill up the pages of this book many times over.

The long-term goal here was to produce a book that would be one of the first sources future historians would turn to and heavily reference when writing about the emergence of the criminal underworld in twentieth-century Ireland. I suppose only time will tell if that will be realised, but, if nothing else, any impressionable young person will almost certainly walk away from this book with a valuable lesson if they read Gilligan’s closing reflections in the last chapter.

‘Crime’, Gilligan repeatedly told me, ‘doesn’t pay.’

TAPE ONE

THE RISE OF THE STREET URCHIN

‘As far back as I can remember, I always wanted to be a gangster.’

– HENRY HILL, GOODFELLAS

It felt like the calm before the storm on a balmy Monday morning in early May 2022 in Torrevieja, a dreary seaside city on the Costa Blanca coastline in Spain. It was weather for suncream and baseball hats, but there was a far more pressing concern to avoid getting burned, in mafia parlance, as I waited, with some apprehension, for a face-to-face meeting with one of Ireland’s most notorious figures.

To the minute, John Gilligan strode into the hotel lobby, dressed as if he had a court appearance, with a folder tucked under his arm. He might have been through the wars, but he looked relatively youngish, even with his trademark shock of grey hair. He also seemed physically strong for someone in their twilight years. It was obvious that he used to lift weights in prison from the way he pumped my hand. The only real sign of old age was his small hearing aids, but they clearly worked their magic because he never told me to speak up or to repeat a question.

He asked if we could